Comfortable with Uncertainty

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, quit 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 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.

  • Tereza

    Great post Jerry. This is a great complement to the ‘ship it fast and iterate’ mandate today, which is an about-face from what we were all taught.

    A great manager I worked for once said, ‘you don’t need perfect information. You just need slightly better info than your competitor. And a more decisive plan of attack.’.

    I do know that every single time in my life I’ve ignored my gut, I regretted it. Gotta tune in to the gut.

    And boy has motherhood been a surprisingly rich place to flex those Uncertainty and Gut muscles, every day. Which school? I don’t know! This nanny or that nanny? Who the F knows! You do all the research you can but no answer will ever appear except in your gut. So you trust it, and be ready to pivot when you learn more.

    And sometimes, the formal “facts” obstruct your view into what’s really going on. Study up, but trust the gut.

    • jerrycolonna

      Great point Tereza…facts can definitely obscure the view. Trust your gut is right…especially, too, your intuitive gut.

      • Charlie Crystle

        gut = informed intuition.

  • bijan

    great post. I reblogged that last quote.

    • jerrycolonna

      Thanks Bijan

  • sea

    I’ve tried to type this comment several times. Each time I delete what I was going to say for fear of somehow being found out.

    What am I so afraid of saying? Something along the lines of I wish leaders were brave enough to admit to being afraid. To tell the truth about risk and cash flow and uncertainty. To stop assuming that employees are so stupid that we don’t know what’s really going on. Especially in 2010, when most of us know enough to make the CEO’s blood run cold.

    I also wanted to say how much I love that you love Pema Chodron. You called her your gateway drug to Buddhism recently and that made me giggle. At work, I often ask myself “what would Pema do?” Usually the answer is “stay, stay, stay.” Although, admittedly, some days it is harder to stay than others. Today is one of those days…

    Anyhow, thanks for the blog. It’s always a joy to spend time here.

    • jerrycolonna

      You’re very welcome…and you’re welcome at this place that’s forming here.
      I can’t tell you the number of times I hear Pema’s voice in my head saying…”Sit. Stay. Stay.”
      Yes, folks, like she’s speaking to a dog. More to the point, it’s a pithy instruction for actually taking charge of your own mind and not chasing every little bouncing ball that shows up.

      Someday I’ll find a way to weave together even more thoroughly all of these amazing teachings and connect them to the every day of business and life.

      • panterosa,

        How does one teach uncertainty with intelligence? Isn’t it a form of know thyself which helps one see the world and know where to fit in and when. Who are you? is a never ending question which remains open even after we die.

        People are often more uncomfortable in knowing (it’s time to break up, quit the job etc.) than in the uncertainty. The uncertainty brings freedom.

        • jerrycolonna

          I think it’s learning to relax with the uncertainty that brings freedom. I think part of what I was trying to address was the paralysis I often see setting in in the face of incomplete data.
          Learning to be comfortable with uncertainty can not only ease anxiety but facilitate decision making.

          • panterosa,

            Can you teach people to embrace that freedom and begin the adventure? Can you rewire their guts to respond with ease not anxiety? Can you build an optimist?

          • jerrycolonna

            Not sure about building optimists but I think people can learn to see the underlying patterns that cause the unease and anxiety and interrupt enough so that no longer become the habituated response.
            Seeing the pattern, becoming mindful of it all, was and remains a powerful tool in my own life and one which I encourage with all my clients. And there are some awesome adventures on the other side of anxiety.

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  • jseelig

    Great post. I have always said that the challenge that we all share is that in life there is no control group. We don’t get to see what would have happened had we made a different choice…

    • jerrycolonna

      I love that image, jseelig. It’d be great if we all had a “control” version of ourselves to see what would happen if we did nothing.

  • Peter Cranstone

    When do you know?

    You don’t – and as long as you know that, then you know. Years ago at my first startup we were building (me and the other guy) a data compression product. At it’s core was an algorithm that would compress all the data in the universe. If we could do it, we’d be able to go back to the big bang with those few elements (which we saw as zero’s and one’s) and from that arrive where I’m typing this post.

    As you know my partner died and I set to reverse engineering the code and learning the math involved. Essentially the algorithm when run correctly could predict the future – can you imagine it, you would know.

    Well when you really, really, dig into the math we ended up with this perfect mathematical “cup” which you would feed in random data. It would do it’s thing and a bit would disappear – sometimes. It didn’t matter because you can always run it again and this time it would disappear. And yes when you reversed the algorithm the bit would pop back.

    One of favorite questions (never answered) was where did the bit go? Another dimension, perhaps? If I could only see into that dimension I said to myself I would know.

    But alas there was this problem of the occasional “bit”.

    Think of this bit as knowing… when do you really know? If we could have predicted when that bit was going to be a problem we could have solved the problem.

    But we couldn’t – of course God doesn’t want us to know the future (what would be the fun of living) so he carefully hides it inside our heads.

    The missing bit described by Pema Chodron (I’ve brought her books – thanks) is uncertainty. I came to grips with uncertainty many moons ago – and I learned that you will never know everything, and that missing bit is the piece that keeps us all going.

    • jerrycolonna

      The missing bit not only keeps us going, it keeps it all interesting.

      • Peter Cranstone

        Absolutely – hard to believe that it’s just a bit. Here’s the other piece of advice I also learned. When you do you really know? When the money runs out. And it always does if you’re not creating value or getting carried away with those expenses.

  • kareem

    Great post, Jerry. I recently watched a movie about Crossfit, an intense / ridiculous workout program that I follow. The movie’s called “Every Second Counts”, and it’s about the annual Crossfit games, where they name the world’s fittest man.

    One of the competitors said something that stuck with me (in Crossfit, business, and life):

    “Crossfit helps you be comfortable with being uncomfortable.”

    One of the biggest unexpected benefits that I’ve gotten from Crossfit is being able to get through a life or business situation despite being (at times extremely) uncomfortable.

    So happy you started a blog, BTW. I heard your interview with my pal Andrew at Mixergy, and am really appreciating your insights here.

    • jerrycolonna

      Thanks Kareem…let’s all keep trying to be a bit more uncomfortable.

  • Mike McGrath

    I believe from experience that intellect and emotions can often inhibit an action that is instinctive. We have grown our intellect, and have developed ways to cope with feelings, but most ignore developing the most primitive part – the instinctual or “gut” reaction. Once you let go a bit, its very liberating.

  • Charlie Crystle

    startups are about bringing light to the darkness.

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  • Dan T

    To me it’s all about possiblities vs. adverse consequences and barriers vs. paths. The more I experience, the more complex the model becomes based on all the new input. I can imagine more possibilites, but I see more potential downsides. I see more potential barriers, but I have figured out more ways to avoid them or get around them. In the end, I get comfortable knowing that I have thought it through, have a clear vision for the possibility, can recover from worse case results, can anticipate multiple barriers and have a few different paths in mind to avoid or get around them. Sounds like a football coach planning for the season or a game.

    • jerrycolonna

      I think that’s right dantinpa. In the end, though, I think you have to relax enough to know that you can’t anticipate all the moves and trust that your gut knows–that the collective wisdom of the team you’ve built knows–the right way to respond.

      • Dan T

        damn, that is a spot-on comment. “the collective wisdom of the team you’ve built knows – the right way to respond”. I had a situation in the past where I failed to build the team I needed around me. In hindsight, I was arrogant – I got comfortable that I (ME, not WE) could respond. Although I tried to build that team, a few key pieces were missing and when WE needed to respond, I did not trust the “collective wisdom”. We/I floundered for a few months and ultimately rebuilt the entire team.

        • jerrycolonna

          So trusting ourselves, trusting the team is a way through the uncertainty.

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  • Deb

    Sit. Stay.
    When the movement originates from the spaces between the breaths,
    from the pause between the note.
    then, oh then the dance is stunning.
    Stop sitting.

    • jerrycolonna

      Exactly so, Deb. Sit. Stay. Dance. The perfect prescription.

  • Bags

    Life is scary… terrifying even. But that’s part of the fun.

    • jerrycolonna

      It’d be pretty damned boring without the fear, now, wouldn’t it?

  • chad

    Jerry, great post. My 2 cents:

    Having uncertainty is it’s own knowing. If you are uncertain about success, you can know you wont attain it.

    Living with uncertainty is creativity in essence and also it’s own knowing. If you live in the uncertainty of the next client, product release, or whatever, you stand in the uncertain position of creatively directing the flow of uncertain events toward success. You will be successful.

  • Julie P

    Great post; I think some people (leaders) have just enough stability to trust their gut and fly into darkness. For me, I need just enough information/cash/hope/love/vision whatever that stability is rooted in to take hold. When I have a bit of stability THEN I can fly into the darkness.

    • jerrycolonna

      Why the need for a bit of stability?

      • FlavioGomes

        Its alway feels worse when your in the middle of crisis then it actually is.

      • Julie P

        Generally stability feels safe – that stability comes in a variety of forms, but feeling safe makes it easier to take risks.

        It may be totally in your head. I am in Whistler BC for a few weeks with my family and I took my sun glasses (with a light perscription for stygmatism) instead of my goggles (w/out perscription) snowboarding on a sunny day last week. I was faster and more aggressive than usual, probably because I could see better and I rely on my sight for seeing ice pockets and flat spots, whatever… that said, the Paralympics are here next week and my yoga teacher works ski-patrol, she told me about a ski-racer who is blind. she races by audio queing and feel, I guess my need for extra-sensory stability is really just in my head.

  • Steven Kane

    Chance favors the prepared mind. – Louis Pasteur

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