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Diary of a CEO · 2023-06-08

TRANSFORM Your Life At Any Moment: Alcoholic Lawyer That Became "Fittest Man On The Planet"Rich Roll

Recovered alcoholic lawyer Rich Roll on becoming an ultra-endurance athlete and using discomfort and self-examination to transform your life.

TRANSFORM Your Life At Any Moment: Alcoholic Lawyer That Became "Fittest Man On The Planet"Rich Roll
The guest

Rich Roll: Former lawyer and recovering alcoholic who became a world-class ultra-endurance athlete (Ultraman) in his 40s, a New York Times bestselling author of Finding Ultra, and host of one of the biggest wellness podcasts.

What this episode covers

Rich Roll traces his life through multiple chapters: a bullied, insecure kid who found escape in alcohol, a top swimmer at Stanford whose career was destroyed by addiction, a functional alcoholic lawyer who hit bottom, and finally a plant-based ultra-endurance athlete. He and Steven Bartlett explore addiction as a broad spectrum (including phones, work, and food), the role of willingness and rock bottom in change, and why balance is a macro rather than a daily concept. Rich argues discomfort and pressure are the pathway to growth and that we vastly underestimate what we can accomplish over a decade. The conversation closes on Rich's current challenge: learning to let go of striving and create from joy rather than self-inflicted suffering.

The guest's own work

BookBy the guestISBN verified

Finding Ultra

Rich Roll

“but making that transition was very challenging even you know after Finding Ultra came out uh I completely severed my ties with the law”— Steven Bartlett

Also referenced (named, not recommended)

BookReferencedISBN verified

The Infinite Game

Simon Sinek

“then I've read Simon's book about infinite games and thinking okay how would I design every system in my life so that I could run those systems for 40 or 50 years”— Steven Bartlett
ProductReferenced

ChatGPT

OpenAI

“I then was like I'll Google it chat GTP went on chatty speed talk to me about time management techniques there's so many of them”— Steven Bartlett

Big reveals from this episode

  • Rich frames addiction as living on a broad spectrum, from substances to phones to relationships, all forms of distracting ourselves from discomfort.
  • His first marriage ended on the honeymoon, which he describes as his emotional bottom as an alcoholic.
  • His parents, on counsel from Al-Anon, told him to cut ties until he was ready to get sober, which became catalytic for his recovery.
  • After rehab he spent roughly 10 years people-pleasing as a corporate lawyer before a second rock bottom around age 40.
  • A health scare, unable to climb a flight of stairs without wheezing despite being a former world-ranked swimmer, broke his denial.
  • His transformation began with a seven-day juice cleanse designed to mimic the discomfort of detox, then going entirely plant-based for 16 years.
  • He did the podcast for years as an unmonetized hobby while nearly losing his house and having cars repossessed.
  • Rich's current mission is learning to let go of striving and step into a place of allowing rather than self-willed suffering.

Worth remembering

  • Rich got into Harvard and Princeton but chose Stanford partly for its number-one collegiate swimming program.
  • He lived in a rehab facility for 100 days starting September 1998.
  • He argues we overestimate what we can do in a year and underestimate what we can do in a decade.
  • Steven describes a book chapter on time, noting a 35-year-old has roughly 17,000 days left.
  • About six months into running, Rich spontaneously ran the better part of a marathon (24 miles) despite never being a runner.
  • He distinguished himself in Ultraman, a three-day double Ironman race, inspired by reading about David Goggins doing it around 2006.
  • His wife Julie was the strength who refused to let him quit and return to law during years of financial hardship.
  • Steven reveals he will play at Old Trafford for the Soccer Aid charity match in June and trains four times a week.
  • Rich admits he was a control-freak perfectionist who tried to do everything himself until building a staff prevented burnout.
  • The episode's closing tradition has each guest leave a question for the next; Rich would call his 18-year-old self to say it's okay to be who you are.