Tech-minded and business-focused founder/CEO of Distillery, an enterprise full-service software development company.
It was my third night without sleep. To be clear, I wanted sleep. I craved sleep. This wasn’t some experiment in self-inflicted sleep deprivation. The sleeplessness was completely involuntary.
I tried hard to calm my brain. I was so tired. I laid in bed, trying to fall asleep, but I simply couldn’t. Why? Somehow, my business had become a plane speeding down a runway that was shrinking rapidly. I couldn’t see past the nose of the plane. And I couldn’t release myself from worrying over what would happen when we reached the end of that runway.
Luckily, these sleepless nights happened more than two years ago. Looking back from the current moment — a current moment in which my business is back to a comfortable seven-figure EBITDA and I’m sleeping like a baby — I now feel a little silly. After all, it’s just business.
In the big picture, the situation with my business hadn’t been that bad. We had enough money — I knew things would pick up. So why would I completely lose sleep over it? Losing sleep didn’t make things any better. In fact, for me, losing sleep does exactly the opposite, because when I’m worried, my mind is simply not at 100%. In that state, I’m not making the best decisions.
When I told him about my predicament, my business advisor, Phil Ressler, who is exponentially smarter than me, asked me, “Did someone put a gun to your head?” Strange question, isn’t it? The obvious answer was “no,” and so that’s what I told him. He responded, “Then calm down.” Such a simple and yet effective way to look at it.
It wasn’t that bad. It was just business. Still, my experience is illustrative of another malaise that entrepreneurs tend to keep under wraps.
If you’re an entrepreneur, you’re prone to stress. On the outside, you are a wall of confidence — always put together, always ready for what’s next. But is it possible to stay always calm on the inside? To never worry about small problems and not lose sleep over the big ones? That’s where I struggle with the answer — because for me, the answer is still “no.”
I believe that entrepreneurial calmness is a myth. “Everything is great” is just a disguise entrepreneurs wear so that employees, investors and partners can maintain their own façades of calm. Entrepreneurs are inspired, energetic and passionate, certainly, but they’re also stressed about losing money. They’re under pressure about that expensive hire or new office. They’re worried about not growing quickly enough. They’re strained about the need to close that next round of investment. And they’re overextended as they rush to roll out new features better and faster than their competitors.