The Day After Selling Your Business

And just like that, with one final signature, I changed the course of my life.

I didn't come to the decision lightly. I made it in January of 2017, on a beach, and I've told that story elsewhere in this sequence. I stepped down as President at the end of December 2017, and January 1st, 2018 was my first day as officially semi-retired, or unemployed, or whatever you call it when you're transitioning to something you can't yet name. The challenging M&A process was over, the cash was in the bank, and I was excited by what lay ahead.

What I thought would be an easy personal transition was anything but. And the first symptom was so small I almost didn't notice it.

Every Fifteen Minutes

In the first weeks after the sale, I caught myself checking my email every fifteen minutes.

It was pure habit, the kind you don't know you have until its reason disappears, like waking early or reading the paper. For 27 years, the inbox was where the problems arrived, and the problems were mine. Now someone else was looking after the issues, and the issues, obediently, went to him. Nothing important was arriving. And still, every fifteen minutes, I checked.

It took me an embarrassingly long time to understand what I was doing. I wasn't waiting for an email. I was waiting for the feeling I had mistaken for purpose.

Some mornings I would go into the office. I still had a minority stake, a reason to drop by. And I would come in half hoping, and I mean this literally, half hoping there would be a problem I could solve. There never was. The new president was busy, working away, handling the things I used to handle. Watching him do it well was satisfying, in the way it's satisfying to watch your succession plan actually work. It also made me feel completely dispensable, in the way nothing in 27 years ever had. The silence of solitude can be deafening, and I had not understood, until then, that the noise I missed was the sound of being needed.

What I Thought It Was

For a long time I told myself the standard story: I missed the company. My identity had been wrapped up in my role, in my relationships with customers and staff and suppliers, and now the role was gone. All true, as far as it goes.

In the years since, I've compared notes with a lot of entrepreneurs who sold their businesses. Almost none regret selling. Nearly all of them are back at work in some form, and the usual explanation is the one I used to give: we love building, we're wired for it, we get bored. I no longer believe that's the real reason. I think they keep working because they don't know how not to. I spent 27 years being rewarded, daily, for being useful. Then one morning, nobody needed me. I can tell you exactly what that is. It's terrifying.

But even that wasn't quite the bottom of it. The bottom of it took me longer to find, and it was hiding in another small habit: for months after the sale, I would sometimes open the old reports, the dashboards I had built and read for decades, half expecting to find something new in them. I knew every metric by heart. Revenue, margin, pipeline, service numbers, all of it. I could tell you any figure from any year. And I kept opening the documents like a man checking a stopped clock.

What It Actually Was

Here is what I eventually understood, and it changed how I read my whole career.

I didn't lose my identity when I sold my company. I lost my scoreboard.

Twenty-seven years of numbers that told me, every single day, whether I was winning. The company wasn't giving me purpose. It was giving me a way to measure myself, and I had been mistaking the one for the other since 1991. The proof came fast: within a couple of years of the sale I had stepped off every scoreboard I'd spent my career on and immediately, instinctively, found new ones. New ventures. Books sold. Followers. Fitness numbers. It's in my DNA the way hair colour is, and no wire transfer changes your DNA.

I used to think entrepreneurs were addicted to building companies. I don't think that anymore. I think we're addicted to scoreboards, and companies happen to be the most absorbing scoreboard ever invented. So what happens when the game you've spent thirty years mastering suddenly stops keeping score?

The Letter I Read to Everyone Else

The day I announced to my team that I was stepping down, I read them a line often attributed to Mark Twain: "Twenty years from now you will be more disappointed by the things you didn't do than by the ones you did. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover."

I meant it for them. It took me years to understand I had also been reading it to myself, and years more to understand that sailing away from the harbor is the easy part. It's the open water, with no markers and no score, that tests you.