Success is when risk-taking self asks sensible self “Can we still be friends?”

Ringmaster David Cohn challenged us to a carnival of #fail. What follows is my total cop out.

In life and in entrepreneurship, I don’t believe in “failure,” “failing” or “fail.” I believe instead that we make mistakes. One minute, I am absolutely right and the next I discover I am absolutely wrong.

It is at these “ooops!” moments when the outlook becomes bleak and I see my project, my ambition, my plan as a failure. My life in entrepreneurship becomes a spectacular succession of risk-taking and disappointed aspirations beginning in awkward childhood, continuing through painful adolescence, blossoming in adulthood and now coming to fullness in middle age.

This is when I have to say “Stop!” Risk-taking self asks responsible self: “Can we still be friends?”

The essence of this lesson is contained completely in Todd Rungren’s brilliant and wise song.

LaLaLa LaLaLa LaLaLa LaLaLa LaLaLa LaLaLa LaLaLa LaLaLa LaLaLa LaLaLa LaLaLa

We shake hands and make up. This friendship with myself means I will see the experience as a learning not a failure. To judge a life experience as a failure is to invite a mindworm into your life, one that will swell to monstrous proportions with every inevitable misstep and block your path forward. Banish the mindworm!

This doesn’t mean I shove my less-than-successes under the rug, but it does mean that I accept them fully. Indeed, in private and with special friends, I honor my failures. This is part of entrepreneurship. It also answers my personal question: What is success?

I won’t bore you with a personal story because I believe that no matter what our material success, disappointment in ourselves is too often the human condition. And after long practice I have learned that self flagellation is the root of more disappointment. So although I might fail to change the world’s view so that it no longer condemns “failure,” I can at minimum adjust my own point of view to be friends with myself, and view my seemingly endless capacity to make monumental mistakes with compassion and acceptance.

“To err is human, to forgive divine,” said Alexander Pope. My goal is to extend this divinity of forgiveness to myself and others as much as I can day by day.

“Make no mistake, Let’s end quickly. But can we still be friends?”

The would-be entrepreneurs among us must nurture self love, because it is with passion and self confidence that we beat back the dark times and shake the feeling of being a total doofus. I know this from personal experience and from interviewing dozens of entrepreneurs about their failures and successes.

What I learned from these interviews is that the key to “failing” well is to understand when to quit. You’ve made a mistake, you’re digging a hole and it is getting deeper. Stop digging — now! Honor the work you’ve done and move on. It’s a new day and a new game.

“Fail” with grace. Be delicate with your fragile self. It’s not about being tough. It’s about being real.

“I try to live my life where I end up at a point where I have no regrets. So I try to choose the road that I have the most passion on because then you can never really blame yourself for making the wrong choices. You can always say you’re following your passion. “ Darren Aronofsky

Easy for Aronofsky to say – look at all his success. But look at all his wackiness too. His first movie, “Pi” was about Hasidic Jews, the Torah and the stock market. Sound like a blockbuster to you?

Life really is about following your passion, because life without passion is empty. But don’t kid yourself and think there is only one passion. There are many, as Silicon Valley’s Randy Komisar told me in an interview nearly a decade ago.

And one very important passion for everyone is family and friends.

“Grains of sand one by one, before you know it – all gone.”

Part of being friends with yourself is being there for your friends and family. With their welfare in mind, recheck your professional passion alignment regularly. The entrepreneurship direction that makes sense at 20 years old might not make sense at 30, 40, 50 and beyond.

To add some grist to the mill, and to fortify what might seem a specious argument, I’ve included a syllabus of sorts and some favorite teaching moments.

Yippie! Another failure!
If you are on the entrepreneurial path, I’d suggest visiting the website of my friend, Barry Moltz. Barry’s books and his website are a treasure of insights on entrepreneurship. I coached Barry through his first book and wrote the stories about start-ups in it.  It’s safe to say that our work together on “You Need to be a Little Crazy,” was a humble breakthrough in  discussing the reality of failure.

Kathryn Schulz is a Wrongologist, and she says:

1,200 years before Descartes said his famous thing about “I think therefore I am,” this guy, St. Augustine, sat down and wrote “Fallor ergo sum” — “I err therefore I am.” Augustine understood that our capacity to screw up, it’s not some kind of embarrassing defect in the human system, something we can eradicate or overcome. It’s totally fundamental to who we are. Because, unlike God, we don’t really know what’s going on out there. And unlike all of the other animals, we are obsessed with trying to figure it out. To me, this obsession is the source and root of all of our productivity and creativity.—Schulz from her TED talk “On being wrong” | Video on

And if you are feeling down, it’s always fun to cheer up with your friends, families and neighbors and don’t forget your online friends. I like to Twitter “You’ve gotta have heart” from the musical Damn Yankees when the Knight Foundation is pruning through its proposals and some are learning that their first volley at entrepreneurship didn’t make it. I especially like Peggy Lee’s version.

Here’s the original assignment from DigiDave.
What: A failure in your life (personal or professional) that has lessons. It must be your failure and you must take responsibility. But this will be a safe space to discuss our failings and what we can learn from them.
The Details
We talk about ‘failure’ a lot in the online journalism community. It can be a bit of a buzzword. “Let’s fail early and fail often” is a motto I personally have adopted. But the true value of failing is if we can share the lessons learned. We probably do this all the time without knowing it – but rather than try to condense our lessons into 140 characters, let’s create a safe space this month to discuss a failure that others can learn from.

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Sally Duros believes good writing is a superpower. You can connect with Sally on , and on Twitter.