The 2AM CEO Moments
I've been there.
Not as a CEO — but as someone who has sat across from enough of them to know exactly what 3am looks like from the inside. The ceiling stare. The mental replay of a decision that seemed right at 2pm and feels terrifying by midnight. The question you can't quite name but can't quite put down either.
Leadership has a public face and a private one. The public face shows up to the meeting, makes the call, holds the room. The private one wakes up in the dark and wonders if it was the right call at all.
Nobody talks about that second one enough.
Here's what I've noticed after years of coaching CEOs and sitting as a Vistage Chair: the 2am moments aren't a sign something is wrong with you. They're a sign you're paying attention. The leaders who sleep perfectly through every hard season are often the ones who've stopped feeling the weight of what they're carrying. And that's actually the more dangerous place to be.
The question isn't how to make the 2am moments stop.
It's what you do with them.
I grew up in a small farm town where big dreams weren't really part of the script. No mentor pulling me aside. No roadmap. I found my way through a series of decisions that were equal parts brave and accidental — and I spent a lot of nights wondering if I'd gotten it wrong. What I didn't have then, and what I try to give my clients now, is a place to take those questions before midnight.
Because here's the truth: most 2am spirals aren't actually about the decision itself. They're about not having anyone to think it through with.
When you're at the top, you can't always be uncertain out loud. Not with your team, who's watching you for steadiness. Not with your board, who expects confidence. Not even sometimes with your spouse, who's already carrying their own load. So the questions pile up — unprocessed, un-pressure-tested, alive at 3am.
What changes things isn't having all the answers. It's having a space where you can ask the real questions before the ceiling becomes your only sounding board.
The CEOs I watch sleep better — and lead better — aren't the ones who've figured everything out. They're the ones who've stopped trying to carry it alone. They've got a room, a peer, a coach, someone who will sit in the hard question with them and not flinch.
That's not weakness. That's the smartest leadership move I've ever seen.
If you're in a 2am season right now, I'm not going to tell you it goes away entirely. It doesn't. The stakes just keep getting higher the longer you lead.
But I will tell you this: the questions that wake you up at night deserve better than the ceiling.
They deserve a real conversation.
Nancy Girres is an executive coach and Vistage Chair based in Fort Collins, Colorado. She works with CEOs and leaders who are ready to stop going it alone.