The Rewards of Failure


I work on 20Skaters, ThreeFortyNine, Ontario Startup Train and a few others. My vanity site is

Failure. It seems we talk about it more than success in the startup world. Mark Evans suggested that in “Canada, unfortunately, failure is a four-letter word”. Our fear of failing here prevents us from reaching, from leaping, from succeeding.

Some other guy suggests that safety nets are for failing. The idea that allowing yourself the space for failure becomes a self fulfilling prophecy.

So which is it? We’re too skeered of failing or we’re too prepared to fail?

3564244382_cb57a92511_mHere’s the rub. Until you accept that failure is a possibility, you’ll get nothing started but until you decide that failure is no longer an option, you’ll never succeed.

Step 1: Accept that failure is a likely and very real possibility. Focus on squeezing every last drip of learning out of every misstep.

Step 2: Decide that failure is no longer an option.

Another rub. There are very real rewards to failing that are attractive and appealing. Yes, rewards. Their appeal is strong, Dorthea Brande calls it the Will to Fail. For starters, having tried and failed allows to spend the rest of your days saying you tried…

“I had that idea”…..”Ya I had a startup but the timing wasn’t quite right”…..”I took a shot at it but I had the wrong cofounder”

Trying and failing keeps you from having to see what your idea looks like when executed on. Executing on a idea is ugly. It’s no longer a pretty, puffy dream with dollar signs, friendly customers and investors. It’s a real business that you had to white knuckle into submission. Chances are it was not pretty and it changed you as a person, not always in a good way. The difference between the finished work and that idea you had is often massive. Not having to ever see that difference is appealing. Leave me to my dreams please!

There are other rewards to failing, the point is that failure isn’t necessarily this ugly endpoint that you naturally navigate away from. It’s important that you consider what’s appealing to you in failing and what may actually attract you to it. You will never succeed until you choose that failure is impossible. Yes, it often is just that simple.