Mastering The Art Of Failure


I find a lot of poetry in the lives of startup entrepreneurs, mostly for their willingness to venture into the unknown. Like poets exploring down the page, across lines, startup adventurers summon their technical abilities, their learning, their audience – their courage – and try to lead us to where we all haven’t been before or to where we can see something familiar in a brand new way. And they teach us a lot about mastering the art of failure.





Poetic Strike Outs

A well-known line and one of my favorites, comes from the poem “One Art” by Elizabeth Bishop: “The art of losing isn’t hard to master.”  Whether it’s the keys to the car or the company we pour our souls into, we lose a lot. Far more often than we win or gain. Think of baseball hitters. Even legendary batters only record a hit about 3 out of every 10 trips to the plate. Yet no one talks about a nearly seventy percent failure rate. That would be depressing, and it would miss the point. Success comes with a lot of whiffs. That’s exactly why we appreciate and applaud victory. In sports anyway, we tend to glorify success and quickly forget defeats. Can we cultivate the same habits and perspective in business?





Nearly every entrepreneur I’ve interviewed for the pages of KillerStartups has had a startup go bust before putting a viable company together. Despite education and training, despite all the accelerators and incubators out there, despite all the resources available online and in the tactile world–not to mention the tales of the ones who’ve gone before–it’s seems that trial by fire is part of the rite of passage. We need to test ourselves, learn our strengths and weaknesses, write lousy poems, take awkward swings, work through things going wrong before we become graceful in our endeavors.


“Lose something everyday. Accept the fluster”


OK, so you shouldn’t make foolish choices for the sake of experiencing failure. Doing things correctly requires meticulous attention to detail, incredible persistence and resiliency. There are smart failures, where our best efforts fall short and we sleep knowing that we did everything within our power to succeed, and there are dumb mistakes that we don’t need to make. But to stay cautious and shy away from the pain of screwing up only delays the inevitable. By not failing, we stunt our growth.


Hip To the Missteps

Another source of inspiration I find helps stare down potential disaster is jazz clarinetist Artie Shaw. In the Ken Burns documentary on jazz, he said something to the effect of: “If you don’t fail, you’re not trying hard enough.” The only way to know the limits of your ability sometimes is to go over the edge.





It hardly needs mention that everyone is still talking about Facebook’s stumbles since going public, yet the company just passed the billion user mark. Insane. Success has a way of magnifying mistakes, making them more visible to more people. It’s not easy to have your shortcomings on full display, but with an ego left on the shelf, there’s almost always room for correction for our errors, and always something to learn.


How many mistakes are truly fatal? That’s a tough question to answer. But not trying, not embracing the risk of failure – that’s the only path that teaches us nothing.


Photo Credits

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