Uncertainty: The real story of leading

Let us now praise those who search, who do not spin a story of imagined success, or a story of Phoenix-like recovery from failure. Let us praise not knowing for sure, because that is the sure thing – in business, in startups. In life. Let me now praise Path. This aptly named startup is getting interesting – that is, if you’re interested in leadership.

“…We’ve made a lot of mistakes,” said Dave Morin, CEO of Path, a San Francisco startup that saw a lot of attention in the business press and from celebrities with real cool cred in tech. (Ashton Kutcher and Brittany Spears. You be the judge.) And, according to the NYTimes update, Morin also played the flashy role of first and best believer in the inevitability of his vision. For a leader like him to confess to mistakes after playing the tech celebrity so well, let us praise that reflection and humility.

dark path

Most of us know two narratives about about leaders and startups. The first is the story of a leader with a brilliant idea. With some adjustments along the way and nod to the hard work behind the curtains, the story is one of seemingly inevitable success. The leader is responsible for it, with appropriate nods to the team that made it possible. It’s the revered American story of individual effort and independence.

The other story is “what I learned from failure.” We love this story because it is in fact mythic. Think Moses in the wilderness, Jesus in the desert, Dante’s hero in the dark wood. If hubris is the hero’s flaw, the desert teaches her humility, also known as self-awareness. I don’t know Dave Morin, but it sounds like he’s in the desert. I’m grateful that his story isn’t a simple version of success or failure. Morin is more like you and me, not knowing for sure. Until “it” happens, we don’t know for certain what “it” is

Uncertainty is almost unbearable for prolonged periods. There’s a good argument for experimenting with action, even any action. It’s the empirical way we cut a path through the dark wood. Those experiments may seem to how we pulled ourselves out of quicksand. But they’re still only techniques. And they don’t always work. Better than a lesson from inevitable success and instructive failure is the lesson that we have to face uncertainty alone and look within. What sort of person makes it out of the desert?

In my experience, leaders – maybe everyone – want something from work. Beyond a living, we are always seeking something else, too. Purpose, power, acknowledgement, respect, community, competition, meaning, and many other things.

The leader who makes it through the desert is the one who finds her purpose under the company, the product, the team. What makes us want to do this, our chosen work? What do we want to get out of it? That is the theme of story we are in.

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