There's no map for this.

Back in 2009, I was a 28-year-old salesperson hawking healthcare software door-to-door in Manhattan.

Many of the doctors I was calling on weren't much older than me. And after forming some friendships, I found myself joining a group of doctors for dinner one night.

We ended up at a new Indian spot in Tribeca. Prem, our host and organizer for the evening, was a gastroenterologist. David was a well-known plastic surgeon. And Jessica was a young dermatologist, just starting to build her practice. They brought along a few of their younger friends who were still in med school. We all crammed into a table in the back, ordered way too much food, and after the second (or third) round of drinks, the conversation turned to careers.

I remember feeling pretty good about mine at the time. I was new to the city, loving my job, and things were starting to click for the first time in my professional life. I was happy to be in New York, to be invited to a dinner with new friends, and not thinking much about where the conversation was headed.

Then a young med student named Kristine started talking.

She seemed to be about my age, if I were to guess. And she commanded everyone’s attention as she walked through her career plan with calm confidence. She’d finish her residency, followed by a fellowship, join a practice, work her way up, and eventually become a partner.

The next two or three decades had been mapped out with such specificity, and I remember noting just how impressive she was. She could tell you, down to the year, exactly which step came next.

I was working for a fast and furious startup at the time. Putting it kindly, we were building the plane as we flew it. Roles were being created and doled out weekly. People were getting relocated on a whim. Nobody knew what came next because "next" was being figured out in real time.

As I sat listening to Kristine that night, I felt just how big the gap was between her world and mine. We were about the same age, just starting our careers, and working hard. But Kristine had a path that existed long before she arrived. And I was on a journey that would change every day, if not every hour.

I thought back on that dinner several times over the years. It was just one of those nights that stuck with me for some reason. And it really popped back into my mind the further I got into building my own business.

I finally understood what I'd felt sitting across from Kristine that night.

No map

Entrepreneurship isn't hard because the work is necessarily hard. It's hard because you're never quite sure what the work even is. You feel confused more often than you feel certain. You sit down to design a strategy and realize that there aren't just a few options to choose from. There are hundreds or thousands. Should you build this funnel or that one? Is it high ticket or low ticket that’s best for you? Audience first, or product first? Twitter or LinkedIn or YouTube or TikTok or Instagram, or all of them, or none of them, or some of them?

And just when you think you've figured something out, the platforms change, the algorithms shift, a new trend arrives, and the entire landscape shuffles underneath your feet.

Sound confusing? It is.

Add to that thousands of people telling you they've cracked the code. Everyone has the cheat code, the framework, the playbook, and a done-for-you system. Some people are scamming. Some of them are telling the truth because it worked for them. The bad news is that their market isn't your market, their timing isn't your timing, and their personality isn't yours. You can follow their steps exactly and land somewhere insanely different.

And that whirlwind feeling never really goes away. Even after years of building, finding something that works, and getting a little traction, there's always a new competitor, or a new tool, or a new threat that makes you feel totally lost. Like you’re starting from scratch again.

I'm not sure I've ever felt like I've truly “made it.” I don’t actually think that feeling exists in this entrepreneurship game. I’ve always felt like, no matter how much success I had, that someone else had cracked the code faster or better than I had. And for a long time, I thought that was a personal failure of mine. Like everyone else had figured out the map, and I was the only one still wandering around asking, “Am I doing this right?”

But, it turns out there’s no map for anyone in entrepreneurship.

Two kinds of careers

Most traditional career paths have a path you can follow that was sketched out long ago. It doesn’t matter if it’s medicine, law, most trades, or even becoming a professional athlete. The stages have been largely predetermined by what’s been proven to work. Do this first, this second, this third, end with this, and ta-da, you’ve made it. A doctor who worked her way to becoming a practice partner back in 1995 can jump on a call with a resident today and give them advice that still mostly applies, because the path is generally the same.

Entrepreneurship has none of that. There are no predetermined stages. And even the things that look like stages aren’t. Getting into Y Combinator isn't a step in the way that getting into medical school is a step. Hitting 100,000 followers means everything to one person’s business and nothing to someone else’s.

The next marker of success doesn't exist until you invent it. And you're out there trying to figure out what the next stage looks like while simultaneously trying to win at whatever the heck stage you're currently stuck in.

And, unfortunately, most good career advice is stage advice. Do this specific thing at stage three of your career, and you’ll move to stage four. But the entrepreneur isn't at stage three of anything. They're at some random, unmarked point on a path they're making up in real time.

That's why so much entrepreneurship advice fails to land. The advice giver tells us what they did, as if the “doing” is the part that transfers. But it’s not. What transfers (if anything) is the judgment they built by living through it. The hard-won instincts. The experience and wisdom they gained in their market, at their moment. But most of the time, you can't even borrow stuff like that. You just have to build your own.

And when the advice and the frameworks and the playbooks don't work? Most people will blame themselves. They weren't focused enough, or didn't execute correctly, or gave up too soon. But working without a map isn't a personal failure. For an entrepreneur, that's just the job. And it’s one of the hardest jobs in the world.

The bottom line

When I think back to that dinner in Tribeca, I think about Kristine. I imagine she's somewhere around step 14 of 20 on her way to practice partner. Of course, there's absolutely nothing easy about that journey. But sometimes I envy the predictability of it.

Mostly, though, I love the challenge of entrepreneurship. I love the fact that I can stop, pivot, and do something completely different tomorrow or next year. I love that when people ask what I do for a living, I'm never quite sure what to say. I love that when I have a new idea, I can go take some action on it and find out if it’s brilliant or moronic. There's a freedom in that which most linear career paths will never offer.

What I didn't know at that dinner table in 2009 is that Kristine and I weren’t on the same path and never would be. We just happened to be about the same age, sitting in the same room, eating the same Indian food. Her map already existed. And mine never would.

So here's my question for you this week:

What path are you still following that was built for someone else's situation?

Reply and tell me about it. I can't respond to everyone, but Jennifer and I read every response, and we love hearing from you.

That's all for this week.

See you next Saturday.