Is there really no work for older intellectual workers like me?

Jack Krupansky
119 min readFeb 20, 2017


My normal work career is essentially over. I have no interest in pursuing my old career as a software developer and consultant. Unfortunately, I’m not even close to being financially well off enough to officially retire, so I need to seek at least some stopgap work to provide income to tide me over until my Social Security and retirement accounts are sufficiently flush with cash that I can officially retire.

Unfortunately, try as I may, over the past two years I haven’t been able to identify even a single solid work opportunity that will work for me. Why is that? What can be done to rectify that? Those are the two questions this informal paper will explore.

My perception is that I am not alone, that plenty of other older intellectual workers are in the same boat, unable or uninterested in continuing their old careers, but too young, too energetic, or too financially insecure to retire.

This informal paper is primarily my own personal career story, but my hope is that enough people will see enough parallels to their own situations that somehow we can all benefit from our collective wisdom.

I know this paper is long — my advice is to read the first few and last few sections and then skim the section headers and only drill down into those sections that appeal to you.

Intellectual workers

Some may be confused by that term. They might be more comfortable with the common term of knowledge worker, but to me a knowledge worker simply uses or disseminates existing knowledge in their work, while an intellectual worker’s primary focus is on producing intellectual work products, new material that is primarily knowledge or other forms of intellectual property, as opposed to physical objects or services.

To be clear, intellectual workers are almost always professionals as well, requiring some sort of intensive education and possibly formal credentials.

A customer service representative certainly must apply a significant degree of knowledge and even manipulate information in customer records and transactions, but they don’t create new intellectual property or knowledge for wide dispersal.

I could have used the term intellectual professionals as well. Flip a coin whether intellectual professional is a better term than intellectual worker.

I didn’t use the bare term professionals since there are quite a few professions that don’t have quite the same emphasis on creation of intellectual property, such as doctors, accountants, lab technicians, or investment bankers. Not to mention the so-called oldest profession.

I suppose I could’ve generalized this paper a little to apply to all professionals, not simply those who produce intellectual property, but maybe that would have watered it down too much and diminished my own role and relevance in the story. I would hope that non-intellectual professionals might at least find enough parallels in my story to relate to their own stories.

In my personal case, in my former career as a software developer I produced computer software, which also included a fair amount of technical writing. Basically, sitting and typing at a computer most of the day, with very little contact with any other physical objects or people.

Writers, journalists, scientists, research analysts, and lawyers would also be prime examples of intellectual workers. Not that they don’t also interact with people a fair amount, but their primary product in some form of knowledge and intellectual property.

Teachers and trainers would be knowledge workers but not intellectual workers since they use and disseminate knowledge but don’t produce new knowledge on their own. But those who develop teaching or training materials or plans would be classified as intellectual workers since they are producing a form of knowledge. Professors engaged in research would be a hybrid — knowledge workers when teaching in class, and intellectual workers when engaged in formalizing and publishing the results of their research.


This informal paper is dedicated to all of those poor lost souls who are in the same boat as me:

  • Primarily intellectual workers, producing knowledge and other forms of intellectual property.
  • Our traditional careers are over, for a variety of reasons, whether we are unable or uninterested in pursuing our old careers.
  • We’re too near retirement to start a whole new career that will end within a few years when we officially retire.
  • Consulting based on our former career is theoretically possible, and we have the interest, but there is no significant interest for our services.
  • Our minds are still very active and we still have a fair amount of energy and enthusiasm that could be applied to intellectual pursuits.
  • Our central focus is intellectual pursuits. We work with ideas and relationships between ideas, concepts, vision, strategies, and plans.
  • We either don’t have PhD’s or other forms of emeritus status sufficient to earn us a financially secure position or even if we do we don’t have quite the intellectual edge to keep us in the game.
  • Even if we do have the ability to continue working at traditional jobs, we simply aren’t interested and don’t have the level of emotional energy to stay engaged with a traditional role.
  • Many of us don’t have sufficient financial resources to live in the lifestyle we would like.
  • We actually do wish to work in productive jobs and to continue making productive intellectual contributions to society.
  • We need work that is satisfying and fulfilling.
  • We need informal work arrangements, such as part-time work with very flexible schedules.
  • We would like to travel more, requiring sufficient income as well as flexible work schedules.
  • Traditional job roles simply don’t fit with our level of knowledge, experience, and wisdom. Generally speaking, any traditional role will not attract and keep our interest.
  • There are too few organizations willing or able to recognize us for who we are, to recognize the value of our talents, or it is simply too difficult to identify such organizations.
  • The work pace, assignments, and interactions must not place us under an excessive level of stress that puts our health at risk.
  • We’re not interested in competing with and taking the jobs that young people deserve and need to get their careers off the ground.
  • We do need a decent level of compensation and benefits, but accept that compensation may be lower due to fewer hours, provided that our more senior and more talented contributions are compensated to the extent that they are of value to the organization.
  • You may also be a young person who is very definitely not in the same boat as me, but you may have parents or aunts or uncles or friends with relatives who are in the same boat as me. This paper can help you understand how they are the way they are, or why some of them don’t have these problems while some of them do.


You might be interested in this informal paper if:

  • You are one of those poor lost souls mentioned in the dedication and might be able to learn something from my experiences or share your own successes and failures so we can learn from each other.
  • You were one of those poor lost souls but found your way and might be willing to share your experience.
  • Your organization is interested in intellectual workers who think and live outside of the box and can accommodate non-traditional work arrangements.
  • Your organization provides services to older intellectual workers who are having difficulty finding meaningful work.
  • You are simply a thoughtful person who relates to all of this and thinks they might be able to offer some feedback or other form of assistance.
  • You are a young person with relatives or friends with relatives who are in the same boat as me. This paper can help you understand more about them, and maybe even help you relate to them at some level.


My purpose for writing and posting this informal paper is to:

  • Clarify my own thinking, to help myself.
  • Confirm whether my thinking is valid or not.
  • Get feedback from others on my thinking, discovering gaps, holes, weaknesses, and other flaws in my thinking.
  • Become aware of opportunities from others.
  • Hope that a clear description of my own situation might help others in a similar situation.
  • Help younger professionals and students understand why older intellectual professionals are having such difficulty.
  • To free myself from my past, so that I can move on, unencumbered.
  • To clear my head so that I can move on to other, more interesting activities.


My specific asks of readers are:

  1. Are you aware of specific work opportunities that would clearly be a good fit for me?
  2. Could you please keep me in mind should you become aware of such opportunities in the future?
  3. Do you think I am missing anything? Are there any clear gaps or flaws in my reasoning?

Technology focus

My main area of focus for my career has been the technology sector, as a software developer and consultant, and that is indeed much of the focus for this paper, but a fair amount of the discussion here should apply to non-technology sectors as well. Not to mention that my personal interests going forward have a strong non-technology component.

Workers in the technology sector should find this paper most relevant. Workers in other sectors should find at least some tangential relevance or parallels to their own situations. Not to mention that most sectors have a strong technology component these days anyways.

Why is this so long?

My apologies if you think this informal paper is too long, but my emphasis is always on thoroughness over brevity. I simply wanted to cover every base imaginable, to leave no stone unturned. That’s my method… even if some consider it madness or even merely very annoying.

Besides, the main point of this informal paper is that I am having great difficulty finding satisfying work — if I didn’t have such significant difficulty I wouldn’t even be writing this paper at all, so by definition it should be longer rather than shorter.

The other odd factor in this paper’s length is that part of my core personality is that I am intensely drawn to seemingly intractable problems, an opportunity for me to dive deeply and explore broadly in search for a solution. Well, my current predicament certainly fits the bill for a seemingly intractable problem, so of course it gets the full treatment, with this informal paper being a thorough examination of my situation in both depth and breadth.

Another factor in the length is my goal of giving the reader the maximal amount of insight into the nature of my predicament, through deeper and broader levels of detail.


I’m very serious about thoroughness. Every. Little. Detail. If you don’t share my passion for thoroughness you’ll be very disappointed with this paper. Just a mild, polite warning. Proceed at your own risk.

How to read this paper

I do offer a polite suggestion to those who do think it is too long: Simply skim the section headers looking for topics that you are most interested in, and then you need only read those sections that really interest you.

Organization of this paper

My apologies in advance if this informal paper comes across as a stream of consciousness rather than having a clear structure. It is verging on book length and in fact would have chapters if Medium had such a feature. I have tried to group sections as appropriate and order them as well, but different readers may have different interests.

In the end, I decided that too much structure might confuse more than help. I focused my attention on the ordering of sections, but frequently found that I had conflicted views about the order that various topics should be presented. I made compromises based on my best judgment, which I expect will not necessarily be the same compromises that some readers might have preferred that I make. Again, my apologies.

Friendly advice for young professionals and students

Although young professionals and students are not the primary audience for his informal paper, I think there are some pieces of friendly advice that I can offer to them to help them avoid ending up in my same boat:

  • Don’t take all of this as too strong a cautionary tale — you may have great success at the same places where I did not.
  • Assess your own motives and interests.
  • Follow your own authenticity.
  • Go your own way. What works for others may not be best for you.
  • Don’t follow in my footsteps! (missteps)
  • Be yourself, but think long and hard before becoming too much of an outlier that most people can’t relate to, unless that is really the real you.
  • Think about who your role models are. If you have none, think long and hard about that.
  • Think, but don’t overthink. Action and forward progress are infinitely superior to overthinking.
  • Get a mentor ASAP.
  • Have some faith in serendipity.
  • Cultivate a second or backup career early, something you can fall back on if your main career falters. Me, all I had was my main tech career and nothing else.

Should I ever work again?

Right now, this is the single biggest question running through my head — should I even bother looking for work anymore or should I simply accept the reality that I am never likely to work again and then proceed to focus on how to go about retiring.

I toyed with using that question as the title of this paper, but my passion for being explicit and detail got the best of me.

Seeking advice

Seriously, I could use some good advice on that central question.

My tentative answer is that I should spend the next year or so seeking some sort of work, and only then make the decision to abandon my search for work.

So, have at it, give me your best advice.

Do I really want to work?

No! I have no desire to work, at least in any traditional kind of job.

Although some sort of informal, part-time work would be acceptable and welcome.

So, yes, I actually do want to work, as long as it is personally satisfying, which rules out any of the traditional work I have experienced or heard or read about.

Sure, I would like to spend much more of my time pursuing personal interests, but I recognize that my limited finances imply that at least some work would facilitate that pursuit.

And my expectation is that there might be some work that actually provides me with a deeper range of experiences in my areas of interest that is more satisfying than me simply pursuing my interests in my own. In other words, experiences that can take my interests to a whole new level, much more than a mere hobby.

In short, yes, I do want to work — provided that it is satisfying, and doesn’t incur a distressing level of anxiety that could negatively impact my health, which is my most valuable asset.

Good riddance

Yeah, that’s what part of me really thinks and wants, to simply walk away, even literally run away from the very concept of working. Good riddance, indeed.

If only it were that simple.

Open to opportunities

Just to be clear, I really am open to opportunities, provided that they provide me with some significant level of satisfaction and don’t entail any level of stress that may jeopardize or compromise my health even the slightest.

What is work?

Not to be flippant, but I would satirically define work as any activity that someone is willing to pay you for that you wouldn’t be inclined to engage in if not for being paid.

But don’t some people enjoy their work, working even when they no longer have a financial need for that income? Yes, but what is the first thing they will tell you? “It’s not really ‘work’ since I really enjoy it!” And if they don’t say that, it probably means they don’t enjoy the “work” as much as they claim.

There is also volunteer “work”, virtually identical to traditional work but without financial compensation, albeit with a fair degree of flexibility in work arrangements.

In any case, the goal here is to find work that doesn’t feel like… work.

My career in technology — it’s complicated

At first blush, the mere fact that I have experience in “technology” should automatically assure that I have employment, for life. If only it were that simple, but… my career in technology is… complicated, as you will soon see.

Why did I end my old career in technology?

It was simply getting way too difficult to pull off the work in my old career in technology, a combination of:

  1. I was no longer interested in the work.
  2. The available work to be far too tedious.
  3. Too much energy to keep up with the growing complexity of the technical matter, which I no longer had any interest in anyway.
  4. My own energy level was beginning to wane anyway. I still have a fair amount of energy, but not the level I had 20 years ago.
  5. My mind did seem to be slowing down and starting to become problematic, but that may have been more my loss of interest than any real cognitive deficit.
  6. Today’s technology work pace is just too frenetic and demanding for my declining energy and interest.
  7. The only reason I was ever able to keep up the pace in past years was sheer force of will, which I no longer have.
  8. I know too much — it is just too difficult working with people with much less experience who are unwilling and uninterested in doing things better and right in the first place, and too happy to engage in trial and error and oblivious to doing things better until they actually stumble and fall, and even then they don’t want to listen. It was all just too painful for me to watch.
  9. I never had much in the way of any real tolerance for BS, office politics, and personality conflicts anyway.
  10. In recent years it was starting to take longer and longer to find new contract and consulting work. I simply ran out of energy without finding new work after my last contract ended.
  11. The many ways that technology is mismanaged, by people who should know better, including senior executives and policymakers, has too much of an unwarranted negative backlash on those who conceive, design, and produce technology.
  12. Turning 62 and suddenly being eligible for Social Security just completely eliminated any desire for traditional work for me.

I have distilled the factors influencing my departure from the tech work scene into five categories:

  1. Technology. I simply wasn’t happy with the current state of affairs with the technology itself. I had much higher aspirations for what was capable, but I encountered essentially no significant (to my mind) interest in improvement of the current state of affairs. Too much incrementalism, no significant revolution, and people seemed very happy with where we are. At least nobody expressed any interest to me in how we could improve things in a dramatic way. Even with leading edge technology, the focus is more on flash than on substance. For example AI, and my personal interest, software agents. Too little attention to hard-core R&D, as opposed to product and market-oriented engineering or product development, and too few R&D opportunities for people like me. The net effect is that I find the available technology far too tedious to be interesting to me.
  2. Complexity. The complexity of technology has gotten out of hand and is not being managed well at work. Worst of all, neither technical staff, technical architects, nor management are bothered much at all by this state of affairs. Cognitive load is out of control. In most cases, no single individual has a full handle on the full system under development. This is flat out unacceptable. The biggest risks are that nobody has a handle on how many bugs are in the system or what cybersecurity risks exist until they gradually emerge from experience in the real world. That is a special and very ominous risk when it comes to AI and systems in which human life is at the mercy of the machines. My single biggest complaint is the “code first, ask questions later” attitude, or the variant “code first, refactor later [rinse and repeat ad nauseum]” attitude. Very common. Far too common.
  3. Management. Not to disparage some of the very decent managers I have worked with during my career, my personal standard of excellence has always been that managers should help you perform better, not prevent you from performing well. Tell them you know how to improve management, and they ask you how. So you tell them how, but they commonly simply respond that you can’t do that and they have no interest in doing so. It’s a very primitive state of affairs. Too much focus on coding and superficial progress, with no real attention to deeper, long term progress, such as robust design and code quality. Too much rework and “pivoting” required. A lot of the work is technical, but much more management support is needed, that simply isn’t there.
  4. People. Without being too judgmental, and not to in any way disparage the vast majority of great professionals I have worked with during my career, I just didn’t find that there was any real synergy between me and the people I was expected to work with. Sure, we cooperated, but that was far short of what I would call synergy. As with management, you tell them you know a better way to do things, and they ask you how. So you tell them how, but they commonly simply respond that you can’t do that and they express no interest in doing so. It’s a very primitive state of affairs. Too much focus on coding and superficial progress, with no real attention to deeper, long term progress, such as robust design and code quality. Too much rework (today called “refactoring”) and “pivoting” required.
  5. Work environment. There have been some improvements such as work from home, remote working, physical work space improvements, and collaborative online tools, but there has been no significant attention to actually making people more productive. There is too much focus on superficial appearance, without concern for real value. Too much noise and too much multitasking, again with too little focus on productivity. Collaborative tools frequently work in opposition to productivity rather than enhancing it. Meetings? Hah! Even further back in the Stone Age than 20 years ago.

To recap that, my exit from the tech space was driven by disappointment with technology, complexity, management, people, and work environment.


Another factor in me walking away from my old career in technology is that I grew depressed and frustrated by all of the many distractions, or what I felt were distractions from my core interests in vision, strategy, requirements, architecture, design, and algorithms, such as:

  • Monetization — which is worse, an obsessive focus on it or a consistent failure to pay attention to it and get it right?
  • Business model — the magical word there is pivoting, an abrupt shift to an alternate business model. Sure, sometimes it is essential to make such shifts, but it is not good and very distracting if it happens too often and feels like more of a reaction than careful thought.
  • Minimal viable product — too much of a rush to market for an incomplete product. All too often more energy is spent trying to make the minimal viable product work at all than getting it right in the first place.
  • Security — an essential feature, but managed so poorly that it became a distraction, as well as not given enough attention and focus to be “by design.”
  • Internationalization (called i18n) — important, but frequently either too much of a disruption or not given enough attention and focus to be “by design.”
  • Too much agility and pivoting — code quality, software quality, and product quality suffer greatly when the mission and strategy change too often or are not thought through clearly enough in advance.

So often, these issues become problematic primarily because they are frequently addressed as afterthoughts rather than addressed using any clear-headed rational process.

The overall effect of distractions falls into my category of complexity, but this is complexity more related to management and product management than the software and code itself.

Last work: January 2015

It has been a full two years since my last billable work in January of 2015.

Oh, I get pings via LinkedIn for open positions on a frequent basis, but they are all looking for the kind of uninteresting and unsatisfying work that I gave up on well before my last contract ended.

Bored and frustrated

A simpler formulation of why I abandoned my career in technology is out of boredom and frustration. Even supposedly “new” technology really didn’t feel so new to me, just incremental or lateral advances and frequently steps backwards. Worse, I just didn’t feel that anybody was giving a priority to doing anything that was both exciting and satisfying. It has been very frustrating, at least for me.

Hands-on is tedious and boring to me

I find hands-on tech work to be very tedious and boring. Endless hours spent madly typing cryptic Unix commands, writing scripts, navigating poorly-designed user interfaces, and cobbling together a plethora of poorly designed software tools simply isn’t my cup of tea.

I actually didn’t mind spending endless hours commenting on issues in Jira, but I never felt that that was accomplishing much of anything. It was needed, given the complexity of the software under development, but that was not productive per se. And so much of it could have easily been avoided if a much more sane design process had been used, which has to start with a much more sane requirements analysis and specification phase. But, that is usually not possible in today’s work environments.

And time spent resolving conflicts and synchronizing checkins for source control was not exactly fun, at least for me, either.

I wasn’t enjoying the underlying coding anymore anyway, so the tedium and boredom were just the straws that broke the camel’s back for me.

Hands-on doesn’t give me enough leverage

My main rationale for abandoning hands-on technical work was that I felt that it limited me to only what I could accomplish by myself, the code I wrote by myself. This drove my early interests in management and my later interests in architecture, vision, and strategy.

But the real point is that I wanted to focus on ideas and let other people do all of the vast labor needed to actually implement my ideas.

But in a nutshell, leverage was the major driver for me. I was no longer content to focus only on my little piece of the much larger puzzle.

Sense of entitlement

I hate to admit it, but a sense of entitlement has crept into my thinking, the sense that I had paid my dues and earned the right to expect an easier ride at this stage.

Intellectually, I acknowledge that such a sense of entitlement is not a good thing, but it is still there. I can do my best to repress it, but undoubtedly it will resurface on occasion.

Fairness to my ideas

One factor that certainly contributed to me loss of interest in the tech sector was a relatively consistent level of unfairness to my ideas. To be fair, many of my ideas are so far outside of the box that most people are simply unable to relate to them at all, but I see that as more of a reality than a reasonable excuse. This falls under my category of a lack of synergy.

It is especially disheartening when people are dismissive, disparaging, or resort to ridicule when confronted with ideas dissimilar to their own.

Criticism is fine, expected, and highly desirable, but it needs to be constructive, not destructive and dismissive.

At best, it is still quite dispiriting when someone merely shows no interest in some novel idea.

Just once I would like to have work where there is actually an expectation that novel or alternative ideas will be commonplace and welcomed warmly.


My entire education and career in technology has certainly been what is now called STEM — Science, Technology, Engineering, and Mathematics. I have always been fascinated by science. I received my college degrees from an engineering (and science) school. I always did reasonably well in math, although it was not one of my top interests. And I got into computers early, in high school back in the days when that was very uncommon.

That said, the crazy thing is that my interests these days are much less about STEM and much more about non-STEM topics such as foreign policy, defense, security, finance, and economics, even though STEM now figures prominently in many more areas of society than in the past.

To be sure, I am still interested in STEM, but at a much higher level of abstraction, concept, policy, architecture, and how it fits into society as a whole, rather than as a hands-on practitioner. No, I have no desire or interest in participating in hackathons. Sure, it is truly wonderful that so many young professional (and some older ones as well) are so enthusiastic about group programming, but I simply have no such interest. And, no, I am not going to help you fix your broken computer.

Beyond STEM opportunities

Given that I have such diminished appetite for traditional, hands-on STEM work, of course I am interested in non-STEM opportunities, but they would have to be non-traditional, which becomes a problem, a virtually impenetrable stone wall. Sure, maybe there are some hidden doors and passageways through the maze, but I am not aware of any at this point in time.

Even with a map of the non-STEM terrain, the prospect of finding an alignment of my interests and actual opportunities is problematic. And then there is the issue of education, training, and credentials — I worked really hard for an extended period of time to get to the starting line in STEM. That’s a level of effort that I simply lack the energy and enthusiasm for, not to mention that the time and finance elements are generally problematic given how close I am to official retirement.

That said, I am sincerely interested in figuring out how to “crack the nut” to find plausible opportunities in non-STEM fields that are a well-aligned match between my interests and my abilities and the needs of organizations. But, again, there also has to be a strong interest on the part of the organization in non-traditional roles and flexible work arrangements.

Uneven energy

Energy level is a key factor in my decision to abandon my former career in the technology sector. Success and even bare survival in the tech business these days takes an incredible level of energy. I simply don’t have that level of energy anymore.

I really do still have a lot of energy, but not quite enough. Not even close.

But the real issue is that I don’t have the level of interest in the work to marshal what energy I do have.

The more problematic aspect of my energy level is its uneven nature. I really do have brief moments and short periods where I have a reasonably high level of energy, but unfortunately those moments and periods are too few and too far between to amount to the minimum needed to thrive in most of today’s fast-paced work environments.

I accept that my energy level is quite uneven, but I also accept that most managers and teams are unable to cope with individuals with such uneven energy levels.

This is also a big part of why I have been much more comfortable with part-time and informal work arrangements for quite a few years.

My health is my absolute top priority

My health is my most precious asset. Even at my age, so many people are beginning to struggle or waste significant levels of energy and time on health issues. I am extremely grateful that I am as healthy as I am. And I want to keep it that way.

My age? I’m 62, going on 63.

Besides nutrition and exercise, managing stress is essential to remaining healthy, especially at my age. The point is that I absolutely cannot afford to take on any work role that is likely to result in any significant anxiety or other stress that might impact my health.

A significant factor in my health is the degree that I walk every day, including the ability to experience nature on those walks, to burn off anxiety and gain a sense of calm. Those “lost” hours do interfere with my availability to work, but my health comes first, in an absolute sense.

My most valuable assets

The things about myself that I value most and will work the hardest to protect are:

  • My health
  • My time
  • My mind
  • My energy
  • My independence
  • My authenticity
  • My curiosity and passion for learning
  • My judgment

My experience isn’t on that list. Maybe part of that is that I am a novelty junkie, so I don’t have an interest in doing anything that I’ve done in the past. Sadly, that experience is what hiring managers are usually most interested in, even as it is what I am least interested in.

The difficulty here is that my most cherished assets tend to work against me when seeking work. Especially note that “being part of a team” is not on my list.

Org chart boxes

As a general proposition, I have always felt uncomfortable being shoehorned into any organizational chart box that I have ever encountered or heard of. I am always short (or uninterested in) some significant job requirements of the box, and simultaneously I am a lot more interested in areas that are clearly outside of the box.

Put another way, I absolutely don’t fit into a heavily structured, command and control sort of environment. I’ve never for a moment imagined that I would be a fit for the military or a defense contractor or a government bureaucracy position.

Luckily for me, there was frequently a need for outside the box and lateral work that managers were always more than happy for me to fulfill. But, over time the availability of such opportunities declined dramatically. Managers these days are most commonly looking to exactly fill each box in their org chart and usually willing to leave the box open for an extended period of time waiting for an ideal candidate. Not that I can blame them.

The bottom line is that if a work opportunity requires fitting precisely in an org chart box, then it’s not a fit for me.


Seriously, even the thought of being smooshed into a traditional org chart box gives me severe anxiety. Yes, I suffer from… organizational claustrophobia, SEVERE organizational claustrophobia.

Hierarchical organizations

A significant part of my anathema for org chart boxes is in fact due to their inherent hierarchical organization. My personality is simply not organized in a way that is synergistic with hierarchy. Somehow I have managed to make do over the decades, although I am not sure exactly how, other than to simply acknowledge that the hierarchy exists and that it is a reality that I have no choice but to live with. I also acknowledge that the vast majority of people actually need such hierarchy to thrive, and even enjoy it, so I have to accept that as well, accepting both the existence of the hierarchy and the need that so many people have for it. I mean, who am I to take away something that other need and love.

At quite a few junctures of my career I have thrived precisely because managers themselves frequently found that their cherished hierarchy was working against their own interests, and that productive and effective results sometimes require bypassing the strict channels of the hierarchy. It was at those times that my dispassion for hierarchy was especially valuable to even the most ardent keepers of the hierarchy. Most of the time this was not true and I kept my head down and tried to ignore the shackles of the hierarchy as best I could, but those occasional moments of freedom were awesome and kept me going.

The trouble now is that I no longer feel any strong drive to accept the traditional rigid hierarchy. That doesn’t make the hierarchy go away, it simply leaves me out in the cold.

Novelty junkie

Put simply, I’m a novelty junkie. In a nutshell, that’s precisely what I am and precisely why I have such difficulty finding satisfying work. I get a thrill from curiosity, adventure, and discovery, but once the mystery has been unfolded, I quickly lose interest.

Maybe that’s part of what drew me to computer software development and kept me going for so many years.

It would appear that I have now exhausted most if not virtually all of the novelty that is accessible to me — and available to me as a work opportunity. That could well change at some point in the future, but right now I have to deal with the here and now.

Relentless curiosity

I’ve always been very curious about just about everything. Maybe that’s a big part of why I am not attracted to most traditional jobs — they involve working with the known and offer little opportunity for me to explore and let my curiosity run wild.

Thinking outside the box

I’ve always thrived when thinking outside the box was a very important criteria for a given project, goal, or task.

That said, I have frequently not been as talented at lateral thinking as I would have thought. Sometimes I am thinking outside the box, but not far enough outside the box. Call it near-box thinking. It has served me well, but not as well as I would have thought or hoped.

In quite a few cases I actually was thinking way too far outside the box, so far away from the box that people simply couldn’t relate to it, to me, or me to them.

In hindsight, I can confidently state that I frequently did a poor job of managing expectations and more carefully targeting a more moderate distance from the box that simultaneously excited and satisfied people but didn’t baffle, confuse, or frighten them.

The flip side of that is that I should be more careful about associating with organizations and teams which simply aren’t prepared to cope with my style of outside the box thinking.


While the ability to think outside the box is a very useful skill, it becomes quite problematic for someone like me who always prefers to live outside the box and to exert great energy to stay outside the box. It can be quite counterproductive and not enthusiastically welcomed by a typical manager or project team.

In short, I’m the guy for a manager who needs an outlier kind of guy, and I’m not the guy when a manager has a well-defined, very inside the box kind of task, goal, or project.


Maybe it always goes with the territory for being an outlier, or maybe it is the cause of being an outlier, but I have always had a strong streak of independence. Ask my mother and my Kindergarten teacher.

The good news is that I thrive when working independently. The bad news is that I only thrive when working independently.

I need to find an organization that values independence and avoid those which discourage it.

Lack of synergy

I think the single biggest disappointment of my entire career has been the almost complete lack of synergy between me and both the people and vision of the organizations that I worked for. Not that I would blame anyone else for the lack of synergy, but simply that I very rarely experienced it.

Work has always seemed more like an endless struggle to me, constantly having to explain myself and even then not really being understood or appreciated, and almost never could someone do me the courtesy of (correctly) finishing one of my sentences for me.

This is the penalty of being an outlier, which I have always been.

Surviving, thriving, and just getting by

I’ve spent way too much of my time and energy during my career simply trying to survive and get by. It’s very tough not fitting in. It’s taken huge amounts of my energy and attention that I could have better spent engaged in productive activities.

Only much later in my career did the lightbulb finally go on inside my head that thriving is the goal I should be shooting for, not merely surviving and getting by.

It’s odd to say it now, but never once in my career did it dawn on me to tell a manager that although things were okay and I was surviving and getting by, that I wasn’t thriving. Never once did I speak up and say that okay was not good enough.

That’s another one of the few pieces of advice that I would urgently given to a young person or student — don’t settle for okay, strive for thriving.

Looking back, it’s rather sad that all too often my top concern was having billable work to pay the bills rather than thriving.

The flip side is that I wasn’t ever ignoring or walking away from better work or turning down better work for more money, but simply that all the work I was finding was mediocre relative to my interests and aspirations.

Only rarely did I encounter an opportunity to turn down a secure position, money, and stock for a more appealing situation.

By the book

I definitely believe in following rules as a general proposition, but not when it comes to the actual content of my work. Too often, people tend to do things by the book rather than to do what is most sensible.

In any case, I’m not a good fit for work that needs to be done by the book. I’m a better fit for work that needs to be done outside the box.


In my younger days I developed a strong interest in moving into management. I even tried it out a few times, sometimes with decent results, usually with mediocre results, and sometimes with disastrous results. The truth was simply that I didn’t have the aptitude for it, particularly when it comes to personnel management — people skills, reading people, hiring, motivation, persuasion, empathy, and all of that. I was great at vision, strategy, organization, planning, and problem solving, but there was no way for me to get the authority to focus on those areas without first getting into a position of authority with competence in personnel management. Game over.

In truth, my primary motivation was not to join and protect the hierarchy, but to escape from the hierarchy. Being an org chart box at the bottom of the pyramid felt incredibly oppressive, to me. I figured that the quicker and higher I could move up the hierarchy, the less oppressed I would be. What a shame that I had no mentor to laugh at me and explain the simple truth that it doesn’t work that way. If I had thought about it myself I would have realized that most people actually enjoy and thrive in their org chart boxes and bouncing between the boxes in the hierarchy, so that no matter how high I moved, I would always be surrounded by people who would view my anathema to their org chart boxes as odd or offensive if not an outright threat.

I had imagined that moving up to a management org chart box would be a form of escape, to freedom. I didn’t seriously consider that I would be deeply unhappy having to deal with subordinates and co-workers at the management level who were passionate believers in the hierarchy and their org chart boxes, and that they wouldn’t view my displeasure with hierarchy and boxes as an amicable and welcome prospect.

So, after quite a few years of yearning and trying, I finally gave up my dreams of being a manager or executive.

That’s when the prospect of being a freelance consultant took root. Free from the hierarchy and org chart boxes. Free at last, free at last! Not totally free, but a lot more free. I remember vividly the weeks after I quit my job and turned around and did substantially the same technical work, at the same company, in the same office, for the same manager (VP of software development at a VC-funded tech startup), but as a consultant, how free I felt. Really free, as odd as it may seem. Even though I still had to work with the hierarchy, I had a lot of flexibility in structuring the work, and my hours. For example, instead of having to work mandatory overtime without extra compensation, billing by the hour actually put more money in my pocket and I had personal control over exactly how many extra hours I was willing to work. I only worked half-time, traveling round-trip every week from Colorado to Boston to a separate consulting gig (half-time as well), but somehow this arrangement worked wonders for me.

Management? Sure, I still fantasize about it, a little, but it isn’t anything I consider a serious prospect for me, now or ever again.


Micromanagement really sucks, especially for professionals with a very strong sense of independence. In my model, staff should be given a goal, a rough, summary of the problem to be solved, and then management should step back and let staff do their own analysis and come up with and execute their own plan of attack, and allow them to follow through on execution without any significant interference or back-seat driving by management.

To be sure, I have in fact had quite a few opportunities to work with decent, competent managers who followed the model I just outlined, refraining from micromanagement, but unfortunately there have been too many instances where this was not the case.

I’m not your slave or puppet

Micromanagement has two problems: lower organizational performance and great dissatisfaction felt by staff. It really does get to the point where you feel like you’re a mere slave, with blind obedience expected, or a puppet always waiting for your puppet master to pull the next string. Not a good thing, all around.


Even now I harbor at least a fascination if not outright interest in leadership. Even so, I’m more interested in the direction-setting aspects of leadership rather than the motivating, persuading, and personnel management people skills aspects of leadership.

At least at an intellectual level I recognize the necessity and value of leadership, even if I don’t have any significant passion for following a leader.

As a general proposition, I have thrived in any role where I was expected to explore, set a direction, and blaze a trail, even if somebody else is ultimately the leader who will lead a team on that trail.

After all these years and decades, I wish I could say that I have an aptitude for leadership, but I simply can’t. And it’s not simply a need for some skill training. I just don’t have the full range of aptitude leaded for a leader, particularly on the people-skills front, which is most of what a leader does anyway.

Presence and commanding respect

One of my most severe personal limitations that has held me back the most is my distinct lack of an real strong sense of presence, the simple fact that I don’t command respect and never have.

Curiously, I never paid any attention to this limitation during my career, until just today while working on this paper. Hey, at least that means that my belief that writing helps to clarify my thinking is not so outrageous after all.

In all honesty, at this stage I am unsure whether this inability to command respect is a personality defect or something that a little training, skill development, and experience and focus couldn’t correct, but I’ll file that thought away to pursue on another day.

Personnel management

As much skills as I might have at high level vision, strategy, architecture, organization, planning, and problem solving, that is all for naught due to my complete and total lack of personnel management skills, such as:

  • Recruiting — selling the organization as a place to work with a great mission.
  • Hiring — selecting staff.
  • Interviewing — asking the right questions and assessing responses to questions, like is the person lying or holding something back?
  • Motivating staff.
  • Persuading staff.
  • Empathizing with staff personal issues.
  • Reading people, understanding body language.
  • Grasping when people are lying or merely uncomfortable with certain questions.
  • Praising people.
  • Assignment of tasks and responsibilities for team members, deciding in advance who was really best for each role.
  • Assessing and managing ego issues for team members.
  • Assessing fit for team members.
  • Assessing overall fit for team members.
  • Deciding how and when to assign stretch goals and how to avoid overloading team members.
  • Coaching staff.
  • Career planning for staff.
  • Firing.
  • Performance reviews — how to give just the right feedback to help staff grow.
  • And so much more. Whatever it is, I just don’t have it.

Intellectually, I am well aware of these things and their importance, but I simply don’t have any aptitude, let alone any talent. Besides, my attitude is that if I can’t be a great manager and a great leader, then I don’t want to manage or lead at all. My attitude is to be something that you are really good at. Mediocrity is not a viable option.

Project management

Managing a project is a hybrid of pure management and mastery of technical content and methods. I’ve had mixed experience with project management, as a project manager or project leader.

The downside was my very weak skill set and aptitude for the personnel management side of management.

The upside was my technical expertise and analytic and organizational skills, such as:

  • Grasp of project vision and strategy.
  • Talent for requirements analysis and specification.
  • Decomposing a problem into smaller problems.
  • Synthesizing solution strategies.
  • Monitoring, tracking, and reporting project progress.
  • Troubleshooting and problem solving — except for people issues.
  • Sequencing the development of components.
  • Integration of components.
  • Testing process.
  • Tracking and facilitating unresolved issues.
  • Documentation.
  • Release coordination with groups outside of the project team.

The one technical aspect that I had no competence with was task and project estimation. I could understand the technical details of any component or task, but judging how long it might or should take to complete was simply beyond my grasp, in large part because it depends heavily on the people part of the equation, which I have no aptitude for.

Many aspects of the project management process are independent of the specific technical details of the subject matter, so much of my project management expertise could be applied to even non-technical projects.

I would think that there must be a significant number of organizations that could use my project management expertise, except that they might insist on hiring someone with people skills and with an expectation of hands-on participation, which would not be a fit for me.

The way I see things, the opportunity I seek is to be a consultant on project management.

Technology mismanagement

Beyond technical management of the conception, design, and development of technology, I also have problems with technology mismanagement, the ways that technology is misused in such a way that it reflects badly on those who produce the technology. This includes senior executives and government policymakers.

A great example is the current frenzy over cybersecurity. It’s a real mess. Some of the mess concerns the technology itself, but even then the technology is deficient primarily due to mismanagement at the technical level, preventing technical staff from properly conceiving, designing, implementing, testing, packaging, and delivering technology that doesn’t have these kinds of issues in the first place. The other major issue is senior executives and policymakers who construct their own imaginary conceptions of what the technology can do, failing to give the technical staff the resources they need to adequately fulfill those imaginary conceptions, and then wondering why their imaginary conceptions were not met.

In any case, I have little if any appetite for working in an environment in which technology is mismanaged, managed so poorly.

On the flip side, I would dearly love to work with any organization with enlightened management who enthusiastically looks to me to help them unravel the tangle of technology, policy, jargon, and mismanagement that plagues them, helping them to find the truth in the apparent madness.

Born to run

I need to run, to move forward, to make rapid progress, not be hobbled by second-guessing, backseat drivers, and endless questions and demands for justification. To be honest, there have indeed been more than a few occasions where management has given me a chance to sprint, unencumbered by the usual bureaucratic ballast, but it hasn’t even been close to the norm.

I am indeed born to run. But how many managers can relate to that, other than to pay lip service to it?


Maybe it’s implicit in being born to run, but just to affirm the point, I’ve always been self-motivated. If I have one problem, it’s coping with environments where self-motivation is discouraged, such as under micromanagement.

Orthodoxy, convention, and tradition

I simply do not thrive in environments which focus on the orthodox, convention, and tradition. My mind and interests simply do not fit into such narrow and confining boxes.

Unorthodox, unconventional, novel

I do thrive in environments that welcome the unorthodox, the unconventional, and novel approaches, and offer plenty of room to maneuver and run.

Rooted in the future

Another way that I am not a good fit for organizations steeped in tradition and orthodoxy is the fact that I feel rooted in the future. I accept the past and the present, but it is the future that is my central focus. Most co-workers and managers are firmly attached to the here and now as well as a strong sense that the future will mostly be a linear extension of the past. Yeah, I can cope with that if I have to, but I simply don’t have any passion for it.

My mind is firmly attached to the future, whether it be 5, 10, 20, 25, or 50 years from now, and the more different from the present and the past the better.

No role model

The concept of role models just popped into my head for no apparent reason and I suddenly realized that I myself do not have a role model and never have. I would not have thought that would be possible, but apparently it is.

To be sure, there are plenty of successful people in whom I have great respect and even whose success I envy greatly, but I have never felt any urgent desire to be just like them. In fact, upon reflection, at times in my life when I have encountered or heard about such people, I have always told myself that I would much rather have my own life, as it is but fully under my own control, than be like these other people, despite their great success.

Sure, there are definitely elements of the successes of others that I might want to emulate, to some degree, but only to the extent that it was my own decision and that I am free to pursue my own approach.

No role models growing up

As unbelievable as it might sound, I had no role models when I was younger or even as a child, but part of that is that I was so independent in my thinking.

I discovered computers in 10th grade in high school, and that became my central focus. I knew I wanted to work as a computer programmer, but I had no role model per se.

Until I discovered computers I had been very interested in science. Not so much in math, but I was fascinated by nature and space, rockets and astronomy. I was fascinated by the Star Trek TV show (in black and white!) in 1966 and Walter Cronkite’s 21st Century TV show in 1967 when I was 12 and 13 years old. They were building a nuclear power plant in the town next to me, which was a mind-boggling concept to me at that age. And I was passionate about leafing through old issues of National Geographic magazine, whether it was science, nature, or faraway lands and distant cultures. Not to mention the wonders of the 1964 World’s Fair when I was 10 years old. I recall the IBM pavilion and the GE pavilion which had a demonstration of nuclear fusion. And the Mercury, Gemini, and Apollo space programs were a really big deal to me.

But I had no idea how exactly I would pursue that interest as an adult. I had a little bit of a Peter Pan mentality — half-hoping that I would never have to grow up into an adult and be forced to give up the magic that the world seemed to have from the perspective of a child.

Luckily, computers came along, so I then had a more clear path to something resembling an adult occupation. But still no role models per se.

No mentor

Beyond simply not having any role models, from a practical perspective I think it is very unfortunate that I never had a mentor, even once in my long career. Looking back, it probably would have helped me greatly, although in truth it would have been a contradiction to the basic independence of my personality. Still, it might have helped me a lot, if it could have happened.

To be sure, there have indeed been a handful of managers and executives along the way who have been helpful to my career. In truth, I think they generally knew better than to offer me explicit advice, preferring to simply get out of my way and let me do my thing, being rather respectful of my performance. You know, content to let the goose that lays golden eggs do its thing. The downside is that they were generally more interested in my raw performance as a low-level technical contributor than in helping me advance up the career ladder. Or, maybe they simply knew me better than I thought and could more clearly see that I had no detectable people skills or management potential.

Sure, I also got a little friendly advice along the way as well, but occasional strands of advice are not a valid substitute for the sustained, long-term relationship of a true mentor.

There was one, unique situation once where I was actually working on a side project with a guy who actually could have become a mentor for me. He was an MIT PhD, one of the original Multicians, if you have any idea what that means. He actually offered me a full-time job in an R&D (not product development) group, surrounded by extremely talented research PhDs, but I turned it down to remain in a more front-line product development group. I could well have leveraged that opportunity to pursue a PhD and focus on R&D. That’s a huge question mark for me, whether I chose the right path or the wrong path at that moment. In truth, I’m not a traditional PhD R&D type either, so choosing that path could well have been equally disappointing.

Not having any true role models to tap as mentors, it would have been difficult for me to relate to anyone as a mentor. Without a sense of relationship, the mentorship would have been an empty shell, a sham.

Not a mentor

Given my significant experience, maybe I would be a great candidate to mentor younger professionals or even students or interns, at least in terms of the wonders of a career in STEM, but given my dramatic disenchantment with the state of affairs in the tech world these days I simply am not in the proper state of mind to do any such thing. Besides, from my experience, the general direction and tone of tech professionals these days is antithetical to my own views.

Besides, given my profound unhappiness with how my own career has turned out, I can hardly recommend that anyone pursue a career path even remotely similar to my own. Although, that is actually quite ironic since any normal professional who had in fact pursued my exact career path would likely have been much more satisfied than me. It wasn’t my path that was wrong, just that it wasn’t a great fit for me. On the other hand, it may indeed have been the closest fit possible. After all, I am unaware of any better path that I should have or could have taken.

Mentorship requires a significant relationship, belief, and trust. Given that I do not particularly relate directly to the young professionals and students of today, there is not any significant opportunity for me to develop the depth and breadth of relationship required for a successful mentorship. That said, I do sincerely wish young professionals and students success at finding mentor opportunities. And that would be my best advice to them: Find a mentor ASAP!


It is abundantly clear that I have always had a vicious streak of independence, which has virtually excluded me from any great success in any traditional work role. I’ve always needed to be myself, which is rarely compatible with most work situations.

I definitely could have benefited from being truer to my personality, character, values, and spirit — my authenticity.


How can you tell whether you are being authentic? A very simple test is simply whether you are attacking the task, goal, or project with a very clear sense of enthusiasm. Do you look forward to tomorrow when you go to bed? Are you cheerfully leaping out of bed to get started in the morning?

Enthusiasm is such a great indicator for authenticity because it is rather difficult to fake unbridled enthusiasm. And if you can, then maybe you should consider a career as an actor out in Hollywood or on Broadway. Or maybe a job in sales.

Repressed authenticity

I am sorely tempted to assert that my biggest mistake throughout my entire career has been my sincere but misguided attempt to repress my authenticity in favor of trying to fit inside all of those cramped org chart boxes which were offered to me. Now, it is abundantly clear that I just should have said no, bitten the bullet, let the chips fall where they may, and proceeded to find or create opportunities that were much more closely in line with my own quirky authenticity.

Now that’s some solid advice that I could enthusiastically give to young professionals and students.

My ongoing conflict between being authentic and being what people are willing to hire has been a clear drag on both my career and my spirits in general.

Nobody’s role model

Even if somebody wanted to look to me as a role model (or mentor), I would strongly advise them against it. I am too much of an outlier for there to be any more than a very tiny probability that anybody could both successfully and satisfyingly follow the path that I have followed.

The only advice I would give someone is that they first need to decide whether they themselves seriously wish to follow an outlier path, and if so, that they should focus on being authentic, to be themselves rather than try to follow a role model per se, let alone try to follow in my footsteps (more like missteps.)

Deferring to my own judgment

As mentioned previously, I see my own judgment as one of my best or at least most valued assets. I defer to it, implicitly. Or at least that is my intention. In fact, a lot of the mistakes I have made in my life would not have happened had I more strictly and confidently deferred to my own best judgment rather than defer to the judgment of others.

My long career

I refer to my long career, although there are plenty of individuals with significantly longer careers, but I count my career as starting with my first paid work that focused on computers when I was in high school, in 1972. I also include my first unpaid work on computers when I was in high school, in 1970.

My first real, professional job with a newly-minted college degree started in May 1976.

In between, I worked during college, programming computers fairly intensively.

Early days of my career

I was first exposed to computers in a major way when I was in the 10th grade in high school, in 1970. I wrote some small programs in BASIC, PL/1, and FORTRAN. I even wrote some programs for the Olivetti Programma 101 calculator.

I took a special online training course in the use of computers during the summer of my sophomore year in high school (1970.) Back in those days, online meant timesharing using an IBM 2741 terminal connected to a remote IBM mainframe computer via a telephone line and an acoustic coupler modem.

Soon thereafter, I was writing PL/1 code, some projects of my own and some projects for the math teacher overseeing the school’s terminal. He was anxious to show other teachers what computers could do, and I was one of his guinea pigs. Hey, it was free computer time back in the days when that was still a rather expensive proposition. So, I was in fact working, just not for pay. These days, it would be called an unpaid internship.

Later the local community college got their own mainframe computer (RCA). Unfortunately, it didn’t have PL/1, so we had to switch to BASIC. The good news is that it was a lot cheaper, so I felt a lot less guilty about spending so many hours on the computer after school and during breaks. Eventually they let me do a little assembly language programing, which felt like real programming.

I was so into computers that I had little interest in driving and didn’t even bother getting my driver’s license. That changed when we got permission to use the computer center at the community college, which I did on some evenings. I began some more serious assembly language programming. I even created my first little AI program, a very simple-minded question-answer program.

I participated in a fairly sophisticated computer science educational program during the summer of my junior year of high school (1971) at the engineering school where I later received my undergraduate and graduate degrees in computer science. It covered machine architecture, assembly language, and numerical analysis, using the Digital PDP-10, a truly awesome computer. We used IBM keypunch cards and batch to run our programs. I spent six weeks living in a dorm room. Well, actually, most of the time I lived in the computer center.

Sure, these days, even kids much younger than than I was learn to code on a routine basis, but back then (1970) there were very few of us.

The culmination of this early training was that I worked as a professional at my local community college in the summer of my senior year of high school (1972), first as a data entry clerk and then as an applications programmer, programming in assembly language, believe it or not.

And when I arrived at college, I was offered work in the computer center the first week I was there, working part-time during school and full-time during breaks and the summer. I also worked full-time at both the community college and the engineering school when I dropped out for a semester.

I did come back after my break, working more hours at the computer center of the engineering school and taking an overload of graduate computer science courses even though I hadn’t even completed my sophomore year. To be clear, I was not one of these prodigy genius types, just extremely motivated and willing to focus really hard to get the work done that a genius type could breeze through.

Despite skipping a semester, I took an overload of grad computer science and electrical engineering courses, so that I was able to graduate with the same class I started as a freshman, but with both a BS and a MS in computer science.

One of the few joys of my college years was having adjunct professors for a number of my grad courses who were from the infamous Bell Labs or other prestigious area companies and commercial laboratories. Curious now that at the time I didn’t even think of interviewing for Bell Labs.

My professional career

Finishing my senior year, I knew without a doubt that I only wanted to go work at Digital Equipment Corporation, maker of the PDP-10, the premier choice at that time. I interviewed at no other companies. One interview — it was actually my first flight on a plane, my first car rental, and my first experience driving in Boston. My manager in the computer center had personally forwarded my resume to my ultimate hiring manager. No on-campus interview. One job offer. I figured that I was all set.

By the time I had my first “real” job out of college at Digital, I was already well ahead of quite a few of the seasoned professionals I had to work with, which was yet another of my early experience not being a true fit for the roles I was offered.

My experience at Digital was both eye-opening and rather disappointing. I did indeed have a lot of positive experiences and was able to meet and work with a lot of truly amazing people, but the actual work I had was far less than what I really needed. My enthusiasm for my work was like nonexistent. I left Digital rather disenchanted.

I bounced around to a couple of other companies, focused more on venture capital-funded technology startups, and eventually shifting to freelance consulting (or contracting.)

You can check out my LinkedIn profile for the later stages of that process.

I remember this one guy I worked with at Digital who quit to go back to grad school at Stanford. Not too many years later he founded a technology company based on his work at Stanford with networking. I ran into him at a Digital trade show fairly shortly after he had founded the company and he told me about it, but I completely forgot about it since it wasn’t really a big success at that stage. Many years later, I saw his name in Wired magazine when the company was a really big deal success. Wow. Meanwhile, I’m just struggling to get by.

Limited success

I am unable to give a solid yes/no answer to the question of whether my career was a modest success or a colossal failure. I was somewhere in the middle — a limited success.

I am not a great success as measured by any of these criteria:

  • Not a billionaire.
  • Never a senior executive.
  • Never a successful entrepreneur.
  • Never a chief technology officer.
  • No PhD.
  • Not a recognized expert in any field.
  • No prestigious awards.
  • No million-dollar retirement account.
  • Unable to retire on 60% of my work compensation.
  • Nobody is knocking on my door begging me to work (on reasonably senior-level.)

On the flip side, I am not a total failure due to these criteria:

  • Able to retire at all on Social Security.
  • A non-trivial retirement account to supplement Social Security.
  • Not penniless and living on the street, in the gutter.
  • My health is intact and reasonably decent.
  • People still contact me for work for my old career.
  • I do a lot of serious writing.

Can’t I retool my previous career?

Technically, the first step for most people who are ending their current career is to figure out a subset of their former career that they can use as a foundation for their encore career. Typically this is as a consultant in the same career space, or an interest from their former career that can branch out in a related but somewhat different direction. Or, they punt and leave all remnants of their old career behind, which is roughly where I am.

Put simply, since I have no interest in any aspect of my old career, there is nothing left to retool.

Outdated experience

I have a lot of really solid experience, but so much of it simply isn’t relevant to today’s job market. A lot of the technology, software tools, and project management methodologies have changed dramatically from 40, 25, 15, 10, or even just 5 years ago. It absolutely is true that technology is advancing at a rapid pace and that your expertise has a very short shelf life that diminishes in value literally by the day.

That said, I do think I have distilled a lot of valuable principles from my experience, that transcend the specific technologies, specific tools, and specific project management methodologies that are in use at any one moment in time.

No current references

All of my old, standby references are now so old that I no longer feel that I can offer any current references. Most of my more recent references are for situations that I wasn’t exactly the most happy with, so I don’t feel comfortable using them, although in a pinch I could.

The bottom line is that I absolutely won’t be pursuing work that requires current references.

Ideal goal

My specific, ideal goal at this juncture is:

  1. Work until I am 70, to maximize contributions to my retirement accounts and maximize investment returns (primarily stock market) for my accounts.
  2. Defer commencing Social Security until I hit age 70 to maximize my monthly benefits.
  3. Find some sort of informal, part-time work.
  4. Any work from here on MUST be personally satisfying.
  5. Any work MUST NOT be stressful in any way that might incur some health risk. My health is my most prized and protected asset.
  6. Full-time work would be acceptable if it is particularly satisfying and/or particularly unstressful.
  7. I have zero interest in any work remotely similar to work I did in the past. In particular, I am not interested in software development or any hands-on technical work.
  8. High-level consulting related to software would be acceptable, if particularly interesting but must be low-stress.

Is my ideal goal feasible or likely?

Technically, my ideal goal is feasible, but… it seems very unlikely to me at this stage.

What work can I see myself doing?

In all honesty, try as I might, I can’t really imagine any work that would be a fit for me at this juncture. Okay, sure, I can indeed imagine possibilities that would be quite acceptable, but my assessment is that they do not exist in this world, or at least I have no knowledge about how to find them.

Okay, technically, I would accept any light office work, at least as a stopgap.

How do I think of myself right now?

These days I represent myself as “a semi-retired former software developer and consultant.” Semi-retired in the sense that I am indeed interested in work, provided that it is low-stress and interesting to me. I don’t say software developer because I have any interest in doing that anymore, but simply to accurately represent the bulk of my background and experience.

I also bill myself as being a freelance consultant, such as when a registration form requires my title.

Ready to retire?

On the one hand, I seriously wish that I could afford to retire right now and never work another day in my life (being a slave to anybody else), but I recognize that my financial resources are not in great enough shape to do that very comfortably at this point in time.

That said, my financial resources are sufficient that I could indeed retire right now although on a shoestring budget that would be a lot tighter than I would like. Like, zero travel and minimal dining out and unable to afford the kind of apartment and location I would like to retire to. I am currently over two miles outside downtown Washington, DC, rather than right at the edge of downtown DC precisely because of my limited budget.

So, yes, I could retire, but that’s not my first preference considering my finances. Alternatively, yes, I could continue working, but only if it is on my terms, being reasonably low-stress and reasonably interesting and personally satisfying.

In short, I would be happy to work, but only on my terms, or I would be happy to retire (cringing a little) if I can find no work on my terms.

Bottom line: I definitely need to try to find some work, ASAP. So, technically, I am not ready to retire, although my current lack of income leaves me technically semi-retired.


Although I sincerely do intend to keep searching for satisfying work, I am nonetheless resigned to the fact that at this stage it is rather unlikely that I will stumble across work that would be palatable.


As resigned as I am to remaining unemployed, I also remain steadfastly hopeful that there is at least some chance, maybe 1 in 1,000 that there really is some opportunity out there waiting for me, if only I had even the slightest clue how to find it.

To be clear, I am hopeful, but not so optimistic.

Go back to school?

Going back to school to retool for a completely new degree is a nonstarter for me at this stage. Given that I want to plan to retire within four to seven years, that wouldn’t leave enough time to both go to school and recoup the costs by the time I would want to retire.

Might community college or some certificate program be an option, taking much less time to get to the job market and at a much lower cost? Possibly. Except for the fact that I don’t know of any such career paths that would make sense for me given my interests and aptitudes.


If I can’t find real work, couldn’t I volunteer? Sure, in theory, but in all honesty, there are no volunteer positions that I have ever heard of that I would be interested in. If I do ever hear of such a position I will definitely consider it, although for now my focus is to try to find real work that provides me with an income.

In truth, volunteer work is mainly for those who are financially secure enough that they no longer need to work. That’s not my situation, at least at this juncture.

That said, I would definitely consider a volunteer position that had a strong prospect of segueing into a paid position.

Also, volunteers are generally expected to have passionate beliefs that are in close alignment with the vision and values of the organization, but I know of no organizations that my neutral and dispassionate beliefs would be in alignment with.


I would definitely consider an internship, even if unpaid, provided that the actual work was acceptable.

That said, I absolutely would not accept an internship if it meant that some enterprising young person would then be deprived of that position.

What is my passion?

I am interesting in everything and passionate about nothing.

That’s what I like to tell people. And it’s true.

Conventional wisdom is that you should pursue your passion, chase your dreams. But with no clear passion (or even a vague passion), I am at a distinct disadvantage.

Labor of love

Closely associated with passion is the concept of a willingness to do work for sheer pleasure, for the psychic reward, rather than the financial reward itself. To be sure, we want to be paid for our labor as well (unless we have the space to commit to volunteer efforts), but the work we really seek is a labor of love.

An idea guy

I suppose you could say that I am passionate about ideas, but that’s a rather broad passion, not the the kind of narrow focus that people are normally looking for when they ask you about your passion.

An idea junkie

I really am very interested in ideas, thinking about them, understanding them, and even writing about them. I like to take an idea and figure out what makes it tick, figure out its nature. I want to discover where it comes from and what are its consequences. But I have no interest in the hands-on aspects of implementing them.

Unfortunately, I am not a card-carrying PhD certified genius, so there does not appear to be any real market for a guy like me.

Still, I am very interested in being alerted to any opportunities that others are aware of.


I do enjoy writing, sort of, but it doesn’t come completely natural, I don’t have any passion for polish and flair, and it commonly feels like more of a forced process than a preferred activity, so it really isn’t something that I can realistically pursue as a work option. Yes, it does work well as a hobby or informally, as I am doing right now, but there is no money in that.

I currently spend a lot of my time thinking and writing about ideas. And wondering how on earth I can figure out how to get some income.

Now that my old career is in the rearview mirror, when I’m not attending think tank events here in Washington, DC, I spend a lot of my time writing informal papers which I post on Medium. Nothing publication-quality or polished in any way or anything that I get paid for, but… stuff I’m interested in and enjoy writing about.

I think I can actually say that much of my current informal writing is a true labor of love. I guess the only hesitance I might entertain in making that claim is that I cannot be so sure that a major portion of my motivation for writing is to develop a portfolio of writings that may indeed open the door to gainful employment or financial remuneration of some sort. In other words, if I won the big lottery, would I still be interested in writing.

By the way, my writing is exclusively nonfiction. I don’t have any affinity for fiction. I wonder if that is related to my distinct lack of aptitude for lying.

Formal writing

I have absolutely no interest and an absolute disdain for formal writing. Granted, I am a stickler for spelling, grammar, capitalization, and punctuation, but my style is strictly informal, to the point of being conversational.

That said, I have to laugh at what an anguished decision it has been for me to decide whether to use contractions in this informal paper. I finally decided that since it is a decidedly informal paper and my intent is to speak to the reader conversationally, contractions make perfect sense. I also struggled with the “always or never” rule for contractions, but finally decided that I would mostly use contractions except where the non-contracted form seemed to read a little better. Huh… I actually refrained from using contractions in this paragraph. Somehow, it actually did seem more natural that way.

I guess this is a key part of the story of my life, always torn between the orderliness of formality and the friendliness of informality. If I could only just settle on one or the other, my life would be so much simpler.

Informal writing

I personally think my informal writing style is reasonably readable (except for frequently being too long!), but that does mean that I will not be a good fit for most positions that require a fairly formal style of writing.

Despite my informality, I still strive to write in a manner that is thorough, plain, and clear. To me, those are the ultimate goals of writing.

I also find that I am much more comfortable attempting to write in a style that speaks to the reader in a friendly, conversational manner. I do hope that people find this style easier to read.

Are there any organizations out there which could utilize my skills at informal writing?


Yeah, at first blush, blogging would seem to be an almost ideal opportunity for my informal writing skills. In fact, years ago, when blogging was still a new thing (2005), I did quite a bit of blogging. But, I never developed much of an audience, so that even with Google AdSense, my blogging revenue was miniscule.

My main problem is that I am frequently so far outside the box that very few people actually relate to me or any of the topics that I blogged about, and I had no interest in blogging on any of the many hot topics (e.g., the Super Bowl as I write these words), or on those rare occasions when I did, I was lost in all the noise of the so-called blogosphere.

I was even very active on Twitter for a few years (@JackKrupansky, last post April 2010), tweeting links to my more significant blog posts. Didn’t seem to help much, so I hit the pause button.

I think of blogging as mini-essays, with an emphasis on brevity, relative short treatments of topics of modest importance. At this stage I prefer more substantial essays, what journalists would call “long form”, or what I would call mini-books, relatively lengthy treatments of topics of moderate importance. feels more appropriate for my style of writing at this stage.

Even if an organization did want me to blog for them, I doubt that I would find it very fulfilling, and I expect that the pay would be fairly minimal, making the benefit hardly worth the effort.

As a general proposition, I enjoy writing for myself — the constraints of writing for someone else would drain away all of the potential psychic gain for me.

Mr. Bullet Point

If I am famous for one thing, it is my penchant for lists and bullet points in particular. I have great disdain for lengthy narrative prose, mere stories, when what I crave is simple lists of facts. Of course the connections between the bare facts are important as well, but that is just another list of more bullet points. I am Mr. Bullet Point.

This informal paper certainly has a lot of text and not really that many bullet points per se, but I am using lots of small sections with section headers effectively as bullet points. It is rare that I can write more than a few paragraphs without feeling the need to label a new section.

Enough with stories and narrative

Yeah, I know, a lot of people, even most people, love their prose, stories, and narrative. If you can’t offer your dry, unpalatable facts as a juicy story with dramatic narrative flow and filled with colorful personalities, they simply are not interested. Fine, so be it, but I will leave it to others to be the storytellers and narrators. I will be content to be Mr. Bullet Point.

Is it really such a sin for me to focus on what I am good at? Why should I be the one who is denied authenticity, forced to fabricate odd stories and winding narrative prose simply to convey very clear, bullet-like points?

I do recognize that some (a lot or even most) people need the structure of stories and narrative to fully and emotionally make the connections and contextual relationships between seemingly disconnected facts. It’s just that I don’t relate to that type of personality.

I also recognize that stories and narrative are more effective at conveying social truths and values for most people. Again, let the people have what they need, but I’ll stick with the raw facts.

One note on stories versus narrative: narrative is essentially abstract and about themes at a high level without details, while stories are more concrete and personalized and reveling in rich detail. For example, a narrative might be about the rich extracting resources from the working class, while a story would add names and faces, places, times, and specific actions to that narrative, detail that real people can relate to. I would prefer the narrative level over the story details, but my real preference is the bullet point level of raw facts and raw relationships.

The point of all of this is that I won’t be a good fit for an organization seeking staff to focus on stories and narrative.

Just the facts

To reiterate, I can only thrive in an environment focused on raw, technical facts rather than colorful narratives and stories.

That doesn’t mean that I absolutely cannot work in such an environment at all, but simply that the organization and staff must agree to respect that my role is rather different from theirs.

Value of my writing: Zero

Alas the feedback from the market is that the value of my writing is… zero. Really. Nothing. Okay, sure, I used to be able to earn $50 a month from blogging with Google AdSense ads, but that was hardly worth my effort. And I currently earn $0 from all my significant writing on Medium.

I did actually author an e-book on the Apache Solr search server that I marketed on Lulu, netting a few hundred dollars, but once again the revenue was certainly not adequate compensation for the effort.

I personally get great value from my writing in terms of clarifying my thoughts, but no revenue stream.

This is sad, but it is a fact.

Why do I write?

Although my writing earns me no direct income, I write for these reasons:

  • To clarify my thinking. Just putting ideas into words on paper helps a lot.
  • To clear my head. All of these crazy thoughts stop bouncing around inside my head once I put them into words.
  • To free myself from my past. To put negative, unpleasant, or disappointing thoughts in a box and put that box out of my mind so that I can move on.
  • Others may give me feedback to help me make some progress.
  • Others may get some value from my experiences.
  • I enjoy writing.
  • It makes me feel calmer.
  • It makes me feel more satisfied.
  • I feel productive.
  • I feel much more comfortable and unconstrained when writing than speaking. I can write, review, and edit until I am satisfied, which I need very much, but which is not possible when speaking, or at least it’s extremely painful to watch, let alone experience.
  • To build up a writing portfolio of my ideas to enhance the prospects of my employment or association with an organization like a think tank or research lab that values ideas and written expression.
  • I feel that some matters are not covered at all or that existing treatments are incomplete, misleading, unclear, vague, or poorly integrated, so that in some way I feel that I can cover the matter or more adequately or clearly describe or explain the matter, including by distilling the essence from existing treatments.
  • I enjoy expressing truth. It’s my thing. Truth and expression of truth are their own rewards. Of course, one does have to discover truth first, which is the really hard part.

I don’t write for these reasons:

  • To make money.
  • To appeal to a broad audience of average citizens.
  • To seek affirmation.
  • To escape from the real world.


Back in my younger days I thought of myself as a creative individual. Mostly that was related to creating computer programs. I wasn’t into art, music, or writing.

Years later I came to realize that I really wasn’t creative per se, but more productive. I tended to focus on recreating things, doing things better, but not really creating new concepts that had never been seen before.

The bottom line is that truly creative work is not my forte.

Although, in more recent years I actually written up some of my thoughts for systems that really haven’t existed before, such as software agents and virtual travel, as well as coming up with more clear models for various social processes.

That said, I tend to be more content performing analysis and being more accurate in descriptions than others than being creative per se.


Imagination is a close cousin to creativity. Technically, imagination precedes creativity. Although I don’t currently think of myself as a creative type, I actually do consider myself imaginative. I am passionate about working with ideas, which focuses on imagination, but I have no real interest in actual hands-on development, the actualization stage, which is where imagination becomes real through actual creation or creativity.

The bottom line is that I could indeed thrive in an environment which valued imagination, as long as the creation stage is not required from me as well.

Asking questions

One special passion that I do have is asking questions. But… I’m far less interested in getting answers than focusing on the questions themselves. In truth, if I come up with a question and am unable to answer it fairly quickly myself, then the odds are that nobody can answer my question in a satisfactory manner. Sure, sometimes I simply don’t have access to the necessary resources to answer some questions, but with the depth and breadth of the Internet and Google these days, so many questions are readily answerable — if they are answerable at all. If neither Google nor I have an answer, forget about it.

I get a lot of satisfaction from asking questions and am actually famous for writing very long lists of questions, but my lack of interest in answers is a distinct disadvantage for most work environments where answers are what matter most.

My special interests

I really am interested in just about everything (exceptions noted in a subsequent section), but there actually are some areas that I am more interested in. For example, here in Washington, D.C., when attending think tank events I am more interested in:

  • Geopolitics
  • Foreign policy
  • International relations
  • Defense
  • Security
  • Intelligence
  • Terrorism and counterterrorism
  • Economics and Finance
  • Critical infrastructure
  • Cybersecurity
  • AI

Missing from that list is technology in general. So, no, I don’t attend hackathons.

At a secondary level I have a moderate interest in:

  • Education
  • Health care
  • Criminal justice
  • Social policy
  • Environmental policy

Some other, more general interests:

  • Philosophy
  • Critical thinking
  • Science
  • Physics
  • Quantum mechanics
  • Psychology
  • Law, especially constitutional law
  • Economics
  • Euthanasia and end of life care
  • Universal Basic Income and Universal Guaranteed Work

Fascination with philosophy

I was never interested in philosophy in my younger years, preferring practical and hands-on efforts, but in recent decades I have been much more interested, especially as a way of pursuing and evaluating ideas and concepts.

To be clear, I have little interest in a lot of the classic and traditional forms of philosophy, or even the newer, post-modern forms, but there are still plenty of strands of philosophy that have proven useful over the years.

I see part of my mission in life as sorting through the masses of material and distilling out the essence that seems most useful and most explicative.

Maybe my interest in philosophy is another part of why I have so little interest these days in practical, hands-on pursuits.

I don’t for even a single moment believe that I can monetize my interest in philosophy, but I do find it useful when conceptualizing and analyzing ideas and concepts.

My non-interests

Back in the days when I really used to enjoy reading the Sunday New York Times, I would first discard these sections since I had no interest in them:

  • Sports
  • Entertainment
  • Arts
  • Leisure
  • Automotive
  • Real estate

My mission: seeking truth

My primary motivating force has always been to seek truth rather than to seek power or greater sense of belonging to a team. Unfortunately, it has always saddened me and distanced me from people who I strongly sensed did not share my passion for truth.

Even in writing, my passion is for mere accurate description while many people are much more interested in an engaging story and appealing narrative than the raw facts. I’m a raw fact guy — give me a story or narrative and I see my first and primary task as stripping and sifting away the story and narrative elements that so many other people adore, to get to the essential facts. I call it finding the needles in the haystacks.

Alas, even in supposedly analytic projects, where assessing facts should be the main interest, I have observed that there is still too much of a focus on some story, narrative, or agenda, and that people are more focused on merely using facts as clubs or weapons to justify some agenda rather than a source of enlightenment. I’m an enlightenment guy, not an agenda guy. I want to help people understand, not defeat them.

Finding needles in haystacks

I have always prided myself with my ability, or at least interest, in finding things that are well-hidden, the proverbial needles in haystacks.

Alas, all of that supposed skill is now failing me — I am virtually positive that there is satisfying work for me hiding somewhere deep in some organizational haystack, but despite my best efforts, I simply can’t find it. I am honestly not sure what to think of that. Or, maybe it simply means that my skills are in fact as sharp as I thought, but my judgment that work exists for me is flat out wrong. So, what exactly is the truth here?

Collecting puzzle pieces

In addition to my predilection for finding needles in haystacks, I also like to say that I collect puzzle pieces — detecting, isolating, collecting and organizing individual facts, what I call puzzle pieces, not so much necessarily ever producing the full puzzle image, but at least assembling interesting collections of puzzle pieces that may at least provide some insight into what larger or smaller portions of that full puzzle image might be.

Team player — not so much

As deeply as I intellectually know that teams are important and the value of being a team player, that’s simply not me. I’m definitely more of a lone wolf player. Sure, I can and have worked with teams many times over my long career, but usually as more of an outlier. Rather than being a well-integrated team player it was usually more that the team tolerated me and I tolerated the team because we needed each other, not because I wanted to be part of the team or that they wanted me to be part of their team.

My main successes were where management considered me an adjunct to the team. I definitely had to work with the team and they provided me with assistance, but nobody labored under the illusion that I was an integral part of the team, although I in fact participated in many team events.

Not a good fit

I generally have not been a good fit for any defined role, usually due to my outlier qualities. In fact, my value to management was typically precisely because they had some special need for which traditional roles were not a solid fit, so my lack of fit was the needed fit.

In today’s work environment management is typically looking for only great fits and is usually prepared to leave a position open for an extended period of time until they find a candidate who really is a great fit.

In the old days, fit was more something that a worker had to explicitly do after being hired rather than qualities that had to exist before getting the job.


Fit is simply a fancy word for compatibility, just with less of a negative connotation, so my general lack of fit is really a general incompatibility for teams and their parent organizations, including incompatibility with organizational values.

Belief alignment

Generally speaking, people tend to work in companies or organizations whose vision and values are in reasonably close alignment with their personal beliefs. Generally speaking, an employee is expected to be passionate about the vision and values of the organization. That’s a problem for me. I tell people that I am interested in everything but passionate about nothing, which means that I would not be sharing the passion that co-workers and management have for such an organization.

That’s a big part of why I have thrived as a freelance consultant — management brings me in for my technical merit, not for any expectation that I share the organization’s mission.

Who would hire me?

Yes, I’m available, but I’m not so sure that anybody would really want to hire me. Well, okay, I do in fact have plenty of evidence that people are unlikely to want to hire me.

In fact, honestly, I would not even hire myself! Really. I mean, in the sense that you shouldn’t hire somebody unless they are very interested in the job, really interested in working, express a clear sense of passion for the opportunity, and there is clear alignment with the values and mission of the organization.

That said, it’s not for me to say. If someone has their own good reasons for wanting to hire me — and the work is palatable to me, I will hear them out. But I am also prepared for the prospect that my work days are now a thing of the past. Good riddance!

Underpaid peon

I guess that concisely states how I always felt when I worked in any traditional roles — underpaid peon. That I was a peon, a mere tiny cog in a large and grinding machine, and underpaid for my peonage to boot.

Once I got myself into a little (tiny, actually) bit of trouble over this. I attended an industry technology conference and actually listed my title as “Underpaid Peon.” Most people at the conference laughed and nodded in agreement, many clearly feeling the same way, but a staff member at one exhibition booth actually sent a copy of my exhibit badge to HR at my company, saying “I’m glad he doesn’t work at our company.” HR forwarded it to my manager who simply left that note and a note of her own saying “Remember that you are representing the company.” I posted both notes on the bulletin board outside my office — EVERYBODY who saw it just laughed and laughed. Hey, I was just being authentic — some people (a lot of people) actually appreciate that. Besides, I seriously don’t want to work at any organization whose management doesn’t have a sense of humor.

Yeah, now I am careful not to do anything that might harm the reputation of any organization I work for, but… there is a negative side effect of that, namely my severe loss of authenticity.

In truth, the right answer is that I should never accept a position where I feel that I am in fact an Underpaid Peon. Good idea… except for the fact that this eliminates like 99.999% of the potential opportunities for me. Oh well. That’s life. So be it. Chips do have to fall where they may.

Long walks and dramatic views

One key way that my interests are incompatible with most work environments and work arrangements is that one of my passionate interests in life is taking very long walks — think multiple hours — on a regular basis. My interest comes from:

  • I simply enjoy walking, a lot.
  • Health benefits of the exercise.
  • Mental stimulus and relaxation from dramatic views.
  • Clears my head.
  • Facilitates mulling over ideas.
  • Visual stimulus surfaces fresh ideas.
  • Reduces my anxiety.

I prefer to take these walks during daylight (although night works in NYC with all the lights, sounds, and energy), which for much of the year interferes with a normal work schedule. As a freelance consultant I would set my own hours, allowing me to walk whenever I wanted. This is not possible for most traditional work arrangements.

Access to thought leaders

Given all my disappointments and disinterest in most work situations, why would I actually want to consider work, besides the mere need for money, that is? Simple: to gain access to thought leaders. Sure, I can learn a lot and do plenty of writing on my own, care of the Internet and Google, but I can significantly leverage my own thinking by listening to what other people have to say. Attending think tank events provides me with tremendous opportunities to access a significant amount of thinking and varied perspectives and experiences far beyond my own. Having a job that allowed me to work with such thought leaders would take me to yet an even higher level of knowledge and insight.

So, even if I can or decide to retire and research, think, and write on my own, I would definitely miss out on the turbocharged benefits of actually working directly with thought leaders.

Given that such opportunities seem unlikely to be available to me, my next best fallback is to continue to attend think tank events. Beside the formal presentation portion of the event, it is very informative to talk one on one with the panel participants, or even fellow attendees who frequently know a lot more than me, especially when they are attending the event due to their own specialized interest and expertise in the event topic.

Afraid to retire

As much as I would dearly love to formally retire, never to work again, and free to pursue my own intellectual interests full time, there is the nagging concern that working on my own severely limits my potential. Giving up direct access to thought leaders is a major loss. Sure, attending think tank events does make up for some of the loss, but it is at a much more subdued level than have much more intense direct access.

In truth, the typical positions that I have worked in generally provided me with only limited access to a very small number of relatively minor thought leaders. There have certainly been exceptions. Think tank events have the advantage of providing access to a broader range of thought leaders, but with a much more limited intensity for one on one interaction.

I really do miss that level of intensity from working at companies active at the front line of their industries, but maybe access to the broader range at think tanks is actually a better thing at my stage of career and life.

Nonetheless, the fear or at least anxiety of retiring remains.

Broader interests

I do indeed feel that I have broader interests now than years ago when work demanded that I have more laser-focused niche interests.

It would be great if some available work opportunity offered me access to pursue broader interests, but the simple truth is that the vast bulk of available work opportunities are more niche and laser-focused, offering only narrow and shallow org chart boxes.

So, pursuing my interests on my own time and own dime may indeed be the only real way for me to pursue my broader interests. I guess that’s the way it is with older intellectual workers.

Too much negativity!

I admit it, up front… negativity is a really bad thing, and I clearly have too much of it. People usually have seemingly solid reasons for their negativity, but that simply isn’t enough to justify any kind of negativity. True, I agree with that analysis, but… what to do when one finds oneself so mired in negativity?

Granted, the answer requires shifting out of the mindset of negativity to the mindset of positivity, but that appears more easily said than done.

What’s the first step? Don’t ask me — I have no clue. If I did, I wouldn’t be in this predicament.

Okay, sorry for that little interlude. Now back to some productive discussion.

Aptitude, skill, and talent

This is simply a mini-tutorial on how I view skills. Clearly there are a lot of areas in which I lack skills. Technically, lack of skills should not be a deal killer — just take a course, read a book, attend a seminar, do a little practice, get a little coaching, do a lot of practice, and bingo, you’ve got skills. But… that presumes that you have a basic level of innate, natural aptitude that can serve as a foundation on which to build skills. If you’ve got the basic aptitude, you can pick up the skills, but if you don’t have the minimal aptitude, no amount of training or practice can amount to anything — zero times even a large number is still zero.

I use talent to refer to innate aptitude that is special and head and shoulders above the aptitude of the majority of people. Sure, skill training and practice may still be needed or to turn a star into a super-star, but visible, awe-inspiring talent is always a joy to behold. So true… if only I had some real talents to exploit.

The point of all of this is that I will focus here on aptitude rather than skill per se. So, if I say that I don’t have an aptitude, like for sales and persuasion, that should not be construed as a simple need for skill training.

Out of the question

Some work prospect requirements are definitely out of the question for me, not so much as a pure matter of preference, but due to a very distinct lack of aptitude as well as passion. Some of these requirements or opportunities are:

  • Requires physical strength, heavy lifting
  • Requires precision dexterity or careful physical coordination (watch repair, surgery, music, drawing, performance)
  • Requires strong people skills
  • Requires working with difficult people
  • Sales, selling
  • Customer service, working with difficult people
  • Hospitality
  • Motivating people
  • Persuading people
  • Managing people
  • Personnel management
  • Requires great patience
  • Requires great tolerance
  • Requires great empathy
  • Requires great sensitivity
  • Requires use of emotion and pressure to influence people
  • Physical contact with people
  • Flesh and blood (health care, or even massage)
  • Foreign language skills, fluency
  • Reading people
  • Detecting lies
  • Negotiation
  • Suffering fools gladly
  • Working with children
  • Working with the elderly
  • Working with the disabled
  • Working with animals
  • Cooking, food preparation
  • Intense mental focus
  • Great writing skills (professional level)
  • Great speaking skills, public speaking
  • Great short-term memory
  • Great memorization ability
  • Impeccable appearance and picture-perfect smile
  • Requires excessive formality, including attire such as jacket or tie
  • An environment marked by convention and orthodoxy and not giving high approval to the unconventional and unorthodox
  • A partisan environment where passionate belief in the organization’s vision is mandatory — such as environmentalism, social justice, racial justice, and conservatism
  • Creative work — arts, fiction, theater
  • Lateral thinking
  • Thinking on your feet — sometimes, maybe, but generally I am more thoughtful than off the cuff
  • Full-time, long-term career path
  • Sports and athletics
  • Entertainment (acting, theater, comedy, dance)
  • Repetitive work
  • Storytelling, fiction
  • Acting
  • Software development, coding (no longer any interest)
  • Hands-on technical work (no interest)
  • User experience design (UX) — I’m not good with visual design, but human factors and interaction analysis is something I am interested in.
  • Complex mathematics
  • Complex forms and paperwork — or any job focused significantly on forms and paperwork
  • Personal connections who can deliver business value
  • Surprises — or at least very unpleasant surprises
  • Cattle calls — large number of applicants with no sense of carefully considering my particular skills or abilities
  • Heavily structured environment, fixed hours, rigid rules
  • Command and control style of management
  • Micromanagement
  • Government
  • Military
  • Defense contractor
  • Academic
  • Intense time pressure, or most other forms of excessive pressure
  • Marketing, especially correctly reading a market
  • Social media (Twitter, Facebook) — although I am on LinkedIn and Medium
  • Microsoft Office — I’ve switched to Google, although I could go back for a decent job, I guess
  • Requires cell phone/smart phone — am I the last person in the world without one?!
  • Fast typing — I’m not a slow typer, but moderate typing speed is not good enough for some environments
  • Multitasking — limited multitasking is fine and even preferable (I like working on multiple projects), but heavy multitasking is simply not a fit for me.
  • Very short-term projects — minutes, hours, or days
  • Very long-term projects — many months or years, except that long-term occasional consulting in fine


I am not at all interested in traditional full-time employment, a classic 9–5 job. In fact, I’ve worked part-time for quite a few years, although I did have a full-time job at Microsoft from 2006 to 2008. Not my cup of tea.

That said, if the work truly was interesting and compelling I’d be willing to work full-time or even overtime provided that I found the work palatable and with a reasonably low stress level, but I’m not holding my breath on encountering such a blue-moon opportunity.

Wearing a jacket and/or tie?

Oh dear. Yes, I suppose technically I could do the “business” attire thing, but it would be a real drag.

I’ve gotten so used to shirt and jeans that it feels too difficult to give up the jeans. I’d be okay with going back to chinos, and I always wear a button-down shirt anyways.

Shoes may be an issue too, since I prefer to wear comfortable, casual shoes (but not outright running shoes or sneakers), but that can be dealt with. Wearing non-casual dress shoes could be problematic for me since I would normally prefer a long walk to and from work.


The real point here is not clothing per se, but the simple fact that the jacket and tie are symbolic of an organization obsessed with formality, while I’m a guy obsessed with informality. So, it isn’t a question of whether I could wear a jacket and tie, but the simple fact that any work environment that requires a jacket and tie is almost certainly not a good fit for me.


More simply, I’m the kind of guy who thrives in an environment focused on informality. The informality is symbolic of freedom and an encouragement to pursue opportunities broadly and without constraint or any narrow sense of direction and not even a hint of micromanagement.

No resume

For many years I kept an updated resume online, but no more. In truth, most of my freelance work was obtained via word of mouth and didn’t require a resume. My belief and attitude is that LinkedIn is a vastly more superior approach than an old-fashioned resume.

For reference here is my LinkedIn profile.

Unable to suffer fools gladly

One of my personality “defects” that has held me back greatly is my inability to suffer fools gladly. That makes it virtually impossible to work in sales or customer service, or for many managers. I feel that I have an almost moral obligation to call out stupidity when I see it. Intellectually, I recognize and agree with the admonition that “the customer is always right”, but I’d be a very poor choice to interact with customers who entertain and speak foolish and stupid thoughts.

Anger management

Yeah, I do get very frustrated and even angry at times. I do have a rather short fuse, but I’m usually very good at coping with frustrating situations. Every once in awhile I do slip up and say something in a tone that is distinctly less than friendly, professional, and productive. That said, I never bear a grudge and quickly revert back to as friendly, professional, and productive a tone as possible. I do think I handle things well enough for most environments, but I certainly recognize that I would be a very poor fit for situations where “the customer is always right.”

Arguments and heated debate

As a consultant, I endeavor to be as professional as possible, adhering as closely as I can to the “customer is always right” model. I used to tell people that I can do anything for six months, but after that I start taking too much of a sense of ownership and becoming resentful of unreasonable requests that might corrupt the integrity of the product.

As hard as I try, occasionally discussions devolve into intensified arguments, and even acrimonious and quite heated debates. Usually the acrimony is very short-lived, but it is still rather unsettling that it happens at all.

Maybe this is simply the price we have to pay for trying to perform really difficult tasks in which really difficult choices have to be made, and where dramatic differences of opinion are not uncommon. Still, I do wish that I could handle these situations more calmly and skillfully.

Borderline obsessive-compulsive disorder?

I’ll readily admit that I have my habits, rituals, and behavioral oddities, but I doubt that I would be clinically diagnosed as suffering from obsessive-compulsive disorder (OCD.) Borderline, maybe.

In truth, there are quite a few work roles where an almost-obsessive attention to detail is highly valued. In fact, computer programming is one of them. But, at this stage of my career I am not interested in work that requires that level of attention to detail. My research, thinking, and writing does get into a lot of detail, but only to the level that I feel comfortable and satisfying, and not to the level of true, professional-level research and a lot of technical jobs.

Borderline attention deficit disorder?

My status as a novelty junkie and an inability to stay comfortably within an org chart box might suggest that I have some some of attention deficit issue, but I doubt that I would be clinically diagnosed with attention deficit disorder (ADD or ADHD.)

In truth, there are quite a few work roles where extreme multitasking and rapid jumping from task to task is essential, but I have no interest in such rapid multitasking. I am much more methodical even when I am working on multiple projects.

No emotional tolerance or stomach for hands-on work

Yes, I thoroughly enjoyed hands-on when in my early days, but I fairly quickly grew tired of it. I did continue to do it for many years, but only because it was a mandatory requirement for the available work. But these days I literally have no stomach for it. I am emotionally unable to cope with the demands of hands-on work, particularly since I have no interest in it.

It bugs me to no end that managers have no interest or need for my various talents, that all they care about is the hands-on work, which is my least interesting skill, to me.

In the old days, my intense interest in the work carried me through the difficulties and tedium of the work, but with a flagging interest, I have nothing to carry me through the burden. It’s just too great a burden for me to bear, especially emotionally. And I feel it in my stomach.

As I’ve noted, my health is my most important asset and biggest priority, so work that makes me feel sick is simply out of the question.

Work I’m okay with

I know full well that my list of no-go work is way too long, but there are at least a few things that really are acceptable to me, such as:

  • Working with people in a general sense, as opposed to customers or patients
  • Working in an office environment
  • Planning
  • Organizing
  • Problem solving
  • Analyzing
  • Self-motivated
  • Travel
  • Standing and walking
  • Part-time
  • Freelance
  • Casual, informal, unpolished writing
  • Explaining complex matters in the kind of simple, plain English that mere mortals can relate to
  • The subset of user experience (UX) that relates to analysis of human factors, interaction, and workflow — just not the visual design stuff.
  • Curiosity
  • Novelty junkie, always something new
  • Working on multiple projects — but not in a Millennialist multitasking sense, more thoughtful, slower transitions, at my own personal pace
  • Unstructured
  • Part-time — maybe more if truly interesting
  • Email — my preferred form of communications
  • Google Apps — Chrome, Gmail, Docs, Sheets, Calendar, Drive
  • Collaborative tools — HipChat, WebEx,, JIRA
  • Modest to moderate-sized projects — weeks to months, not hours/days or years

My black box skills

One of my special skill areas, effectively a talent, is looking at a black box and figuring out what may be in the box when you can’t actually see inside the box. This involves deducing the answers to a collection of questions:

  • What can’t be in the box.
  • What is unlikely to be in the box.
  • What might be in the box.
  • What might not be in the box.
  • What is likely to be in the box.
  • What must be in the box.
  • Design experiments to further limit the range of possibilities. Even if you can’t see directly inside the box, you can always do indirect experiments that give you fragments of information related to what might or might not or could not be in the box.
  • Rinse and repeat using the results of the experiments to increasingly limit the range of possibilities.

Customer consulting experience

Although I have clearly expressed the notion that I am not a good fit for sales or customer service, I actually have had some limited success at consulting for customers.

First, as a freelance consultant, I have by definition interacted with a fairly wide range of customers, although most of that was more contract programming than consulting per se.

Beyond that, I did do some amount of customer consulting for a database vendor, participating on sales calls, answering technical questions, and offering advice on complex data modeling issues, both for core database use and for advanced search engine features.

I was actually okay with that, to the degree that I was able to stay away from hands-on work. I didn’t mind assisting them with advice for troubleshooting, as long as they did the actual hands-on work.

Unfortunately, virtually all of the positions available for that type of work require the hands-on portion of the work that I have no interest in.

Qualities I’m mediocre at best

There are some work qualities that are not strictly no-go for me, but not my best qualities, such as:

  • Confidence — at least strongly projecting confidence
  • Communications skills — issues of polish and presentation
  • Persistence — sometimes I give up a little too easily unless incredibly motivated
  • Patience — I tend to be impatient, preferring to act or move on
  • Training, teaching — technically possible, but no real interest since it is too repetitive


I will be the first to admit that my communications skills are not so great, especially when it comes to persuasion, selling, motivation, and polish.

Technically, I believe that I do have fairly decent communications skills, at least when it comes to speaking and writing plainly, simply, and clearly, focused on clear description of raw facts.

But I am definitely not a storyteller, and completely uninterested in so-called narrative. Just the facts, that’s me.

Jack of all trades, master of none

My software development career covered a very wide range of software technologies. As a novelty junkie I always enjoyed branching out into technology areas where I previously did not have experience. The downside of being a jack of all trades was that I was no longer a master of a single trade. My main focus coming out of school and in my first few years of professional work was programming language and compiler development, with a side interest in software tools.

I generally learned only as much as I needed to get each individual project completed, so that I was never a true expert in any of the areas I worked in. In specific niches I really was expert, but for broader areas I certainly was not an expert.

As such, I am not qualified to be a nationally-recognized expert, writer, or trainer for most of the areas in which I worked.

That left me qualified to be a consultant for specific narrow niches, but not in a broader, general sense for any of the areas in which I worked.

Not a recognized expert

Having the jack of all trades mentality, I always eschewed taking the time and energy to be an expert in anything. That approach served me fairly well during my main career, but unfortunately means that my career doesn’t qualify me for the kind of emeritus and consulting status that prior status as a recognized expert would convey. That said, I don’t think I would have done anything differently over the years. That wouldn’t have been me, I wouldn’t have been authentic.

No emeritus status

I am indeed envious of those who have been so successful in their careers that they have achieved an emeritus level of status that essentially allows them to gain income with little effort. I myself have neither achieved that status nor do I have any prospect for doing so.

Technically, emeritus status is simply the retaining of a title, a formality, but the point is that it is an acknowledgement that one’s contributions have had great significance.

My point is simply to refer to an emeritus level of status as a qualification for contributing a level of wisdom that younger, less-experienced professionals simply do not have to offer.

No PhD

I enthusiastically pursued getting a masters degree in computer science in college, but didn’t even consider for one moment getting a PhD. My main interest was on getting to the front lines of commercial, professional software development as quickly as possible. As soon as I picked up my diploma in May 1976 I promptly left town, starting work the following Monday, and never looked back. I correctly perceived that a PhD was not a required credential for commercial, professional software development. I encountered only a very few individuals with one over most of my career. That has changed a little in recent years, but still seems to be the exception rather than the norm.

But once I ceased being interested in garden-variety software development, the lack of a PhD began to take its toll. Once my interests were more focused on ideas and research rather than code, a PhD seemed to be more the cost of admission to that level of work, meaning that I was out of luck.

Looking back, I definitely should have pursued a PhD at some stage in my career, such as when I had the opportunity to work as an assistant to a PhD researcher in the R&D group at Digital.

That said, things are what they are. I never did decide to pursue a PhD, so that is the reality that I have to live with.

There is also the open question of whether I actually possess the raw intellect to thrive at the PhD level. There is a fair bit more to a PhD than taking a few more courses and working on a project. I had the intellect to achieve an MS, but there is a night and day difference between an MS and a PhD. A PhD is more a matter of native aptitude and raw talent than simply skills training. In truth, my own intellect is probably in limbo, somewhere above an MS, but still short of a PhD. I accept that reality.

The main point is that the lack of a PhD deprives me of a key credential needed to work at the lofty levels of ideas and research.

The flip side is that I have also noticed that many computer science PhD holders are really doing more mundane software development and incremental advances these days, not the kind of more advanced research on far out ideas that hold much greater appeal to me.

Not a thought leader

Thought leaders are basically experts whose opinions have the ability to shape public discourse on some matter. This also makes them highly sought out for consulting opportunities. Alas, I’m not in that class, not even close, nor do I have the prospect for being so.

That said, it is good advice for young professionals to seek to achieve a level of competence and innovation and to establish a pattern of communicating ideas that leads you to becoming a sought out thought leader.

Minimal entrepreneurial efforts

I have indeed made a couple of attempts as an entrepreneur. I had a couple of small software products, software tools, that I designed and implemented myself and was marketing to software developers, back in the 1990’s. I had only very modest success, insufficient to sustain a viable business. I simply was unable to gain enough traction to maintain a presence in the market.

I made another modest attempt back in 2012, but all of my technical effort did not lead to a viable product.

I dearly would have liked to have been a successful technology entrepreneur, but it clearly wasn’t in my stars, cards, or whatever.

My primary difficulty was an inability to accurately read the market. Marketing simply is not my forte. Intellectually I know all the pieces, but reading market demand is not within my range of aptitudes.

Quick study

Although I don’t have status as an expert, one of my strengths has always been as a quick study, that a manager or executive could throw me at a vague problem and I could very quickly figure out the true nature of the problem and be able to explain its nuances in relatively plain English that mere mortals can relate to.

That said, it is far more common these days for managers and executives to reflexively reach for recognized experts for their pre-prepared pitches, even if these so-called experts are far less skilled than I at presenting the essence of their area of expertise in the relatively plain English required by mere mortals.


I have made a couple of attempts to be an entrepreneur, but with little success, the main problem being an inability to properly read markets and customer demand. You could build the best product, but if there is not a large market ready and willing and able to buy it, you are out of luck.

I simply have no detectable ability to read markets, to get a handle on what real customers really want. I’m just too much of an outlier, too lacking in empathy for what customers really need.

Social media

I think social media is great — I am a shareholder of Twitter, Facebook, Google (bought Blogger and YouTube), and Microsoft (formerly a shareholder of LinkedIn before Microsoft bought the company.) Technically, I do still have profiles on Twitter, Facebook, and Blogger, but LinkedIn and Medium are the only social media platforms on which I am currently active.

I’ve never gone near SnapChat, Instagram, or WordPress, or any of the many more minor social media platforms.

I am a semi-frequent viewer of YouTube videos, but I’ve never uploaded or commented on a YouTube video, and video production is definitely not in my skillset.

I am modestly active on Jelly, but very few people know about that new question and answer platform. And I am active on occasion on the Seeking Alpha social media platform for investment and financial markets.

Quite a few digital-savvy organizations are now very active on social media, so that becomes a job requirement that I am both unable and uninterested in meeting. So, any position with a requirement for significant social media activity is effectively out for me

Sure, I was quite active on Twitter for several years, but I pulled the plug back in 2010 when I realized that I was not getting any significant benefit from the investment of my time.

I was also quite an active blogger for a number of years, but even that dwindled in more recent years, and has now ceased since I began focusing more intensely on my more serious longer-form writing on Medium.

I keep my professional profile updated on LinkedIn, occasionally posting status updates, which is a little like Twitter.

Work I’m unlikely to be good at, but…

  • Working outside, in all weather — possible, but it depends, and not so likely.

Work I’m unsure about

  • Paralegal — except I’m not into forms and paperwork, even though I find law and contracts fascinating. I wouldn’t mind working in a law office doing some relatively menial work if it exposes me to legal minds.
  • Menial work with no intellectual content — maybe as filler or a stop-gap if the pay is decent and the stress level is low.


Part-time work, such as 10–15 or 20–25 hours per week, is most ideal for me. I would really like to have a full four hours a day, during the day, to pursue my non-work interests.

Technically, I am willing to work more, even full-time or even overtime if the work is truly interesting and compelling, to me.

Full-time consultant?

I am certainly interested in work as a consultant, but I would have to think carefully if the specific position required a full-time commitment. At a minimum it would set off yellow warning flags for me. Yes, it could work, but not so likely. Still, I would consider it. Beggars can’t be choosers, right?

My preference would be a heavier part-time commitment, 25–30 hours a week, with the option of expanding to full-time or even overtime upon mutual consent. I’ve done this more than once in the past and it seems to work well. Management is typically pleased with the prospect that I would be available in a crunch, but wouldn’t have to budget the expense of full-time the rest of the time.

Reason and merit vs. emotion and pressure

At heart, I am Mr. Reason, and also Mr. Merit, focused on the use of reason and merit to analyze and advance ideas and proposals, and diametrically opposed to the use of emotion and pressure to influence and manipulate people. In my book, the ends do not justify the means — only reason and merit are justified.

Any organization or team that doesn’t share these values is unlikely to be a good fit for me.

Mental blocks

What possibilities might I be missing due simply to mental blocks?

Some possible causes of mental blocks for me:

  • Tired and burnt out.
  • Just getting old and losing my energy and mental edge.
  • Limited network and circle of friends.

So, how exactly can I identify specific blocks and then overcome them?

Outside the box, lateral thinking possibilities

So, what exactly might I be good at or consider that I am presently aware of?

  • (list is empty so far)

Now, I need to ponder exactly why that list is empty, other than the distinct possibility that if an opportunity is out there then I have probably already thought about it.

Okay, technically that list is empty because it should only be opportunities that I am unaware of, but by definition I cannot be aware of what I am not aware of. Of course, that is the function of imagination and speculation, to bring into our minds things that we are not yet even aware of.

The point is that this is where I seriously need help from readers to put some potential opportunities on that list so that I can consider them and then take them off the list.

Currently available jobs for me

Trust me, I’ve looked with significant energy and discipline, but nowhere can I find any available jobs that are a good fit for me. Nada. Zilch. Nothing. The vast majority of jobs out there are relatively traditional jobs, a box in an org chart, which makes them uninteresting and poor fits for me.

And it’s not a matter of credentials either, per se. If the work interested me, I’d be willing to put in the effort for the credentials (degree or training.) In truth, virtually all credentialed jobs are also traditional jobs, which by definition are not a fit for me.

Boring work

Boring work is certainly not my first or even the bottom of my top 100 preferences for work, but it actually would be marginally acceptable if the pay were semi-decent and a low-stress environment. In other words, sure, I could accept some “filler” work while searching for more fulfilling work.

Unfortunately, that “low stress” requirement is a deal killer. Sure, I would bet a lot of money that somewhere out there there is such work, but as before, I am at a loss for how to find it.

Repetitive and tedious work

My core personality makes it extremely difficult if not outright impossible for me to accept work that is repetitive, tedious, or otherwise boring, even if the money is fairly decent or even great. Some people get a psychic boost from repetitive work, with each repetition reinforcing the psychic benefit of the activity, but not me. Maybe this is due simply to me being a novelty junkie.

I simply could not thrive working as a chef, cook, electronic repair technician, or even a salesman giving the same pitch over and over, or even a judge, presiding over endless cases with the same basic fact patterns governed by the same laws and with the same outcomes.

Granted, much of software development was commonly quite tedious for me, but I guess there was just enough novelty along the way to keep me going. But now, software development is like 99.9% tedium, at least for me, effectively putting it in the tedious work basket and earning my disdain rather than my passionate interest, even if the money is quite decent.

Envy of those who enjoy their jobs

I truly do envy those many individuals who have managed to find work that they really enjoy and are truly passionate about. Insanely jealous even. Who knows, maybe they worked a lot harder or a lot smarter to get to that point of happiness.

To be sure, there were numerous moments when I found my work interesting, but they were the rare exception.

I once had a boss whose belief was that you should consider yourself lucky if you were happy in your work 10% of the time, the other 90% being the price you had to pay to get that 10%. I thought that was an absurd proposition, but the simple truth is that I would have been lucky if I had managed to get to that 10%, which never happened for me. Even in my best weeks, maybe I hit 5% satisfaction. Satisfaction 1% of the time was probably the norm for me, and frequently I did not hit that mark.

Should work be fun?

I would like to say that, yes, work should definitely be fun, but I recognize that for so many people work is simply a source of money to support their families and lifestyle, where their real fun happens. Many people do in fact have some degree of fun at their jobs, but typically during breaks and between tasks or chatter during tasks, but the work itself is more likely to not be fun at all. That said, I think most people would agree that they really, really, really would prefer to have a job that is very satisfying, if not outright fun. Sadly, for far too many of us, you take what you can get.

So, yes, part of my goal is to find work that is fun. My real goal is satisfying work, but I’d settle for fun.

That said, I feel that life is conspiring to offer me only work that is both unsatisfying and distinctly un-fun.

Nonetheless, for the purposes of this stage of my career I plant my stake in the sand as saying that I will only take new work on the condition that it is fun, to at least some degree. The satisfaction absolutely needs to be there for me at this stage, with at least a minimal of fun.

Career counseling?

Could a traditional career counselor help me? Maybe, theoretically, but… my personality, aptitudes, interests, and background is likely to be way too atypical for any normal career counselor to be of any assistance.

Still, I would be open to a consultation if after reading this lengthy assessment some very special counselor thinks they could be of great assistance.

Just to be clear, no, I am definitely not interested in taking a career test or survey. If a counselor can’t tell from what I have written here, then they are definitely of no use to me.

Special services for workers over age 50

Yes, there are indeed quite a few special services and programs available to help workers over age 50 find employment, but for the most part they focus on:

  • Helping people get into traditional job roles — the kinds that people covered by this paper are unsuited or uninterested in.
  • Reminding employers to refrain from age discrimination, but the candidate must still fit all the qualifications for the traditional job.
  • Companies who pay special attention to attracting or at least retaining workers over age 50, but again they are essentially the same traditional jobs that people covered by this paper are unsuited or uninterested in.
  • Those actually interested in going back to school for a full career, which is not an option for those of us very near retirement age.
  • Relatively unskilled work, which will not be of any interest to the kinds that people covered by this paper.
  • Helping people turn hobbies and interests into businesses.

I don’t want to disparage such serious efforts to help workers over age 50, but simply want to focus on the distinct category of us who simply do not fit into the traditional roles covered by such programs.

Just to give a sense of the flavor of the kinds of very real job opportunities that such programs offer that are clearly not of any significant interest to the people covered by this paper, consider:

  • Interpreter/translator
  • Tax-return preparer
  • Ride-hailing driver
  • Park ranger
  • Direct salesperson
  • Dog walker or pet sitter
  • Retail cashier
  • Craft worker
  • Package courier
  • Your old job, part time
  • Curator
  • Clinical counseling and school psychologists
  • Instructional coordinators
  • Library technicians
  • Postsecondary teachers
  • Museum technicians and conservators
  • Morticians, undertakers, and funeral directors

Other elements of these programs include services that are probably already used or unlikely to help those covered by this paper:

  • Resume writing tips
  • Networking tips
  • How to use LinkedIn
  • Job fairs — especially for over-50 workers
  • Advice for starting your own business
  • Job listings focused on over-50 workers

Some of the organizations offering programs for older workers are:

My review of those resources found nothing that met my interests or situation. Mostly their focus was on variations of traditional work roles, or for roles which do not intersect my interests.

But, hey, if anything mentioned in this section helps you find gainful work, that’s great.

General model for older workers

Just for the sake of completeness, here is a general model for older workers seeking work:

  • Did you lose a job or encounter difficulty finding work due to age discrimination? You can consider legal action. No need to give up simply because your legal rights were violated.
  • Do you just need to broaden your search geographically? Consider a move.
  • Do you need some variety, a variation of your current role? Talk to your boss, HR, or check job listings.
  • Do you like some or most aspects of your job but the hours are a problem? Talk to your boss or HR to arrange flex hours, or seek another employer who does offer flexible working arrangements.
  • Is there a modest lateral job move that would appeal to you (money, type of work)? Get the required training or degree — if you are still young enough to afford the degree and the time working required to earn back the cost.
  • Are you young enough to jump to an entirely new career that interests you a lot more than your current career? Go for it, if you can afford the cost of the jump and the time working required to earn back the cost.
  • Are you disabled in some way? There are government programs for that.
  • Are you just tired of working, period? Retire, if you can afford it.
  • Are you simply burned out, but not ready to retire? Consider a sabbatical or just take some time off on your own, but then continue the same or similar job.
  • Do you need the structure of a job to feel fulfilled at the end of the day? Keep working or find a traditional job.
  • Do you have a great idea for a new business and really want to be your own boss? Plenty of resources for that. Just make sure that you have the skills, passion, and a ready market before making the leap and investing your time, energy, and money.
  • Do you have a craft skill or hobby that could be turned into a modest business for some supplemental income? Go for it. Again, just make sure that you have the skills, passion, and a ready market before making the leap and investing your time, energy, and money.
  • Are you comfortable with traditional part-time or menial roles and won’t be bothered by tedium and boredom? Go for it.
  • Consider a formal or informal skills assessment to see which career direction you should pursue.
  • Do you really need the money, or are you financially secure and just want something interesting, productive, and socially valuable to fill your time? Consider a volunteer position, such as with a non-profit whose cause you believe in.
  • Are you out of work, need the money, and none of the above seems to fit the bill for your particular interests, abilities, and situation? Okay, you’re in the same boat as me.

That should cover the lion share of older workers who are not content to continue working in their current jobs. And that last one tells you whether this paper is particularly relevant to you.

Jobs for the kids

One thing I am really serious about is that I absolutely do not want to take a job that some deserving young person would be eligible for. The future belongs to the kids. They come first.

My interest is in work that needs a little of my accumulated wisdom, something where the kids would not be competition.

Age discrimination

Personally, I’m not willing to go there. Sure, maybe I might have been discriminated against because of age — you can never know, but it wasn’t at all obvious to me. My perspective is that I simply don’t have the energy, enthusiasm, or interest that a lot of younger workers have. Or maybe I’m just burned out. But nothing I could attribute to age per se.

There is the aspect of team fit and cultural fit. Work environments are a culture today (not that they haven’t always been), so maybe I’m simply no longer a cultural fit, and maybe I simply do not share the same (work) values as members of teams and their managers do these days. Even then, that’s not an age issue per se either.

And my bottom line thesis is simply that I am no longer interested in any of the jobs that are appropriate for young people anyway, so even if there were age discrimination, it would be a moot point for me.

To reiterate, I don’t even want to consider taking a job that a deserving and enthusiastic young person would want. I want work that focuses on what I can bring to the table in terms of talents, skills, experience, and wisdom that young people simple do not have, yet, or haven’t sufficiently developed, yet.

Foreign workers

Another place that I’m not willing to go is to assert that the presence of foreign workers or outsourcing or offshoring is in any way a factor in my own predicament. The simple truth is that virtually all of them are doing work that I have no interest in.

The ugly truth is that there are indeed a lot of native workers who could do the work of foreign workers, brought here on special visa programs on an assertion that they are fulfilling an unmet need, except that:

  • Existing native workers do not have the specific skills and training. And companies are unwilling to pay to train native workers to develop those skills. Offshore schools and companies focus tremendous attention and resources on training these foreign workers on the latest technologies and project management techniques before they come here, so it’s difficult for most native workers to compete with that.
  • Many native workers are not a good fit for modern technology teams. Old dogs and all of that — too proud, too much ego.
  • Some fraction of older workers simply aren’t a good fit for younger, faster-paced teams. Not all of them, but finding a good fit is problematic.
  • Foreign workers are more compliant — they are more desperate to do whatever it takes to succeed, otherwise they will be sent home.
  • Many native workers feel too much a sense of entitlement.
  • Much of the work is either more entry level and lower pay, or more structured than many native workers would tolerate.
  • Foreign workers will be much more likely to tolerate a sweat-shop type of environment than entitled native workers.
  • We simply don’t have the kind of of skill and ability databases to identify native workers who could in fact be ideal candidates for the positions that foreign workers fill.

You’re fired!

Yes, I have actually gotten fired, twice. Technically, there was a third time as well, if you count termination as being fired. Sure, getting fired is no fun, but I like to assert that one of my biggest regrets is that I didn’t get fired more — not getting fired suggests, to me, that I wasn’t taking enough risks.

To be fair to myself, in both cases I was seriously considering resignation well before actually getting fired. In other words, these were not situations where I thought everything was fine and oblivious to underlying problems.

In both cases, I explicitly decided to hang in there and try to turn unworkable situations around, but the situations were simply too unreasonable for me to have any real chance of success.

In one of the two cases I had actually just finished typing a pre-resignation email (requesting a discussion to try to address my concerns) a mere few seconds before the rep came to my desk to escort me out of the building. It was actually a relief to me to know that they terminated me rather than me giving up and quitting.

And in the other of the two cases I actually continued to work at the company in a different capacity, although they declined to renew my contract a few months later when it expired. Ironically, within a few months of that, my boss, his boss, and her boss, all of the layers of management between me and the CEO had also moved on, so it’s difficult to say whether the non-renewal of my contract was due to my performance or not. In truth, as much as I enjoyed the excellent pay, I was quite relieved to no longer have to deal with the internal company politics.

The third situation was where I submitted my resignation but the company had a policy of immediate termination if you went to a competitor. They’d had a problem where a project leader had spent his final two weeks after resignation recruiting colleagues to go work with him at the competitor. In my case, I actually went to work for my old boss who had himself been terminated under the same strict policy. Since I gave four weeks notice, the company was obligated to give me all four weeks as termination pay. Just reward?! So ironic. In truth, the policy was a joke among staff, managers, and HR as well. I let them know a couple of weeks in advance of when I would formally submit my resignation, and they were okay with that, although not happy to see me leave. In fact, we had a going away lunch, the day before my official notice. The funny, comical, ironic thing was that I arrived at work at around 8:25 AM and my manager frenetically ran up to me saying “Where’ve you been?! Your exit interview [HR] is scheduled in five minutes and you haven’t yet given notice!!” LOL. So, I quickly typed up the resignation letter and marched off to HR for my exit interview. My usual HR rep was out, so another rep walked me through the paperwork. Consistent with the irony of the whole thing, I noticed two appropriate (inappropriate?) cartoons on the HR rep’s bulletin board: “Doing a good job around here is like wetting your pants in a dark suit. You get a warm feeling, but nobody notices.” and “Getting anything done around here is like mating elephants. It’s done on a very high level. There’s a lot of stomping and screaming involved. And it takes two years to get any results.” Ouch. Sad, but so ironically relevant.

There were also two situations where my contract was terminated for business reasons rather than anything related to my performance. In one case they were terminating all consultants. The other was the same, due to the financial crisis in September 2008.

I quit

I submitted resignations a number of times, but usually that was simply to move to another company.

Only once did I actually submit a resignation in an angry “I quit!” frame of mind. Even then, I actually turned around and immediately started consulting for the same company, but with more flexible, generous, and acceptable terms.

More productive networking

My networking abilities are mediocre at best. Sure, I have 500+ connections on LinkedIn and I do my best to connect with people at events, but the simple truth is that none of these connections has any current value to me in terms of finding informal part-time work at this stage of my career. Yes, these connections would work like a charm if I sought traditional work roles (those damn org chart boxes!) or even the kind of work roles that I held in the past, but I am not interested in any of those traditional roles at this stage of my career. And as I just said, I am unwilling to take work that a deserving young person might want.

What I really need is networking connections that have some interest in the kind of work I am interested at this stage of my career — either senior consulting roles where my talents and accumulated wisdom brings some value to the table, or some relatively unskilled office work that at least covers a fair fraction of my monthly living expenses so that I can keep most of my savings intact for my eventual retirement.

The simple truth is that I have no idea how to establish such networking connections. Maybe that is because the even simpler truth is that they do not exist. But, hey, I am very, very, very willing to be proven wrong on that front!

Golf anyone?

No, I don’t play golf, or tennis, or squash, or like any sports or card games, or generally hang out at social gatherings. That’s my preference, but it does leave me out in the cold in terms of social connections that frequently lead to professional or business connections.

That said, it would not make any real sense for me to take up golf (or any other activity) solely for the purpose of professional or business networking — it would be patently obvious that I was a fish out of water, so it simply would not work. And I would be very unhappy doing it. Generally, you should only take up activities that you are passionate about, and it is that passion that makes you authentic and appealing to others interested in professional and business networking.

Actually, I did take golf lessons once — I worked at a computer company that owned a small country club with a golf course. I’ve taken skiing, scuba diving, and even flight instruction. It was all fun, but my interest waned once the novelty wore off. I was more interested in the learning process than the activity itself.

Calling all organizations that do hire people like me

I don’t for one minute believe that there are no organizations out there who are interested in a guy like me. The problem is that I have been unable to find any of them. Yes, I’ve poked around the Internet and done a fair amount of searching. And I’ve exploited my networks of connections to the best of my abilities, but my search has so far turned up empty.

Sure, some organizations do go out of their way to recruit and hire older workers, but the truth is that they are simply saying that they will not use superficial age as a hiring criteria — you still have to meet the same technical criteria as for younger workers, so if it was the job requirements which were your turnoff in the first place, such an establishment is not going to be a satisfying solution. You are still going to have to fit into a formal org chart box.

No, I don’t want to look at your job listings!

It seriously annoys when when I carefully explain to someone the nature of my situation, particularly my need for a part-time, informal arrangement and their primary response is to look at their formal job listings. Duh… if I wanted a position from a job listing I would have already done that.

In truth, maybe they are just being polite or are too insecure to say outright that there is no place for a guy like me in their organization.

My dream job

Oh, I almost forgot… my dream job: Congressman. They get paid a reasonable amount and don’t really have to do very much except get reelected. They get to attend a lot of very cool meetings (I love going to congressional hearings and talking to people in hallways.) They get to say and do whatever they want, being responsible only to the voters. And if they are independents, they don’t have to toe any party line.

Alas, election and reelection are deal-killers. I wouldn’t be able to promise and lie about doing things I knew I wouldn’t be able or willing to do. And I’m not a party-line kind of guy. Definitely an independent, an outlier. Giving speeches, kissing babies, and so much smiling and being nice to people I may not be able to stand would be deal killers as well.

The jacket and tie would be deal-killers for me as well. But as noted earlier, the jacket and tie per se are not the deal-killers, but the fact that they are symbols of an organization obsessed with formality while I’m more obsessed with informality.

As I like to say, I have found that fantasy is usually so much more satisfying than reality. So, yes, being congressman is my fantasy dream job. Unfortunately, I need a reality dream job, not a fantasy dream job.

My real dream job

My real dream job would be to have $10 billion to run a technology research and development lab and business incubator — with nobody to answer to. Listen to people pitch ideas and decide which to bet money on, especially young people and even college dropouts, accepting that a fair fraction of these efforts would fail to bear fruits.

Is that likely to happen? Not very, but hey, we’re supposed to dream big, right?

My dream of working in venture capital

I had harbored a passionate interest in working with a venture capital firm, but my best efforts never turned up any opportunities. I actually wrote a long essay on that effort: My Venture Capital Swan Song.

In truth, I would have been less happy at a venture capital firm than my dream of an R&D lab and incubator, particularly due to my passion for ideas rather than business plans and finance.

Working from home

I’ve actually gotten used to working from home, since that is common for freelance consultants. I’ve worked in an office as well, and I am perfectly willing to work in an office again, but it does seem more than a little outdated and obsolete given advances in technology over the past 15 years.

Stuck in a circle

So far, no matter how hard I try to apply my analytical skills I remain stuck in a tight circle of circular reasoning:

  1. My first preference is to engage in work that I am passionate about.
  2. Search as I may, I can’t find any.
  3. Not being aware of any acceptable work, my second preference is to exit the rat race and retire.
  4. But I am not financially set enough to retire in my preferred minimum level of comfort — I can’t afford NYC (which I can accept) and I can afford DC only if I never travel and rarely eat at a nice restaurant and I can’t afford to live directly downtown.
  5. The only way out of that is to find some stop-gap work since I can’t find acceptable work.
  6. My health is my main asset — I am absolutely unwilling to risk my health with any stressful work or work environments.
  7. I have no special qualifications for any work other than the kind of technology work that I have no interest, no passion, and no energy for.
  8. Search as I may, I can’t find any work that I am qualified for or interested in and that would be low-stress.
  9. I can accept that state of affairs and continue to live off limited savings for a few years before starting Social Security benefits, but that drains a significant portion of the savings that I would prefer to have available for a more comfortable retirement as well as emergency expenses.
  10. Given that financial risk, my conclusion is that my first priority should be to try even harder to find stop-gap work for at least the next few years.
  11. Now I’m stuck, back to the top of the loop.

Sure, the easy way out is to accept reality as it is, that my retirement will be on a very limited budget and not even remotely as comfortable as I would claim as my minimum (a little travel every year, dine in nice restaurants a couple times a week, live in a comfortable downtown apartment.)

Yes, I could easily do that, but “easily” leaves me stuck with a very strong lingering feeling that somehow I am missing something and that if I just try a little harder, I’ll find it.

Rinse and repeat.

Tentative conclusion

Currently my tentative intention is to stay in the loop for a little longer, at least a year, maybe two or even three, keeping my eyes and ears open for even remotely palatable work at even minimal pay, before commencing Social Security benefits.

Exactly how long can I afford to do that? It gets complicated. Should I start taking distributions from IRA accounts? I could, but my plan was that I would need that money at age 70 for my plan of semi-comfortable retirement. Should I leave my IRA accounts alone and draw down my non-IRA savings and investments? I could, but a fair amount of that should be kept in reserve for rainy days, and most of it was supposed to be available at age 70 for that imagined semi-comfortable retirement.

The short answer of how long I can hang is there is anywhere from three months to seven years, all depending how I make those various tradeoffs. Technically, I actually could live off IRA distributions, provided I stick to my current very-limited budget, for the full seven years to get to my age 70 goal for maximum Social Security benefits, but then my IRA accounts will be drained to the level of provided only a very minimal supplement to social security.

Right now, I figure the optimal tradeoff is to hang in there for at least three more years, to age 66, and then start Social Security, with more than half of my savings and IRA accounts intact.

That seems like a tentative, workable, semi-decent, reasonably low-risk plan that protects a good chunk of my savings and leaves the door open to the sudden appearance of some acceptable work that could let me be more financially secure all the way to age 70 when I can get maximal Social Security combined with maximal savings and IRA account assets.

The big issue even there is how much effort to spend (waste) on fruitless job searching, as well as the resulting anxiety. The flip side is that the lottery ticket-style hope that something could pop up could balance the anxiety and make the next couple of years more mentally comfortable even if not financially comfortable. In other words, try to look at each successive day as a fresh lottery ticket. Hey, at least that’s a positive spin on a gloomy outlook.

Right now, my tentative, default plan is that I will semi-diligently continue my work search, considering myself only semi-retired, for the next year, and only then pull the plug, stop searching, and call myself fully retired, even though I will continue living on savings only for a couple more years.

It is also my tentative plan to revisit my thinking every three months, to check in and see if the finances still seem to be working and ask the question of what it is that I am missing.

Goals and milestones

Setting goals and milestones for those goals is an important task in any pursuit. My ideal goal for official retirement at age 70 is reasonably clear, but given my limited finances and lack of any reasonable path to acceptable work to get there, the whole project gets quite fuzzy and problematic, such that I do not have a reasonably actionable set of goals and related milestones.

Instead, I have only these weak goals and milestones of remaining open to potential opportunities as I might become aware of them, revisiting my finances every three months, deciding in a year whether to give up on job search, and whether and when to tap into my retirement accounts to fund my monthly expenses until I finally bite the bullet and commence receiving monthly Social Security retirement payments, preferably no sooner that a year from now.

Part of me wishes that I had more specific and concrete goals, but I accept that this may be the closest I can get at this stage. I accept reality. Grudgingly. Sort of. Maybe. We’ll see. Stay tuned.

Clarifying my thinking

I started this paper at the beginning of the year precisely as an effort to review my status and to clarify my thinking, especially the question of whether I am missing anything. I think that it has been successful in that sense, even if I didn’t uncover specific work opportunities in the process.

Managing my time for my work search

The biggest struggle I have right now is figuring out how much of my time and energy should be dedicated to the job search over the next year, and exactly what tasks that should involve.

Absent any great ideas, my preference is to simply keep my eyes and ears open, but not do any explicit job-search activities per se, other than simply chatting with people at think tank events.

It just feels like I should be doing a little more than that, but I simply don’t have any decent ideas what exactly that little more might be.

Daily struggle

That endless loop of doubt and anxiety plagues me on a daily basis, not to the point of making me completely dysfunctional, but it is a frequent source of low-grade anxiety. At least a few times a day the thought pops into my head that I need to be doing more to find work. If not that, then I frequently encounter activities or interests that are outside of my reach due to my limited finances. Similarly, at least a few times a day the thought pops into my head that I need to just give it up and accept that work is just not going to happen for me. Rinse and repeat. Ad nauseum.

Either way, I continue my attendance at think tank events, keeping up on world events in my areas of interest, my long walks around DC, and my informal writing, including this informal paper.

Dotting all the i’s and crossing all the t’s

Part of my method here is to exercise a significant degree of diligence, to make sure that I have dotted all the i’ and crossed all the t’s.

Generally, one shouldn’t need to go to that level of effort to solve a problem, but when confronted with a particularly thorny problem, or where the apparent solutions are universally unpalatable, it is a reasonable last resort.

In a very real sense, that is what this paper is all about, a last resort.

Think but don’t overthink

A lot of people stumble forward without thinking. I don’t typically have that problem.

On the flip side, overthinking can be downright unproductive, as with my being stuck in a tight loop. I do occasionally fall into the overthinking trap. Usually it is when I encounter an insoluble problem. No so much that no solution can be found, but that all available solutions are roughly equally unappealing. In which case, the optimal solution is frequently to simply randomly pick one of the unappealing solutions, or pick the least unappealing solution, and then drive forward with commitment and confidence but with a heightened sense of awareness that if the chosen solution suddenly becomes much more unappealing, you can quickly change horses in midstream to one of the alternative solutions.

In any case, the simple solution to overthinking is to simply stop doing it.

So, I’ll do that, right now. That happens the moment I hit the Publish button in Medium to broadcast this paper to the whole world. At that point my thinking and overthinking ceases and I can comfortably move on to the next topic on my long list of research and writing interests.

Am I missing anything?

Okay, I think I’ve covered everything, so am I missing anything? My history is that if after serious deliberation and diligent searching I come up empty, then there is very likely nothing there, that I didn’t miss anything, but I honestly and sincerely and seriously hope that just this one time I could be wrong and that someone can quickly point out what I missed.

Please, please, please, somebody prove me wrong!

What a mess — no clear way out

The more I look at this problem, the more I keep coming back to the same conclusion, that there is no clear and obvious way out. It’s all just too much of a mess. No amount of additional insight or analysis seems likely to identify a clear way out. This is a very ugly mess indeed.

To be sure, I do have a way out, of sorts, but the problem is that it is far less than even remotely being palatable.

Can AI help me?

Theoretically, a sophisticated AI algorithm would be able to quickly identify work opportunities that are a near-perfect fit for me — if such opportunities actually exist. But, from a practical perspective, such algorithms, and the databases needed to enable them, simply do not exist. Still, it is an appealing thought.

One of the great difficulties is that such an algorithm would depend on inferring what degree of flexibility hiring managers and their organizations have. This is an example of tacit knowledge — capabilities that you can observe people as having, but which they are unable to express in plain English, and nor can even smart professionals discern and codify those best practices. Frequently it involves significant judgment and even wisdom, which are much different beasts than the kinds of hard knowledge that traditional AI has been good at.

The long-term prospect is machine learning — discerning the truth without being directly told the truth. Unfortunately, that either takes a very long time of direct experience, or requires mind reading, and even with mind reading, the inference of true capabilities is likely to be quite problematic until the secrets of mental processes can be fully plumbed.

And the wisdom part of the equation is a much longer-term prospect. We may have to wait for Ray Kurzweil’s Singularity to come to fruition.

Ultimately, AI should be able to help the laziest, dumbest, most ignorant, most untrained, most ill-educated, most disabled, most unmotivated, and most incompetent individuals find productive and satisfying work. A tall order indeed.

Work is guaranteed, if…

As things stand, you can only be assured of finding work if:

  • Your needs and background are a solid match for a number of opportunities in your area.
  • You know somebody who knows somebody who has a position that would be a match.
  • You encounter a very enlightened hiring manager who can see your potential despite not having a solid match for stated job requirements. And you are lucky enough to find such a manager.
  • You are very lucky. Serendipity can be very satisfying, but very elusive.


It is not a goal per se, more of a strategy, but I do at least harbor fantasies that sometimes serendipity does bear fruit — discovering opportunity by running into just the right person by being in just the right place at just the right time by complete chance, boosting that chance by diligent efforts to expose yourself to a reasonably wide range of opportunities. In my case, I attend a lot of think tank events which gives me an opportunity to interact with both the expert speakers and a range of interesting attendees who are active or retired from a variety of interesting fields.

Alas, so far, despite my best efforts, no fruitful work opportunities have resulted, but I do thoroughly enjoy chatting with these people and having access to the knowledge and wisdom they possess.

Part of the secret of serendipity is that you have to be patient, which is rather difficult for some of us.

But maybe the most problematic aspect of serendipity is that you have to really keep your eyes open since opportunities may not always be readily apparent. An opportunity may present yourself but in a form that you don’t immediately recognize. That’s a difficult problem.

Stock market

My current thinking and plans don’t in any way depend on the stock market, which is where the bulk of my retirement and savings assets are invested. Everything will proceed as discussed independently of what happens with the stock market. I will sell increments of stock to pay for monthly expenses regardless of market conditions.

That said, if the economy picks up a bit and the stock market follows, I may be able to capture some windfall profits that will allow me to end up with more money in my savings and retirement accounts in coming years, so that I may indeed be able to live on savings and retirement accounts until age 70 without excessively depleting those accounts. I might then have a much healthier addition to my monthly income combined with the healthier monthly Social Security checks I would get by waiting until age 70.


I always cringed at even the mention of law in my younger days, although I actually did enjoy working with a corporate lawyer on a technical contract. I was amenable to the conceptual stuff, but not all the boilerplate and mumbo-jumbo.

When I semi-retired during the dot-com boom I moved to Washington, DC due to my fascination with government. I loved going to Congressional hearings, for some reason. This was a side of law that I could relate to, somehow, in a way that I couldn’t grasp, then or now.

I arrived in Washington in August 1998, just in time to hear the news of the big Microsoft antitrust case. I attended the initial hearing and was mesmerized by the process. I had no intention of attending any more of the trial which threatened to be quite long and dragged out, but at each step I felt enticed to attend just one more day of the trial. Eventually I thought I could write a book about the experience, then realizing that I would have to commit to attending the entire trial, which I did. I met and chatted with countless lawyers, technologists, and journalists. I even had my own Pacer account to directly access court electronic records. One of the law professors I met even added me to the ABA antitrust email list. A full page interview and picture of me were published in the National Law Journal. In the end, I decided not to write the book since I figured that by then everybody was kind of tired of the whole process and there were two books out already anyway. Nonetheless, the bug had bitten, and now I was hooked. I actually enjoy reading legislation and statutory law and regulations.

I’m positive that I wouldn’t enjoy being a practicing lawyer, but I would enjoy working at the fringes of the law profession. I’m unaware of any specific roles or opportunities that would be a good fit for me, but I suspect that there might be something out there for me, if only I had even the slightest clue of how to find it.

Backup career

Looking back, one of the greatest risks of my career was that I did not have a backup career, some kind of basic, always in demand, work that would always be available if or whenever your main career falters or peters out. Whether it is being a taxi driver, bartender, singer, photographer, or whatever, it is something for those stretches when you have nothing.

For a lot of people this could simply be the kind of work you did for a summer job when in school.

Me, I had no backup career. Technology was my only career. My summer jobs were technology jobs, so I had no automatic backup career like a lot of my less-fortunate peers.

If I had to do it all over again, I’d… I have no idea, simply because all of the options I can imagine right now have no appeal.

If money is your primary motivation for work…

Yeah, I know, there are plenty of people whose primary motivation for work is to fund their lifestyle, especially to raise a family, but once you’ve taken care of those necessities (or evaded them, like me), such as arriving at retirement age, money is a rather poor motivation for work. At least to my tiny brain, work for older workers, especially those with an intellectual bent, should be a great joy and a real treat, not an obligation and a profoundly depressing source of anxiety. Work should lift your spirit, not drag it down.

Near-poverty subsistence

I’ve resigned myself to the simple fact that I will likely live the rest of my life at a near-poverty level of subsistence. To be clear, I will certainly be free of poverty — not living on the street or wondering where my next rent check or meal will come from or living in a dangerous neighborhood, but my budget will be severely restricted:

  • No travel. Zero travel budget.
  • No eating out at nice restaurants on a regular basis. Occasionally, or appetizers and a drink, but that’s about it.
  • Zero entertainment budget. Luckily there is plenty of free entertainment and my walking is free.
  • Less than luxurious apartment. Not living in an outright dump, but a lot less than I would have hoped, and not as close to downtown as I would have hoped.
  • Not afford to live in New York City. That had been my goal.

Universal guaranteed work

One far out idea that I am still working on is the concept of what I call Universal Guaranteed Work (or Employment), which is my response to proposals for Universal Basic Income (UBI.) The basic idea is that anybody who cannot find normal work could go to a neighborhood work center where they would be paid to engage in training and education of their choice, primarily through online courses. In recognition of their training and education efforts they would then receive a paycheck comparable to a super-minimum wage job — an enhancement to minimum wage, comparable to say $15 per hour, based on how much time they spend on training. A database of completed training can then be mined by normal employers to recruit and hire these individuals.

Counseling and career planning services would also be available. Free meals would make sense as well, reducing the pay needed. Daycare and healthcare facilities would make a lot of sense as well, further reducing the need for pay to cover those expenses.

The online courses would also support skills assessment. Helping to build a database of who has measurable skills in every area, helping organizations to find workers who fit their needs.

Intelligent AI agents could detect learning patterns that need remediation as well as opportunities for growth, guiding those with potential to their true potential.

In-person counselors and career assistants would also be available to help people bridge the gap to real employment or to at least keep them engaged in the process and active in the training process, which is the basis for their pay.

The goal in all of this is to transition people to productive work when possible, but also to train and provide income for potential workers in the interim, assuring that they do not lose skills or opportunities to learn new skills.

In some cases it would make sense to combine these work centers with traditional community college facilities. Maybe these facilities would be satellite facilities for community and even state-level colleges and universities.

A premium pay could be offered for courses aligned with the needs of particular organizations, subsidized by those organizations.

Traditional organizations could also rent space at these work centers to outsource work to trainees and also to have traditional workers come and work side by side with trainees, both to perform actual work tasks and to provide more hands-on support for what originally was purely online training.

How would UGW be funded? I’ll take the easy way out and say it’s beyond the scope of this paper. Dovetailing with community colleges and subsidies and fees from organizations benefiting from the program would be a major component.

If such a program was in place, I would definitely spend more than a few hours a day taking courses on law, psychology, economics, international relations, strategic studies, quantum physics, climate science, genomics, or whatever.

In short, UGW would solve or at least be an acceptable stopgap for my immediate work problems. The database of completed courses might indeed hook me up with real work opportunities.

Is UGW likely to come into existence anytime soon? Nope. But one can dream, right? Hey, I’m just trying to offer a productive contribution to the discussion rather than simply venting and whining.

Strengthening Social Security

Since I do have such an urgent dependency on Social Security, it is probably in my best interests to focus at least a small fraction of my attention on strengthening the Social Security system.

I don’t have any current plans or ideas for how I can best participate, but I will give it some thought.

Passage of time

I have had a number of situations in my life where I couldn’t have work when I wanted it, where patiently waiting for the passage of time, without any other action on my part, yielded good results.

It’s a tough call. You can’t be sure whether you need to change things or whether simply waiting longer is the right way to go. That doesn’t work all of the time, but enough of the time that one must be mindful of it.

So, even though I can’t think of additional steps to take right now on the work front, it may very well be that I have indeed made all the right moves and that now the only thing left to do is wait and the passage of time will do the rest.

That said, placing a time limit on any activity can be a very good idea. In my case, I’m giving myself another year or so. I can extend that if it seems advantageous and promising, but I recognize that I will need to be very clear-eyed and clear-headed about such a decision.

Lingering doubts

Even with my best plans as outlined above, I still have significant lingering doubts, but since they remain after even my most diligent efforts, I guess that’s the nature of these kinds of intractable problems, where there is no great clarity for even the best of solutions.


I really do need to double-down on my efforts to find some palatable work. I’ll probably spend the coming year diligently and desperately seeking such work. I have no realistic expectation of finding it, but I’ll remain committed to the search. Only a year from now will I finally consider throwing in the towel, pulling the plug, and considering myself officially retired. Even then I will continue to live off savings for as long as I can before finally commencing my Social Security benefits, maybe 15 months from now, trying as hard as I can to keep pushing that date out to push my monthly check amount at least a little higher.

Meanwhile, I really am open to suggestions on all fronts, as long as the prospect is palatable and consistent with maintaining my health and sanity.

Although I am willing to take less than optimal work, satisfaction and some degree of fun are definitely a goal of my ongoing search. Okay, in truth, they are nice extras rather than absolute requirements, but I at least want to have satisfaction and fun in the front of my mind as I continue my search.

Every three months I’ll check in on both my finances and work prospects and tune my thinking and plans as needed.

My final thought is that I sincerely hope that there aren’t too many other people in my same boat. Unfortunately, I suspect that there are. Maybe only 10–15% of the workforce at my age and older (my educated guess), but that’s still a lot of people. Even if only 2–5%, that’s still millions of disappointed and disenchanted potential workers. I may not be able to offer these people solutions, but at least I can offer them my very sincere condolences. Yes, I really do feel your pain. My empathy is quite real.