My Education and Career Path

I was homeschooled, but in practice that meant playing Legos most of the time.  My mom felt guilt over her failed attempts at creating a more structured learning environment and curriculum.  At the time I thought I was probably embarrassingly behind my peers in “normal school”, but I didn’t much care.  We (my siblings and I) always had lots of chores to do, and I had paid jobs from age ten or earlier (weekly then daily paper routes, golf course, grocery store, construction…).  I had no interest in any kind of intellectual life until I was about sixteen.  Up until then, it was sports, Legos, earning money, playing guitar, and whatever I had to do to get decent grades in my few homeschool classes or textbooks.

When I was 15, I attended a small private school for my sophomore year in high school.  I enjoyed the sports and made some friends, but after years of loose homeschooling, it felt stiflingly prefabricated.  I don’t think I took homework home with me the entire year, since so many classes required almost no attention, I’d do homework right there at my desk.  The whole thing seemed artificial, and I found it absurd that we all followed the same bells and schedule, like cattle corralled through the halls.  I was not too smart for school – plenty of kids there were smarter than me – but too impatient with the lack of individualization.  I was also irritated that it severely restricted the hours I could work.  I decided to quit.

I’ll never forget when I told the music teacher of my decision to leave and enroll full time in the local community college.  I considered him a friend and something of a mentor.  He helped awaken my musical interest and gave me opportunities to sing and play that I was not qualified for, something I’m still grateful for.  But he just didn’t get it.  I came in to class after running around outside in a rainstorm with a few other students and broke the news.  He stared, mouth agape with a bewildered, wounded look in his eyes and said, “College!?  Isaac, you’re not ready for college.  You’re still a kid who runs barefoot in the rain!”  Any doubts I had about my decision vanished then and there.  It was a well-meaning plea, but I took it as a challenge.  I felt he underestimated me, and that was a great motivator.

I spent the next two years taking a full load of classes, packed into two or three days a week, and working as many hours as I could the other two or three days.  I loved it.  I could choose the classes I wanted, make my own schedule, and interact with a variety of people much wider than in the private high school, and even more than at the university I later attended.  Most of the classes were ok, some bad, some good.  The best classes I ever had were business and marketing from a crazy, middle-aged, self-proclaimed capitalist fanboy who ran a successful business but taught for fun.  It was around this time that I awoke to the world of ideas.  It had nothing to do with any of my classes, but for some reason (probably a breakup with a girl) I started picking up books, something I had, with a few early exceptions, hated.

I found myself mesmerized by philosophy, theology, and eventually economics.  My job had me travelling across the state and installing phone and computer cables (pre WiFi), and taking on scary amounts of responsibility, mostly making things up as I went.  My education, which came almost entirely from books I read on my own and late-night conversations with friends at church, the used bookstore, and coffee shops (which were kind of a new thing in Kalamazoo, MI at the time) was moving at breakneck speed.  It was like my whole childhood I was just doing whatever I had to to get by educationally, but the dam broke in my mid-teens and I was in love with the life of the mind.  I also had something of an entrepreneurial spirit and helped start a nonprofit and did a lot of international missions work, which at the time I thought was the best way to make the world a better place.

After community college I continued the work/school split while attending the local, generic, massive state university where I majored in political science and philosophy.  I changed majors several times, but finally settled on subjects I most enjoyed and would let me finish as fast as possible.  I didn’t mind school, but hated the amount of money I had to pay, and just wanted to get the piece of paper that was supposed to be a ticket to a job.  Trying to save money, I went two whole semesters without purchasing a single textbook and still got good grades.  It seemed like a racket.

With the exception of one professor and one TA, none of my fellow students or faculty really aided my intellectual development in comparison to what I was pursuing on my own and with friends outside of school.  I used to walk around an old building downtown and imagine buying and turning it into a real college, where students only bought the items they wanted from the bundle, and where work and classroom were not in competition, but complementary.

Despite never having a single meeting with an advisor, somehow I graduated.  At least I assume I did, since they sent me a certificate in the mail.  I was 19 and I started a business with my brother.  It was something of a failure, with a few high points.  We folded it up after just nine months.  I spent the next five years as a very young and very poor married guy working in the state legislature, then at a think tank.

I loved ideas, and had come to believe the way to make the world a better place was through political and policy change.  But the more I studied and observed the machinations of the political world, the less faith I had in it as an avenue for change.  While at the think tank I took night classes and got a Masters in Economics.  It was a uniquely amazing program, as we used no textbooks but instead read all primary works beginning with Hesiod all the way through Marx and Mises and Friedman.  I drove across the state three hours each way, one night a week for a year and a half during the program.  By the time I was done, my belief in the inability of politics to improve the world had become firmer.  I had little interest in anything besides educating people about the perils of government intervention and the wonders of the market.

My wife and I took a chance on a great job offer running libertarian educational programs in Arlington, VA, a city we weren’t too fond of before we moved, and one that, after leaving I wouldn’t wish on anyone.  The job was amazing.  Over my four plus years there I ran fellowships, seminars, mentoring programs, and raised money.  I interacted with hundreds of bright students and dozens of successful entrepreneurs.  I began to observe troubling trends.  So many young people were stacking up degrees and educational accolades, yet wandering aimlessly, insecure and unsure about their career prospects.  They had degrees and debt, but couldn’t find a job.  Many of the smartest decided, since they didn’t know what else to do, to go to law school.  So many came out the other end with massive debt, no closer to finding a fulfilling career.  (If I had a nickel for every lawyer that told me they wished they hadn’t done law school…)

Meanwhile, in fundraising I met countless business owners who claimed they were always hiring, even in a supposedly down economy, but couldn’t find enough good talent.  Something was amiss.

My views on changing the world were shifting too.  Education as I thought of it – convincing people to change their worldview – seemed insufficient.  I began to observe areas where change happened, it seemed to have a great deal to do with entrepreneurial innovation.  You could spend your life trying to convince people the Post Office is inefficient or immoral, or you could invent FedEx or email.  I got the itch to disrupt the status quo as an entrepreneur.

A culmination of desires I had in college and opportunities, skills, connections, and worldviews I’d developed since came together.  Cliché as it sounds, I went for a walk on the beach and had an epiphany.  A single word, “Praxis”, popped into my head.  I could almost see it in bold letters floating on the horizon.  A relentless flood of ideas filled my mind, and I ran to my car and drove home as fast as I could to type it up.  I was going to create an alternative to the university system.  Better, faster, cheaper, and more individualized.  I wanted to create a new class of entrepreneurial young people.  I wanted to seize the best online educational material, organize it, add a powerful credentialing signal, and combine it with work experience at dynamic companies that couldn’t afford unproductive interns.  I was tired of seeing young people languish and drown in debt.  I was tired of seeing business owners struggle to find good workers.  I was tired of seeing so many entrepreneurial opportunities and so few people with the confidence to pursue them.

Thus Praxis was born.  It’s kind of the incorporated version of my philosophy on education.

While living through the various phases I was only sometimes conscious of these things, but in retrospect I can draw several lessons from my educational and career path:

  • Free time is more valuable than planned time.
  • Work is more valuable than school.
  • Responsibility and ownership at an early age are irreplaceable.
  • College is what you make it, but nearly everything good you get from it can be had better and cheaper elsewhere.
  • Your education belongs to you, and no institution can give it to you.
  • Discovering what you hate is more important than finding out what you love. As long as you’re not doing things you hate, you’re moving in roughly the right direction.
  • Seeing geography as a constraint is a major impediment to your educational and career progress.
  • Your personal philosophy and educational and career path should feed each other.
  • Wandering and experimenting are great, but not at any price. Meandering through an educational path you’ll be paying off for a decade or more is different than dabbling in a free class or internship that will only cost you a few months.
  • Don’t fear how you compare to your peers.
  • If the interest isn’t there, don’t put energy there. But when it is, go all the way.
  • You always get more out of things you choose over things you’re made to do. Find ways to have more of the former, and fewer of the latter.
  • Work ethic can overcome knowledge deficit, but not the other way around.
  • Mentors can be great, but they can also hold you back. Don’t take them too seriously.
  • If the process isn’t fun, you’re doing it wrong.
  • If the process isn’t hard, you’re doing it wrong.
  • You’ll be doing it wrong at least some of the time. That feedback helps you figure out how to do it right.
  • Push your imagination to see yourself as capable of great things. Continue to do this.

The few regrets I have for the path I took boil down to one: I wish I had more confidence, and earlier, about going my own way.


Excerpted from The Future of School


*If you are a teen or you have a teen that’s interested in entrepreneurship, creative thinking, and out of the box living, check out the Praxis Teen Entrepreneurship Course!

Praxis Teen Entrepreneurship Course