To Succeed, Get to Failing

How failure drives us to be our best selves

For anyone who’s unsure about the future or just unsatisfied with their current job or life circumstances, Roadmap: The Get-it-Together Guide for Figuring Out What to Do with Your Life by Roadtrip Nation provides real-world wisdom collected from our 15 years on the road interviewing inspiring individuals to find out how to create a career doing what you love. This is an excerpt.

Never has a letter had more maligned associations than “F.” F is for failure, F is for fake, F is for fear, F is for fraud. F is for f . . . (Okay, we walked into that one). It starts in school with the dreaded grade F. Getting an F means you under-performed to the fullest extent; you failed, brought shame to your name. There is no lesson to be learned, no helpful takeaway for bettering your performance the next time. It’s no wonder we develop such a deep-seated fear of failure.

Oddly though, despite our fear of it, failure is just part of business as usual — the daily process of missteps and improvement that’s part of getting the work done. Even though this is a bona fide fact, we still hold onto outmoded ideas about the shame and fallout of failure.

Organic life itself is the product of millions upon millions of years of trial and error — why shouldn’t our lives follow suit? Without failure, you can’t improve, modify, or move on. Failure is what gives you the impetus to recraft the beta version of yourself; it redirects your Roadmap. Ultimately, failure is a good thing. Before the first Roadtrip, we couldn’t even fathom the idea that successful people failed. But everywhere we’ve been, accomplished people have shared stories of the failures that changed and improved them.

  • David Neeleman, the founder of JetBlue, was fired from his high-level VP job at Southwest Airlines. His failures and successes at Southwest helped him create JetBlue.
  • Wanda Sykes, acclaimed comedian, actress, and Emmy Award–winning writer, bombed on stage before she became a household name.
  • Howard Schultz, chairman of Starbucks, approached 240 potential investors with his vision for European-inspired coffee shops — 99 percent said no.
  • Jesse Jacobs, owner of the Samovar Tea Lounge chain in San Francisco, was rejected for a business loan by seventy-one banks before finding funding.
  • Ben Zander, conductor of the Boston Philharmonic, experienced failure at a young age when his mother entered his compositions in an arts festival. When the time came to present the awards, the judge held up Ben’s work and said, “These compositions are so bad that this young man should be discouraged from ever composing again.”

Video game designers often cite studies showing that during a game, the most enjoyable moment for the player is actually when they fail and are spurred to try again. You know the feeling: that moment in Tetris when the blocks stack over that top line, or Mario loses his last life, and you feverishly hit “retry” because now you know more about that level, and you know you’re one step closer to beating it. Your undeterred video game brain doesn’t view starting over as reason to give up, rather you see it as an exciting challenge. You keep going until you save the world (or, until your fingers cramp into a claw).

We thrive on trial and error, on solving problems and overcoming obstacles, and no reward is more satisfying than overcoming failure and seemingly insurmountable challenges. Failure incites movement, and a chance to do better.

Using failure as a tool for both self-reflection and further action is something that Paralympian and six-time world champion wheelchair racer Jeff Adams excels at. It would be easy to slot Jeff, paralyzed at age nine during treatment for cancer, into a movie-of-the-week “I overcame my disability” story, but that’s not where the true power of Jeff’s story lies. And while he has never let his disability get in the way of his zeal for sports, and his unwavering determination was certainly a huge factor in his success as a Paralympian, Jeff’s wisdom and growth stem from his relationship with failure.

“When I go out and speak to students, I talk about races I lost. Because I’ve learned more in losing. Those are the times when I’ve grown.”— JEFF ADAMS, Paralympian

One of his crucial failures was in the summer games in Barcelona. “I went into the last lap on a breakaway with two other guys, and in my head it was like, ‘My life is gonna change today. The last lap is the best thing I do. I’m on a breakaway with only two other guys, and they give three medals. Mathematically, this is working!’ But I made a mistake by not checking my equipment enough.”

Jeff’s chair broke in that last lap, spilling him face-first onto the track.

“I lost. It went from being the best day to the worst day. We have it so ingrained in us that it’s always about winning. Maybe it’s about losing, and suffering, and overcoming, and having that courage. But we don’t value that as much as the ‘win.’ So, I won a race in Sydney, and it was a great day. But what did I learn? That it’s fun to have a great day? That’s the weird conundrum in life: You learn so much more when things aren’t easy, when things aren’t fed to you, when things aren’t perfect.”

Consider this: Failure is nothing more than a result. It may not be what you hoped for, but it is an unchangeable fact. You can’t fight or hide from facts. Experiencing failure is like downloading information. It’s a new fact to process. You now know something that you didn’t before. Results — favorable and unfavorable — lead to new actions, more informed actions, more calculated risks, all of which move you closer to the center of your Roadmap.

So let’s agree to take the “F” out of failure. In fact, let’s change society’s definition of the word.

The traditional definition of failure:

Failure
noun (ˈfāl-yər)
Lack of success. Synonymous: Nonfulfillment. Defeat. Collapse. Foundering. Loser.

Let’s try this instead:

Failure
noun (ˈfāl-yər)
A critical action in the process of growth and the acquisition of experience. Synonymous: Create personal growth. To learn. To experiment.

Activity: Think about instances in your life that you, either now or at some other time, labeled as failures. Using the new definition, make a list of those failures. But take it a step further. Make a column next to your list of failures titled “What I Learned” and see if you can identify one — or many — lessons you learned from each failure.

Take a look at these lists. Your failures may still make you cringe, but that’s okay. Focus on what you learned and what you took away from the experience. How have you grown since then? How has your life changed in a good way? How are you doing things differently from how you were before? How are you developing and rebuilding your self-confidence to try again?

Failure itself is not bad. What’s bad is the inability to learn or grow from a situation that might not have gone your way the first time. That is true failure.

Craig Brewer, the renowned director of gritty hits like Hustle & Flow and Black Snake Moan, doubled down on this philosophy when speaking with us, urging us to seek out failure. Early in his career, he and a few friends and family members joined forces on a quest to create a masterpiece. Shirking their jobs and responsibilities in favor of pursuing their dreams, they pooled their savings together and set out to make the great American movie. How did it work out? As Craig revealed with a wistful smile, “It failed, miserably. I mean, there’s close to $30,000 of film that sits undeveloped, and I don’t think I’ll ever develop it.” That flop wasn’t Craig’s last. It was simply the first in a string of many failures along Craig’s road.

Like Craig, we all fail. A lot.

The specter of fear that failure engenders is deep inside all of us. Craig’s solution is the old stare-the-demon-in-the-eye approach. Failure is a part of life, a painful part, a rough and messy part, but an unavoidable one. So embrace it.

When Craig met with our crew, one Roadtripper, Michael, spoke with Craig about how his fear of failure was holding him back from pursuing a film career.

“Are you perfectly clear on the fact that you will fail?” Craig asked. “Are you cool with that? I mean, you know you’re going to fail, repeatedly. The only way you’re going to get good is if you fail. So get to failing. Get that process going. Don’t put that process off, because it’s going to hurt more when you’re older. Because what ends up happening is people don’t want that hurt, so they get married and have kids, and then they blame their families and their circumstances for the fact that they didn’t want to fail. . . .

So if you want that enrichment of success, get busy failing.”

Randii Wessen, a systems engineer at NASA’s Jet Propulsion Laboratory, applied for the shuttle astronaut program twelve or fifteen times in a row. He has never been accepted. In his files he has rejection letters from grad schools, internships, aerospace companies, and even the very laboratory where he now works. “You can measure the caliber of everything by how it handles adversity,” says Randii. “What do you do when you get a lousy grade? What do you do when you get rejected from a university? What do you do when someone dumps you in a relationship? It’s how you pick yourself up that makes you stronger, and that really tells you something about the caliber of who you are as a person.” With that mantra in mind, Randii left us with a chestnut:

“Those who dare, risk defeat. Those who don’t, ensure it.”

Failure is never the end of a story; it’s not even really a failure. Mistakes, and even epic blunders, are helpful instruments as you make your own road. Take risks. Get to failing! If things don’t turn out how you imagined, or you fall flat on your face, modify your method and try again. Failure is an outcome, nothing more. It’s a series of lessons to be learned along the way to better versions of yourself.

From the book Roadmap: The Get-it-Together Guide for Figuring Out What to Do with Your Life by Roadtrip Nation.

Available for pre-order here.

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