Is it time to quit?

Is it time to quit?
Photo by Payton Tuttle / Unsplash

As someone with three tours of duty (totaling 11 years) of searching for P/M-fit as part of seed-stage startups of my own making, I'm often asked why — or perhaps how, I didn't quit.

This question has tendrils that cast shadows over and permeate nearly every article I've written as part of this newsletter. 'Sure, finding fit is awesome, and it almost appears as if, given enough time, it's inevitable.

But how did you know not to quit?!'


Were you there at my first startup when I:

  • Quit working on it full-time and got a job again?
  • Quit trying to get people to visit our site directly and gave away the value 🐙 as an embed?
  • Quit trying to monetize ads even though it was making us $100k+ a year?
  • Quit offering a free tier to millions of visitors a year?
  • Quit providing self-service even though we had 2,000 subscribers?
  • Quit bootstrapping and diluted our ownership?
  • Quit trying to fundraise and reduced the team?
  • Quit my position as CEO?

No? Huh. Did you only catch the ending, maybe? The part where it was acquired and all of the above became a story of success?

No worries. Maybe you were there at my second startup when I:

  • Quit selling a forecasting wizard for SaaS even though it had a few customers and clear roadmap?
  • Quit trying to build it as a solo/lifestyle business?
  • Quit providing — and I mean burned down 🐙, a high-touch SaaS financial modeling tool even though it had customers and revenue?
  • Quit positioning the new thing as a horizontal platform even though it was growing?

Okay. Well then it makes sense you don't think of me as a quitter!

In truth, all I do is quit.

The Key To Avoiding Burnout

Yes, I understand you meant 'how come you didn't quit — like, I mean, really quit on, you know, the Whole Thing?'

And yet, this is the answer.

By letting go of the parts that weren't working — quitting those, and only holding on to the parts that still contained promise.

Yes, sometimes that meant I was left with a shred. But that shred worked, and that shred gave me hope 🐙. And that shred fit into the life I was able to live.

Yes, I was fortunate to still have anything at all. To have the flexibility and margin in my life to still allow for something. But it was equally vital to look at the part I controlled, to be willing to redefine it, and to force quit the things that would have driven me towards permanent failure.

Early and often, again and again, I quit so that I can hold on to the promising bits. Maybe later someone will use those fragments to weave a success story.