How to Quit Your Job (and Find Work You Actually Love)

By Bill Jackson July 7, 2026 2 mins read 34174 Views

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Hey friends, if you’ve ever felt like you’re “winning” on paper (good job, good salary, impressive titles) but still feel weirdly empty inside, this video is for you. I sat down with Paul Millerd (author of The Pathless Path and Good Work) to break down a 10-step roadmap for quitting the default path without needing some perfect master plan, from running the numbers to dealing with the shame and fear that comes up. Hope you enjoy xx

🔗 LINKS MENTIONED IN THIS VIDEO

Paul Millerd’s post on money: https://newsletter.pathlesspath.com/p/eight-years-pathless-and-money-reflections

Pathless Path by Paul Millerd: https://geni.us/6LNq8

Good Work by Paul Millerd: https://geni.us/BodACSP

⌚️ TIMESTAMPS

0:00 Introduction
0:41 Step 1: Win The Prestige Game
4:39 Step 2: Spot the Misalignment
7:27 Step 3: Face the Shame
17:07 Interlude: Are You Actually Wired for This?
21:20 Step 4: Run the Numbers
28:08 Step 5: Take the Leap - Without a Perfect Plan
32:33 Step 6: Hack a Living
43:42 Interlude: Work Doesn't Have to Suck
48:37 Step 7: Follow Your Energy
55:55 Step 8: Declare Retirement
59:00 Step 9: Handle the People Around You
1:09:44 Step 10: Keep Playing the Infinite Game

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