Over-Indexing on Identity, A Fallacy
Embracing the unknown in 2024
Welcome to Startup ROI!
I’m Kyle O'Brien (that’s me 👇🏼)
This newsletter has seen many iterations over the years. TL;DR: I’m an American living in Paris. I write about tech, startups, investing and some learnings along the way. Historically, I’ve written long-form deep dives; in 2024, I plan to share more of my personal journey in more regular, short-form pieces.
Aside from writing this, I do a few other things:
Co-founding an early-stage deep tech fund with
— if you want to read more about our work, check outHosting monthly dinner parties for the Parisian/European tech & venture scene: The DM Dinner Club (subscribe to our event calendar)
Interviewing founders and investors about the our impossibly cool future via video podcast: _Unit Testing
My DMs are dangerously open on LinkedIn & Twitter. Hit me up!
Now onto our regularly scheduled programming…
There’s a quote that’s been rattling around in my head for some time. It must have shown up in some Instagram reel (back when I was on the gram) and lodged itself deep in the recesses of my overworked temporal lobe. Following some extensive Googling, I recovered the full text with a (questionable) attribution to Oscar Wilde.
“If you want to be a grocer, or a general, or a politician, or a judge, you will invariably become it; that is your punishment. If you never know what you want to be, if you live what some might call the dynamic life but what I will call the artistic life, if each day you are unsure of who you are and what you know you will never become anything, and that is your reward.”
— Oscar Wilde
I relate so deeply to this quote because I’ve fought so hard to pursue the dynamic life, despite my better judgement. I’m a creature of habit, one that enjoys the pleasures of consistency, self-improvement, peer recognition and a clear path to success. Nevertheless, a life of career certainty (read: monotony) also scared the shit out of me. Death by tedium simply wasn’t an option. The amount of limbic friction required to to overcome this base desire for comfort and predictability was (and remains today) immense. But there is a reward, as Wilde points out, in never becoming anything.
In high school, I was dead set on playing soccer in college (I had also deluded myself into thinking a professional career was in the cards — it was decidedly not). In a borderline cringey way, I made soccer my personality (or at a least a large proportion of it). My AOL screen name was soccerplaya7491. When Facebook introduced statuses, mine was fixed as Kyle is playing soccer for an unreasonably long period of time (we’re talking years). I over-indexed on this identity, kept doubling down along the way. Eventually, I did get into a great soccer program in college, and instantly regretted it (after one season, I quit the team and transferred schools).
I learned this lesson the hard way many times over, without much success in changing my approach. In college I replaced soccer/discipline with a social life/drinking. When I joined the tech world, I was intent on one day becoming a successful B2B SaaS founder. When I first started this newsletter, I hoped to be the best tech newsletter writer in the game. I exchanged one identity for the next in hopes of finding one that matched some imaginary internal resonance frequency. There’s nothing wrong with any one of these ambitions. My problem was not recognizing them as milestones instead of endpoints. You have to constantly reinvent yourself, retain the good and learn from the bad. You must be a “Day One” human — for those unfamiliar, it’s a reference to Bezos’ Day One Culture, originally articulated in a now-famous 1997 letter to shareholders. If you’re wondering what Day Two looks like, watch this (hint: it’s bleak).
I think the closest approximation to the dynamic life is a modern day renaissance man, a gentleman scholar, a jack of all trades or a live player. Someone who can context switch between industries, roles and cultures and excel. I’m not sure I qualify as a renaissance man just yet… but I — as my girlfriend likes to say — do so many things. This year alone I played many roles: marathon runner, podcast interviewer, emerging fund manager, dinner club host, jungle trekker, meditator, biohacker, concert-goer, community manager, cold-plunger, fundraiser, and Spanish-speaker.
At its best, identity keeps many of us sane; at its worst, it leads to culture wars (not to mention real ones). Don’t be fooled by the allure of permanence. Identity is an ongoing project in life as it is in career. If you take Wilde’s approach, embracing the versatility will be the reward in and of itself. In the end, identity — the self — is merely an illusion. So you may as well fill it with dynamism, art, poetry, curiosity and an unending thirst for knowledge and discovery.