Dreams in a World of Systems

Letters to a friend #33 - On creativity, coffee, and carving your own way

Dear Friend,

I’m really bad at following instructions. If you were to watch me build a LEGO set, you’d probably be surprised at how impatient I am. I like to free-form, it’s what draws me to philosophy and writing. I love the limitless paths with the only constraint being your imagination.

When it comes to life, though, I admire the instructional path. The systems. Four years of undergrad, four years of med school, four years of residency, then becoming an attending. Or the corporate version: undergrad, internships, job, manager, and eventually retiring at sixty. And while all paths carry some ambiguity, there’s comfort in having solidified steps to work toward. It’s like a rock climber seeing the next handhold; the move is still hard, but the direction is clear.

Still, my admiration for the instruction-based path is from a distance. I know I wouldn’t enjoy it. The creative path feels more like climbing blind, on the same mountain, but constantly wondering if I’m even on the right one. And in that climb, there’s a strange tension between the comfort of my day job and the pull of the work I actually want to do. I often wonder if I’m overthinking the path itself. Am I making the right moves? Am I putting in enough effort? Though I typically find worrying about these questions rarely solves anything.

But effort is slippery. Success, after all, doesn’t always map cleanly to work. If my very first blog had gone viral and reached a million people, would I call that the result of effort, vs if my 1000th one did? A part of me will probably always feel like I’m not doing enough. And maybe that’s the point. Naval Ravikant has a line Do what looks like work to others but feels like play to you.

This week, I attended a Coffee Ceremony hosted by two people who decided to go all in on their dream. The level of detail they poured into the event was remarkable. Their goal is to build interest in their future brick-and-mortar café. One of them even quit his comfortable software engineering job and moved to San Francisco to pursue it. Almost the exact opposite of what most people come here for. Instead of joining tech, he walked away from it.

I loved his willingness to chase his dream of creating a space for people to slow down and gather over a cup of coffee. It feels like a quiet rebellion in a city obsessed with speed, progress, and “forward thinking.” It reminded me that there is space, even here, for different kinds of dreams. While some push us into the future, others hold space for the present.

Watching them inspired me to solidify my own. Even in a city where tech dominates, I want to carve out a place for storytelling to help document and carry ideas into the world. I’m grateful I could play even a small role in their journey, and ironically, their pursuit has helped me continue mine.

That’s all for now; I hope your week was fantastic and that this helped you dive a little deeper beneath the surface!