The Pathless Path with Paul Millerd

Cate seemed to be fully entrenched on the default path — she had graduated from Yale and became the Supreme Court advocate on her way to becoming a partner in her law firm. But she didn't want to live the lives of the people around her. She pivoted hard, you could almost hear car brakes squeaking as she made the turn, and over a year she became the number one female poker player in the world. She later started art and perfume companies and led operations at Avlea — a pandemic medicine company. One might think she's simply a superhuman, and what she did is beyond the grasp of mere mortals, but Cate claims that agency is learnable and joins the podcast to tell us how.

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⌛TIMESTAMPS
  • (00:00) - Intro
  • (02:29) - The scripts that Cate grew up with
  • (06:54) - Doors-opening credentials?
  • (10:45) - Leaving law for poker
  • (18:59) - Developing agency, learning form the others
  • (24:04) - Deterministic vs probabilistic economy
  • (27:15) - Risk and the diminishing prestige of the traditional paths
  • (31:32) - Burnout
  • (37:42) - Asking dumb questions
  • (42:21) - Defining ambition
  • (44:01) - Seeking actual feedback and how everything is learnable
  • (50:33) - The surface area of luck
  • (58:07) - Closing remarks

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What is The Pathless Path with Paul Millerd?

The Pathless Path is hosted by Paul Millerd - a writer, creator, and consultant. He has conversations with freelancers, self-employed entrepreneurs, creators, and vagabonds who share their perspectives on their relationship with work, burnout, bootstrapping, indie hacking, remote work, reinvention, creativity, sabbaticals, leisure, self-employment, unconventional living, and digital nomadism. Past guests include Ali Abdaal, Khe Hy, Ben Hunt, Wade Foster, Dan Vassallo, Kris Abdelmessih, Steph Smith, Amir Salihefendić, Alex Pang, Visakan Veerasamy, and more.