He was one of the most respected executives in the room — and one of the most paralyzed by his own thinking. Here's how he got out.
He had the title. He had the track record. He had the respect of his peers. And he was spending three hours a night replaying decisions he'd already made.
Overthinking at this level isn't about intelligence — it's often a sign of it. High-performing leaders in high-stakes environments develop the habit of running every scenario because at some point, that thoroughness served them. The problem is when the habit outlives its usefulness.
What we worked on wasn't how to think less. It was how to recognize when thinking had stopped being productive and started being a way of avoiding the discomfort of uncertainty.
He started using what I call a 'decision close' — a deliberate moment at the end of his analysis where he named his decision out loud, wrote it down, and then physically closed his notebook. It sounds simple. It worked because it created a ritual that signaled to his brain: this chapter is done.
He also started distinguishing between decisions that were reversible and decisions that weren't. Most of what he was agonizing over fell into the first category. Recognizing that didn't make the decisions easier — but it made the cost of getting them slightly wrong feel proportionate.
Six months later, he told me the replaying had mostly stopped. Not because the stakes got lower. Because he'd built a different relationship with the uncertainty that comes with them.
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