When I sold my wire harness company, the closing day went exactly as planned.
I signed the papers at 2:00 PM. The wire hit my account by 4:00 PM. Years of risk and hard work had turned into generational wealth, truly life-changing money.

I’d done everything “right.”
I hired a President two years earlier, built systems that no longer depended on me, and spent months preparing a seamless handoff. It was a textbook exit, a one-year transition period, no surprises, and a perfectly executed plan.

That first month after fully stepping away felt incredible.
On Friday, I slept in for the first time in more than three decades.
Saturday, I went on a four-hour hike.
Sunday, my wife and I went out for a long celebratory dinner.
I thought, “This is it — I’ve finally made it.”

Then came Monday.

I woke up at 5:45 a.m. out of habit, made coffee, opened my laptop… and realized there was nothing waiting for me.
No emails that mattered. No fires to put out. No one who needed a decision or direction.

After 35 years of building something from the ground up, I had sold not only a company, but also my purpose.

It didn’t take long for my wife to notice. I’d pace the house with my coffee, check my phone every few minutes, and start projects I’d never finish. The house at the beach didn’t help. Travel didn’t help.

My financial advisor told me to relax.
My M&A advisor had moved on to the next deal.
But nobody told me about that Monday morning, the one after the dream came true.

What Founders Don’t Plan For

Now, sitting on the other side of the table as a sell-side advisor, I’ve seen this story play out many times.
Before we ever talk about EBITDA, customer concentration, or valuation, I ask every founder a straightforward question:

What are you going to wake up for on Monday morning?

Not the Monday after closing, the one six months later, when the champagne has gone flat and the congratulatory calls have stopped. That’s when many founders realize something unsettling:
The 60-hour weeks, the constant problem-solving, the sense of responsibility, it wasn’t just what they did. It was who they were.

The deal may close in 90 to 120 days. The identity crisis can last for years.

Founders plan for enterprise value, tax optimization, and deal structure. They build transition plans and integration roadmaps. But few prepare for the emotional and psychological shift that comes when the company no longer needs them.

Purpose Is the Part of the Deal You Can’t Wire

Here’s the truth: purpose doesn’t show up on a closing statement. You can’t wire it, and you can’t invest it.

Before you sell, take the time to ask yourself a few hard questions:
• What will give you meaning when the company no longer depends on you?
• Who will you be when you’re not the founder?
• What problem will you solve when this one is gone?

The “perfect exit” nearly broke me because I optimized for everything except the one thing that mattered most, what came next.

The exit should be the beginning of something, not the end of everything.

If you’re thinking about selling, let’s have a different kind of conversation, one that starts not with closing day, but with Monday morning.