Lessons

Lessons

The Case for Caring Less

Molly Graham
May 07, 2026
∙ Paid

A founder friend of mine — she runs a multi-billion-dollar company — said something recently that I haven't been able to shake.

A few years ago, she was completely gripped by the outcome. She wanted to build something huge, and she felt personally responsible for everything — every decision, every number, every swing in the business. You could feel it when you were around her — how much she cared, but also how much it weighed on her.

Fast forward to now. It’s the same company, though now it’s actually a much harder macro environment. But she’s different. Being around her, you can tell she feels calmer and less reactive, like she has more ground under her feet.

She told me: “I think I’m actually a better CEO now because I care a little less.”

What she meant wasn’t that she lowered her standards or stopped showing up. It was that she stopped needing the company to turn out a certain way. She accepted that there are things she can’t control, that she’s going to do her best in the face of cha…

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