From “walking in the desert” to Escaping Flatland

“Ok, but what if you think more concretely about what you want to do? Like, what are the precise day-to-day activities that make you feel alive and proud of yourself?”

Regarding music, the activities he actually likes are (1) coming up with new songs and (2) performing live.

“What would be the most effective way to design your life so that you get to... See more

An update, 3 years into this next chapter of my career: 3 years ago in May 2021 — after nearly 20 years in traditional tech roles as an engineer and a product manager — I left Stripe to start this 2nd chapter of my career. I don’t write often enough about this stuff, so here’s an update both for long-time followers and new followers: - I absolut... See more

This clarity highlighted something I had unconsciously been doing for nearly twenty years, even before going out on my own, and that was building a business full of resilience, driven by a desire for autonomy and, on most days, enjoyment. In other words, by scaling down every aspect of my life, I realized this was how I had successfully built my bu

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-1 to 0 is when you figure out what you want to work on. It’s when you decide where to allocate the next 5-10 years of your life.

This may sound simple, but it can be overwhelming and isolating in practice. That period before SPC was not my first -1 to 0 experience. I spent the year after leaving Facebook to start Cove feeling like I was banging my... See more