Fail Your Way to a Successful Business

"If you're not failing every now and again, it's a sign you're not
doing anything very innovative."
-Woody Allen

Although we may all agree that some of Woody’s failures weren’t innovative, you can’t argue with the wisdom.

So many entrepreneurs (myself more than most) fail to succeed because we fear failure itself. You can’t blame us though , can you? We live in a society where every minute detail of our lives is available to the public through a simple Google search. We’ve seen so many people’s lives destroyed because of a very brief lapse of judgement. People get too scared to colour outside of the lines, just in case it results in public scorn.

In our businesses, we worry about picking too narrow of a niche market. We’re nervous about sharing too much of our personality on the company blog. We are downright terrified about promoting ourselves online. Instead, we keep running our boring business, never taking risks. Maybe we don’t actually “fail”, but we also never make it big.

Although not my favourite sport, let’s use baseball as a prime example.

Josh Hamilton, a left-fielder from the Texas Rangers, batted .359 to lead the league last year. He had 518 at bats  in the season. That means he technically failed 332 times he went to the plate. As a reward for failing almost 2/3 of the time, he was paid just over $3,000,000 last year. I don’t know about you, but I’d be more than willing to publicly fail 332 times a year for $3,000,000. How about you?

What about in the business sector?

  • Coke and Pepsi are still the 2 big names in cola; the companies that brought us New Coke and Crystal Pepsi.

  • Google has failed many times with its products; most recently with Google Wave.

  • Apple waited a long time to finally call their latest version of iTunes version 10.0. The big new feature? Ping. How often have you used Ping lately?

  • Facebook constantly updates its product without letting the users opt in, often enabling private information to go public. People are frequently enraged by this behaviour, yet over 600 million people use the service.


These are all big, public companies, all making really dumb decisions. And, at the time, consumers were outraged (or worse, unexcited and silent). Despite these failures, these are still among the biggest companies on the planet.

You won’t always succeed. You might not even succeed most of the time. That’s not the point. Take risks, lots of them. Try out new things, go off on tangents from time to time.

  • Pick a really specific niche to market to. (“moms in their 30’s with teenage daughters” instead of just “moms”)

  • Advertise somewhere you haven’t before.

  • Try cutting out services you usually spend lots of money on (no, utilities don’t count).

  • Launch a new product you’ve been too nervous to try out.


Some of these will fail miserably. Great! Now you’ve just narrowed down your list of possibilities. If you know that 1/10 of your ideas will be great, and you’ve failed 9 times in a row…guess what? You’re about to do something brilliant!