What the Biggest Year of My Life Taught Me
Jay marks his birthday by reflecting on five lessons an unpredictable year taught him. From making career choices based on the skills you want to build, to trusting yourself through discomfort and pro...
4 Sep 38min
Ask Jay: The Right Opportunity Might Not Be What You Expect
Jay answers four listener calls about what to do when the path forward feels uncertain. From career rejection and financial risks to knowing when openness becomes self-abandonment and how to keep goin...
2 Sep 32min
EILEEN GU: “The Ground Was Cracking Beneath Me.”
Jay sits down with Eileen Gu, the most decorated freestyle skier in Olympic history, to go behind the resume and into the mindset that built it all. Eileen opens up about the grandmother and mother wh...
31 Aug 1h 5min
The Psychology of Financial Freedom
Jay explores why our relationship with money is about so much more than what’s in our bank account. He breaks down five lessons, from how childhood shapes the way we spend and save, to what we’re real...
28 Aug 34min
Ask Jay: How Do I Forgive?
Jay answers four listener calls about the messy, unresolved side of forgiveness, from custody guilt and bias in parenting, to forgiving yourself after the sudden loss of a parent, uncovering a spouse’...
26 Aug 36min
Alison Wood Brooks: The Science Behind Great Conversations
Jay sits down with Harvard Business School professor Alison Wood Brooks, author of Talk: The Science of Conversation and the Art of Being Ourselves, to explore what makes great conversations actually ...
24 Aug 1h 42min
The Surprising Reason You're Still Unhappy
Jay breaks down the difference between healthy self-reflection and the kind of rumination that keeps you stuck in your own head. He shares four practical shifts to help you break the cycle, from redir...
21 Aug 32min
Ask Jay: How Do I Let Go?
In the very first episode of Ask Jay, a new series where listeners send in voice notes with their biggest questions, Jay explores what it really means to let go when your heart is still holding on. Th...
19 Aug 38min
