Oh, to be 18 (or 22) Again!

What decisions would I be making if I was now in the same shoes as the kids who are 18 or 22 today? I’m at the end of my normal work career, but now I have the luxury of pondering what I would do if I had the opportunity to do it all again but in today’s world. If I was graduating high school or college these days what exactly would I do? I actually have no idea, but it’s an interesting question to ponder.

More importantly, what exactly are kids age 18 or 22 doing these days in terms of education, career, and life decisions?

As importantly, what advice and recommendations are well-meaning adults (parents, older siblings, aunts and uncles, grandparents, family friends, guidance counselors, career counselors, teachers, and professors) giving kids these days — or SHOULD they be giving them — about:

  • What to do with the rest of their lives?
  • What career should they choose?
  • Where should they go to college?
  • What should they study?
  • What companies or agencies should they work for?
  • Should they start a family soon, or wait a few years after they finish school?

Not that kids should ever do what their elders dictate, but what advice and guidance resonates with them that they might WANT to take?

I’m not intending to present or even seek answers here, but simply trying to get a more solid handle on what the right questions are.

When I ask a question here, I have three audiences:

  • Myself.
  • My peers. Aging Baby Boomers.
  • Young people, age 18 or 22.

Just to reemphasize the context for the questions again:

  • If you were 18 again or are 18 now and considering your post-high school options.
  • If you were 22 again or are 22 now and considering your career choices after graduating college.

And that includes the few years before those milestone ages when you may have been considering your options with a little less urgency and time pressure. Granted some of us may know exactly what we want our futures to be when we’re 15, 12, 10, 7, or even 5 years old, but for the rest of us, what logic should be used to make these decisions?

Quick summary of the questions I’m interested in:

  1. Would you go to college?
  2. What career would you choose?
  3. Plans to get married and raise kids?
  4. Management or leadership aspirations?
  5. What values would guide your decisions?
  6. What is your main motivating force?

My retrospective

College was a slam-dunk no-brainer in my day — 1972. Of course, Vietnam and the Draft were incentives for college as well. And college was dirt cheap then compared to today. And jobs for kids with degrees were plentiful as well.

I was into computers back then in high school, but computers were the size of large rooms in 1970, so college and working at a big company, a college, or in government were the only real choices if you wanted to do anything of any significance with computers.

Personal computers were nonexistent except in some specialized and primitive forms. If you wanted to do any real, serious computing you needed access to one of those room-size monsters.

And if you wanted a decent job at a big company you needed that 4-year college degree.

The point is that these days a career in computing doesn’t require or demand a college degree or a job at a big company, so the choices are dramatically different for kids these days.

The wealth of free open source software and free online courses and plentiful venture capital argue against the absolute necessity of college and big-company jobs as well these days.

BTW, I did drop out in 1973 and worked at a local community college — in their nicely air-conditioned computer center, but went back to the big-deal engineering school after a semester since I really wanted that big-deal job working at a big computer company. I even worked part-time in the computer center of the school I had dropped out of, which sounds a bit weird if you ask me.

I also simultaneously got a masters degree in computer science in my 3–1/2 years in college. I think that was quite useful, but once again, there is so much advanced material available from top schools and experts online for free these days. Still, it was useful to be directly exposed to some real industry heavyweights — a bunch of the adjunct graduate professors were noteworthy individuals from the infamous Bell Labs and elsewhere in industry.

A big part of the reason I went into computers in 1972 was the prospect of working in an air-conditioned room; that’s not an issue these days.

The key reason I went into software development was probably that it allowed me to create something significant without actually having to build something in the real world, which was problematic for me due to my lack of fine motor skill, dexterity, patience, and physical strength.

These days, 3-D printing presents fantastic creativity opportunities for even the most physically clumsy of us.

Still, software allows you to create things that simply aren’t realizable in the physical world. Beyond mere objects, we have information systems, virtual reality worlds, and online communities, existed or were very sophisticated back in my day, but are commonplace today — and don’t require a college degree, a big company job, or lots of capital.

The options available to kids today are a breathtaking quantum leap ahead of what I had to choose from back in 1972.

Sure, the Intel 4004 microprocessor chip was introduced in 1971, the 8008 in 1972, the 8080 in 1974, the MITS Altair 8800 in 1974, and Microsoft BASIC for the Altair in 1975, while I graduated college in 1976, but they were all far too toy-like for the kinds of software I was doing at the time. It wasn’t until 1982 that the Motorola 16/32-bit 68000 microprocessor and large amounts of RAM memory, 8-inch hard disk drives, high-resolution bitmapped graphics displays, and the optical mouse input device were available that people like me could do really interesting software (a high-end CAD workstation in my case.) I had to work at a venture capital-funded startup to get access to all of that technology. That was my first exposure to Silicon Valley venture capital and the denizens of the infamous Sand Hill Road.

Now, all of that kind of work can be done within the budget of anybody, with no need for a college degree, big-company job, or significant amounts of capital.

BTW, I knew next to nothing about computers until 1970 when I was in the 10th grade and an advanced placement math teacher introduced them to my high school via a Computer Club. I took a specialized introductory online course (they called it timesharing in those days) that summer at the local community college and the following summer I took a more intensive six-week residential advanced course at the engineering college I would attend after graduation. But there were no formal classes in computer-related topics in my high school at that time. How times change!

The questions

Summary of the questions to be detailed:

  1. Would you go to college?
  2. Would you take time off before starting college or before starting a job?
  3. Would you go to grad school before starting a job?
  4. What career would you choose?
  5. What exactly draws you to such a career?
  6. What sector of the economy would you choose?
  7. Would you start your own company?
  8. Would you be content to be a non-managerial worker, modest supervisory or management role, or do you have a passion for being a senior executive or leader?
  9. How do your family plans (marriage, kids) affect your answers here?
  10. Would you start your own company or go work for a big company first?
  11. If you had to work in government, which agency?
  12. If you had to be in the military (think draft), which branch?
  13. Would you be content to be a grunt soldier, sailor, or airman, a modest officer rank, or do you have a passion to be a senior officer?
  14. What values would guide your decisions?
  15. What is your main motivating force — belonging, power, or truth?
  16. Do you feel a strong desire or obligation to go to school or work near your family?
  17. Which is a stronger motivation for your decisions, money, people, or personal happiness?
  18. How likely are you to simply follow the advice of your parents?
  19. How likely are you to follow the same path as your friends or peers?
  20. What should you study in college?
  21. What should you study in high school?

Question #1:

  • Would you go to college, like a big-deal 4-year university?
  • If not, what would you do instead?
  • Or would a 2-year community college degree or vocational training be good enough for a start for you?

Question #2:

  • Would you take time off after graduating high school before starting college (a gap year)?
  • Would you take time off after graduating college before starting a job?
  • How much? A year? More?

Question #3:

  • Would you go to grad school before starting a job?
  • Just a masters, or a PhD as well?
  • JD?
  • MBA?

Question #4:

  • What career would you choose?


  • Academia — professor, researcher
  • Military
  • First responder (police, fire, EMT)
  • Justice system (courts, corrections)
  • Politician — state, local, federal
  • Doctor
  • Other medical
  • Lawyer
  • Other legal
  • Engineer
  • Software developer
  • Business executive
  • Management — organizing work and people, motivating people
  • Sales
  • Customer service — solving problems for people
  • Scientist
  • Social science
  • Teacher
  • Analyst
  • Finance — banking, investment, investor
  • Journalist
  • Technician
  • Diplomat
  • Nonprofit executive
  • Creative work — visual, writing, performing, speaking
  • Social work
  • Volunteer work — helping others
  • Construction worker
  • Manual labor
  • Drifter — only work as needed at odd and part-time jobs
  • Bum — never work, depend on largess of others
  • Criminal — hey, some do
  • Other

Question #5:

  • What exactly draws you to such a career?


  • Economic opportunity — the money.
  • Desire to raise a family — the money.
  • Passion about the work.
  • Satisfaction of being productive.
  • Excitement of learning new things.
  • Excitement of travel.
  • Thrill of negotiating deals.
  • Thrill of persuading people to buy things.
  • Desire to be a part of a team.
  • Desire to be a part of something much bigger than yourself.
  • Spiritual enlightenment.
  • Joy of the work itself.
  • Fun of the work itself.
  • Thrill of the work itself.
  • Challenge of the work itself.
  • Great inner satisfaction that you are helping real people with real needs.
  • Desire to protect people.
  • Desire to protect your community.
  • Desire to protect your country.
  • Desire for peace in the world.
  • Desire to help protect the environment.
  • Desire to correct economic injustice.
  • Desire to correct racial or ethnic injustice.
  • Other.

Question #6:

  • What sector of the economy would you choose?


  • Government (other than military)
  • Military
  • Business
  • Industry
  • Finance — banks, insurance, investment, venture capital
  • Media
  • Leisure and hospitality
  • Small business
  • Nonprofit
  • Academia
  • Religious
  • Artist, writer, or performer
  • Volunteer work
  • Other

Question #7:

  • Would you start your own company?
  • Right away?
  • Maybe even drop out of college?
  • Or join a big company to get experience?
  • Or join a startup to get startup experience?

Question #8:

  • Would you be content to be a non-managerial worker?
  • Would a modest supervisory or management role be your goal?
  • Do you have a passion to be a senior executive or leader?

Question #9:

  • How do your family plans (marriage, kids) affect your answers here?
  • Do you expect to get married?
  • How soon after graduating?
  • A traditional marriage or something more… “modern”?
  • Do you expect to have kids at all?
  • How many kids?
  • How soon after getting married?
  • Does adoption appeal to you?

Question #10:

  • Would you start your own company or go to school and then start at a big company first to get experience and save some money first?

Several questions are less core, but could be enlightening.

Question #11:

  • If you had to work in government, which agency (or the military)?
  • That can include the military, astronaut, park ranger, diplomat, etc.

Question #12:

  • If you had to be in the military (think draft), which branch?
  • Or conscientious objector.
  • Or leave the country.

Question #13:

  • Would you be content to be a grunt soldier, sailor, airman, marine, or coast guardsman?
  • Would a modest officer rank be sufficient for your interests (sergeant, lieutenant, captain, major?
  • Do you have a passion to be a senior officer (lieutenant colonel, colonel, general, admiral)?

Variations of those last three questions could be asked for any other sector of the economy, whether the tech sector or any of the major religions, for that matter.

Question #14:

  • What values would guide your decisions?
  • Whose values are these really?
  • Are they American values, shared by everyone?
  • Are they personal values which you have adopted of your own volition?
  • Are they values you inherited or learned from your parents?
  • Are they values you learned in school?
  • Did you pick them up from a mentor of significant advisor?
  • Are they values you were instructed about by a religion?
  • Are they values you picked up from the media, from movies, from books?
  • Do these values represent everything that you stand for?
  • How much of what you stand for do you need to have represented in your career?

What are some of the values guiding your decisions?

  1. Absolute
  2. Altruism
  3. Benevolence
  4. Certainty
  5. Challenge
  6. Chance
  7. Charity
  8. Collective action
  9. Comfort
  10. Commitment
  11. Community
  12. Compassion
  13. Country
  14. Courage
  15. Creativity
  16. Diligence
  17. Economic justice
  18. Empathy
  19. Environmental justice
  20. Equality
  21. Equity
  22. Excellence
  23. Experimentation
  24. Fairness
  25. Faith
  26. Family
  27. Fate
  28. Freedom
  29. Friends
  30. Future generations
  31. Grit
  32. Happiness
  33. Hard work
  34. Harmony
  35. Honesty
  36. Hope
  37. Imagination
  38. Independence
  39. Individualism
  40. Integrity
  41. Justice
  42. Leadership
  43. Leisure
  44. Liberty
  45. Live up to your full potential
  46. Loyalty
  47. Luck
  48. Meaning
  49. Merit
  50. Money
  51. Obligation
  52. Opportunity
  53. Organization
  54. Passion
  55. Peace
  56. Perseverance
  57. Protect the environment
  58. Prudence
  59. Racial justice
  60. Relative
  61. Relaxation
  62. Responsibility
  63. Sacrifice
  64. Search for meaning
  65. Service
  66. Social justice
  67. Spirituality
  68. Structure
  69. Success
  70. Teamwork
  71. Truth
  72. Universal
  73. Other

See the papers from my series on In Search of American Values for more discussion of values.

For a full list of values (over 2,000!) See: Master list of Values in America.

For lists of values for various groups see Values of Significant Groups, Organizations, and Figures in America.

Question #15:

  • What is your main motivating force — belonging, power, or truth?
  • Is belonging to a team or a movement your main aspiration?
  • Is getting to the top your big goal?
  • Are you adamant about truth and justice at all costs?

For more details, see my paper What’s your motivating force — belonging, power, or truth?

Question #16:

  • Do you feel a strong desire or obligation to go to school or work near your family?
  • Does leaving your home and community give you anxiety or excite you?
  • Which gives you greater satisfaction, staying around people you know or getting to know new people?

Question #17:

  • Which is a stronger motivation for your decisions, money, people, or personal happiness?
  • Do you need only a moderate level of income, enough money to cover your basic needs plus a little more for comfort, or do you feel a strong drive for the big bucks?
  • Would becoming a billionaire be a strong motivator for you, or more of an unwelcome distinction and burden?

Question #18:

  • How likely are you to simply follow the advice of your parents?
  • Out of fear? Fear of what — their judgment or your own lack of confidence in your own judgment?

Question #19:

  • How likely are you to follow the same path as your friends or peers?
  • Desire to be near your friends?
  • Desire to keep up with your friends?
  • Faith that their judgment is better than yours?

Question #20:

  • What should you study in college?
  • Focus on career/vocation-oriented program?
  • General, liberal education?
  • Or do you simply have significant personal interests regardless of whether they lead to significant income?
  • How much do you need to know or anticipate before you enter college about potential careers and educational plans for college?
  • How might decisions and plans evolve as you progress through college?
  • When during college will you need to make a final decision about your final course of study in college?

Question #21:

  • What should you study in high school?
  • What course of study would you pursue?
  • Do you intend to go to college?
  • If so, what prerequisites would you need for college?
  • How much do you need to know or anticipate before you enter high school about potential careers and educational plans for high school and college?
  • How might decisions and plans evolve as you progress through high school?
  • When during high school will you need to make a final decision about your final course of study in high school?

Time machine

The main focus here is what any of us would do today, but those of us who are well past 18/22 could also examine the same set of questions from the perspective of:

  • If I had it all to do over again, going back in time, what do I now wish that I would have done then, in the world of then as opposed to today’s world?

Just as a thought experiment, to get a sense of whether different decisions would necessarily have made a big difference in your life.

My point: Sure, maybe I could have avoided some bad decisions or exploited lost opportunities, but for every decision I could change to my advantage, there might be any number of decisions that previously worked out quite well for me but wouldn’t necessarily work out so well given the other changes.

On the other hand, I could understand that some people whose lives turned out fairly poorly, might be quite happy to go back in time and simply roll the dice, expecting that almost anything would be better than a fair chunk of their current life.


As I indicated, the answers to all of these questions are less interesting to me than getting the questions right.

To me, this is all a thought experiment — the goal is not the answer, but the thought process.


I suppose all of these questions could be packaged into a formal survey, but I’m less interested in actual answers or statistical distributions than I am in the philosophical value of understanding the questions themselves and getting the questions right.

If any enterprising Millennials wish to convert my questions to a modern online survey, you have my blessing.


Oh, yeah, right… my original purpose had been to answer the questions for myself. Not to answer them per se, but to contemplate and understand them.

Two points:

  1. I honestly don’t have good answers to ANY of my own questions.
  2. They’re moot since I am not 18 or 22 and won’t ever be.

That said, even though I am not going to be starting any new career at this stage of my life, I do have a choice of what I write about and what I read about or study.

I have made the choice to spend my time in Washington, D.C., which is essentially all about the federal government and government policies.

I have also made the choice of spending much of my time writing, as well as reading and research in support of that writing.

Which agency of government? I’m most interested in stuff like:

  • Foreign policy
  • Defense
  • International security
  • International relations
  • International institutions
  • Democracy promotion
  • Justice
  • Order
  • Constitutional law
  • Law in general, including supreme court cases
  • Finance
  • Monetary policy
  • Economics
  • Investment
  • Energy
  • Efficiency
  • Seemingly intractable social problems — not so much to solve them as to understand their true nature
  • Values

My values? See My Personal Values.

My main motivating force? Truth — at all costs.

I’m an idea guy at heart; I am passionate about working with ideas. The messy hands-on effort to put ideas into action is definitely not my interest. Sure, it would be great to see some of my ideas put to good use, but that goes in the nice category, not my primary focus.

I do a lot of writing now, but… I’m not at all convinced that if I was 18 or 22 again that I would really be so interested in spending most of my days writing. Interesting. Maybe the thought is that young people should focus more on actually DOING things — writing, musing, speculating, and all of that can come later in life or in your spare time rather than taking time away from real life.


Personally, I had zero interest in the military when I was 18 or 22. Not that I had anything against the military per se (and ignoring Vietnam, which was still going on when I was 18 in 1972), but simply that the rigid organizational structure, formality of a chain of command, the concept of “orders”, and little room for flexibility, all made the military a non-option for me.

Little did I know then how badly organization and structure sucked in most companies. Sure, there is some more flexibility, sort of, but still way too much structure and rigidity for my own personal tastes.

In fact, knowing what I know now, the military would not be completely out of the question if I were 18 or 22 again.

A plus for the military is the prospect of going to school on their dime while in the service.

And there is no question that a lot of the toys you get to play with in the military are far more interesting than those available to the average civilian.

In short, the military is certainly a much more viable option these days than in my day.


I really wasn’t interested in a government job when I was 18 or 22 either. I just didn’t see that government had anything exciting to offer me. I was into technology, computers, software, development tools, and working for a computer company was the hands-down, slam-dunk, no-brainer choice to make. In fact, I knew exactly what company I wanted to work for and only interviewed for that one company (Digital Equipment Corporation — DEC, Digital.)

Sure, government is doing a lot more leading edge technology stuff these days, across the board, but if you’re a really hard-core technology guy, tech companies are still the first choice.

BTW, the main government positions I was superficially aware of in my day were working for the NSA.

Or, a stone’s throw from government itself were technology contractors closely associated with the federal government such as BBN — Bolt, Beranek and Newman, who had a key role in inventing the technology behind the Internet. But, I was more interested in working for a computer company (Digital Equipment Corporation) than anything remotely associated with the government.

And Bell Labs was part of The Phone Company, which was too much like government for my tastes.


Although I got a masters degree, I never considered myself PhD material or had any interest in spending my days in classrooms or having to deal with students.

Sure, research labs are interesting, but being a perpetual grad student never suited my tastes.

And formal academic papers never suited my tastes either.

These days, there are plenty of tech companies who hire research-grade scientists and have entire divisions with the word “Labs” in them.

But I don’t want to denigrate young people who have a passion for teaching or shepherding grad students through exciting research projects.

One possible transition going forward is that there is a complete lack of clarity about how strong government spending for academic research grants will be in the coming years and decades. If commercial firms are willing to pick up the slack, it takes a lot of pressure off Congress to foot the bill.


What would I do today even if I wanted exactly the same career?

I’m not an application software guy, so Google, Microsoft, or Apple might be the only choice for me. Sure, quite a few of the big tech companies have lots of non-applications software groups, but that’s a sideline for them rather than their main thing.

Actually, these days I would probably be considering hot areas like:

  • Artificial intelligence.
  • Quantum computing.
  • Distributed computing.
  • Distributed databases.
  • Search engines.
  • Software agents.
  • Cybersecurity.
  • Advanced computing approaches that haven’t even been invented yet.

Also, I would consider physics as well. There is a lot of interesting stuff happening that has potential to intersect with technology and computing. But the simple truth is that while I am very interested in physics, I’m confident that I wouldn’t have any interest in working in the field on a regular basis, day in and day out.


I’m actually quite interested in law, particularly constitutional law, but I am quite confident that I wouldn’t want to work in law on a regular basis, day in and day out, eight (twelve??) hours a day. Besides, I could probably only squeak through a mediocre law school; if you can’t be the best, why bother.


I’m a firm believer in the value of serendipity — taking advantage of unplanned events and chance encounters. Or at least I imagine that I am even if I don’t practice it as often as may be appropriate. I consider it one of my values, even if not quite one of my virtues.

So, regardless of how I might imagine a replay or repeat of my life to look like if I had to go back and live it all again, I recognize that a wide range of alternative serendipitous events might come my way.

So many events of my life were indeed serendipitous. Totally unplanned.

How that might play out for me, even if I wanted to keep parts of my life exactly the same, is of course completely up to chance.

I can of course control my own actions and my own decisions — to some extent, but I can’t control the unknown, the chance events that life will throw my way.

Best laid plans of mice and men

The companion of serendipity is the old saying about how the best laid plans of mice and men can so easily go awry.

So, even if I (or anybody else) knew exactly how they wanted their life to play out from age 18 (or 22) onwards, don’t bet on it.

Sure, maybe sometimes that actually happens, but… don’t bet on it.

And besides, sometimes those serendipitous events will yield much better or more interesting outcomes than those best laid plans.


Personally, I’m not a big fan of detailed, immutable plans anyway. I’m a big fan of flexibility.

But that is a factor for others to consider — how rigid or how flexible do you want to be? What works out best for your own personality?

Your degree of flexibility needs to at least roughly sync up with your own authenticity. Otherwise, life could get rather unpleasant. There is no point trying to be more flexible than you are comfortable with, and no point trying to be more rigid than you are comfortable with. Sure, you should be willing to occasionally detour out of your comfort zone, but not so far that you lose your way.

Comfort zone

Indeed, what exactly is your comfort zone?

Oh? How can you tell?!

Me, I don’t feel that I ever had a true comfort zone, so getting out of a box that I was never in is a rather absurd proposition.

Still, the concept is at least worth contemplating as one contemplates the life ahead of them.

On the one hand you don’t want to get stuck in some confining comfort zone.

And on the other hand you don’t want to spend your life uncertain what you should do next at every moment of every day.

What’s next?

Once I click the Publish button I can finally consider the questions complete and only then can I seriously begin the process of contemplating what my own personal real answers really are.

Update 4/8/2018: Added sections for Serendipity, Best Laid Plans, Flexibility, and Comfort Zone. Still contemplating my own answers. Actually, I haven’t really been contemplating them much at all as I’ve been too busy writing, attending think tank events, and otherwise enjoying life as it presents itself to me.

Actually, I have contemplated this topic on occasion, but I keep circling back to the simple fact that I have no real clue how I would relive my life if I had to do it all again. If someone suggested that I just flip and coin and roll the dice and do something random, that would sound as appealing as reliving my life as it happened, modulo variations in the serendipitous events and chance encounters.

Freelance Consultant