Comfortable with Uncertainty

Posted on: Friday, February 26th, 2010

When do you know? I mean, really know?

Slumped into my couch, pale from a lack of sleep, nose red from the cold he can’t shake, the CEO shook off my suggestion about this being the time to hire an assistant.

“I know, I know,” I said, “you’re a cheap bastard,” and we both laughed.

“It’s not that,” he said after a pause, “it’s just that—well I know we should be hiring for what the company is going to look like in six months but what if it turns out I have to fire them down the line. What if I’m ahead of the game?”

I told him: “You’re at that point when, if you don’t hire enough firefighters, you’ll never get out of firefighting mode.”

“This little start-up of yours,” I continued, “is about to become a company.”

And he looked at me with a mix of relief and sheer terror—and just a touch of nausea.

Later that week, I got an email from another client returning from a board meeting.

“We’re not dead,” he said in a slight nod to Monty Python. They’d given him one more quarter before they’ll decide if they’ll fund that last half million everyone thinks will take the company to break-even. Of course the problem is this is the third “half-million to break even” the company has needed in the last year.

Still another client calls. He’s preternaturally calm. Spooky, even.

“Well my man…we’re burning a quarter million a month and I’ve got a million in the bank. If we don’t close this deal [a deal that will net the company a few million as the result of a sale of an asset], then it’s all over.”

But then he says the really spooky thing; he says: “I think.”

When do you know it’s time? When do you know it’s really time to start the business, shut the business, expand the business, invest in the business, quick your job, end the job search and take the offer on the table, leave your spouse, marry your girl/boyfriend, move to Australia, come home from Australia? When do you know?

“A warrior accepts,” writes Pema Chodron in Comfortable with Uncertainty, “that we can never know what will happen to us next. We can try to control the uncontrollable by looking for security and predictability, always hoping to be comfortable and safe. But the truth is that we can never avoid uncertainty. This not-knowing is part of the adventure. It’s also what makes us afraid.”

I think the only answer to the plaintive poignant question of “When do you know?” is embedded in the bit of Buddhist wisdom: You can’t know–not really, anyway.

Maybe the hardest part of leadership—be it leading a company, a family, a relationship or simply your own life—is that often times you don’t know and you have to still have to act. Leadership in some ways is built on learning to be comfortable with not knowing, with imperfect knowledge, with the inherent uncertainty of it all.


this came from Jerry Colonna, Fred Wilson's old partner at Flatiron Partners.