Today, I'm joined by my old friend Tim Urban, the mastermind behind the wildly popular blog Wait But Why. Known for his ability to break down complex topics with humor and stick-figure drawings, Tim has captured the attention of millions worldwide. From his early days as a blogger to the release of his first book, "What's Our Problem?: A Self-Help Book for Societies," Tim has consistently delivered thought-provoking content that challenges our understanding of the world around us.

In this episode, we dive into pressing issues like unfettered tribalism, the concept of "idea prisons," and the potential impact of AI on society. Tim also shares personal insights as a new parent and teases his upcoming book. It'll challenge your perspectives and leave you craving more of Tim's signature blend of depth, wit, and accessibility. Don't miss this captivating conversation that tackles the complexities of our modern world head-on.

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Tim’s blog: Wait, But Why?: https://waitbutwhy.com/

Tim’s book: What’s Our Problem: https://www.amazon.com/Whats-Our-Problem-Self-Help-Societies-ebook/dp/B0BTJCTR58

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Chapters

01:55 The virtue of changing your mind

05:31 What has Tim changed his mind about

11:43 Are we on the other side of insanity yet?

18:05 How new media platforms shape culture

29:30 AI and tribalism

40:11 Internal and external wars

44:04 Tim on being a new parent

47:34 How Tim's views changed after having a kid

50:29 Tim's next book

Theme music: “Icarus Lives” by Periphery, used with permission from Periphery.

Ever feel like culture’s splitting into countless micro-worlds where everyone’s just vibing to their own thing? In this episode, I introduce my theory on the "Jazzification of Everything." Drew and I dive into how our subcultures of music, entertainment, and even personal obsessions have evolved into these aging communities, totally detached from the cultural monocultures of the past. Whether it’s metal fans in their forties or electronic music lovers growing older with their favorite DJs, we explore how the media landscape and algorithms have encouraged us to stick to what we know—and why this shift could be both a gift and a curse.

We also dig into why “premium mediocre” is taking over our consumer habits, and whether or not that’s actually a bad thing. We discuss how these tiny, exclusive-seeming trends might be fooling us, offering superficial luxuries instead of anything truly valuable. We cap it off with a big question about whether chasing after anything is worth it, or if we’re just dooming ourselves to disappointment. Give it a listen. Enjoy.

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Chapters

00:00 Mark has a theory... 00:24 The F*ck of the Week: The Jazzification of Everything22:11 Brilliant or Bullsht: "Premium Mediocre" 38:03 Q&A: Why chase anything at all?

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Theme song: Icarus Lives by Periphery , used with permission from Periphery.

In this special New Year's episode of The Subtle Art of Not Giving a F*ck podcast, we dive into the perennial challenge of making meaningful changes in our lives. Rather than falling into the typical "new year, new you" trap that leads most people to abandon their resolutions by February, Drew and I explore a different approach to personal transformation. We share our own struggles with perfectionism, control, and finding purpose.

We also dig into some research about how evolution may have shaped our sense of purpose, the science of habit formation, and offer practical strategies for making lasting changes. Whether you're setting goals for the new year or just trying to build better habits, this episode will help you approach personal growth with more wisdom and less pressure in 2025. Enjoy.

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Theme song: Icarus Lives by Periphery, used with permission from Periphery.

This week, we dive headfirst into the messy, uncomfortable topic of regret. From the aches and grays that come with hitting a new decade to the deeper realizations about relationships, selfish mistakes, and missed opportunities, we unpack how regret shapes who we are. And there's a twist: what if regret isn’t something to fear or avoid? What if it’s a tool for growth? I share my own stories of taking people for granted, self-destructive habits, and the lessons I’ve learned about self-forgiveness and choosing your regrets wisely.

We also tackle some fascinating questions about whether empathy is actually good for society. Is it always a good thing, or can it sometimes lead us astray? To round things off, we share our thoughts on AI and its impact on creativity and human connection.

Enjoy.

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Chapters

01:14 The F*ck of the Week: No Regrets?

19:36 Brilliant or Bullsh*t: Is Empathy Always a Good Thing?

40:45 Q&A: Is AI coming for us all?

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Theme song: Icarus Lives by Periphery, used with permission from Periphery.

Today, we dive into the fascinating world of luck, risk, and how they shape our lives. We explore the delicate balance between playing it safe and taking chances, and why understanding this balance is crucial for personal growth. If you've ever wondered whether you're too cautious or not cautious enough, then strap in for this one.

We dig into the psychology of luck, examining how our perceptions influence our outcomes, and why taking calculated risks can lead to outsized returns. We also tackle the tough question of how to cope with life's inevitable hardships. Hopefully this gives you a fresh perspective on risk-taking and a new appreciation for the role of chance in your life.

Enjoy.

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0:00 Mark’s in the doghouse

2:44 The F*ck of the Week: Making Your Own Luck?

19:00 Brilliant or Bullsh*t: We should take more risk in life?

36:47 Q&A: How should you approach taking bigger risks?

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Theme song: Icarus Lives by @Periphery , used with permission from Periphery.

You ever notice how some people can’t stand being told what to do—even when the advice is good? Yeah, that’s me. In this episode, Drew and I dig into why so many of us rebel against advice, why others chase it like their life depends on it, and whether all that “actionable advice” we’re constantly fed is actually helping anyone. Spoiler: I’m not a fan of cookie-cutter solutions, and I’ve got some opinions about the self-help industry’s obsession with telling people exactly what to do.

We also get into the bigger picture—how advice often misses the mark when it’s not tailored to someone’s unique situation, and how therapy culture might be trying to replace something deeper that’s missing in our lives. I’ll share why I don’t give rigid life hacks, the trouble with universal solutions, and the surprising reason why most breakthroughs aren’t about the advice at all. If you’re tired of “do this, don’t do that” advice, this one’s for you.

Enjoy.

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Chapters

01:26 - The F*ck of the Week: Actionable Advice

21:26 - Brilliant or Bullsh*t: Therapy vs Therapy Culture

38:04 - Q&A: Taking Your Own Medicine

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Theme song: Icarus Lives by Periphery, used with permission from Periphery.

Have you ever felt like there’s more to life than the daily grind, like your dreams are buried under all the obligations and expectations life throws at you?

In this episode, we sit down with The Buried Life co-founder and New York Times bestselling author, Ben Nemtin, to explore why so many of us feel disconnected from our true purpose—and how to reclaim it.

For Ben, it all started as a group of friends chasing wild bucket-list dreams and helping strangers achieve their dreams too. In the process, they discovered what it means to give yourself permission to dream and then make those dreams a reality.

We dive deep into the psychology of fear, the power of accountability, and the surprising benefits of doing what you love—not just for yourself, but for everyone around you. We discuss why most people regret not living authentically, how to overcome the social and emotional barriers holding you back, and practical strategies for rediscovering your dreams, even if they’ve been buried for years.

If you’re looking for inspiration to take that first small step toward a life that feels truly yours, this episode will get you there.

Enjoy.

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Ben’s Stuff:

The Bucket List Journal by Ben Nemtin: https://www.amazon.com/Bucket-List-Journal-Achieve-Fulfilling/dp/B09VX2LMY2

The Buried Life (TV Show): https://www.bennemtin.com/tv-show/

The Buried Life (Poem): https://www.poetryfoundation.org/poems/43585/the-buried-life

Ben’s Website: https://www.bennemtin.com Ben’s TED Talk: https://www.youtube.com/watch?v=H6Y7mfxEaco

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00:00 What is the buried life?

06:57 Finding your gift and giving it away

11:07 The impact of The Buried Life TV show

18:06 Your goals don't have to be big to be meaningful

21:17 Your authentic self changes over time

26:15 Buried lives and the modern world

34:50 How to uncover your buried life

50:22 Leveraging emotions in your favor

59:41 Ben's Bucket List Journal

Theme music: “Icarus Lives” by Periphery, used with permission from Periphery.

Life has a way of just kind of happening to you. And while exactly what happens is unique to each of us, we all seem to go through very similar stages of our lives.

Today, we talk about the challenges of these stages. Each stage comes with its own “crisis” that, if navigated well, can propel us to the next stage. It is this never-ending struggle where life happens.

And then… Drew gets all new age and Mark just isn’t having it. And we round it out with a very simple, yet very difficult question from a listener: How much is enough?

Enjoy.

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The Four Stages of Life by Mark Manson: https://markmanson.net/four-stages-of-life

The Art of the Interesting by Lorraine Besser: https://www.amazon.com/Art-Interesting-What-Pursuit-Cultivate/dp/1538743205

Chapters: 00:00 Introduction

02:48 The F*ck of the Week: The Four Stages of Life

26:09 Brilliant or Bullsh*t: Psychological Richness

38:27 Q&A: How much is enough?

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Theme song: Icarus Lives by Periphery, used with permission from Periphery.

Wouldn’t it be great if we dropped all the bullsh*t about modern dating? No more games. No more fake, flaky people. No more texting back and forth for weeks or even months only to find out you have zero chemistry when you meet up in person. No more f*cking bots and AI generated dating profiles…

Sabrina Zohar definitely thinks we can skip all of it and get right down to the fun stuff (oh yeah, baby!). All it requires is brutal honesty with yourself and the people you’re interested in. So if you can stomach that, this episode is right up your alley.

We ask Sabrina: What does your attachment style really tell you about how you should date? Are dating apps really that terrible, or can we change the way we use them to get better results? And do we have high standards, or are our expectations just too f*cking high?

And a whole lot more.

We had a lot of fun in the studio with Sabrina. I hope you enjoy it too.

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About Sabrina Zohar

Sabrina Zohar is the multi-faceted entrepreneur and media figure responsible for coaching hundreds of thousands of people to start doing the work to improve their dating life, their relationships with others–and more importantly: their relationships with themselves.

Sabrina’s online presence shifted from talking about her sustainable clothing line, SoftWear, to sharing about her personal dating life. Sabrina’s message spread like wildfire, and the rest is history.

Sabrina’s message has earned her features in NBC California live, The LA times, The Drew Barrymore show, Daily Mail, Newsweek, US Sun, Yahoo, MSN, and more. Sabrina is a multi-faceted force guiding individuals to success in the entrepreneurial space, fashion, podcasting and media, and of course, the intricate world of love and relationships.

Sabrina’s website: https://www.sabrinazohar.com/

The Sabrina Zohar Show Podcast: https://www.sabrinazohar.com/podcast

Follow Sabrina:

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Chapters

00:00 Introducing Sabrina Zohar

04:25 The F*ck of the Week: Attachment Styles

21:36 Brilliant or Bullsh*t: Dating Apps

46:28 Q&A: Are my standards too high?

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Theme music: "Icarus Lives" by Periphery used with permission from Periphery.

Today, we’re diving deep into the subtle difference between a healthy routine and a rut. How can you tell if your daily grind is keeping you grounded… or just grinding you down?

Next, we tackle the question of boredom: Why does it feel so unbearable, and could we actually be missing out on its hidden perks? Spoiler alert—boredom might just be the key to unlocking your most creative, inspired self.

Finally, we confront one of life’s biggest dilemmas: When is it time to walk away, and when should you double down? Whether it’s a project that’s going nowhere or a relationship that feels like it’s on life support, we’ll give you insights on knowing when to quit and when to stick it out.

Enjoy.

Brilliant or Bullshit Paper: Just think: The challenges of the disengaged mind https://pmc.ncbi.nlm.nih.gov/articles/PMC4330241/

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01:19 F*ck of the Week: Routines vs ruts

17:50 Brilliant or Bullsht: How painful is boredom?

31:06 Q&A: When to quit vs when to grit?

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Theme music: “Icarus Lives” by Periphery used with permission from Periphery.

What are you called to do in life? What is your life’s task? And once you figure that out, how do you pursue it?

The one and only Robert Greene sat down with us on the pod to talk about all of these questions and a whole more.

We discuss finding and pursuing one’s life task, the nature and causes of “Peter Pan Syndrome”, science vs timeless wisdom on life, figuring out what do in midlife after you’ve taken the wrong path, and a much more.

Enjoy.

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About Robert Greene

Robert Greene is the author of the New York Times bestsellers The 48 Laws of Power, The Art of Seduction, The 33 Strategies of War, The 50th Law, Mastery, The Laws of Human Nature, and most recently of The Daily Laws.

In addition to having a strong following within the business world and a deep following in Washington, DC, Greene’s books are hailed by everyone from war historians to the biggest musicians in the industry (including Jay-Z, Drake, and 50 Cent).

Greene attended U.C. Berkeley and the University of Wisconsin at Madison, where he received a degree in classical studies. He currently lives in Los Angeles.

Robert’s Website: https://powerseductionandwar.com/

Robert’s Books: https://powerseductionandwar.com/books/

Robert’s social media:

YouTube: https://www.youtube.com/@RobertGreeneOfficial

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

X: https://x.com/RobertGreene

Facebook: https://www.facebook.com/p/Robert-Greene-100085341047380/

TikTok: https://www.tiktok.com/@robertgreene

Chapters:

00:40 The F*ck of the Week: Finding Your Life’s Task

29:37 Brilliant or Bullsh*t: Peter Pan Syndrome

43:15 Q&A: Science vs Timeless Philosophy, How to Start Over in Midlife

Theme music: “Icarus Lives” by Periphery, used with permission from Periphery.