On Purpose with Jay Shetty

Robert Greene: The Surprising Reason You Feel Unhappy Even When Life Is “Good”

02 nov 2026 · 01:31:06

Bestselling author of The 48 Laws of Power and The Law of the Sublime, Robert Greene, joins Jay to explore why so many of us feel unfulfilled, even when we're achieving everything we thought we wanted. He opens up about the life-threatening stroke that changed his perspective and inspired his new book, and shares how reconnecting with our childhood interests can help us discover our true purpose. Robert also explains why boredom, struggle, and confronting our mortality can lead to a more meaningful life, how to turn envy into gratitude, and practical ways to navigate workplace politics, complicated relationships, and the feeling that life has become stagnant.

With Love and Gratitude,

Jay Shetty

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What I Discuss:

00:00 Introduction

02:18 Why We Feel Disconnected and Unfulfilled

06:27 Pursuing The Right Goals

11:32 Near-Death Experience And Writing The Sublime

13:13 Uncovering Your Authentic Self

19:51 The Looking-Glass Self

22:20 Overcoming Boredom Through Slow Disciplines

27:38 What is The Difference Between Happiness And Fulfillment?

32:15 Resisting Modern Culture And Embracing Difficulty

36:08 Building Confidence Through Small Steps

41:03 The Anxiety of Feeling Behind in Life

48:00 Connection To Others vs. Chasing Wealth

51:17 Turning Envy Into Gratitude

55:12 Real Fulfillment Beyond Financial Success

58:32 Money As Oxygen, Not Fulfillment

01:00:13 Workplace Politics And Power Dynamics

01:02:46 Why We’re Drawn to People Who Send Mixed Signals

01:04:53 Breaking Out of Repetitive Life Patterns

01:07:23 Confronting Mortality To Feel Alive

01:14:45 Transcendence, Evolution, And Spirituality

01:19:37 The Anti-Sublime Vs. the False Sublime

01:25:02 Robert On Final Five

Episode Resources:

Pre-order The Law of the Sublime https://sites.prh.com/lawofthesublime

Instagram | https://www.instagram.com/robertgreeneofficial

YouTube | https://youtube.com/@robertgreeneofficial
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