Home / BigDeal / #105 The Confidence Expert: How To Build UNSHAKEABLE Self Confidence | Mark Manson

#105 The Confidence Expert: How To Build UNSHAKEABLE Self Confidence | Mark Manson

BigDeal

Dec 04, 2025

1h 17m

Description

Most people think confidence is about believing you'll succeed. Mark Manson knows better — it's about being comfortable with failure. After writing one of the best-selling nonfiction books of all time and spending nearly two decades studying human psychology, the author of The Subtle Art of Not Giving a F*ck has cracked the code on why Gen Z is struggling with relationships, why therapy culture might be making us worse, and why your emotions are a system that needs managing just like your business.

In this raw conversation, Mark breaks down the alarming statistics behind today's confidence crisis, why dating apps are optimizing for all the wrong things, and how adopting labels as identity actually amplifies your problems. We dive deep into the hidden costs of success, why the happiest country in the world has low expectations, and the brutal truth about why 20-25% of Gen Z has cut off at least one parent. He reveals why AI therapy is both promising and dangerous, the single question that exposes red flags on first dates, and why marrying well is the highest leverage decision of your entire life.

But this isn't just about what's broken — it's about what actually works. Mark explains why failure is the only currency that matters, how to stop being a people pleaser without being a dick, and why your bank account reflects the difficult conversations you're willing to have. If you've ever felt like you're chasing happiness instead of meaning, or if you want to build real confidence that comes from action instead of affirmation, this episode will change how you think about success, relationships, and the problems you're willing to have in your life.

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00:00:00 Introduction
00:01:16 The Paradox of Being Likable
00:05:19 The Dating App Crisis and Modern Relationships
00:07:45 What Real Success Actually Means
00:09:16 The Happiest Country: Low Expectations in Finland
00:11:28 Social Skills: The 80/20 of Happiness
00:13:21 Confidence is Comfort with Failure
00:15:14 Building Failure Muscle: From Small to Big
00:24:07 The Post-Exit Existential Crisis
00:27:33 Stop Labeling Yourself: Identity and Mental Health
00:45:07 Emotions as a System to Manage
00:48:37 The Why Game: Peeling Back the Onion
00:49:45 Therapy Culture and Cutting Off Family
00:53:48 ChatGPT as Therapist: The Malignant Narcissist Problem
00:56:27 Building Purpose: AI That Challenges You
01:02:40 AI Limitations: Brilliant Idiots
01:06:21 Choosing a Life Partner: More Than Romance
01:09:37 The Best First Date Question
01:11:18 Everything Comes with Bullshit
01:12:17 What Pain Do You Want?

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