What’s Keeping You Up at Night?

Introducing the Sleep 5000: the real measure of a healthy business (and a healthy owner).

I believe the best way to measure business health isn’t revenue growth or headcount or even profit. It’s about getting enough sleep. Sure, most of us have a rough night here and there, but over time: Are you sleeping well? Or do worries keep you awake, carrying business stress deep into the night?

I’ve joked that in my next life, I want to create a “Sleep 5000” list to replace the Inc. 5000—a ranking of the entrepreneurs who sleep the best. The ones who have built something sustainable, not just something fast. Because I’ve seen too many successful entrepreneurs who are anything but healthy.

A few weeks ago, I had dinner with a friend who runs a large manufacturing business. By most traditional measures, he’s doing very well. But he told me he’d been in and out of the ER several times in recent months. I couldn’t quite figure out what was going on, so I asked him a question I often use when talking to business owners: What’s keeping you up at night? He didn’t hesitate: cash.

As we dug in, the situation became clearer—and more troubling. He had access to a line of credit, exactly the kind of tool designed to smooth out the ups and downs of a manufacturing business. But he wasn’t using it. Instead, he had chosen to manage everything with operating cash, putting enormous pressure on himself. In other words, he was torturing himself unnecessarily.

That moment stuck with me—not just because of his situation, but because of the question. “What’s keeping you up at night?” cuts through a lot of noise. It gets past the surface-level answers we tend to give—things are good, we’re growing, no major issues—and goes straight to the real pressure points. It can reveal what’s actually going on.

But recently, a friend challenged me on it. She pointed out that the question itself is negative. It assumes there’s something wrong. And she’s right. There are times when nothing is keeping you up at night, and that’s not denial—that’s a sign you’ve built something stable.

So I’ve started to adjust the question: What, if anything, is keeping you up at night? It’s a small change, but it matters. It creates space for both realities—the entrepreneur who carries a quiet burden and the one who has earned the ability to sleep well.

And it’s also worth remembering that what’s keeping you up at night may not be a business issue at all. It may be something personal: health, family, relationships. That’s not a failure of leadership. It’s part of being human. The lines between business and life are never as clean as we might like to pretend they are.

The goal isn’t to eliminate every worry—that’s impossible. The goal is to build a business and a way of operating that doesn’t require you to carry constant, unnecessary stress. Sometimes that means fixing a real problem. And sometimes, as in my friend’s case, it means recognizing that the problem isn’t the business—it’s how you’re choosing to manage it.

So here’s a question worth asking yourself—and your peers: What, if anything, is keeping you up at night? If you’re in a peer group or forum, start your next meeting with this question. It shifts the conversation from updates to honesty. And if the Sleep 5000 ever exists, you’ll be ready to apply.