“I have a rule: no meetings before 3pm,” Lenny Rachitsky says. The retro analog clock on the wall ticks past 9:30am. “This is an exception.”

Our writer spent hours with Rachitsky — the PM turned reluctant influencer — to see what happens when the podcast camera turns off. He learned that after you peel back Rachitsky’s layer of equanimity, what you find is someone who has something to prove.

Rachitsky started Lenny’s Newsletter to live a “chill life.” And on the surface, it seems he’s achieved that: walk into his home and the floors are heated, there are lit candles, steam rises from the mug Rachitsky sips. 

But with all his success and how much he works, our writer wonders if that goal of living a chill life is still even possible. 

This is the central contradiction of Rachitsky. The chill life made his insanely high quality bar possible. The quality at which he does everything made the chill life sustainable.