Failing to Fail

definition failure

As I venture (or should I say “re-venture”?) into the world of the self-employed creative knockabout, my mind is very much centered on the business side of the business. Sure, I’d love to dwell solely on the creative side, but this other realm is a necessity if I want to be able to live long and prosper doing what I love.

I have been here before. I couldn’t wait to be here again — after almost a decade attempting to inspire the creativity in hundreds of young high school minds. On the journey back I discovered that my goal of running my own business again is not something I share with many other creatives to whom I’ve spoken. Most of them would rather deny that the “other side” exists and not deal with it at all, but there is something rewarding and empowering to me in balancing both the business and the creative. (God did not create me ambidextrous just for His own kicks!)

I think the biggest obstacle to venturing on one’s own (okay, the second biggest after being able to afford things like food and proper shelter), is the fear of failure. Do I have this fear? Abso-freakin’-lutely! Is it stopping me? No.

Why is that?

There are many things I’ve learned in my 42 years, and one of the biggest is that you never know unless you try. At the end of their lives, more people regret the things they didn’t do, than the things they did. If I didn’t try, I would always regret it. Plus, I’d be a hypocrite. Every year that I was teaching high school English and Reading, I read a passage from a book written by Michael Jordan, I Can’t Accept Not Trying (Harper San Francisco, 1994). He points out that when you think about the consequences of missing “a big shot,” you think negatively and that, in turn, becomes fear, fear of failing.

So, can there be a positive way of spinning it? Positively. “Sometimes failure actually gets you closer to where you want to be. If I’m trying to fix a car, every time I try something that doesn’t work, I’m getting closer to finding the answer,” writes Jordan.

“Designers Must Learn to Embrace Failure” written for Time by Tom Kelley and David Kelley calls the fear of failure “the single biggest obstacle people face to creative success.” Although creatives are more likely to experiment more often than non-creative types, they are prone to more failure, but as Jordan said, they learn constructively from their failures.

According to the two Kelleys, “The inescapable link between failure and innovation is a lesson you can only learn through doing.” If you never try, you never have the opportunity to create something great, regardless of how many tries are necessary. The Time article offers an example from John Cassidy’s book, Juggling for the Complete Klutz, that struck home. Cassidy begins with “The Drop.” Toss three balls in the air at once and let them drop. Repeat. There, you failed. Now when the balls hit the floor, again and again, it’s the norm. When learning to juggle, the balls are on the floor more than in the air, but the more you try, the more times they end up in the air. The more the success you can celebrate.

This analogy reminded me of my son’s early attempts at skateboarding. What did he spend 90 percent of his time doing when he was teaching himself to skateboard? Falling in the grass, very dramatically … on purpose. Yes, he was 3 or 4, and very demonstrative by nature, but he was learning how to fall the right way. By the time he was 7, he was on giant ramps and in huge bowls, or pools, skating in competitions against teenagers twice his size. When he changed sports to wakeboarding at 13, he spent his time trying and landing consistently all the small basic tricks before going big. All those people who came out to go big first are no longer even in the sport. My son had to fail/fall a lot to become world-ranked in the sport he loved. Did he know he was teaching himself to fall first to be successful later? Probably not.

Watching him and telling students for years they could do whatever they wanted in life, finally sank in with me. I’m not planning to fail, but I will learn from it and grow from it, and make it worth the fall.

As Jordan said, “If you are trying to achieve, there will be roadblocks…. But obstacles don’t have to stop you. If you run into a wall, don’t turn around and give up. Figure out how to climb it, go through it, or work around it.”

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