Ambitious people often waste their lives by leaving things too early.
Everyone (i mean everyone) has switched lines at the grocery store and regretted it. You're in one that isn't moving, the one next to you is, so you cross over. Then yours starts, the new one stalls.
I run a company that has raised over a hundred million dollars. I switched lines to start this company. I switched lines, when we pivoted. I am not going to argue that people should never leave.
But I have watched enough of these decisions by now, across many companies and domains. The people who left almost always left at the moment things got hard, and very few who ended up where they had been hoping to go.
The people who stay through the ugly often seem to end up ahead, and they are the ones who now look lucky.
I know people who struggled for years, until it hit. I've also seen overnight pivots to success. There's no one recipe. But below is some sincere thoughts on when to stay, and when to leave. And why switching lines usually ends up failing.
I. Your Line
The line you're standing in is the only one you know from the inside. You know exactly what's wrong with it. You've been watching the slow cashier for six minutes and you have opinions about her. The other line you see from across the store, and from across the store almost anything looks fine, because you can't see the coupons or the price check or the man reaching for his checkbook. You're not learning anything about that line. You're seeing it from an angle that hides its problems.
Nobody switches lines because they've studied both. They switch because their own line's problems are visible. A la.... the grass is always greener... Then they get to the new line and its problems become visible, and now there's another line, one aisle over, that looks fine.
II. It Feels Good
Switching feels like taking control. Staying feels like giving up. So when someone leaves a job at month eight, or a startup changes markets in year two, or a founder rewrites the strategy the week before the old one would have started paying, it registers as bold. People congratulate them. Nobody congratulates you for staying in a line.
But most of these moves are the same move. The thing got hard, another thing looked easier, and the person went toward the thing that looked easier, dressed up as ambition. It's hard to tell the difference from the outside, and sometimes from the inside, because the feeling is identical. If you're leaving right when it got hard, you're probably switching lines.
III. The AI Era
This was always a problem, but it has gotten a lot worse, and I think it's worst for people just starting out.
A new grad today looks at a job market where the fastest money is in AI, where twenty-three-year-olds raise rounds off a demo, where every week someone with fewer years of experience than you announces something enormous. Every line looks shorter than yours. And these lines are visible in a way they never were, because the whole thing plays out on a feed. You see the announcement. You do not see the four years of nothing that came before it, or the two years of nothing that will come after it for most of them.
So people move. They leave the solid job at a company that's learning slowly for the startup that's moving fast. They leave the startup at month ten for the one that just raised. They leave engineering for founding, founding for investing, investing for whatever gets written about next. Each move makes sense on its own. Together they add up to someone who is twenty-nine and has been new somewhere five times and deeply good at nothing.
The AI era rewards depth more than any period I've seen, because the tools make the shallow parts of most jobs free. What's left is the part you only learn by staying. And the era tempts people out of staying more than any period I've seen. That's the trap.
IV. Leave On the Way Up
If you take one thing from this, take this. The best time to leave a company is on the way up, not the way down.
Most people do the opposite. They stay while things are good, because it's comfortable, and leave when things get hard, because it's not. Which means they leave right before the hard part would have taught them something, and right before the company would have needed them most, which is when the people who stayed get the equity and the title and the story.
If you're leaving because it got hard, wait. Hard is where the value is. Hard is the part everyone else quits, and the people who don't quit are the ones with the résumé everyone wants five years later.
If you're leaving because you've won, because you shipped the thing and learned what there was to learn and the next mountain is somewhere else, go. That's the good kind of leaving. You'll leave with people who'll hire you again and a reputation for finishing. You'll also leave with a clear head, which you don't have when you're fleeing.
V. The People Who Stayed
The founders whose stories we tell mostly didn't switch lin…
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