The moving line
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The finish line you’ve been running toward doesn’t exist. It never did.
When I was twenty-two I had one goal that I thought about more than anything else: a six-figure salary.
I don’t know where the number came from. Probably from growing up in Ottawa, where a six-figure government salary was the ceiling most adults I knew were building toward. Probably from the math I was doing in my head at that age, where a hundred thousand dollars a year meant I could pay rent without thinking about it, go to restaurants without checking my account first, and feel like I’d separated myself from the pack. At twenty-two, a hundred thousand dollars was the finish line. I was sure of it. If I could get there, I would know I’d made it.
I got there at twenty-three.
And for a few weeks, maybe a month, it felt like I thought it would. I’d look at my paycheque and feel a small pulse of confirmation. I’m here. I did it. The number I’d been chasing was real, and it was mine. I remember buying a dinner I didn’t need to think twice about and feeling the specific pleasure of being someone who could do that.
Then the number became normal. The salary I’d spent years thinking about became the salary I had, and having it felt the same as not having it had felt before I got it. The finish line I’d been running toward was behind me now. I was standing on it. And I could see a new one, further out, that I hadn’t been able to see before I got to the first one.
A few years later, after I’d started my own business, I crossed a million dollars in revenue. I’d like to tell you I popped a bottle of champagne or called someone or sat down and took a breath. I didn’t. I’m not even sure I noticed when it happened. There was no single day where the number appeared on a screen and I thought, this is the moment. It was more like I looked up one quarter and the number was behind me, and I was already thinking about the next thing.
The part that would have shocked twenty-two-year-old me was how little it registered. A million-dollar business had come and gone without ceremony. The finish line had moved so many times by then that crossing this one felt like crossing any other one. A brief registration that something had happened, followed by the awareness of how far the next line was.
I can hold the rational understanding that I’ve built something most people would be proud of. And I can feel, at the same time, that I haven’t started yet. Both of those things are true. They coexist without resolving.
I used to think something was wrong with me. Then I had a conversation that changed how I understood the whole pattern.
The question that changed it
I had a guest on the podcast last year who sold his company for nine figures. I asked him when he knew he’d made it.
He laughed. Not a polite laugh. The kind that comes out before you can stop it, because the question is so far from what the answer looks like from inside.
“I still don’t think I’ve made it,” he said.
He meant it. The man had sold a company for more money than most people will see in ten lifetimes, and the internal experience of that achievement was the experience of looking up and seeing a new line further out than the last one. I recognized it because I’d been living inside a smaller version of the same thing for years. The scale was different. The feeling was identical.
He told me his original goal had been to pay his rent without stress. Then it became employing a few people. Then building something that could compete in a real market. Then building something worth acquiring. Each time he arrived, the person who arrived was bigger than the person who’d set the goal. The new goal matched the new person.
That’s when he said the thing I haven’t been able to stop thinking about. He said, “The line moved because I moved.”
Which raised a question I hadn’t considered before. If the line moves every time you reach it, and it moves because you’ve grown past the person who set it, then is the moving line a problem? Or is it just what ambition feels like from the inside?
