In this episode, we sit down with Mark Manson, bestselling author of The Subtle Art of Not Giving a F*ck, for a wide-ranging conversation about pain, purpose, momentum, and what it actually takes to build a meaningful life. Mark explains why you can’t want the reward without wanting the cost, how suffering is often self-created through the stories we tell ourselves, and why momentum—not motivation—is the real driver of progress.

We go deep on relationships and dating — romance vs compatibility, conditional love, commitment, self-sabotage, and how to know if you’re actually ready for a serious partnership. Mark shares the biggest dating mistakes people make today, and how alignment beats excitement. We also explore creativity, writing, money, building and scaling a new AI company, and why Mark believes AI will fundamentally reshape personal growth, therapy, and the future of self-help.

201. Designing Discourse Opportunities that Build on Each Other