Why I’m an Entrepreneur Who Is Afraid To Fail, and You Should Be Too

Success isn’t about risk tolerance, it’s about risk mitigation

Joe Procopio


Photo by Fionn Claydon on Unsplash

I’d like to debunk some conventional wisdom about success and failure in business. Namely, this broken circle of logic:

A. Entrepreneurs and business leaders have to take risks in order to succeed.

B. Younger people are more likely to take risks than older people.

C. When taking on a new challenge or starting a new business, older entrepreneurs and business leaders are more likely to be successful than their younger counterparts.

A plus B does not equal C. Why?

Conventional advice about risk and failure is usually poetic garbage

Most of the platitudes associated with risk and failure are often just a bunch of word salad — phrasing that sounds profound when you first hear it, but on reflection doesn’t make a whole lot of sense.

Take your pick from these Successory-style mantras that I know you’ve heard before:

  • Fortune favors the bold.
  • Go big or go home.
  • Fail nine times and get up 10.

To hammer my point home, that last one is not a quote from Steve Jobs or Michael Jordan, but rather from Jon Bon Jovi. For the risk-takers among you, he was a musician who found success in the 1980s with hair-metal hits like “Livin’ on a Prayer.”

It’s very romantic stuff. But in a vacuum, those slogans are just a salad of nice words tossed with a low-calorie motivational dressing and served by a guy on top of a mountain with his arms outstretched.

Failure is something you should expect, not strive for

I’ll be the first one to tell you that it’s OK to fail. And in fact, I’m right there with the throng of folks who will encourage you to go out and take risks, especially when you’re young.

The thing I don’t want you to do is spend years — or even an entire career — not realizing your potential because the system told you that success can be found in a title or a corner…



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