Why ‘Fail Early and Often’ Is Wrong

You should be learning from your successes, not your failures.

Written by Joe Procopio
Published on Jun. 30, 2021
Why ‘Fail Early and Often’ Is Wrong
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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.

More Expert Analysis From Joe ProcopioHow Founders Save Their Startups


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 customers, or when you explore new ideas to expand your offering, all of these decisions have measurable consequences and results.

Often when we make a decision and it pays off, we may celebrate a little, but that’s where it ends. We rarely take the time to understand how the decision resulted in success and, more crucially, how we can exploit those learnings to expand on that success. In other words, when something we do works, we’re content not to change it again until it stops working.

It’s the difference between “Hey, that worked!” and “Wait. Why did that work?”

Want to take the leap and start playing to win instead of playing to fail? Here’s what I’ve learned with some of my successes, both large and small.


Stop Doing What Other People Think You Should Do

Don’t mold your startup to look, sound and act like other businesses. This is the top play in the playbook of playing not to lose.

In every single successful startup I’ve ever founded or been a part of, there has been a constant buzz of voices telling me that my startup should do this or that because that’s what successful businesses like mine do.

These voices can be numerous, experienced and trusted. They can also be an army of the wrong customer that you initially chased because you thought they would get you to revenue quicker.

You didn’t start your company to be a clone of another company. You did it to execute a great idea. Don’t modify that idea because other companies found success with ideas that aren’t yours.


Stop Leaning on Others as Your Path to Success

Your business is not one brilliant person away from success. Actually it is, but that person is you.

This sounds callous, but the people you bring into your startup are going to be interchangeable parts to do the things that you don’t have the time or the skills to get done. If your idea and vision is correct, you don’t need the world’s best coder, you need someone who can code to your idea and vision within your budget.

Your success — or your failure — is all on you. It’s not fair. Own it.


Stop Thinking Money Is the Answer

Don’t spend money until you have to, don’t raise money until you absolutely need it, and don’t sink more money into your startup than it deserves.

Spending money feels like progress. Raising money feels like success. Investing money into your own venture feels like legitimacy. But none of that is true.

As an entrepreneur, your job from day one is to generate money. Most of the time, you have to spend money to generate it. But until you can nail down what that equation looks like, keep your powder dry.


Stop Overthinking What You’re Building

This is a common trap for all entrepreneurs, no matter how experienced they are. The pursuit of perfection is a big part of what drives us. We bake it into our company, our product, our messaging and our culture.

Distill your idea of perfection down to a single sentence, and use that as your guide. When you do this, you’ll discover that a lot of the initiatives on your plate move from definitely-need-now to can-wait-until-later.

“Later” should be defined by a number of paying customers or a revenue milestone.


Listen to Your Customers

The easiest way to build a successful business is to let your customers tell you what to build. But just like “fail early and often,” this is advice that’s much easier to give than take.

When I look back on my successes, the one actionable strategy I keep coming back to is spending time listening to customers. This means figuring out how to best get their feedback, determining what feedback is honest and useful, deciding how that feedback is going to result in growth — and then delivering a return that benefits both customer and company.

When this is done right, it’s almost unfair how easy it is to avoid failure and maintain a constant push towards success. It doesn’t happen overnight, but little successes become bigger successes. And growth, while slow at first, becomes steady.

You may still fail. And if you do, you’ll learn from that failure, but at least you played to win.

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