Jan 15, 2017

An unconventional education

In the last two years I’ve spurned a proper career path for an independent route. In that time I’ve started a travel research project, took the GRE and considered going for a PhD, cofounded a startup, became a mentor for Defy Ventures, and spent 4 months developing a new ’entrepreneurial lab’ for a private equity investor. That last one ended abruptly and was a tough deal for me to move past. I had committed to jump in with both feet before the investor was fully aware of his machinations and the lab was shut down before it even started. I don’t prefer to dwell but suffice to say I learned a couple of key lessons. In my effort to shake off a number of false starts, I’ve felt the sense that can best be described as stuck. How do you move forward when you are stuck? “I think when you are truly stuck, when you have stood still in the same spot for too long, you throw a grenade in exactly the spot you were standing in, and jump, and pray. It is the momentum of last resort.” - Renata Adler, Speedboat

It’s been quite a ride and I’ve learned a great deal. Once you’ve heaped a great change upon yourself, that change can become an addiction. The personal growth derived from struggle is worth the agony. Yet, there is a fine line between trying new things and spinning your wheels. After a number of failed ventures, I find its time to move on from this phase of entrepreneurial efforts. That decision doesn’t come easy, it’s hard to leave after successive failures. But that’s just ego talking. I’m a firm believer in making lemonade from lemons and it pays to be creative. Before I move on, I’d like to put this period into perspective. I've long had a curiosity about entrepreneurship. For over a decade my sweet-spot has been helping a proven startup scale past the 1 - 2 million dollar mark. I felt the urge to put something into the world from scratch having spent so much time cleaning up the detritus of early startups. I can confidently say that I’ve given a sincere effort at building 0 - 1. I’ve studied books on entrepreneurship, consulted with entrepreneurs, and spent time building a business from scratch. I’ve learned more than an MBA could teach by learning AND doing in my time as an entrepreneur.

As it turns out, my transition period has opened up an opportunity to seize upon another life goal. For my parents generation the typical life phases looked something of the following: schooling (perhaps including college), work, family, then retirement. Today, attitudes are changing on the prevailing paths of contemporary professionals . The paradox is that your best and most capable years went to work, while your freedom to travel and pursue your passions was well after your physical prime in retirement. It’s a Faustian bargain to believe that the sacrifices you make now justify the for the rewards later. Momentum is a powerful force. This logical fallacy can contort your values over time. What you wanted 5 years ago may no longer relevant today. The pernicious hand of consumerism takes root and its easy to give our labors away for the lifestyle it affords. But that path has gnawed at me for the last 7 years. 13 years ago my father was diagnosed with terminal cancer, months after his retirement. My parents had bought an RV and put their home up for sale, ready to hit the open road. He had planned his exit for years. When I was a teenager I remember my father talking about the good life after he hits retirement. But instead of touring the country he made numerous visits to the Mayo Clinic for surgery and chemo, was forced to sell the RV, and plan for a more amenable lifestyle to terminal cancer. That has made an obvious impression on me. So painfully clear that we must take the time to do the things we want while we can. Why can’t we take the time to pursue other goals during our prime working years? After all, I’m fortunate enough to do so. Something I realize many people are not.

My wife and I have talked about taking a mini-retirement since we were only in the professional workforce for a couple of years. All my friends that know me, know that long term travel has been on my bucket list. But everyone, including myself, doubted that we'd actually make the leap. My wife and I are both competitive and career driven. Invariably over the last 15 years one of us has been ‘ready’ to hit the open road, but never both at the same time. Furthermore, as time goes on obligations grow and comfort settles in. Things like owning a mortgage, golden handcuffs at work, and wanting not for the recreational parts of our life have created barriers to exit. But the alternative is a life well lived. I’ve harbored the deep instilled narrative that it's worth forsaking these comforts.

As it turns out soon after my last failed adventure, my wife’s company was going through an Oracle acquisition. She has no interest in working for the the Oracle machine. Then the election happened. It’s time to get the fuck out of dodge. We’ve outlined a plan for a mini-retirement, and have taken steps to make it stick. Now I get to do things I’ve always wanted: learn a new language, live in another country, surf in exotic places, discover other cultures, and continue learning new skills. My philosophy on travel is that travel, unlike vacationing, is learning. Its active engagement and participation in the world at large. In fact, I’m extending my unconventional education. I’ve completed my studies in entrepreneurship and now am looking towards the humanities (anthropology, foreign language) and staying abreast of modern computer science trends (MOOCs in deep learning). The plan is as follows:

  1. Take on an R&D role at my startup
  2. My wife quits her job
  3. Sell our house and store our stuff
  4. Find a Spanish immersion program where I can surf
  5. Plan an education in deep learning
  6. Find other countries where I can surf and work
  7. Budget for at least 6 months as a nomad

So far things are going to plan. I hired a remote dev to take over coding responsibilities at Brandcards. I was able to FSBO our house in North Boulder. An endeavor worthy of its own post. We’ve found a great immersion program in Bocas Del Toros, Panama. We’ll live with a local who will cook for us, attend 4 hours of Spanish a day, I’ll enjoy surfing in boardshorts, and my wife will enjoy the beach + yoga. My wife has just quit her job, and we have keyed in a few more places we might like to visit and practice our new language. I’m a big fan of simultaneous learning + doing. Our travels are built around the combination of learning and doing. I’ve targeted a MOOC in deep learning and books for my education in AI. I’m currently kicking the tires on a deep learning project. For now I've left out alot of details in favor of a simple overview. If you want follow along, we’ll be updating our adventures in our old travel blog . For this blog I plan to continue to explore software projects and perhaps how our travels can relate. For example, our Spanish Immersion program offers great parallels in AI. Stay tuned.