Mark Manson: When Quitting Is the Smartest Business Move

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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.

00:00:00 Trailer
00:01:30 What Is The Most Important Question in Life And Why?
00:04:21 Pain is Inevitable, But Suffering is Optional?
00:06:31 When Should You Quit vs. Push Through?
00:11:17 What's Your Actual Thoughts on The Self Help Industry?
00:15:43 Creativity is Boring. What Do You Mean By That?
00:19:45 Buy Low and Sell High With Ideas?
00:24:12 When Was The Moment Where You Were Like I Need to Write This Book?
00:29:11 When Writing a Book, What Do People Need to Know?
00:32:51 What Does The Economics of Book Publishing Actually Look Like?
00:39:55 Where Do You Think The Future of The Book Industry is Going?
00:45:21 What's Your Philosophy on Habits?
00:48:06 What is Manson’s Law of Avoidance?
00:51:31 Were You Ready to Confront the Cost of Being Famous?
01:00:33 Love vs Romance vs Compatibility
01:08:14 Do You Put Yourself or Your Partner as #1 Priority?
01:13:34 Conditional vs. Unconditional Love?
01:21:52 Respect or Communication, Which is More Important?
01:22:23 What Are Questions You Should Be Asking Your Partner?
01:24:50 How Do You Think You're Actually Ready For a Relationship?
01:26:18 What's the Biggest Problem With Dating Today?
01:30:22 The Business of Mark Manson
01:39:50 What's Been Your Best Hire?
01:43:26 What Has Been the Biggest Changes From Being a Writer to a Business Operator?
01:44:52 You Have a Paid Subscription Community. Why Has It Worked For You?
01:47:17 How Have You Not Burned Out?
01:48:53 What's The Best Advice for a Creator Building A Media Team?
01:51:09 AI Startup, Tell Us About It?
02:02:03 Quickstrike Questions

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🔗 Links Mentioned
Purpose AI - https://purpose.app/
Mark Manson “Solved: Friendship” Episode -    • Making Friends as an Adult, Solved  
Subtle Art of Not Giving a F*ck - https://amzn.to/3MDWv3o
Stumbling on Happiness - https://amzn.to/3YyiE5G
The Denial of Death - https://amzn.to/4iXudNg
The Blank Slate - https://amzn.to/3KPFNxq
The Road Less Traveled - https://amzn.to/4pDHqxb
Will - https://amzn.to/3XUSCcN
The 4 Hour Workweek - https://a.co/d/igh4EKm
Tools of Titans - https://amzn.to/48Jojfn

🎙 Guest: Mark Manson, Best-Selling Author / Creator
YouTube:    / @iammarkmanson  
Website: https://markmanson.net

📬 Get in Touch
Instagram:   / openresidency  
LinkedIn:   / markmastrandrea  
Website: https://openresidency.com/
Email: [email protected]