Why “Fail Early and Often” is Wrong

You should be learning from your successes, not your failures

Joe Procopio
5 min readJul 12, 2021


Failure is not good for you. Entrepreneurs who are told that failure is a treasure chest full of valuable startup lessons are being sold a false — and sometimes self-fulfilling — bill of goods.

“Fail early and often” is another one of those tired advice soundbites I dislike. Not because it’s flat-out wrong, but because it rarely comes with the necessary context.

I know the stench of failure. I’ve wallowed in the misfortune of my own making more than I care to admit. And I’ll be the first to tell you that those failures came with very poignant lessons about what not to do. But seriously, I could have read those lessons online — or at least somebody could have given me a heads up.

The truth is that you need to minimize failure and all the painful learnings that come with it. Instead, you should be learning from your individual successes, small and large, at every step of the journey. Not only are these lessons more frequent, they come with a lot fewer setbacks.

Learning from success is a much more valuable opportunity than learning from failure, as long as you remember to take the time to do it — which very few entrepreneurs do.

Let’s change that.

Play to win, not to not lose

Learning from failure only keeps you from failing the same way next time.

But no successful entrepreneur goes into their startup genuinely hoping to fail quickly. That’s where the self-fulfilling-prophecy part of “fail early and often” rears its head.

Any decent sports coach will identify a team or a player that’s playing not to lose and immediately correct that behavior. How many times have you seen a team that’s leading late in a game switch their strategy to protect that lead and ultimately lose the game? There’s even a saying in football, “A prevent defense just prevents you from winning.”

Learning from success is what propels real growth.

In business, almost everything you do is an experiment. When you make changes to a product or a process, when you attack new markets to acquire more…



Joe Procopio

I'm a multi-exit, multi-failure entrepreneur. NLG pioneer. Building TeachingStartup.com & GROWERS. Write at Inc.com and BuiltIn.com. More at joeprocopio.com