I Closed An $800M Deal And Felt Nothing

The biggest deal of my career closed, and I felt nothing.

Eight hundred million dollars. Years of work behind it. The kind of number that's supposed to mean you've arrived. I waited for it to land. It didn't. I drove home the same person I'd been that morning, just more tired.

That was the alarm.

For most of my corporate career, I wasn't really there. I was working. Chasing the next title, the next win, the next bit of approval from a boss, a board, a room full of people whose opinion I'd decided mattered more than my own.

I built my whole sense of worth on the outside and worked my way in. Living outside in. The trouble with living that way is that it works, right up until it doesn't.

The wins keep you fed. Then a big one lands and you notice you can't feel it.

I thought about all of that this week because the word burnout is everywhere again. Searches for it are at record highs this year. The one that stopped me cold: searches for parental burnout hit an all-time high too. So this is landing on a lot of people. A lot of parents.

I'm not going to tell you what that means for the culture. You can read that anywhere. I'll tell you what it means if you're the one carrying a company.

When an employee burns out, the company loses productivity and time.

When the founder burns out, the company loses its judgment. You're the one who decides. The one who's supposed to stay clear when nothing else is. When that goes thin, everything downstream goes with it.

What you prioritize. What you avoid. What you decide too fast because you don't have the energy left to sit with it.

Here's the part that never shows up on the P&L. Most of what drains a founder isn't the workload. It's the loose ends running in the background. The decision you keep postponing.

The client who takes more than they give. The number you suspect is wrong and keep not looking at. None of that hits the calendar.

All of it follows you to the dinner table.

People treat being present like a feeling you summon. Breathe, unplug, be here now. That's not wrong. It's just downstream.

The reason you can't be present is usually that something unresolved is pulling at you, and a surprising amount of it is financial.

The founders I work with who feel scattered almost always have two or three things in their numbers they've been avoiding.

We put those on the table and deal with them, and something loosens. They sleep. They're at the table instead of in their own head at the table. Clarity isn't a soft thing. It's what gives you your attention back.

That's most of the work.

Sit down and ask the plain questions. Where am I actually today, not in the version I tell investors. What needs to change. What am I not seeing. How do I keep more of what I make, with less effort and less capital tied up.

None of those are comfortable. All of them are quieter than the thing you're already avoiding.

It's Father's Day.

I'm not going to pretend I have this solved.

I'm still working on being a better dad, a better friend, a better partner. It doesn't end. That's not a flaw in the plan.

That is the plan.

But the work got easier the day I stopped chasing the feeling and started getting honest about where I actually stood.

The deal didn't make me present. The clarity did.