How I got here: a nonlinear career path, and why it worked

A nonlinear career path works when each turn keeps the same question alive, even while the job title changes. You do not need a straight line; you need to know what you were looking for, and to go all in on the one thing that decides it.

I know this because my own path looks like a list of unrelated things: a tennis player, a crêpe stand, a nightlife app, a shirt brand, a community I joined and then rebuilt in my head, and two years of software I set aside to start over in days. On paper it zigzags. Looking back, it was one question the whole time.

The short answer

A career path that zigzags is not wasted time if something carries over each time you turn. Look for the question you kept asking, name it in one line, then put your next turn on the one thing that decides that question right now. The zigzag becomes the proof, not the problem.

Where my path actually started

As a kid I wanted to be an architect. I wanted to design buildings that thousands of people would walk past every day for decades. In high school I spent my free time drawing an apartment building for downtown Birmingham in a design program and getting every detail right.

A year or two before college I let that go, because the buildings I wanted to design would not come until I was old. City planning pulled at me next, because it shapes how whole communities live. Then I decided that governments move too slowly, and that a better society starts with one person changing what they do. That idea, start with one person and let it spread, is still the core of what I build.

The drop shot

At 12, seeded at a junior tennis tournament in North Carolina, I lost 6-0, 6-0 to a boy who drop-shotted me the whole match. I had no answer. I went home and practised nothing but the drop shot for weeks, until it was mine. I still have it.

I did not have words for it then, but that was the pattern I would repeat for years: find the one weakness that decides the result, and fix that before anything else. Not the forehand, the backhand and the serve all at once. Just the one thing.

Later I quit tennis. After about 15 years of training, the game had become routine and I felt nothing about it. I stayed away for about four years.

Turns that looked unrelated

Here is what the middle looked like, and what each turn carried into the next.

• A crêpe stand on campus. In my last year of college I bought a crêpe machine and sold crêpes late at night. Within weeks it was the talk of campus. It taught me I could start something people loved and run it in public.
• A nightlife app. I spent about 2,000 hours building it before I had customers. Plenty of people signed up, and almost no bars did. It taught me to find the people who will pay before I build.
• Back to tennis. I came back to understand learning itself. I rebuilt my own swing and found I could turn a student's weakness into a strength in weeks. The drop shot pattern, made into a way of teaching.
• A shirt brand with a friend. We were texting about training shirts one summer, and I wrote: we should just make our own shirt brand. We called it Ethos. The idea was to become your 2.0 self, and someone close to it read the two dots over the O as two people: you become your best self faster with others.
• Pickleball events and college campuses. Then I stopped. I could not do everything, so I set the brand down and went all in on teaching tennis.

Every one of these looks like a detour. Each one handed something to the next: running something in public, testing before building, fixing the one thing, and doing it with other people.

The thread finally showed itself

The thread became obvious when I joined a founder community. I kept thinking, they should be connecting us. So I built a small matchmaking hub for the members in a couple of days, with suggestions for what two people might talk about.

Then I noticed I did not want to launch it as a one-off. Every app I wanted to make needed the same parts, so I started building the parts once: a screen engine, a workflow engine, a formula engine. I called it Architect. The kid who wanted to design buildings was now designing software that builds software.

That grew for about two years into a much bigger system. Then, one week, I questioned the one requirement I had never questioned: why did everything have to run on it? I kept the principles, set the rest aside, and started again. The new version was running in days.

That was the drop shot again. Find the one thing that decides the result, and go all in on it, even when it means setting down something you spent years on.

How to read your own path

You can do this on one page in about twenty minutes.

1. List every turn in order, including the ones you dropped and the ones you are a little embarrassed by.
2. Next to each, write what you carried into the next turn: a skill, a question, a person or a lesson.
3. Circle the question that keeps showing up. Write it as one plain line.
4. Ask what single thing decides whether that question gets answered in the next few months.
5. Put your next turn there, and let the other good ideas wait.
6. Say the line out loud to a friend. If it sounds true, keep it. If it sounds like a slogan, rewrite it.

For example, picture someone who taught school, ran a food truck and now builds spreadsheets for small shops. Their line might be: I help people turn a messy day into a plan they can actually follow. Suddenly the food truck is not a detour. It is where they learned how a day really runs.

What I would tell myself at 12

You will turn a lot. That is fine. Keep a note of what each turn teaches you, and every so often, ask what the one thing is that decides where you want to go. Fix that first, the way you fixed the drop shot.

My own line, written on a morning walk: I help people figure out what is worth pursuing, find the one thing that moves it most, and act on it faster, in a way that serves the greater good of bettering human society. It took a drop shot, a crêpe stand, a shirt brand and two years of software to be able to write it.

The short version

• A nonlinear career path is fine when each turn carries something into the next.
• Name the one question you keep asking, in one plain line.
• Find the single thing that decides that question now, and put your next turn there.
• Be willing to set down good work, even years of it, when it is no longer the one thing.
• Say your line out loud, and rewrite it until it sounds true.