peak decisiveness

knowing when to stay and when to leave

Sep 29, 2023

PS: This is late, but I noticed this newsletter hit >6K subscribers! Grateful for this small, growing, community here and thank you for your kind words, they mean more than you know :)

Two years in California, the golden state. Two years of learning how to cultivate my voice. Building up decisiveness. Feeling okay in my body. Two years of delicate wisteria, light-soaked windows, deepening friendships, long drives along the bluest coast with the window cracked open. All my lapses in judgment, some of my most tender moments. In California, dusk moves slowly.

At dinner a friend recounts the exact moment he dropped out of college to build his startup. He walked out of his lecture, laptop under arm, and booked a ticket to San Francisco on a whim. At the time, it felt easy. Obvious. He says he only realized the gravity of that decision far later down the road.

I told him I thought it was a demonstration of strong will. That decisiveness is actually exceedingly rare. Veering off-course is hard. It’s hard when the default is powerful.

Decision making usually operates with a long lag from realization to action. There’s a long tranche of comfort and familiarity coupled with the sunk cost and pain of switching. It might take you 1 week to make the decision but 6 months to actually execute it. I’m sure you know people (or are in this position) who realize in their hearts what ultimatum they face, but are in the painstaking liminal space of living that decision out.

In North Beach, K and I continue our ongoing conversation about how frighteningly easy it is to float through life when your default is comfortable. We call it running on autopilot.

Autopilot looks like staying in relationships, jobs, living situations, environments, you’re not fully happy, psychologically safe, in. It’s Not Bad though. It’s easy to just float on. Then in hindsight, possibly years after, it becomes obvious that it wasn’t optimal and it took you way too long to act on it.

I’ve always been in awe of people who are particularly gifted or have trained themselves for good judgment, quick instinct. They make decisions swiftly and with confidence. I respect that immensely and try to learn from it.

Decisiveness really is an art. Knowing when to stay and when to leave is an art. If you’re growing rapidly, inflection points bubble up to the surface quicker.

At some point you have to decide what you really want, and that’s the hardest thing in the world. The search is important. The reflection is too. But that means standing your ground on your decisions. Accepting the aftermath, the tradeoffs. Culling the branches. Letting go of what you will inevitably lose, with grace. Acting quickly once you’ve made your choice, not dragging anything out for too long.

Conviction is an extension of self-knowledge. That requires spending time alone, tending to the richness of your internal landscape. Can you perceive yourself fully, all your desires, all your fears, without turning away? When something comes along can you tell if it’s a good thing or not? I told you I don’t like ambivalence. I know what I want. I’m good at waiting a long time for the right thing, but when it comes I need to be ready to commit. More recently I’ve kept repeating to myself, don’t abandon your vision. Decisiveness is knowing myself well enough to take the plunge, then the rest is all faith.

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You might like one of my oldest and potentially my favorite post I’ve ever written, default states, or some of my reflections on ambition and san francisco

PPS: Stay tuned for 2! exciting! things! 1) I finally got an iPad and will be doing original illustrations/art for this newsletter, and 2) I’m organizing my first newsletter community meetup in SF (details to come soon)

Life Inputs

📚 Glimpsing God by Nadia, on her complex relationship with writing. “Writing is a sensory appendage, like having a nose or set of hands, that I use to experience the world”.