The Day After Selling Your Business

The first day after I sold my company, I checked my email twenty-seven times.

There was nothing in it.

Not nothing literally. There were newsletters, a couple of promotions, someone trying to sell me office furniture. But there was nothing that needed me. No customer whose phone system had gone down. No manager asking for a decision. No salesperson wanting approval on a discount. No emergency waiting for the man who had spent twenty-seven years believing emergencies were his job.

So I checked again.

By lunchtime I had checked it eleven times. By dinner, twenty-seven.

I wish I could tell you I noticed what I was doing. I didn't.

For weeks, every fifteen minutes or so, my hand drifted to the phone almost without asking permission. Tap. Refresh. Nothing. Tap. Refresh. Nothing. It was as automatic as breathing, the kind of habit you don't know you have until the reason for it disappears.

I thought I was looking for an email. I wasn't.

I was looking for the feeling that someone, somewhere, needed me.

That realization took me months.

The sale had gone exactly as I had imagined. Twenty-seven years after opening the company with little more than optimism and a leased office, the lawyers had finished their paperwork, the money was in the bank, and I had walked away with something I had spent most of my adult life trying to build. I made the decision to sell in January of 2017, on a beach, and that story comes later 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.

By every conventional measure, this was supposed to be one of the happiest periods of my life.

Instead, I found myself standing in my kitchen, refreshing an inbox that no longer belonged to me.

The Sound of Being Needed

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.

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 I Was Actually Missing

It would have been easy to tell myself I simply missed the company. For years, that's exactly what I said. It sounded reasonable. Even flattering. I loved building. I loved solving problems. I missed the people. Entrepreneurs say those things all the time after they sell.

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. 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.

I don't think that's what I missed.

I think I missed the scoreboard.

For twenty-seven years my days began with a question that always had an answer. How am I doing?

Revenue answered. Profit answered. Cash flow answered. Customers answered. Employees answered.

The business had become a machine that quietly measured me every single day, and somewhere along the way I had stopped noticing the difference between measuring my performance and measuring my worth.

Selling the company didn't take away my purpose. It took away the instrument I had been using to measure it.

I didn't understand any of that in January of 2018. Back then, I just knew I couldn't stop checking my email.

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. Sailing away from the harbor is the easy part. It's the open water, with no markers and no score, that tests you.

Looking back now, I think those twenty-seven refreshes told me more about the previous twenty-seven years than any financial statement ever did.

How does a kid down to his last five hundred dollars end up with a company worth selling? That story starts in 1991, with security guards.