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THE TWO MINUTE DRILL

The $70,000 win that set me up to lose


Compete Every Day

The Winners' Trap

Welcome to The Two Minute Drill, two minutes of actionable ideas to help you fight drift and compete every day for your best career, relationships, and life.

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My Win was only the starting block.

I'll never forget the 2016 South Central CrossFit Games Regionals in San Antonio.

We sold more in three days at that one event than I'd done in months of online sales - close to $70,000. I remember double-checking the numbers, just sitting there thinking, oh my god. We'd never done anything like it.

So I started painting a picture in my head. We'd made it. We were set. We were finally going to compete with the big boys.

And I started making bigger bets to match that story - signing us up for events we'd never run, chasing anything that would "validate" us.

That same year, someone offered me a spot in a professional speaking program. $22,000, plus travel. My gut said that's a lot of money. But we'd just had our best year — why wouldn't we keep climbing?

I signed up for it - and a dozen other events and investments - confident that things would keep going up on their own.

A year later, our event sales went off a cliff. By early 2018, we were losing money at events. I felt like an idiot.

It took me a while to see that the win itself set the trap - and there's research that shows exactly how.

In 2022, researchers ran five experiments: they let people win or lose a contest, then offered them a risky choice.

The clear winners walked away feeling more powerful, and that power pushed them to gamble bigger on the very next decision. The narrow winners got no such bump.

The size of the victory — not the fact of winning — was what made people reckless.

Translation: a decisive win doesn't just feel good. It inflates your sense of power, and inflated power loosens your grip on risk.

You bet bigger because winning quietly told you that you can't lose.

That's Victory Drift - the drift that attacks right after you win. Victory creates the conditions for drift. The scoreboard goes quiet, your ego whispers "you're fine," and you start coasting on a number that's already in the past.

I wasn't competing anymore because I was too busy celebrating.

The interrupt is a humility move, and it takes ten minutes.

Pick the one decision you're most confident about right now: the hire, the spend, the new market, the bet that feels like a no-brainer because things are going well.

Before you commit, write down how close your last win actually was. Not the headline number. The margin - the deal that almost didn't close, the quarter that came down to the final week. Then make the call from that number, not the highlight-reel version.

Ask one question: "If that win had been by a hair, would I still make this bet?" If your answer changes, that's not caution. That's Victory Drift, caught in the act.

The win felt like a finish line. It was a starting block. Treat today like the score's still 0–0 - because it is.

Go compete.


What decision are you about to make on the strength of a win that was closer than you remember?

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Win your day, Reader,

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THE TWO MINUTE DRILL

No fluff. No rah-rah. Just tactical, real-world strategies to help you compete today - at work, at home, in life. Because life’s too short to drift through it.

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