27 Things I’ve Learned From 150 Million Podcast Downloads

Ryan Holiday
10 min readNov 2, 2023

In ​his letters​ — the pre-digital medium for distant long-form conversation — Seneca instructs his friend Lucilius to find one thing each day that will fortify him against death, despair, fear, or adversity. Just one thing. One nugget. And that’s what most of Seneca’s letters to his friend are about. They have a quote in them. Or a little prescription. Or a story. But in each case, Seneca is explicit. Here’s your lesson for the day, he says. Here’s your one thing.

Obviously that’s the logic behind the daily emails I write (​Daily Stoic​ and ​Daily Dad​), but it’s also the way I try to live. Every time I listen to a podcast or record one myself, I try to walk away having grabbed at least one little thing. That’s how wisdom is accumulated — piece by piece, day by day, book by book, podcast by podcast.

It’s not much, but considering the scale of ​The Daily Stoic Podcast​, it’s actually added up quite a bit. I’ve interviewed roughly 200 people over the last five years. That’s maybe 300 hours of audio with people who’ve won Academy Awards, the Super Bowl, and sold millions of records. I’ve also probably appeared on ~250 shows myself since my first book came out in 2012. Here’s a list of stuff I have learned that I think is worth passing along…

  1. The novelist Philipp Meyer (whose book The Son is an incredible read) ​said​, “You have to be very careful about to what (and to whom) you’re giving the best part of your day.”
  2. When I ​interviewed Gretchen Rubin​, one of the most thought-provoking and influential experts on happiness, she told me about one of the things she learned from her former boss, the Supreme Court’s first female justice, Sandra Day O’Connor. Shortly after Gretchen published The Happiness Project, she asked O’Connor who she had clerked for, what is the secret to happiness? O’Connor replied, “The secret to happiness is work worth doing.” Perfect.
  3. Something I’ve started implementing ​from Adam Grant​: in addition to coaches and mentors, you need to have judges. Adam was a competitive springboard diver growing up, “and I found it enormously helpful to get a 0 to 10 score every time I came out of the water.” When he transitioned from sports to the work world, he found it hard to get useful feedback. “So I started…

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Ryan Holiday

Bestselling author of ‘Conspiracy,’ ‘Ego is the Enemy’ & ‘The Obstacle Is The Way’ http://amzn.to/24qKRWR