Why Entrepreneurs Should Practice Pessimism

Entrepreneurs are conditioned to tell themselves, “This will work. It has to work!” That might be a dangerous habit.

Why Entrepreneurs Should Practice Pessimism
[Photo: Flickr user Justin Pickard]

Editor’s Note: This story contains one of our 10 Best Business Lessons of 2016. Click here to read the full list.


Drew Houston always hoped that Dropbox would change the world, but he wasn’t certain. Sure, he loved his file synchronization app, but if the market didn’t, he wanted to know as soon as possible so he could change it or scrap it altogether.

With investors on board and product development well under way, Drew created a YouTube video explaining the most important features of his service. If the video gained traction, he would persevere. If it didn’t, he would take it as evidence–devastating as it might be–that he should change course.

Drew uploaded his video and prayed, “God help me. I hope it works”–fearing, of course, that it wouldn’t.

Entrepreneurs And Their Anxiety

Decades ago, the father of cognitive behavioral therapy, Aaron Beck, pointed out something simple yet incredibly profound: Behind every feeling of anxiety we experience is a thought. This automatic thought, which often goes unnoticed, is actually the source of our discomfort. Beck’s suggestion: if you want to combat the anxiety, identify and address the thought.


Entrepreneurs experience plenty of anxiety, to be sure, but few things make them tremble as much as having to test their beloved ideas. Can you imagine the fear Drew must have grappled with, knowing that a simple YouTube experiment might have proved DropBox dead in the water? Faced with this anxiety, some either don’t test their products or fail to look honestly at the results, rationalizing away the signs of trouble.

Before becoming a best-selling author and successful serial entrepreneur, Seth Godin struggled on the verge of bankruptcy for eight years. Even now, every time Seth launches a project, the familiar anxiety resurfaces. In a recent interview, he confessed, “Deep down, if you cut me open, inside is the struggling entrepreneur who’s sure that tomorrow he’s going to have to go back to eating macaroni and cheese.”

In reality, failure won’t seriously threaten Godin’s livelihood. However, these catastrophized thoughts can make him feel as though it might. That’s why whenever Godin launches a new project, he says he constantly has to remind himself, “This might not work.”

The Power Of Defensive Pessimism

Eric Greitens, a former Navy SEAL and author of Resilience: Hard-Won Wisdom for Living a Better Life, points out a curious phenomenon. Many cadets, he says, quit immediately after the first day of training during the infamous “Hell Week”–but not during it. Why not quit at the peak of the pain? According to Greitens, cadets quit not because of the actual pain they experience in real time, but of future pain they imagine awaits.

To beat this anxiety, Greitens suggests visualizing future scenes of failure in realistic detail–for instance, being out of oxygen 30 meters into a 50-meter swim. Then, instead of letting your unconscious conjure horrific images of drowning, think through the likely consequences, in this case the embarrassing prospect of having to be rescued.


This is an example of what psychologists call “defensive pessimism”–a strategy for consciously rehearsing the worst-case scenario in a calm and rational manner. By accepting that catastrophe is possible, the mind can reject it as implausible.

What’s The Worst That Can Happen By Asking, “What’s The Worst That Can Happen?”

Amazon CEO Jeff Bezos still uses defensive pessimism to help combat his own anxieties, keep thinking rationally, and ensure he isn’t throwing good money after bad.

At a shareholder meeting in 2011, Bezos confided, “On the day you decide to give up [on an unsuccessful project], what happens? Your operating margins go up because you stopped investing in something that wasn’t working. Is that really such a bad day?” Bezos’s willingness to imagine giving up allows him to de-catastrophize the consequences of doing so.

And ultimately, it was the same type of strategic pessimism that helped Drew Houston overcome his anxiety about testing DropBox. The video he released ended up driving hundreds of thousands of people to his website overnight, validating his hypothesis, and emboldening him to double down on his product.

Still, Houston recognized it could just as easily have gone the other way. At a 2010 conference called Startup Lessons Learned, he said, “Not launching is painful, but not learning is fatal.” It was only by consciously admitting that having to pivot would be “painful” that Houston was able to grasp that it wouldn’t be “fatal.”


Most entrepreneurs are taught to be stubborn optimists. They’re conditioned to dogmatically tell themselves “this will work–it has to work.” But it’s avoiding the possibility of failure that permits the unconscious mind to explore otherwise unfounded catastrophe scenarios. Ironically enough, that’s the surest way to actually bring them about.

Al Pittampalli is the author of Persuadable: How Great Leaders Change Their Minds to Change the World and Read This Before Our Next Meeting: How We Can Get More Done. He is an independent speaker and trainer, working to help organizations like NASA, Boeing, Hertz, and Nokia prepare for a fast-changing world, by revamping how they hold meetings, make decisions, and collaborate in teams.