Prompt the experiences you want

A dinner with Sasha Chapin at Casa Nautilus

Jul 31, 2025

San Francisco,
July 22, 2025

Dear young polymath,

This is the fifth installment of a series where we share insights from guests at Casa Nautilus. Nautilus is a 3-month residency for young polymaths. Proteges’ stay in SF is fully funded with accommodation, food and equipment included, so they can dive into their craft and build ambitious projects.

Did you know you can just prompt the experience you want?

You’ve probably seen the meme: “You can just do things.” But Sasha Chapin— famous writer, former musician, and professional lore-generator taught us something deeper over dinner.

You can just prompt the world to respond to you differently, simply by behaving differently within it. We talked about identity, scripts, systems, silliness, and the underrated power of choosing to write your own story.

I. You can just retire versions of yourself

Sasha opened the evening with some lore: his early days chasing a career in music. He loved writing songs and performing. He worked hard to become a good musician. He believed he had a future in it. And for a long time, that belief sustained him. But then a quiet knowing began to stir—first an idea, then a truth he couldn’t ignore.

He was a good musician. But not great. And more importantly: he realized he was lying to himself.

“For one, I could just feel that people weren’t as into me as other artists. And I knew… if I worked really, really hard, maybe I could one day open for Tame Impala.”

That wasn’t enough to quit. Eventually, a friend told him what he already knew:

“Your music is good. But your writing? That’s special.”

So he pivoted and retired a version of himself. He let one dream die so another could breathe. That’s terrifying, but also freeing. Most of us are haunted by outdated versions of ourselves so consider this your permission to dive deeper into what resonates most, to grieve previous parts of ourselves in order to grow into who we really are.

II. You can just break script

This was the most fun part of the dinner. Because what is polymathy about, if not learning to mess with the world’s formulas?

Before Sasha was a celebrated writer, before the music gigs and award winning essays—he was a waiter at a fine dining restaurant. Now, you might think, what can waiting tables teach you about narrative power? Always assume the answer to these questions is everything! Sasha introduced us to a concept he calls responsiveness—the capacity to sense impact. Most systems are unresponsive. They don't care what you do. You clock in, clock out. You write the essay, get the grade. You say hello, and the world doesn’t even see you.

But Sasha argued that even if a system is unresponsive, you don’t have to be. You can bring life into the system.

By breaking the script. For example, instead of mechanically asking his customers, “Still, tap, or sparkling?”, Sasha would pretend he forgot how to ask. The awkwardness was the point—it invited presence and space for connection through creating friction.

He told us about the time he spilled olive oil on a woman’s skirt. (*cue collective gasp and chuckle*)

And yet, she still tipped him big. Why? He told her,

“Sorry, I was distracted by how special you are"

I thought to myself, Who even says that? But I guess Sasha does—and it works for him, because he breaks the script! It’s not about being reckless; it’s about play, and about re-enchanting the moments most people sleepwalk through.

When you start behaving differently, people have to respond. They get curious. They open up.

So learn how to prompt yourself to break script.

III. You can just be silly

Why are we so serious all the time?

Why do we grip so tightly, try so hard to be profound, to be right, to look impressive?

What if you just let go? What if you laughed at yourself first?

Sasha taught us: you can just be silly. Being silly helps you feel things.

You can be silly by breaking script but also through the realization:

“People are not your experience of them.”

That quote hit different for me because we like to think we know others; but all we really know is how they feel to us through our own lens: meaning at that moment, in that context, and in our timeline. Silliness is his strategy to loosen that grip onto reality, and to allow feelings and emotions to be felt instead of locking them in a box.

“When I stop trying to fight fear, rejection, pain and just feel them—it’s kind of electric.”

We also talked about Jonathan Haidt’s “elephant and rider” metaphor: your emotional brain (the elephant) and your rational brain (the rider). When those two are out of sync—you suffer. You drag your body around, confused and exhausted. So be silly.

Let the elephant dance. That’s how you sync up your rider and elephant again.