Why Entrepreneurs Must Steer Into Uncertainty

Andrew Maguire
Mar 10, 2015 · 3 min read

Startups are known for their ups and downs. Entrepreneurs operate in an environment of constant uncertainty that in any other industry would be a sign that something is seriously wrong. Generally speaking, humans do not like uncertainty. We don’t like the unknown because it gives us anxiety. Our automatic response is to try to make that anxiety go away, not embrace it.

Sometimes, to mitigate anxiety we create false certainty. Faced with the unknown, we have a tendency to pick any course of action and go with it, desperate to stride purposefully in any direction, even if it’s the wrong one. It is incredibly important for startup leaders and their teams to reject false certainty and embrace the unknown.

Subscribing to false certainty is one of the most dangerous things in the world of startups for a team and, more importantly, as its leader. There’s a popular school of thought that the CEO should know exactly what to do and what should happen at all times, which only compounds that anxiety and increases the chances that you’ll find yourself with slow growth and an underperforming product.

It’s true, paralysis can absolutely kill startups as well. The industry and the competition moves too fast for you to do nothing. As they say, “any decision is better than no decision.” And to some extent that is true. But to succeed in startups, you have to strike the balance between the two extremes. The right decision a week later after additional A/B tests, customer development, or advice is better than going down the wrong path for 6 months.

When I was a CEO, acknowledging how I felt and what I was thinking to my team was the best way to deal with uncertainty and the anxiety that comes with it. The most important thing is to express confidence that we’re going to figure it out. We don’t have all the answers, but I trust my team to help me find them.

Of course, you have to draw a line somewhere. You can’t be completely transparent with your team, no matter how much stress relief you might feel in the moment. Mark Suster wrote a great piece on this a while back, which I highly recommend for entrepreneurs. Personally, I brought all of the biggest challenges to my executive team, because I needed them to help me find solutions.

What I presented to my team as a whole varies, but you get a sense after a while for how much information pushes people past the point where it’s helpful. Some information creates more anxiety and makes your team less productive. Leaders have to make sure that people are able to do the best work they can, and CEOs need to carry the rest of it themselves.

It’s a lot of responsibility for an entrepreneur. The bigger your startup gets, the heavier the weight of that responsibility, because you have more to lose. Acknowledging that we sometimes don’t have all the answers is huge. We have to embrace The Struggle. Facing the biggest risks to our business head on provides the quickest route to a solution. It makes us better leaders.

With every up and down of the startup roller coaster, we have to assess where we are and where we’re going. You have to accept that you might not have all the answers right, but you can find them.

I expected the same from my team. I wanted them to tell me when they’re facing deep uncertainty in their own work. I would rather they steer into the uncertainty than recommend a course of action that they don’t believe will fundamentally solve the problem. Better yet, I want them to bring me a thoughtful analysis of a given situation that we can review together to arrive at a solution.

In order to really embrace that process, we have to be able to exist in this space of uncertainty, acknowledge it, and thrive in it.

Oakhouse Partners

Oakhouse Partners invests in companies that use…

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store