Humans are majestic creatures. Thanks to millions of years of evolution they are somehow the most adaptable beings Earth has ever produced yet still experience terror at the idea of change.
Sasha Chapin, one of my favorite modern writers, wrote in praise of blowing up your life. He espouses that "generally…blowing up your life is a good idea.” I agree.
I love watching people blow up their lives. Explosions release energy and properly directed energy leads to massive change. According to advanced lifestyle seismic monitoring the resulting change is rated as “good-to-great” among those who spontaneously combust. Depending on what yield counts as a life detonation, I have blown up my own life at least five times, and all the best parts of my life I owe to these blast waves and their aftershocks. Given these results I’ve decided to share a bit about my own detonations.
I grew up in the Midwest. Nobody I knew traveled independently. Nobody I knew started companies. Almost nobody I knew wrote on the internet or made art or recorded videos or otherwise did anything which Paul Millerd would later refer to as The Pathless Path. I initially went to college to please other people, to gain status, and to maybe position myself as employable by one industry that seemed to have decent pay and creativity aligned with my interests—Game Design.
After a few years I realized something. It wasn’t game design I cared about, which at the time often involved rigging 3D models or creating particle effects, it was storytelling and, more universally, creating experiences. Everything I was learning in school, from web design to illustration to animation, was almost entirely self-taught. I followed tutorials online and bent projects toward my own interests. I realized I was paying tuition to an institution yet living as an autodidact. I wasn't quite ready to blow up the standard script just yet, but I did decide to blow up that particular path of education.
I transferred to another college, enrolled in an English degree, and moved back to my hometown where I would be able to focus on writing and creativity and potentially set myself up to produce the next great American novel. Instead this particular explosion caused me to meet my first love and undergo a lot of social growth, but generally solidified my disdain for the proffered cost/benefit of higher education in the United States.
After graduating, despite having two degrees, I was working part-time in tech-support with no real job prospects. So I decided to blow up my life. I sold all my stuff, got rid of my apartment, broke up with my girlfriend, and bought a flight to Bangkok. I ultimately spent seven months backpacking around Southeast Asia. This decision led to everything that would come next. I learned you can be heartbroken in paradise. I also confirmed that the stories of arbitrage were totally true (my inflation-adjusted daily burn was equivalent to the cost of a single burrito in the Bay Area today) and I met a huge number of interesting people from around the world. I heard firsthand accounts of meditation retreats, mushroom trips, and even unique events back in the US which might be worth a venture, like South by Southwest and Burning Man.
I finally returned home because my grandfather was dying and for a brief period I got stuck again…same job, same relationship, same lack of prospects. And though I did make it to both South by Southwest (by Couchsurfing) and Burning Man (by finding a stranger on the internet to share a ride with), it would ultimately take me 18 months to break out the Midwest gravity well for a second time. This was a giant lesson on the power of habits and environment. And I learned that re-learning felt truths was a core part of life.
At that point I was cold-emailing anyone doing anything interesting and offering to help. I was saving my meager earnings and looking for an ignition source. Finally one guy, who ran a media company for entrepreneurs and was planning a national event series, said “sure!” This became my exit and second life-blow-up. I hopped into a Honda Element with three strangers and spent months driving around the country organizing events. Objects in motion tend to stay in motion. This gig set off a flurry of movement which ultimately concluded with an anthropological journey deep into a Mexican jungle, in the shadow of the Palenque ruins, where a couple thousand hippies expected, as foretold by the Mayans, the world would soon end.
The world continued and I returned to a more normative path (well…after an additional two-month stint as a writer and pothead building websites for money while living on a lake in Guatemala). I took my first full-time job—marketing for an ergonomic furniture company in San Francisco (though dreams to start a company or break into tech bubbled in the background). I settled in and built a life, a career, and a new relationship (with a woman I had met years before in Asia). And it was great for a while, a huge improvement over my Midwest stagnation, but after a thousand nights or so I felt the call for another quantum leap. Another detonation of chaotic good.
So I blew up my life for a third time. I quit my job with nothing lined up. Muscle memory kicked in. First, I traveled. Weeks in East Africa, months in South America. I read a lot. I felt lost. I aged. I questioned. I spent a winter in a cabin in Utah meditating and learning to code and pushing snow off the solar panels so we could have power. All told this sabbatical was an 18-month saga that, again, is an entire story on its own. It ultimately ended with me landing my first tech job. This meant more money, more flexibility, more status, and the beginning of another few years of a relatively stable lifestyle.
And then again came the call. This time it was January of 2020. Fourth bomb. I quit my job again with nothing lined up. This was the first blow up that didn’t immediately start paying dividends. And when you see the date it’s rather obvious why. But even though I felt like I got kicked in the nuts by a black swan, I used my majestic innate human superpower of adaptability. As the gears of the world became clogged by a virus, I used my free attention to create an embarrassing YouTube vlog about a man losing his mind, and despite this, managed to meet my future wife on the Internet. I ended up, somewhat shamefully, returning to the job I left and spending this weird historical period filling my war chest and investing in my exciting new relationship.
Now, a few years later, I’ve just done it again—the fifth bomb. As of this writing I am about six weeks into another seismic event. I’ve quit my job at an inopportune time. I’m getting married this year. The economy is suspicious. I’m unsure of my next steps. My main quest is based around the thesis that how we feel is the most important thing. I’m focused on reading, writing and meditating while I patiently wait for my next thing to emerge from the debris, much of which is still falling. I’m sure it will be fun. We will analyze the crater in a year or two.