Over 10 years ago, for about a year and a half, I was in a mastermind group with two other agency owners. We were all young. All hungry. All convinced we were about three good decisions away from figuring this whole thing out.

We met once a month. Each of us got an hour, divided into four neat little chunks: problems, wins, asks, and future goals. Very structured. Very serious. The kind of meeting where you nod a lot and say things like “that’s a great insight” while quietly wondering if everyone else is as lost as you are.

When it came time to talk about goals, I always said something like, “I want five new clients by end of quarter.”

X, the first guy, always went bigger. “I want to hit a million by Q3.” “I want $200K in sixty days.” He dreamed in tax brackets.

Y, the second guy, said things like this:

“I want to make one more dollar off my website traffic.”

One dollar.

I remember sitting there thinking, brother, dream bigger. We’re in a mastermind. This is where you’re supposed to manifest your empire, not your lunch money.

But Y didn’t flinch. Every month, some version of the same answer. “Fifty more dollars in savings.” “One more conversion than last month.” Tiny, boring, almost embarrassingly humble goals.

I smiled politely and quietly filed him under “nice guy, limited ceiling.”

We did this for eighteen months.

My goals changed constantly. X’s goals stayed huge. Y’s goals stayed small.

Then, at what turned out to be our final meeting, someone suggested we look back. Tally the scorecard. See how we’d actually done against all those goals we’d been setting.

I went first. The results were, let’s say, humbling. I’d picked up some clients. But nowhere near what I’d been projecting. Not even in the same zip code.

X went next. Same story. He’d made more money, sure. But the million-dollar quarters? The six-figure months? Nowhere close.

Then Y.

Y had hit his goals. Every single one. For eighteen straight months.

Not most of them. All of them.

The guy I’d mentally labeled “small thinker” had a perfect record. And the two of us with the big visions and the ambitious projections were batting somewhere around .200.

That meeting was our last. Not because of drama. Because Y had decided to join a higher-level mastermind. The expensive kind. Five thousand a month expensive.

I started to ask him about it. Why spend that kind of money? Why now? What’s the expected ROI on—

And then I stopped.

I stopped because I realized how stupid I would sound. Here’s a guy who, for a year and a half, had set a goal every single month and hit it every single time. Meanwhile, I’d been whiffing on my goals while privately judging his for being too small.

He wasn’t thinking small. He was thinking compounding.

Here’s what Y understood that I didn’t:

Every time you set a goal and hit it, your brain registers a win. It’s small, but it’s real. And when you do it again the next month, that’s two wins. Then three. Then twelve. Then eighteen.

After a year and a half of that, you’re not just someone who sets goals. You’re someone who hits goals. It’s your identity now. All you know how to do is win.

X and I were doing the opposite. We’d set these big, cinematic goals, miss them by a mile, and then spend the next meeting explaining why it wasn’t our fault. The market shifted. Client ghosted. Mercury was in retrograde. We were training ourselves to expect failure and rationalize it.

Y was training himself to expect success and compound it.

Same meetings. Same hours. Completely different results.

I think about Y all the time now.

When a prospect tells me they have $50,000 to spend on marketing, I don’t take it. I tell them, “Let’s start with two grand. Let’s see what traction we get. Then we’ll know what we actually need to spend.”

People look at me like I’ve lost my mind. You’re turning down money?

No. I’m trying to get a win first. A small one. Something we can learn from. Then we stack another one. Then another. That’s how you build something real. That’s how you build trust.

The agencies that grab the whole budget and immediately start “scaling”? Sometimes they hit. Most of the time, they’re back in ninety days blaming the algorithm for why they lit fifty grand on fire.

Y and I still keep in touch.

After that last meeting, he went to the $5K mastermind. Kept setting small goals. Kept hitting them. And because he was in the right room, with the right people, doing the right work, he got introduced to a globally known author.

That author hired him.

To this day, that author is Y’s only client. One client. He makes more than enough taking care of that one person’s marketing. He built his entire business on a foundation of small, boring, compounding wins, and it put him in a room that most people will never see.

Meanwhile, I’m still here, telling you about the guy who taught me everything by asking for one more dollar.