Your Map Is Outdated

Why the people most capable of doing hard things alone are often working from stale information about themselves.

In Open, Andre Agassi argues that tennis is the loneliest sport there is. You stand across from an opponent you can never touch or speak to, and the rules forbid you from even talking to your coach. People bring up distance runners as the rival for loneliest athlete, he writes, and he waves them off: at least a runner can feel and smell the competition a few feet away.

His real point is that isolation traps you with your own inner monologue. Agassi would know. He spent an entire career winning at a game he has said he hated “with a dark and secret passion.”

I am the runner he waves off. And for most of the last five years, he was right about me, just not in the way he meant.

What the solitude cost me was not company. It was an accurate picture of myself.

When the work is solitary, the map in your head slowly stops matching the territory under your feet, and you are usually the last to know, because you are the one holding the map.

I came back to running about a year into the pandemic, when the isolation had ground me down and I had stopped taking care of myself. I signed up for the Malibu Half Marathon to force some structure back into my weeks, and it worked better than I had any right to expect. By that fall I had quit drinking, lost twenty pounds, and finished the race.

The discipline stayed. Fifty to seventy miles a week, usually before dawn, became the scaffolding under everything else: marriage, the sale of the company I had built, and eventually the start of my own fund and advisory practice. I also went from a decent runner to a genuinely good one. I broke three hours in the marathon, qualified for Boston, and then cut another ten minutes off the time.

Almost all of it happened alone. Running was solitary. So was building a company, even with a co-founder. So is running a fund as a team of one. When a marathon build was already consuming so much of my time outside of work, I did not want to spend my limited social hours driving across the city for group runs. So I rolled out of bed and ground out loops around my neighborhood by myself, just me and an audiobook and the inner monologue Agassi was talking about, the voice that on bad mornings sounds a lot less like a coach and a lot more like a prosecutor.

A few months ago I finally joined a run club, a Wednesday night track workout under the lights with about a hundred people of every level. I had always written off run clubs as either glorified dating clubs or workouts for semi-pros, and I am not sure which I was more afraid of.

What I found instead was a mirror.

I was not the fastest person there, but I could run with the fast group without much trouble, and I could push harder in the 400-meter repeats than I had ever managed on my own. The part that actually rearranged something in my head was the warmup. For years I had treated ten-minute miles as my easy pace, because that was true back in 2020.

Jogging the warmups and cooldowns with the group at eight- and nine-minute pace felt like nothing.

It was not that I had suddenly gotten faster that night. The fitness had been there for months. I just had no way to see it while I was running alone. I had been carrying a five-year-old picture of myself and calling it the truth.

That is the trap of doing hard things in isolation. The same discipline that lets you get good at something alone is the thing that hides how good you have gotten. You put your head down and do the work for years, and because no one is beside you keeping score, your estimate of yourself quietly stops updating.

The people most capable of achieving hard things in isolation are often the ones running on the most out-of-date information about themselves.

So we wait. We tell ourselves we will have arrived once the round closes or the whale customer signs or the next milestone certifies the person we are trying to become. But sometimes we passed that point a while ago and never noticed. It is almost the inverse of “fake it till you make it.” We are not pretending to be something we are not. We are refusing to notice we already are.

I have done this my whole career. When I was running my last company, I did not count myself as a CEO, even while I was managing a team and raising money. When I started writing angel checks, I did not count myself as an investor. When I launched my fund, I was still operating off the self-image of someone trying to figure out how funds work.

None of that was modesty. It was stale information. Other people had updated their read on me years before I updated mine, and my easy pace was eight-minute miles long before I let myself run them.

I see the same lag in nearly every founder I work with. Not long ago I spent a few weeks with a first-time CEO building software for one of those sleepy, paperwork-heavy industries nobody disrupts because it is genuinely hard. He had a real product, a couple of paying customers, and one specific type of customer he could win again and again.

But every time we talked, he pulled toward a bigger, shinier, untapped segment, convinced the real prize was out in the territory he had not reached yet. He was still the founder who had to push in every direction at once and personally touch everything, when the business had quietly become something steadier than that.

The thing already working was the business, and he could not see it, because seeing it meant admitting he was further along than his picture of himself allowed. Most days, my job is just to be the mirror that shows a founder which part of the map has gone out of date.

You still have to do the work alone. But solitary work quietly erodes your ability to calibrate, and at some point you need something outside your own head to tell you where you actually stand.

Sometimes that is a coach or a peer. Sometimes it is a hundred strangers on a track on a Wednesday night.

So check your map. The danger is not that you are incapable of the thing in front of you. The danger is that you are navigating by an old version of yourself, a picture drawn years ago and never revised, and you cannot redraw it entirely from the inside.

Put yourself somewhere your assumptions get measured against other people: a track, a dinner table, a pitch meeting. Not to become someone new, but to find out, faster than you ever could alone, where you already stand.