Not your daddy’s Freud

In the fall of 2020, Ilan Zechory stepped down as president of Genius, the annotation site he founded with two friends from Yale. After more than a decade at the startup, he could have been forgiven for taking a break.

Now Zechory is hard at work again, though not running another zeitgeisty digital media site. Instead, the 39-year-old is training to be a psychoanalyst.

Five days a week from an office on Manhattan's Upper West Side in New York City, Zechory helps his 20 or so patients - some of them supine, in the classic style - plumb the depths of their unconscious minds. Having gained an appreciation for the method during his own multiyear analysis, Zechory loves his new role.

"For the first time in my life I feel at peace with work, and have stopped dreaming about what else I should be doing with my days," he said.

Zechory is part of what may be a...