Seeing patterns

Some reflections from a week away from the laptop

I spent the last two weeks in Kenya for my sister’s wedding. Friends, family, speeches. Reflections on my sister, and on our relationship. A couple of Indian dances to the latest Bollywood songs, and a song I performed on guitar for her procession.

I’ve wanted to discuss music for some time because my relationship to guitar feels foundational; I consider non-musical problems in terms of how it relates to playing an instrument. I’ve found, for example, that improvising is far easier when I’m only softly focused on what I’m playing. When I overthink the notes – the theory behind it, or the perfect intonation – my performance becomes stilted. This realization permanently lives somewhere in the back of my mind, on call whenever I’m trying to force my way through a complex problem at work.

An early, pivotal moment with guitar: I noticed how a song I had previously memorized outlined a scale I just learned. Connecting theory to repetition gave me a new intuition for recognizing musical patterns. This intuition accelerated my advancement in music. Perhaps not coincidentally, most of my training, academic or professional, mirrors this approach: learn the basics, recognize patterns, and apply the process across various context. It’s generally served me well.

But back to the wedding: the process of writing my wedding speech forced me to consider one topic – my relationship with my sister – over the course of my entire life. I’ve built an increasingly diligent approach to reflecting on my life as it unfolds, but rarely do I consider a particular life situation and consciously compare it to a prior one.

Masai Mara, where my sister’s wedding was held

To put it concretely: the startup ideation has been intensive and complicated, and its relatively long timeframe has caused me to consider how I can better approach it. I’ve been thinking about this problem in isolation: Should I go broad or narrow? Should I spend more time researching or building? This approach has merits, and loosely resembles the first principles mindset that’s become almost sectarian in startup land.

But I hadn’t really considered how I’ve approached intensive and complicated problems before, such as deciding whether to attend business school or finding a startup job in Europe at the outset of COVID. I’m referring more to personal characteristics than tactics. Or to put it more plainly: everybody goes through their own journey when it comes to hard problems. Parroting other people typically ends in insecurity and failure.

But I’ve never sat down to put words to what approach feels most like me. I theoretically have the skillset – it’s the same one I’ve learned throughout my career. I’ve just never thought to put myself as the object of an analysis. The disconnect between work and self should be no surprise. When it remembering their younger selves, people typically fall into one of two categories: continuers (those who see roughly the same person) or dividers (those who see something resembling a stranger).

I fall into the former category; I’ve never really felt any different than I did before. At least one drawback I’ve noticed is that it makes analyzing prior decisions much more difficult. I have a hard time thinking about the process of finding a startup job in Europe as anything that could inform my startup ideation right now. I assume those patterns have held ground somewhere in my mind, but I’m not conscious of ever having created them or what role they serve in my life today – and wasn’t, until my sister remarked this weekend that I’m approaching startup ideation much like how I found Gorillas. An outcome, to my relief, that worked out.

This post was a noisy attempt to direct myself to a cliché I reflexively know but often forget: Run your own race, because you won’t win at someone else’s. The past week has been an exercise in re-familiarizing myself with different points in my life that I don’t consider much anymore.

We hear often about creating space separate from work, but I’d suggest we need to foster healthy distance from ourselves, too. Only then can useful patterns emerge.