An Outsider's Search For Meaning
The choices that led me to the startup world
I am a slow but diligent reader, and of the ~240 books I’ve read since I started tracking in 2014, just two have changed my life.
The first is Dan Millman’s Way of the Peaceful Warrior. It’s not the best book I’ve ever read — it’s not even top 20 — but it hit me at a perfect time, and in a perfect way. The book’s protagonist is a frustrated striver, and I saw my 23-year-old self in him. I often recommend it to young, ambitious people; it is profound and practical, and it helped me chill out a little.
The second book that changed my life is the the subject of today’s post: Man’s Search for Meaning, by Viktor Frankl. I just finished reading it this week, and I loved it so much that I’ll buy you a copy. (Seriously. Just reply to this email and tell me where to send it… get it while supplies last!)
This might strike you as a strange choice for this newsletter, but given the thesis of the book — that “the meaning of life” is nothing more or less than the process of you finding meaning in your own life — it struck me as germane.
The rest of this post talks about my personal search for meaning, and why I made the choices that led me to a life in Silicon Valley.
I’m not sure that my path through life is particularly admirable, repeatable, or even advisable, but I hope that is can show you how it’s possible to find meaning through a career change into the startup world.
Searching for meaning through opposition
I grew up as a skeptical kid: I wasn’t sure what I wanted or who I was, but I never had trouble finding faults my surroundings in the Minneapolis suburbs.
One of my first (mostly unknowing) decisions was to choose not to invest in the social scene of my hometown. I found very little community in Lakeville, Minnesota — I was more compelled to connect with my debate friends who lived all over the country (and even with my internet friends) than with the kids in my high school.
I also decided early on that I didn’t want to follow in the religious footsteps of my parents. I wrote about this at length in Agnostic-ish, where I admitted that this rejection of faith wasn’t all that admirable:
My early quest for meaning was more immature than principled. I cared about my beliefs being correct, and I wanted to live in a broader world than Lakeville South High School had to offer. But my response ended up being precisely the opposite of what Frankl suggests in “Man’s Search for Meaning.” He wrote:
“It did not really matter what we expected from life, but rather what life expected from us. We needed to stop asking about the meaning of life, and instead to think of ourselves as those who were being questioned by life—daily and hourly… Life ultimately means taking the responsibility to find the right answer to its problems and to fulfill the tasks which it constantly sets for each individual.”
I didn’t accept what responsibilities life had given me; I rejected them. And as I would soon find out, that strategy was unsustainable.
Searching for meaning through suffering
I had a quarter-life crisis when I was about 23 years old. After landing a prestigious, well-paying job in consulting, I realized that I had no idea what I wanted to do with my life. I felt like I had just woken up from sleepwalking: dazed, confused, and listless.
Tim Urban, author of one of the best blogs of all time, Wait But Why, explained this feeling as only he can:
My response to the “oh f*ck” freefall was to become a crazy person in the opposite direction, and to find meaning by creating a bucket list and desperately, furiously, maniacally trying to cross items off of it.
I thought that I wanted to be a writer, so I wrote a book. I thought that I wanted to be an athlete, so I trained for and ran a marathon. I thought that I wanted to live internationally, so I tried (and mostly failed) to learn Spanish with an intense Duolingo regime. And this was all in one calendar year, while working on some high-burn projects in consulting. It was wild.
It felt noble at the time — as Frankl wrote, “…suffering may well be a human achievement, especially if the suffering grows out of existential frustration.” But Frankl also wrote that “unnecessary suffering is masochistic rather than heroic,” and my suffering in pursuit of my goals was self-imposed, just a coping mechanism to fill the void of purpose and meaning in my life.
It may have looked much better from the outside, but I felt just as empty: no amount of achievement could make up for my lack of self-knowledge.
Finding meaning in self-knowledge
As I matured in my mid- and late-twenties, I became progressively less manic in my desire to make something of my life as I became progressively more aware of who I was and what the world around me had to offer.
Most notably for this newsletter, I learned a lot about what I want in a career. As I summarized in “don’t be afraid of working at a startup,”
I want my company’s work to matter for the world
I want my work to matter for my company
I want my financial success and career advancement to be tied to my personal effort
Consulting wasn’t living up to those three standards, at least by my calculations. If the world’s consulting companies disappeared tomorrow, big enterprises might make less money next year, but everything would mostly be okay. Similarly, if I had disappeared from 2013-2017, my consulting firm probably would have been just fine. The last point, however, was the crucial one that led to my departure from consulting: the lack of incentive alignment. I found that success at a big company depended equally on doing great work and telling people how great your work was; I wanted to do effectively none of the latter, so I sought out a career that was less political.
And, to skip a few steps of trial and error, I found that the startup world fulfilled all of my criteria and then some:
Working in the startup world has given me a chance to pursue meaning in my career.
I’m not raging against anything at Astranis, I’m working towards an epic goal of getting the world online. My personal work matters; my company’s work matters; and my effort has been rewarded (both internally and externally). Although success in this world is challenging to achieve and, at times, painful, the pain of startup life is categorically different from the struggling-against that I felt in my early life, and my quarter-life crisis angst.
Frankl again has wise words to offer:
Mental health is based on a certain degree of tension, the tension between what one has already achieved and what one still ought to accomplish, or the gap between what one is and what one should become. Such a tension is inherent in the human being and therefore is indispensable to mental well-being.
We should not, then, be hesitant about challenging man with a potential meaning for him to fulfill. It is only thus that we evoke his will to meaning from its state of latency. I consider it a dangerous misconception of mental hygiene to assume that what man needs in the first place is equilibrium or, as it is called in biology, "homeostasis," i.e., a tensionless state. What man actually needs is not a tensionless state but rather the striving and struggling for a worthwhile goal, a freely chosen task.
Working towards a really, really challenging goal that I freely chose to pursue is precisely what I love about Astranis and the startup world. It gives me meaning in my career, and in my life — meaning it’s exactly what I hoped to during my days as a disgruntled consultant.
What I have still yet to learn
My fiancée often reminds me that I am still a work in progress, and I don’t want this post to sound either preachy or conclusive. I am still in the middle of my story, and am actively learning every day — hence why I expect Viktor Frankl’s book to change my life.
This graphic, also from Tim Urban, explains it well:
This post has focused on the left side of the graphic for me, and I like the current path that I’m on. But there are still so many more decisions to be made! (Related: it’s a shame that most autobiographies are written by folks only after they have succeeded. Watching a highlight reel is way less existing than hearing from someone actively in the arena.)
If you, like me, feel like you want more from life — and particularly if you feel like moving to the startup world might be part of the answer — I’d strongly encourage you to read “Man’s Search for Meaning.” It might just help you navigate the many paths available to you in a way that is true to who you are.
If you do give it a read, you can help keep me honest. Even in the previous section, where I claimed to have figured some things out, I still sounds like classic me: striving for control; taking ownership of my life; remaining self-centered. I still have yet to internalize Frankl’s point that the way to self-actualization is through self-transcendence:
“…success, like happiness, cannot be pursued; it must ensue, and it only does so as the unintended side-effect of one’s dedication to a cause greater than oneself or as the by-product of one’s surrender to a person other than oneself. Happiness must happen, and the same holds for success: you have to let it happen by not caring about it.”
I don’t (yet) know how to reconcile that with his advice to find meaning by struggling towards a worthwhile goal, but I do know that I have a lot more to learn about myself and the world around me. And if I can remember that much, I think I’ll end up just fine.
Thanks for reading Silicon Valley Outsider! Here are a few past editions that you might like if you enjoyed this one:
If you want to join 470 folks in getting an email from me each Monday, I’ll help you understand Silicon Valley using normal-human words. (And, apparently, understand the meaning of life.)