3 Ways to Redefine Your Relationship with Failure

Have you ever heard anyone praise failing?

What a great job you did failing! I wish I could fail like that. Or, I heard you failed, congratulations!

Failure and me have a long and troubled relationship. I keep trying to ditch it and it keeps chasing me. It makes me feel less than and not good enough. It holds me back from trying new things (because I failed the first time) and keeps me from living freely, authentically, and whole-heartedly (because I’m afraid of failing.)

As it turns out, I owe failure an apology. One of those It’s not you, it’s me apologies, because it actually turns out the problem in the relationship is not failure. It’s me.

I know it’s counterintuitive to think failure can help you succeed, but here’s 3 ways to turn your relationship with failure around:

1. Try to fail.

Steve Levitt, professor of economic at the University of Chicago says, “I always tell my students — fail quickly. The quicker you fail the more chances you have to fail at something else before you eventually maybe find the thing that you don’t fail at.”

At first glance it seems Levitt is a posterchild for success. He was listed as one of Time magazine’s “100 People Who Shape Our World” in 2006 and is co-author of the best-selling books Freakonomics and SuperFreakonomics. However, in a recent interview on failure he states, “I’ve mostly failed at everything I’ve ever done.”

Failure has a profound and powerful stigma associated with it. Developing a healthy relationship with failure is challenging. What I’m finding is the more I fail the more comfortable I’m getting with it, the less attached I am to the label and the idea that it defines me somehow. By putting myself out there to fail or succeed I’m having to dig deep for that nugget of self-confidence that can withstand both failure and success.

Thanks to Levitt, these days I can’t fail fast enough. What a relief. I get to throw myself into everything I love because I’m actually trying to fail.

2. Do a pre-mortem.

A pre-mortem is like a post-mortem, where a medical examiner figures out what killed a patient, except it’s done before. Before the patient theoretically dies, but for our purposes before your project fails, before your big effort disappoints, before your product falls flat.

Pre-mortem is a phrase coined by Gary Klein, a cognitive psychologist practicing since 1969 who studies decision-making. Klein illustrates this by having listeners envision a hypothetical failure of a six-month effort at the beginning of the project. The project doesn’t just fail, it’s an outright disaster. He then has participants spend two minutes writing down all the reasons this project failed.

By doing this at the beginning of a project we get clarity that hindsight provides before it’s over. Instead of focusing on all the ways our project (yours, mine) is destined to succeed, he’d have us reverse that process and see all the ways it can fail. He calls this “prospective hindsight,” imagining that an event has already occurred, and says it reduces over-confidence, something most of us have too much of at the beginning of a good idea.

Klein asks participants to come up with one thing that would help the project, which drums up helpful ideas that would have never come to the surface otherwise.

Doing a pre-mortem on a company level takes away the fear of individuals not looking like a team player because everyone is being asked to assume failure instead of one person trying to find the courage to speak up. It also reduces the likelihood that a postmortem will have to be done on a failed project.

3. Celebrate failure.

Our economist mentioned above, Steve Levitt, suggests that celebrating failure is the only way to make it acceptable and shift the stigma.

Yes, celebrate as in throw a party. Tell your friends. Post it on Facebook. I failed!

If that’s too much too fast, try exploring the feelings failure draws up for you from a nonjudgemental perspective or making a list of the positives that come from failure, such as an opportunity to improve the next time.

If we allow for Levitt’s concept that “failing gets something out of the way that keeps you from finding the thing that you’re actually going to be good at,” that’s definitely a reason to celebrate if you ask me.

(As a sidenote I failed miserably in trying to publish this article. I submitted it to two major online sites and was rejected by both. Thankfully it helped me revise it about ten times to make it a piece I’m really proud of. Cheers to that!)