feeling it out.
intuition, fluidity, getting good, and impressing myself.
I’m writing this early on a Saturday morning. The sun isn’t up yet and for the first time in a while, I have the day to myself. These past several weeks have been long — 80 to 90 hours without very much of a break. Running a business is hard.
Last year, I explored. I called it my startup gap year and used it to bring my startup to market. I built a couple side projects that gained traction but ultimately didn’t make it very far. I fell in love for the first time. After a while, I felt lost.
This year started with the deconstruction of the former version of my life, moving on from a deep relationship and the business I’d spent four years of my life building with some of my best friends. When you do something deeply, obsessively, you risk forgetting yourself at the other end. It took me a while to find myself again.
I rebuilt quickly. In the past, I’d optimized for optionality—keeping doors open. The problem was that I never walked through them, because that felt irreversible. I felt that I was supposed to do something great, but I found that I’d hedge my bets instead of going all in. This time, I was playing with a chip on my shoulder and nothing to lose. I went all in.
That was in May. Seven months later, my world feels fundamentally different. With an incredible team behind it, Relay is now a seven-figure company with twenty people in the Slack. It’s constant chaos, but what matters is that we’re moving in a direction. Personally, it’s been illuminating.
learning by doing
One thing that’s become clear to me is that the way to learn about yourself (or a company) isn’t by sitting inside and ruminating — it’s by getting out into the world, doing something, and then reflecting afterwards. And like any good thing, it’s an art more than a science.
Selves and organizations are complex, multivariate systems — you must treat them with humility. Even with controlled input, you can never cleanly predict an outcome. And you cannot truly rationalize a complex system, even if its parts are dissected and laid across a table. The sum is more than its parts, and the complexity of a system—its magic—is a function of its totality.
The way we must deal with complexity is to feel it out. Unlike an equation, which you can solve, you must learn a system the way a sailor learns to read the wind upon the water. You get acquainted with it. You learn to sense it—to adapt to it—and if you’re really good, you might even learn to predict it. Just because something is complex doesn’t mean it can’t be predicted — but meaningful predictions must be made at the level of the forest, not the trees.
It is inefficient to acknowledge totality. A question I’ve asked a lot recently is “what do you sacrifice for the sake of efficiency?” Western thought seems predicated on efficiency, on turning every art into a science. Aristotle’s parsing of the world into individual parts has taken us to great heights — associating a list of common, generally understood attributes with everything makes it far easier to make decisions. Like money with trade, it has enabled the transaction of thought to happen at an exponential rate. But just as money is a false representation of value, so is definition with meaning.
Breaking a fluid world into discrete parts makes it navigable, but at the risk of lower resolution—like film to pixels. As the systems we exist within become more complex, our capacity for nuance degrades. But the invisible grey area is where the magic lies. It is how we assign value to a thing we cannot measure, or meaning to a thing we cannot describe.
It is true for ourselves, too. To break something apart in search of its meaning is sometimes to miss the point entirely. “Make a [thing] available to the eyes,” says Joan Didion, “and in certain ways it is no longer available to the imagination.”
The totality of oneself is staggering and confusing and disparate and always changing, reactively and recursively. And that’s okay.
in the arena.
I learned fairly young that the world was mutable; that it unfurled in the direction you engaged it with. If you ask someone nicely for something, they might just do you a favor. But unless you’re looking for chaos, agency—your capacity to act, your willpower—means nothing unless you know what you want, and you trust yourself enough to get it.
I’ve never been very good at trusting “the process.” Due to a mix of curiosity and impatience, I always at least tried to do things myself. It wasn’t necessarily that I thought I could do it better myself; instead, it was a curiosity about whether I could figure it out in the first place. At the very least, if the object of my effort failed (and it often did), I thought I’d know why.
In the same vein, I sometimes feel that my ‘formalizing process’ took a lot longer than it did for others. I spent a long time being unsure—unable to define myself with the ease or sureness of my peers. I felt that stapling down a personal purpose or mission statement felt disingenuous, like a canned sales pitch. Others seemed so certain of themselves in a way I couldn’t always understand.
This year, maybe as a result of uncertainty and heartbreak, the object of my curiosity turned inward, and I’ve been learning to trust myself. This is an uneasy thing. Trust, I’ve learned, is less about understanding than it is about humility.
Rationalizing something is much simpler than understanding it. But a rational interpretation is not always an honest one. When we look for meaning, we submit to reasonable-sounding answers to things. We find security in incontrovertible, absolute truths.
As I’ve grown older, I’ve come to regard this dogmatism as a weakness. Seeing that we’re historically more wrong than we are right, why do we feel that it’s a bad thing not to understand? Why is it so difficult to take a posture of humility to the complexity of the world, a system, or a self? The great expression of power is sometimes not to have an answer; to simply shrug, say “I don’t know,” and listen ever more closely.
The surest way to resolve this uncertainty is by taking action—by just doing it. Output isn’t a perfect proxy for progress, but at the very least, it serves to demonstrate the reps we’re putting in toward a direction. Immersion is the truth-teller. And this more than anything is how we develop the instinct to feel, to adapt, to predict — to read the wind upon the water.
mastering yourself
This part of life seems to be defined by iterative growth—getting good. Relay is a forcing function for extremely disciplined growth in three skillsets:
Operations (starting, running, and growing a business)
Product (0 → 1 discovery, design execution, and product management)
Consulting posture (trusted advisory, developing and managing relationships, etc.)
I’m super proud of the work we’ve done so far, and grateful for the opportunity I’ve had to start, operate, and grow a profitable business with an incredible team. The objective for now is simple: know myself and get good. But there’s one thing that still evades me: impressing myself. More to come.