July 16, 2025

Never enough: The Founder Trap

I think a lot of founders struggle with the feeling of never enough. Because the startup world teaches us to chase more.

More funding. More customers. Bigger teams. Louder headlines.

There’s always someone scaling faster, raising bigger, hiring more.

But here’s what I’ve learned, both personally and through the founders I coach:

More Isn’t the Metric

You don’t need 200 employees.

You don’t need to be in TechCrunch.

You don’t need a Series D to prove you’re building something meaningful.

You need a business that works. A life that feels good. And an identity that isn’t shackled to your last round.

Because when your sense of self is tied to startup success, nothing is ever enough.

Ask This Instead:

Not: “Am I doing enough?” But: “Is this good enough for the life I actually want?”

  • Is your pace sustainable?
  • Is your work aligned with your values?
  • Are you proud of what you’re building, and how you’re building it?

You don’t need more. You need clarity.