“Success is becoming in middle adulthood what you dreamed to be in late childhood.” - Nassim Taleb
“For I have a single definition of success: you look in the mirror every evening, and wonder if you disappoint the person you were at 18, right before the age when people start getting corrupted by life. Let him or her be the only judge; not your reputation, not your wealth, not your standing in the community, not the decorations on your lapel. If you do not feel ashamed, you are successful. All other definitions of success are modern constructions; fragile modern constructions.” - also Nassim Taleb
Debbie Millman recently recounted the story of a drawing she made as a kid on the Tim Ferris podcast. In a drawing she created as an 8 year old, it correctly depicted and predicted what she would do when she grew up. The drawing described bustling life in a big city, like going to the bank, laundromat, and having an important career as a designer. She described how she eventually found her way to that life, but there were many detours along the way. Tim Ferris mentions a similar story in his interview with Chris Sacca, who as a kid, described in a journal what he would do at age 40. Chris, in his 40s, stumbled into his parents attic one day, rediscovered these journals, and realized it had depicted exactly what he would be doing at age 40 (start-up investor). He had completely forgotten about them.
As a kid, I loved two things: writing and investing. My crazy high school English teacher opened up the world of creative writing and poetry to me. Value investors like Warren Buffett and financial concepts fascinated me as a kid. If you asked the 15 year old version of me “what do you want to do when you grow up?”, without hesitation I would have said: “write and invest money”. I’m not sure there’s a more polarizing combination of professions, but hell, those were what I wanted to do. For most of my working adult career, I ignored this childhood desire.
I spent my early career eschewing money, spending time in nonprofit work and strongly considering time in the Peace Corps. I can only laugh at myself for how far off the mark I was at finding work that fit me. There’s nothing wrong with the nonprofit world, but the work was bureaucratic, slow, revolved around asking people for money, and most importantly, didn’t utilize my economic minded brain. The experience in nonprofits swung me into the other end: corporate. I did an internship at a private equity fund and eventually took a first job out of college in consulting. Working at a private equity fund was as impersonal as I imagined. While I enjoyed numbers, I didn’t like drowning in spreadsheet work in a cubicle. Consulting was high flying: accumulating free hotel and airline points, fancy dinners with partners, and a corporate card. I lasted 4 months. I took one look at the senior people in the firm and instantly knew their lives were not the ones I had aspired to create for myself.
Eventually, I worked my way into the startup world. It felt like home. Work kept me close to operating businesses and early stage product iteration. It not only opened up opportunities to invest in early stage companies, but how to even think about the process. A startup has a single advantage: the people they attract. They were as interesting and rebellious as I aspired to be. These experiences gave me a rich foundation and the courage to write.
Without realizing it, most of my career led me back to my childhood aspirations. It’s a winding journey and as Taleb says, we get corrupted by life. That corruption came in enticing forms: money, titles, prestige, status—name it and I’ve chased it.
For me, it was difficult separating out what others told me I’m good at from what I wanted to pursue. It’s hard to ignore what you’re good at when they come with all kinds of tasty prizes. I’ve realized the dirty secret: when you line up what you’re good at with what you want to pursue, the tasty prizes naturally come. And if they don’t come? The act of finding and doing what you want to do is an achievement most people don’t realize in their lifetimes. You’ll be willing to go through hell or high water to stay on your path, because it’s hard to imagine an alternative.
I think we have a life crisis when we stray too far from what we wanted as a kid. We spend a lot of time either running away or ignoring the child in us. We justify this dismissal with the restraints of our social environment and the demands of our busy lives. A major life event or moment of clarity is needed to shake us awake. But before the sudden realization, there’s a slow build up, often unnoticeable. It’s something our analytical brain can’t comprehend: an internal, subconscious feeling, a tremor of a quiet child we’ve suppressed and ignored for so long that we don’t know what they sound like. Listen to that kid and listen without judgment. What are they telling you?