choose the life you already have

the opposite of settling

Katsushika Hokusai, The Great Wave

This is part 1. You can read part 2 here.

---

For better or worse, most of my life followed a well-worn pattern. I’d set my sights on something—usually a new job or city—and work feverishly to get it. Once mine, I’d pour myself into it for a year. Coast for two. Feel the slow itch of outgrowing it. And move on to the next thing that felt right in the moment.

By the time I was thirty-six, I’d lived in five major cities, held three different jobs, gone to grad school, written a book, and spent a year traveling the world. From the outside, my itchy feet could look like confusion, maybe even an avoidance of commitment. From the inside, it felt different. It was just my own iterative process. I was young. I didn’t know who I was or what I wanted. And there were parts of myself that only seemed to come to life through relationship with the Other—people, jobs, locations, experiences. Those relationships helped me map my own internal territory. I learned my frontiers, my edges, my altitudes. Each move got me closer to some sort of alignment, something like a personal resonance.

The pattern worked. Until it didn’t. What I couldn’t see yet was that I wasn’t moving toward anything. I was always half-in, half-out of life.

The constant movement kept me in the shallows. I’d wade into a new environment, get tossed around in the rough waves for a bit, find my footing, get bored, and head back to the shore. Once there, I’d look back out on the horizon and scout a new path, a different adventure to embark on.

It took me awhile to realize I liked getting tossed around. There’s something about newness—falling in love, starting a new job, moving to a different city—that ignites a sort of furious energy, like an all-purpose amplifier. The laziness, shyness, and indifference that sometimes plagued me would temporarily fall away, replaced by motivation, excitement, and desire. It was in those moments I felt most alive. Feeling like I had something to prove only added to the intensity. But that aliveness had a ceiling. It was borrowed, always temporary, always dependent on the next new thing.

It took me even longer to realize I might have crossed an invisible line or something like an inflection point. It’s true that staying near the shore preserves optionality. Life is pure potentiality when every possible path is still available, but the trouble with optionality is that it can become habitual. And the more you do it, the harder it is to stop until “the dreams that those options were meant to enable slowly recede into the background.”

There’s value in surveying your options before you make a choice, but there’s also an optimal stopping point. It can even be calculated. The math goes something like this: if you have a fixed number of options to evaluate, the optimal strategy is to spend 37% of your time just observing—not choosing—and then commit to the first option after that which is better than anything you’ve seen so far.

Decide too soon, and you haven’t seen enough to know what “good” looks like. Decide too late, and you’ve already said no to the best options. 37% is the mathematical sweet spot. The intuition behind this is probably why parents encourage children who want to marry young to “date around” and admonish those still single later in life to “settle down.”

It’s not just that the optionality diminishes in value over time. When you stay on the shore too long, the water becomes one-dimensional. The best it can offer me now is a surface that reflects back what I already know about myself, nothing more than a mirror. It doesn’t show me what I could become. If I instead choose one path and dive in, that same water becomes something else: a portal, transporting me not to a deeper sense of self, but to a place where the self merges into something bigger, something beyond itself.

But to do that I have to leave the shore. I have to swim past the breakers. I have to make a choice.

So what do I choose? And more importantly, how do I choose?

There’s a moment I keep coming back to. I was two years into living in my dream San Francisco apartment, two years into my dream startup job, when I woke up with a familiar thought.

None of this is right.

As Elizabeth Gilbert asks at the start of Eat, Pray, Love, looking around at the house she shared with her first husband: “I had actively participated in every moment of the creation of this life—so why did I feel like none of it resembled me?”

San Francisco was near perfect. Good weather, great parks, and better views—punctuated by steep hills, rolling fog, and one-of-a-kind architecture. The ideal place given my preferred leisure activities were long walks with my dog, beach strolls, and weekend hikes. To top it off, I had a group of friends I loved and a life that made sense on paper.

The same could be said for my job. I worked at an early stage startup that a friend and former co-worker had founded. The team was comprised of what an old mentor would affectionately call “good people”—smart, curious, capable, kind. And the role was a sort of choose-your-own-adventure that offered both the flexibility I needed and the autonomy I craved.

When I had the thought that none of this is right, what I really meant is none of this felt enough like “me.” You see, when you’re looking for external things—the Other—to define you, any perceived mismatch feels existential. And there were mismatches.

The tech bubble in San Francisco was hard to penetrate. The city struggled with a “curse of Aboutness” that left social interactions feeling like another productivity hack. And most people caught the California Soft Virus eventually—an over-therapized and under-accountable ethos that got rebranded as “protecting your energy.”

I felt out of sync at work, too. I wasn’t excited about the product we’d landed on after a series of pivots, and I felt pressure to define the vision and direction—things that should be done with genuine conviction, which I didn’t have.

When I woke up that morning, what I felt was constriction. The world I’d built suddenly felt too small for everything inside of me, everything I wanted to do, everything I wanted to be. The mirrors I’d chosen didn’t reflect the vastness of my internal world, and how could they? If it wasn’t San Francisco and the startup job, it would have been another city and another role. Anything would have felt too small because I was using an exogenous fuel source to power my being.

For a long time, my only available response to that feeling of constriction was one I’d always used: to leave. So I did what I’d always done, I rejected the mirrors. I said no—not this place, not these friends, not this job, not this team.

I quit my job, packed up my bags, and moved home to the Midwest. I considered new roles and moving again, maybe this time to Europe, but something in me resisted in a way it never had before. I stayed put. I hunkered down. I started writing.

When I finished my first book, something shifted in me. To say it was one of the most profound moments of my life feels like an understatement. It’s more like it tilted my world onto a new axis. For the first time in my life, I hadn’t needed anything outside of myself to feel alive. I had generated that aliveness from within, then poured it into something that now existed independent of me. A self-contained universe that other people could enter, play around in, maybe even return to. Before that, I hadn’t fully understood the gravity of creation—that the same force that wrote that book could build a life. I was never supposed to find the right external conditions and come alive inside of them. I was supposed to create the conditions myself.

There’s a lot of talk about agency and how a highly agentic person is one who can “just do things.” I could always just do things. I could decide to move to a new country and a month later, it would be done. There are a lot of people running around just doing things in very shallow ways, like I was. Real agency isn’t just the ability to do things. It’s the ability to choose things, and then build a life around those choices. To look at something—a person, a place, a path—and decide it’s yours. Then take action to make it so.

And for me, that was the missing link. When something felt off in my life, I thought the solution was to wipe the slate clean and start over, to let go of everything that felt wrong and pursue the opposite. I’d spent years doing what Brianna Wiest describes in Great Callings, “throwing out every verse just because you can’t get the chorus to sound right.” The alternative seemed revolutionary to me. Commit to getting the song right. Fix the chorus. Swim past the breakers and keep moving toward the horizon instead of returning to the shore.

Cate Hall describes a moment in her life where “the seam through the center of things ripped open and the machinery of the universe spilled out.” Something similar happened to me when I moved home, only on a much smaller and more personal scale. It was more like the seam through the center of me ripped open and the machinery of my life spilled out. I was left to sort through all the guts, all the bits and bobs, with fresh eyes and re-assemble them.

I kept picking up the San Francisco bit and the career bob, twirling them around, investigating them from this new perspective, wondering why I’d been so quick to put them down before.

Over time, I started to feel a new-to-me kind of itch: to go back. To return to my old life and resume my old work. Why not that place? Why not those friends? Why not that career? Why not that team?

Why didn’t I believe that I could build the life I wanted from the bits and bobs I already had? I could take these things as starting points and turn a beautiful city into a home and a good job into a career. I didn’t need to find myself in these things anymore. I could create meaning, purpose, even my sense of self, through my interactions with them. I could just decide I’d found it. That’s all it takes to stop searching—the decision that nothing’s actually lost. And more than that, I could create something for other people too. The energy I’d spent looking for my reflection in the Other could become something generative instead.

But the romantic in me grieved. I’d been telling myself that wandering was the story. It was hard to admit that the false starts were nothing more than the prologue to a deeper life. All those years I’d spent looking outward for something that could only be built from within. The searching hadn’t been wasted exactly, but it had come at a cost, and I was beginning to feel it.

A younger version of myself might have thought of this as settling: to land somewhere and say, "This is good enough. I’ll build a life here.” But that’s not settling. It’s the most radical kind of agency. It’s saying I choose this life—the one right in front of me—come the good and the bad. And I have the power to build it into anything and everything I want it to be. A life isn’t something you excavate. It’s something you construct. Excavation assumes it’s already there, buried somewhere, waiting to be uncovered. Construction assumes you have the raw materials and the will to build.

On some subconscious level, I must have thought that commitment would shrink my world. That choosing one path meant closing off all the others. That the circumference of my life would contract. And in the most literal sense, that’s true. Your world does get smaller when you make a choice. But contractions are a precursor to expansions, and when you stop spreading yourself thin across all the possibilities, something in you concentrates. Your world might get smaller, but you expand to fill the space you claim. You go deeper instead of wider. A life built around commitment has dimension that one built around potential can’t have.

It’s hard not to feel behind in some way, but I try to remind myself that the timing—that this epiphany happened at the age of thirty-seven, on the cusp of thirty-eight—feels almost karmic. If I’m lucky enough to live a long life, say to one hundred years, thirty-seven puts me exactly at the 37% mark. Maybe I’d spent the optimal window observing, experimenting, and learning.

Maybe I’m right on schedule.

There are ships in the water, just past the breakers, ready to set sail, loaded with people, experiences, and entire lives you can’t imagine from the shore. The horizon holds a different kind of infinite. Treasures abound. You can keep waiting for newer, better ships to arrive. You can hold out for the perfect one.

Or you can just choose one, climb aboard, and start rowing.

---

Read part 2 here.

We don’t have to play every game to know what winning feels like. We don’t have to hear every piece of music in the world to understand music. We don’t have to have tried every variety of grape from every vineyard to know the pleasure of wine. Love and laughter and fear and pain are universal currencies.

We just have to close our eyes and savour the taste of the drink in front of us and listen to the song as it plays. We are as completely and utterly alive as we are in any other life and have access to the same emotional spectrum.

We only need to be one person.

Matt Haig, The Midnight Library

This newsletter is where I make sense of the world—philosophy, tech, esoteric rabbit holes, and the future we’re headed toward.

Everything here is free. If you want to support my work, you can subscribe or grab a copy of my novel Dark Days Ahead.

Keep in touch—drop a comment below or follow me on Instagram @ndocherty.

the slow outsourcing of the self

losing the human touch

breaking the career script