Success Solved Everything Except the Important Questions

Nine years ago I wrote down the first morning after the deal closed. Coffee, the kitchen table, twenty-seven years of somewhere to be and then nothing. I remember thinking the silence would take a few weeks to get used to.

This is the check-in nine years later. I am still not entirely used to it.

This is not a complaint. I know exactly how this reads coming from a man who sold his company and never has to work again. But that is precisely why I am writing it, because nobody who wins the game tells you what the trophy actually feels like in your hands. They post the announcement, they say they are excited for the next chapter, and they go quiet. I went quiet for years too. Here is what happened in the quiet.

The Chase Didn't End. It Lost Its Excuse.

The first thing that happened is that I kept going. This surprised me more than it should have. I had told myself the point of building Digitcom was to someday not have to build anything. Then the someday arrived, the wire hit the account, and within a couple of years I had started theicenetwork, a community for entrepreneurs who had sold or were selling their companies. Then I started another business, Cloudstrike. I bought and managed apartment buildings. I told myself these were projects, hobbies with revenue. But if I am honest, they were the same thing I had always done, wearing casual clothes. The chase had not ended. It had just lost its excuse.

The People Who Caught Bigger Fish

Through theicenetwork I got to know a lot of people who had done what I did, and many who had done far more. People who sold for numbers that made my exit look like a garage sale. And here is the thing I noticed, slowly at first and then everywhere: almost none of them stopped either. Within a year or two of their exits, most were back in the hustle. New ventures, new funds, new grinds. And the ones I knew well enough to see clearly were not doing well on it. Heavier. More stressed. They were not chasing money. They already had more than they could spend. They were chasing something they could not name, and the not-naming was eating them.

I would love to tell you I watched all this from a wise distance. I was one of them. I just had not admitted it yet.

The Design Flaw

For a long time I thought the problem was that I had not found the right next thing. The right venture, the right project, the right structure for the days. So I kept applying the tools that had always worked. And they are good tools. Set the target, measure the progress, work the system, close. Those tools built a company from a cold start in 1991, when I spent months getting dragged out of Toronto office towers by security before the phones ever rang. Those tools grew profits year after year for decades. Those tools got me the exit.

But somewhere in year six or seven, I finally saw the design flaw. The skills that built my career were designed for problems with finish lines.

Revenue has a finish line. Valuations have a finish line. A software product ships. A company sells.

But significance doesn't. Enough doesn't. Meaning doesn't.

I had spent my whole life getting exceptionally good at finishing things, and the questions in front of me now could not be finished. I kept running them through the old machinery anyway. What is this next chapter worth? What is the return on my time? Is this project succeeding? The machinery worked perfectly and came back with nothing, over and over, and I mistook the nothing for my own failure to find the right project. It was not that. It was a hammer meeting a piano.

Six years is a long time to spend swinging a hammer at a piano. I want to be precise about why it took that long, because I do not think I was being stupid. I was being consistent. The machinery had been right about everything it had ever been pointed at. When it came back empty, the only conclusion available to me, inside the machinery, was that I had aimed it wrong. There is no reading on the instrument that says the instrument is wrong for this. That is what makes it a design flaw rather than a mistake. A mistake announces itself eventually. A design flaw just keeps returning valid measurements of the wrong thing, year after year, and every one of them looks like a reason to try again.

What Ended the Debate

Then, in August 2023, my body settled the argument the way arguments get settled when one side stops talking. I have written that day down in full, and I am not going to run it again here. This chapter is the accounting, and the accounting starts the morning after, with a reordered list I did not choose and had not earned.

What I want to put in the ledger is not the event. It is what the event actually moved, and what it did not.

The Clearest Proof

The clearest proof of the new list is what I stopped doing.

Cloudstrike, the company I started after the exit, was growing before the heart attack. In the three years since, my involvement has been reduced to occasional oversight, maybe fifty hours in total. It is dying a slow death, and I am letting it.

For a builder, this is the strangest sentence I have ever written. Every instinct I own says save it, it is savable, you know exactly how. And I do know exactly how, which is the part that makes it hard. This is not a business I would have to learn. It is not a market I would have to study. It is the fourth or fifth time in my life I have stood in front of this exact problem with the exact tools that solved it before. I could fix it in six months of the old effort. I have the six months. That is what retirement is. I am choosing my mornings instead.

Fifty hours in three years is not a decision I made once. It is a decision I have made a few hundred times, in the small hours where these things actually get decided, every time I have picked up the phone to start and then not started. Nobody is watching that. There is no room full of fifty people to announce it to. It is the least witnessed thing I have ever done and it has cost me more than most of the things that were.

Some days that feels like wisdom. Some days it feels like watching something I made starve. I have stopped pretending I know which it is. What I will say is that a man who had truly reordered his list would not be counting the hours he did not spend. I count them. I know exactly what fifty is.

Where the Wanting Went

And the chase? It did not end. I want to be careful here, because the tidy version of this essay says the heart attack cured me of wanting, and that would be a lie. The wanting is still there. It just changed targets.

Then I could not keep it to myself, which anyone who knows me could have predicted. I hosted a conference on cardiovascular disease and filled the room with two hundred people. I partnered with Heart and Stroke and did it again. I have walked more than a dozen friends into bloodwork that found the silent thing building in them too. Whether that is generosity or just the same appetite pointed somewhere useful, I genuinely cannot tell you, and I have mostly stopped needing to know. When the engine was pointed at another company, its exhaust was stress. Pointed at this, its exhaust is friends who caught something early. If the ego insists on a scoreboard, that is the best one it has ever had.

But read that paragraph again and notice what it is. It is a man reporting attendance figures. Two hundred people. A dozen friends. I did not choose those numbers because they are the meaningful part. I chose them because they are the countable part, and nine years after I stepped off every scoreboard I had, I am still handing you the ones I have. I did not lose my identity when I sold the company. I lost my scoreboard, and I have been quietly building replacements ever since, and this essay is one of them.

Nine Years In

So, nine years in, the honest check-in is this. Getting what you want does not stop the wanting. Nobody warns you, and I understand now why they do not, because from the outside it sounds like ingratitude, and from the inside it takes years to even see. The finish line I chased for twenty-seven years was not one.

While writing this, I went back through the manuscript of a book I drafted in 2018 and never published. In a chapter about selling, one year after my own sale, I had written: "even now, I'm still trying to figure it out." That was eight years ago. I could have written it this morning. I used to find that continuity discouraging. I am starting to suspect it is just what this question looks like from inside.

The questions I have now do not have finish lines either, and I am slowly learning to work on things that cannot be finished, which at my age means being a beginner again, and I was never much good at being a beginner.

Some of it is wonderful. The mornings are mine. The list is in the right order, finally, even if it took what it took. And some of it I am still working out, which is what the rest of this site is for. The friends who went back to the hustle are the next thing I want to write down, because they are the clearest mirror I have, and because none of us has said any of it out loud.

I am writing it down, in case you are chasing something too.