On Failure

If there’s one thing you’ve got to love about Silicon Valley, it is the embracing of failure. I know and love this because I fail early and often—well at at least often any way. I like to mix up my failures, diversifying them like investments in a well-balanced portfolio. Sometimes I’ll choose to fail at something that requires studying, other times I’ll fail at something that requires coordination, and still at other times I’ll just fail at something brand new.

failure is great

As you might suspect, I wasn’t born loving failure—but it’s one of those things that can just wear you down grow on you. So it makes sense that I have formed more than a secret crush on the SF Bay area. People here fail because they try things out of their comfort zones, and I seem to do that instinctively.

And so this romance with Silicon Valley would have continued blossoming into perhaps a relationship, or at least a dating app—except that I have recently been jolted from my belief of the common acceptance of failure.

The gritty truth was revealed to me in the corner of a crowded hipster-chic hangout in downtown San Francisco. Just 12 hours earlier I had joined two other panelists in presenting a conference session on social entrepreneurship—complete with generous audience participation, inspiring tales of defeat and triumph, and mission-driven work. In the expanse of those two hours we shared intimate emotions of pain and joy—and not just when the audience went from 3 to a multiple of that number.

With all of the good energy flowing, there was an excitement to connect further with attendees and speakers at the post-event mixer. There I met a number of people interested in topics we covered. And it was with one such fellow, that I launched into a conversation about the topic of failure in Silicon Valley. He, a funded entrepreneur straddling two successful startups, lent an ear as I pulled out my pocket violin and waxed poetic about entrepreneurship, the untapped potential of social enterprise, and the amazing embrace of failure in ‘the Valley’.

failure sucks

Though he was listening, he was definitely not buying it. He shrugged off the kumbaya attitude toward failure and revealed that in his experience, those who fail wear a badge for all to see. Like gamification gone wrong, he mentioned that it can tag a person as they seek out new ventures. They are compromised goods in the eyes of investors and potential co-founders. Worse, he said, is how failure ravages the mind. Apparently the knee-jerk reaction to failure is enough to kick your own future efforts in the face—as it can toy with your strategic thinking and make you do things you wouldn’t normally do and avoid things doing what you otherwise would have done, just to sidestep the wrath of a repeat fail. Plus, in the world according to him, you have to be of a certain level or stature to fail forward—if you’re Joe Schmoe a failed attempt may puncture your efforts—causing you to drift and eventually sink; but as a serial entrepreneur with past successes—a failure will probably fetch you an invite to deliver a keynote at a high-traffic event, maybe even a #customhashtag.

along came Diana

My balloon of fragile optimism slightly deflated, I mulled over his candor. The failures that I believed were perhaps leading somewhere, to something greater, a promiseland even, were perhaps—not. And the mere existence of multiple failed attempts might be more an indication to find a new sandbox to play in rather than to find new ways of building.

But you see, just as I was taking the stage for the panel discussion on Aug 31st, 2500 miles away a swimmer was taking to the ocean for a fifth attempt. And while I faced my views on the concept of failure, swimmer Diana Nyad was facing her actual past failure head-on as she set off to swim the open waters of the Pacific Ocean from Cuba to Florida. By the morning of September 2nd 2013, Nyad made history–swimming 112 miles, on her fifth attempt in 35 years, at 64 years old, without a shark tank.

we fail, we are, we move on

Nyad’s feat reframed my meditation on failure. Failure is everything that the successful entrepreneur explained. It is defeating, it can level you, it can brand you ‘uncool’, and it can make you never want to try again.

But if you live to tell about it, that can impact you too. If you can reflect on how you feel about failure, you see, you survived it. What you may have been most afraid of—what would happen if you didn’t succeed—you made it far enough to find out. The road ahead might be messy, uncomfortable, and unknown at times, but you still, are. And there’s that.

After the dust settles on a failure a few things might happen: you might decide to step away—recognizing “the upside of quitting” and freeing yourself to try and potentially succeed at new endeavors.

Or, you might pull a Nyad. Say, “f— it” (not an actual quote of Nyad) I can do this". And then try new methods until you do. For Nyad, she was able to dissociate her past attempts from her ability to eventually succeed. And perhaps the attempts that fell short just fueled her drive to achieve.

It’s the view I have intuitively adopted. Try, fail, quit some, and re-affirm pursuit of some. Playing here–at the edge of rationality, skill, and possibility– is where I feel true potential lies for innovation, progress, and empathy. So, while I don’t doubt that I have many fails in my future, you just can’t spell success without fail. Oh wait….


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