8 Ways to Fail Your Way to Success

8 Ways to Fail Your Way to Success

One designer's take on how to fail to succeed
Megan Crabtree
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“The real measure of success is the number of experiments that can be crowded into 24 hours.” —Thomas Edison

Most projects start with confidence. We’re going to crush this! Then come the mistakes. We squirm. We become riddled with self-doubt. Suddenly the prospect of success seems like a dim light bulb.

At some point, though, we come to accept that screwing up is a key part of the creative process. Think about how kids play: They don’t think, they just do. And if the whole contraption comes crashing to the floor, they laugh at the mess and start over. (Or throw a fit, but hey, they’re learning about emotion, too!) Point is, when you embrace setbacks and don’t let them cripple you, you’re more likely to get across the finish line.

Maybe we should stop talking about failure and call our botched projects “experiments." And let’s take a cue from Edison and crowd as many experiments into 24 hours as we can. Here are eight ways to fail your way forward.

1. Keep it basic

Don’t start by trying to find a fully developed solution to a problem. Keep fidelity low at first to allow others to see the possibility in the idea, not the flaws. The higher the polish, the more likely you’ll get the wrong kind of feedback.

2. Design impossible tasks

Such as: How might we create a new color? How might we live forever? Moonshoot thinking frees us from limiting ourselves, helping us produce a bunch of wild ideas. None of them will be right, but they’ll rev the engine of our imagination.

3. Don’t assume your final format

What are you making? Will you be hand sketching? Wireframing? Sculpting out of modeling clay? Drafting a written piece? Even when our end goal is to end up on screen, it is often helpful to start in a different medium—and maybe a tactile one.

4. Set a goal for failure

Follow this advice from 100 Days of Rejection by Jian Jiang: “We will fail at least 30 times before we figure out the right solution.” Lowering the stakes and making a solution less precious makes it easier to generate a bounty of ideas to build from.

5. "This is a bad idea, but…"

Every time you throw out an idea, start with, “This is a bad idea, but what if…” That helps you practice non-attachment and prepare for the reality that most of your ideas won’t stick.

6. The Shame Gong

Every time someone makes a mistake or fails, hit the gong and have the team whisper "shame" in unison. It actually lowers the barrier for admitting to failure and makes for more honest, less bullshitty brainstorms. It also lightens the mood when you’re struggling with a particularly tough challenge or client. Plus: Ringing a gong is just fun. Missed a line item from the plan? Shame. Couldn't guess the grape of the wine at happy hour? Shame!

7. The mis-name game

Walk around the room and loudly, courageously, and boldly point at objects and yell out the wrong name for them. Do this for three to four minutes. Then pause and debrief. What was that like? Why was it difficult? There is a stubborn voice in your head telling you what is wrong, infeasible, impractical, too risky. The exercise reminds us that there’s a voice enforcing our fear of failure that can overpower our ability to take creative risks. Our job is to learn how to quiet that voice at the right moments to break out of the expected.

8. Worst experience ever

Design the WORST _blank_ experience ever (airplane/shopping/dining/laundry) and really encourage people to visualize it. Then use that to design the best version using an insight you learned from the worst. So, if the worst dining experience involved a waiter who would not leave you alone on a romantic date, what does that say about the key elements that make or break a date?

One final note for aspiring leaders: Don’t be afraid to talk about past failures and what you learned from them. Admitting failure will help your team gracefully shut down initiatives that aren’t working and move on to the next thing. Now get out there and gong.

Thanks to Tom Kelley, Kenneth Robertsen, Neil Stevenson, Olivia Vagelos, Eri Sugiura, and Sally Madsen for contributing to the piece.

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Megan Crabtree
Megan is a designer, illustrator, crafter, southerner-at-heart a little too obsessed with board games, bookstores, and pictures of babies.
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