When Breaking a Rule Feels Earned, You're in Trouble

The month you feel most in control is the one you should worry about.

Not the drawdown. Not the losing streak. Those hurt, but they keep you honest. The real danger shows up when you’ve strung together a handful of green days and started to believe you finally get it.

I call it the cautious-success trap, and it has taken more money from me than any single bad trade ever did.

Here’s how it works. You start small. You’re careful because you’re new to the strategy, or coming back from a loss, or just naturally risk-averse. You follow the rules exactly, because you don’t yet trust yourself to break them. And it works. Three wins. Then five. Your account creeps up and something shifts quietly in the back of your head: maybe I’m better at this than I thought.

That thought is the beginning of the problem.

Barber and Odean...

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