A Bit of Optimism | Podcast

Episode 17

The AI Skills Nobody is Teaching (And Everyone Needs) with AI Expert Ethan Mollick

Be honest: AI makes you a little nervous. Maybe you're afraid it'll take your job. Maybe you're overwhelmed by all the advice about prompts and agents and which chatbot to use. Or maybe you're just quietly hoping it'll all slow down. Ethan Mollick says we're underestimating our own agency in the age of AI. Instead of worrying about what AI will do to us, we should focus on what we choose to do with it. Ethan is a Wharton professor, the author of the bestseller *Co-Intelligence: Living and Working with AI*, and the writer behind “One Useful Thing,” one of the most popular newsletters on AI, work, and education. He's spent twenty years studying how people actually use technology, and he's become the go-to voice for making sense of AI without the hype or the doom. And in his new book, *Co-Existence: The Next Phase of AI*, he explores what comes next as AI moves from a tool we prompt to a presence we live and work alongside. In this conversation, Ethan shares the practical playbook most of us are missing and makes the case that our experience, taste, and point of view aren't things AI replaces. They're exactly what make us better at using it. In this episode you'll learn: ➡️ Why young people are NOT "AI natives" (and why experience is the real AI advantage) ➡️ The $20 decision that instantly upgrades how you use AI ➡️ Why AI agrees with everything you say + the simple prompt that fixes it ➡️ How to make AI write in YOUR voice instead of sounding like everyone else ➡️ The "jagged frontier": what AI is surprisingly bad at (and why that's your opportunity) ➡️ Why taste may become the most valuable skill of the AI era ➡️ How much agency we really have over where AI takes us Ethan believes that the future of AI isn't something that will just happen to us… It's something we get to build together. This… is *A Bit of Optimism*. \+ + + To pre-order Ethan’s new book, *Co-Existence: The Next Phase of AI*, head to: [https://co-existence.ai/](https://co-existence.ai/) Want to hear more from Ethan? Check out his Substack “One Useful Thing”: [https://www.oneusefulthing.org/](https://www.oneusefulthing.org/) \+ + + Chapters ### Chapters - **00:00:00** Why are AI Experts Are Either Doomers or Zealots? - **00:02:05** From Video Games to AI: Ethan's Unexpected Journey - **00:09:16** AI's Profound Impact on Knowledge Workers - **00:14:50** How AI Kills Traditional Talent Pipelines - **00:15:57** Why AI Art Doesn't Bother Me, But I'd Never Hang It on My Wall - **00:20:40** How To Overcome AI's Complication of Competitive Edge - **00:22:06** The 20 Dollar Investment That Changes Everything - **00:24:40** The 84 Percent Rule: Why AI Can Now Do Your Seven-Hour Job in 15 Minutes - **00:25:59** Your Voice Matters More Than You Think: Why AI Can't Replace Taste - **00:19:53** The Discomfort-Avoidant Generation Meets the Efficiency Machine - **00:13:08** Why Young People Are Worse at Using AI - **00:43:35** The Brain We're Sacrificing: From Phone Numbers to Critical Thinking - **00:51:39** Two Prompts That Will Transform How You Use AI - **00:52:58** How to Use AI As Co-Intelligence - **00:54:57** The Agency You Have Right Now: It's Not About Policy, It's About How You Use It \+ + + Simon is an unshakable optimist. He believes in a bright future and our ability to build it together. Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do. Simon is the author of multiple best-selling books including *Start With Why*, *Leaders Eat Last*, *Together is Better*, and *The Infinite Game*. \+ + + Website: [http://simonsinek.com/](http://simonsinek.com/) Leaderful: [https://simonsinek.com/leaderful](https://simonsinek.com/leaderful) Podcast: [http://apple.co/simonsinek](http://apple.co/simonsinek) Instagram: [https://instagram.com/simonsinek/](https://instagram.com/simonsinek/) Linkedin: [https://linkedin.com/in/simonsinek/](https://linkedin.com/in/simonsinek/) Twitter: [https://twitter.com/simonsinek](https://twitter.com/simonsinek) Facebook: [https://www.facebook.com/simonsinek](https://www.facebook.com/simonsinek)

June 16, 2026 59 min

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Episode 227

What Happens When You Stop Optimizing and Start Committing with Former LA Lakers President Tim Harris

In a world of job-hopping, side hustles, and an endless LinkedIn feed, Tim Harris did something almost no one does anymore. He stayed put. Few executives spend an entire career helping build a dynasty. Tim Harris spent 35 years with the Los Angeles Lakers, rising to President of Business Operations and helping transform the franchise into a global brand. Through championship eras, iconic athletes like Kobe Bryant and LeBron James, and decades of change in professional sports, Tim's influence was felt not on the hardwood, but in the culture, leadership, and business excellence that powered one of the NBA's most storied organizations. In this episode you'll learn: ➡️ Why clarity of role is the most underrated tool in any leader's arsenal ➡️ The three unspoken words that silently destroy any team ➡️ What Kobe Bryant taught Tim about mindset (+ why it matters off the court) ➡️ How the Lakers built one of the most powerful brands in sports ➡️ What elite athletes do differently + how it translates directly to business ➡️ What caring, high-performing leadership actually looks like ➡️ Why giving away free tickets to strangers was a brilliant + caring business decision ➡️ The cost of short-termism + what we lose when we stop playing the long game Even a brand as iconic as the Lakers wasn't built by championships alone. Tim says its foundation was built one small, genuine human moment at a time. This… is *A Bit of Optimism*. \+ + + Chapters ### Chapters - **00:00:00** You Have to Love Them in Order to Win - **00:01:54** Why Tim Stayed 35 Years With One Company - **00:04:30** From Soccer Player to Lakers President: Tim's Unlikely Journey - **00:07:54** Coaching as Leadership: Don't Play on the Field - **00:09:39** The Long Game vs Day Trading Success - **00:11:00** The Underrated Tool of Clarity of Role - **00:13:29** Kobe's Compartmentalization: Nice Guy Off Court, Competitor On Court - **00:15:19** The Mental Game: What Separates Elite Athletes From Everyone Else - **00:22:08** The Three Unspoken Words That Ruin Any Team - **00:24:16** Meeting People Where They Are - **00:36:45** Caught You Being a Laker: Empowering Employees to Create Magic - **00:30:31** The Empty Seat Philosophy: Turning Sunk Costs Into Memories - **00:31:35** Building Brands One Tiny Act at a Time - **00:38:42** Remember That Business Is Always Human - **00:42:04** The Jenga Theory: Every Interaction Either Builds or Destroys Your Brand - **00:46:31** Caring Structure: What People Actually Crave at Work - **00:47:26** Never Miss Your Kid's Game: The Accountability Agreement - **00:50:09** Learning From Legends: Phil Jackson and the Human-First Philosophy - **00:48:48** The Work Happens in the Dark: What Made Kobe and LeBron Great - **00:50:56** Stop and Look at the Joy: Championship Lessons and Kobe's Legacy \+ + + Credits **Footage:** NBA Entertainment **Photos:** [http://bit.ly/43Fb37Z](http://bit.ly/43Fb37Z) (Full List) \+ + + Simon is an unshakable optimist. He believes in a bright future and our ability to build it together. Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do. Simon is the author of multiple best-selling books including *Start With Why*, *Leaders Eat Last*, *Together is Better*, and *The Infinite Game*. \+ + + Website: [http://simonsinek.com/](http://simonsinek.com/) Leaderful: [https://simonsinek.com/leaderful](https://simonsinek.com/leaderful) Podcast: [http://apple.co/simonsinek](http://apple.co/simonsinek) Instagram: [https://instagram.com/simonsinek/](https://instagram.com/simonsinek/) Linkedin: [https://linkedin.com/in/simonsinek/](https://linkedin.com/in/simonsinek/) Twitter: [https://twitter.com/simonsinek](https://twitter.com/simonsinek) Facebook: [https://www.facebook.com/simonsinek](https://www.facebook.com/simonsinek)

June 2, 2026 57 min

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Episode 226

Revisited: Choose Your Seven Humans Wisely with Author Fredrik Backman

Hello from Team Simon! We're taking a quick break this week and will be back with brand-new episodes of *A Bit of Optimism* next Tuesday. Until then, we're revisiting one of our favorite episodes — when bestselling novelist Fredrik Backman joined the show to talk about the thing he's spent his whole career writing about: the quiet, radical power of showing up for people. And Fredrik says great friendships aren't found by luck. They're built deliberately, repeatedly, and, sometimes, inconveniently by people who choose to do the work. Fredrik is the internationally bestselling author of *A Man Called Ove* (adapted into the film *A Man Called Otto*), *Anxious People*, and the *Beartown* series. His book, *My Friends*, is a love letter to the relationships that quietly shape who we become. In this conversation, Fredrik opens up about his best friend of over 30 years and what 30 years of real friendship actually requires. His words will have you thinking hard about the friends you might be taking for granted. In this episode you'll learn: ➡️ Why great friendship is a skill + what the work actually looks like ➡️ The concept of your "people” vs. “humans" ➡️ Why your friends are your best editors ➡️ The friendship rule that changed how Fredrik's entire friend group thought about relationships ➡️ The unexpected value of quantity of time vs. quality of time ➡️ How to be genuinely happy for someone else ➡️ The difference between healthy self-deprecation and low self-esteem ➡️ Why the work in a relationship is never solely on the relationship — it's always on you A great relationship isn't a stroke of luck. It's a choice you make every day, in small ways, often when it's inconvenient. This conversation is a reminder of why it's worth it. This… is A Bit of Optimism. \+ + + To buy Fredrik’s book, *My Friends*, visit: [https://www.simonandschuster.com/authors/Fredrik-Backman/411545926](https://www.simonandschuster.com/authors/Fredrik-Backman/411545926) \+ + + Chapters ### Chapters - **00:00:00** We Don't Need Algorithms to Find Our People - **00:02:45** Fredrik's Viral Speech: Fueled by Pure Panic - **00:05:55** The Power of Authenticity: Why Imperfection Resonates - **00:07:29** Choose Your Seven Humans Wisely - **00:08:56** The Friend Who Taught Him Everything - **00:15:43** Quality Time vs Quantity Time: The ROI of Presence - **00:17:53** The "I Want To," Not "I Have To" Philosophy - **00:20:55** Your Friends Are Your Best Editors - **00:13:23** Writing as Self-Editing - **00:15:06** Learning to Be Happy for Others - **00:22:41** The Gift of Time: Showing Up When It Matters - **00:23:56** Be A Great Friend, Get Great Friends - **00:28:55** The Work Is On You: Relationships and Self-Growth - **00:36:23** Algorithms Would Never Match Us: The Value of Difference - **00:34:21** Trying Is Everything - **00:35:55** People vs Humans - **00:37:18** Self-Deprecation vs Low Self-Esteem - **00:39:22** The Jantelagen: Swedish Humility Law - **00:45:26** The Fear of Disappointing People - **00:48:00** Expectations vs Reality: Letting Go of Fantasy - **00:49:00** Understanding Bullies: Finding What We Have in Common - **00:51:21** Fighting Narcissism: Surrounding Yourself With Better People - **00:52:08** Being Comfortable Not Knowing: The Gateway to Learning - **00:55:28** The World's Best Cardamom Bun Debate \+ + + Simon is an unshakable optimist. He believes in a bright future and our ability to build it together. Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do. Simon is the author of multiple best-selling books including *Start With Why*, *Leaders Eat Last*, *Together is Better*, and *The Infinite Game*. \+ + + Website: [http://simonsinek.com/](http://simonsinek.com/) Leaderful: [https://simonsinek.com/leaderful](https://simonsinek.com/leaderful) Podcast: [http://apple.co/simonsinek](http://apple.co/simonsinek) Instagram: [https://instagram.com/simonsinek/](https://instagram.com/simonsinek/) Linkedin: [https://linkedin.com/in/simonsinek/](https://linkedin.com/in/simonsinek/) Twitter: [https://twitter.com/simonsinek](https://twitter.com/simonsinek) Facebook: [https://www.facebook.com/simonsinek](https://www.facebook.com/simonsinek)

May 26, 2026 58 min

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Episode 225

How to Stop Being Socially Awkward (According to Science) with Behavioral Scientist Vanessa Van Edwards

Maybe this sounds familiar: you leave a party and spend the rest of the night convinced everyone was upset with you. Or you replay something you said in a meeting for days and second-guess every last word. Vanessa Van Edwards has been there. As a self-proclaimed "recovering awkward person," she’s spent two decades decoding the hidden dynamics of human interaction to make those skills teachable for introverts and extroverts alike. Vanessa is a behavioral researcher, bestselling author, and founder of Science of People. In her book, *Conversation: How to Be Instantly Likeable in Any Interaction*, she makes the case that social skills aren't a personality type, they're learnable. And she believes we are living in the most critical moment in history to *start* learning them. In this episode you'll learn: ➡️ Why "just be yourself" is unhelpful advice + potentially cruel ➡️ The important everyday interactions technology + AI replaced ➡️ Where to stand at a party so someone always talks to you ➡️ How to have better conversations (+ why you already have the skills) ➡️ What the real antidote to awkwardness is ➡️ How to practice micro-social skills without turning people off ➡️ Why we’re all ambiverts + how to understand ambiversion ➡️ How soft skills drive major career inflection points ➡️ The concept of social fitness + the “nutrition” of your relationships In this conversation, Vanessa lays out how even the most socially anxious among us can build real connections and become more likable… even in a world that has quietly removed all the places we used to accidentally get good at being human. And the secret isn't confidence. It's something far more generous. This… is *A Bit of Optimism*. \+ + + Watch *A Bit of Optimism* on Spotify, and Spotify Premium users can enjoy the show ad-free. \+ + + To pre-order Vanessa’s new book, *Conversation: How to Be Instantly Likeable in Any Interaction*, head to: [https://www.scienceofpeople.com/conversation/](https://www.scienceofpeople.com/conversation/) Want to learn more people skills from Vanessa? Check out The Science of People: [https://www.scienceofpeople.com/](https://www.scienceofpeople.com/) \+ + + Chapters ### Chapters - **00:00:00** Social Skills in the Digital Age Crisis - **00:01:47** Vanessa's Journey: The Accidental Social Skills Expert - **00:05:45** Mistakes Everyone Makes Learning to Improve Social Skills - **00:08:09** Where Did Our Places to Practice Being Human Go? - **00:11:17** Where to Stand at a Party When You Don't Know Anyone - **00:14:17** The Ambivert Reality: Social Fitness and Friendship Nutrition - **00:18:07** The Discomfort Problem: Why Young People Avoid Rather Than Adapt - **00:21:33** Put the Shoes in the Box: The Art of Knowing When to Stop - **00:34:54** Intention Matches Action: Defining Authenticity - **00:46:56** The Power of Being Seen: How Love Changed Everything - **00:49:51** The Ultimate Social Skill: Helping Others Feel Normal - **00:42:20** Micro-Social Skills: Finding the Parts of Yourself You Like \+ + + Simon is an unshakable optimist. He believes in a bright future and our ability to build it together. Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do. Simon is the author of multiple best-selling books including *Start With Why*, *Leaders Eat Last*, *Together is Better*, and *The Infinite Game*. \+ + + Website: [http://simonsinek.com/](http://simonsinek.com/) Leaderful: [https://simonsinek.com/leaderful](https://simonsinek.com/leaderful) Podcast: [http://apple.co/simonsinek](http://apple.co/simonsinek) Instagram: [https://instagram.com/simonsinek/](https://instagram.com/simonsinek/) Linkedin: [https://linkedin.com/in/simonsinek/](https://linkedin.com/in/simonsinek/) Twitter: [https://twitter.com/simonsinek](https://twitter.com/simonsinek) Facebook: [https://www.facebook.com/simonsinek](https://www.facebook.com/simonsinek)

May 19, 2026 59 min

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Episode 224

Stop Telling Us Everything Happens for a Reason with Anti-Victim Tom Nash

We often comfort ourselves with the idea that things happen for a reason, or define our struggles as a test of strength. Tom Nash might ask you to reconsider. Tom is a speaker, former DJ, and globe-trotting advocate for agency, anti-fragility, and the radical idea that your worst moment might be your greatest asset — as he argued in his TED Talk, "The Perks of Being a Pirate.” He’s also the mind behind *Last Meal with Tom Nash* where he asks his guests what their last meal would be if the world ended tomorrow, and then actually cooks it for them. In our conversation, Tom shares how, at 19, a rare bacterial infection left him a quadruple amputee with a 2% chance of survival. And he'll tell you it's the best thing that ever happened to him. This isn’t just another conversation about resilience. It’s a deep dive into agency and the difference between a life that happens to you and one you actually choose. In this episode, we explore: ➡️ Why the story you tell yourself about your own life is the most powerful force in it ➡️ The difference between resilience and anti-fragility (and why it matters) ➡️ Tom’s framework for navigating adversity: The Artist, the Author, and the Alchemist ➡️ The counterintuitive reason why we actually need support networks ➡️ Why "everything happens for a reason" can be a trap (and the perspective that works better) ➡️ What your last meal choice reveals about what you're really searching for ➡️ Why the concept of being "self-made" is a dangerous illusion Tom joins me to ask a fundamental question: who is really holding the pen when it comes to your story? This… is *A Bit of Optimism*. \+ + + Watch the new season of Tom’s show *Last Meal with Tom Nash* and head to: [https://www.lastmealwithtomnash.com](https://www.lastmealwithtomnash.com/) Want more Tom? Check out his website: [https://www.tomnash.com](https://www.tomnash.com/) \+ + + Chapters ### Chapters - **00:00:00** Adversity Can Be The Best Thing You Experience - **00:03:45** Tom's Story: Contracting Meningococcal Disease - **00:07:47** The Gift of Agency: Choosing to Amputate - **00:16:18** The Artist, The Author, and The Alchemist: A Framework for Anti-Fragility - **00:20:28** The Alchemist: Turning Adversity Into Advantage - **00:23:52** Learning to Walk Again: The Momentum Metaphor - **00:26:57** The True Purpose of Support Networks - **00:34:33** Why 'Everything Happens for a Reason' Robs You of Agency - **00:47:37** The Last Meal Question: What Your Choice Reveals About Freedom - **00:42:23** Joel Robuchon: Leadership Through Teaching, Not Commanding - **00:58:34** The Problem With Inspirational Affirmations - **01:00:59** Stop Saying Everything Happens for a Reason \+ + + Simon is an unshakable optimist. He believes in a bright future and our ability to build it together. Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do. Simon is the author of multiple best-selling books including *Start With Why*, *Leaders Eat Last*, *Together is Better*, and *The Infinite Game*. \+ + + Website: [http://simonsinek.com/](http://simonsinek.com/) Leaderful: [https://simonsinek.com/leaderful](https://simonsinek.com/leaderful) Podcast: [http://apple.co/simonsinek](http://apple.co/simonsinek) Instagram: [https://instagram.com/simonsinek/](https://instagram.com/simonsinek/) Linkedin: [https://linkedin.com/in/simonsinek/](https://linkedin.com/in/simonsinek/) Twitter: [https://twitter.com/simonsinek](https://twitter.com/simonsinek) Facebook: [https://www.facebook.com/simonsinek](https://www.facebook.com/simonsinek) Simon’s books: The Infinite Game: [https://simonsinek.com/books/the-infinite-game/](https://simonsinek.com/books/the-infinite-game/) Start With Why: [https://simonsinek.com/books/start-with-why/](https://simonsinek.com/books/start-with-why/) Find Your Why: [https://simonsinek.com/books/find-your-why/](https://simonsinek.com/books/find-your-why/) Leaders Eat Last: [https://simonsinek.com/books/leaders-eat-last/](https://simonsinek.com/books/leaders-eat-last/) Together is Better: [https://simonsinek.com/books/together-is-better/](https://simonsinek.com/books/together-is-better/)

May 12, 2026 1 hr 2 min

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Episode 223

The Real Reason You Feel Empty (Even When Life Looks Good) with Musician Mike Posner

If at some point, you've looked at your life—your job, your relationships, your achievements—and thought: “*is this it?”* This episode is for you. Mike Posner had that moment at 30. His life, by every external measure, was extraordinary: he had hit songs, Grammy nominations, millions in the bank. He was a pop star… And he was miserable. What followed was one of the most honest reckonings we've ever heard on this show. Mike walked across America, survived a rattlesnake bite, climbed Everest, and came out the other side with something no amount of success had ever given him: peace. Mike Posner is a multi-platinum, Grammy-nominated recording artist, songwriter, and producer. But the reason you should listen to this conversation has nothing to do with any of that. It has everything to do with where he was and his incredibly human journey getting to somewhere better, more peaceful, and more meaningful. He even wrote a song about it—a follow up to his hit song “I Took a Pill in Ibiza” called “I Went Back To Ibiza.” In this episode you'll learn: ➡️ Why achieving your biggest goals can leave you feeling emptier than before you started ➡️ The difference between real vulnerability and broadcasting your pain online (and why intention changes everything) ➡️ Why comfort (not failure) might be the thing quietly hollowing out your life ➡️ What walking across America actually taught Mike about who he was and who he wasn't ➡️ Why self-improvement taken too far becomes selfishness ➡️ The one pursuit more valuable than success, grit, or getting to the top You don't need a Grammy nomination to relate to this conversation, you just need to have ever wondered if the life you're building is actually the life you want. This… is *A Bit of Optimism*. \+ + + Watch *A Bit of Optimism* on Spotify! If you’re subscribed to Spotify Premium, you don’t get any Spotify ads on my video. If you want to watch Mike’s new music video for “I Went Back To Ibiza,” check it out here: [https://www.youtube.com/watch?v=UDL6SEW4xKU](https://www.youtube.com/watch?v=UDL6SEW4xKU) You can find “I Went Back To Ibiza” wherever you stream music. \+ + + Chapters ### Chapters - **00:00:00** The Real Reason You Feel Empty - **00:06:51** Art as Alchemy: Turning Pain into Beauty - **00:18:12** The Asymmetry Between What We Have and What We Give - **00:20:32** Walking Across America: Getting Out of His Comfort Zone - **00:24:54** The Snake Bite: When Attention Came From Pain - **00:30:13** The Problem With Avoiding Discomfort - **00:33:47** From Fraud to Peace: Mike's Transformation - **00:36:31** Walking Each Other Home: The Purpose of Art and Life - **00:38:56** The Pursuit of Peace, Not Just Hardship - **00:48:48** Getting to the Top of Everest: Only Half of the Journey \+ + + Simon is an unshakable optimist. He believes in a bright future and our ability to build it together. Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do. Simon is the author of multiple best-selling books including *Start With Why*, *Leaders Eat Last*, *Together is Better*, and *The Infinite Game*. \+ + + Website: [http://simonsinek.com/](http://simonsinek.com/) Live Online Classes: [https://simonsinek.com/classes/](https://simonsinek.com/classes/) Podcast: [http://apple.co/simonsinek](http://apple.co/simonsinek) Instagram: [https://instagram.com/simonsinek/](https://instagram.com/simonsinek/) Linkedin: [https://linkedin.com/in/simonsinek/](https://linkedin.com/in/simonsinek/) Twitter: [https://twitter.com/simonsinek](https://twitter.com/simonsinek) Facebook: [https://www.facebook.com/simonsinek](https://www.facebook.com/simonsinek)

May 5, 2026 53 min

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Episode 222

The Real Reason Young People Don't Have 'The Hunger' for Work (And What Leaders Need to Hear) with Generations Expert Dr. Eliza Filby

Admit it, you've complained about at least one other generation. Boomers, Gen X, Millennials, Gen Z—somehow, they all end up with reputations built around what's wrong with them. Dr. Eliza Filby has a different suggestion: *stop* asking what's wrong with them. And *start* questioning what world they were handed. Eliza is a contemporary historian, generations expert, and the author of *Sunday Times* bestseller: *Inheritocracy*. And with more generations in the workplace than at any point in history, she is precisely the person we need to show us a new way to win… together. In this conversation, Eliza makes connections about how generational change is reshaping work, wealth, and modern life that I’d never thought to connect. She might just change how *you* see the world (and people) around you. In this episode you'll learn: ➡️ Why calling Gen Z "entitled" is the wrong diagnosis (and what's really driving the behavior leaders complain about most) ➡️ How retirement planning and eldercare became the new midlife crisis ➡️ How the economy changed after 2008 + quietly rewrote the rulebook for every generation that followed ➡️ Why belonging is becoming increasingly rare (even though we need it) ➡️ Why Millennials + Gen Z are more likely become homeowners by being loyal to their parents than by being loyal to their jobs ➡️ 3 things no AI will replace in the workplace… ➡️ What’s driving hyper-individualism + how do we fix it We all may have strong opinions about one another, but it’s time to focus on building greater understanding. This conversation is a good place to start. This… is A Bit of Optimism. \+ + + To buy a copy of Dr. Eliza Filby’s bestselling book *Inheritocracy: It’s Time to Talk About the Bank of Mum and Dad*, head to: [https://www.elizafilby.com/books](https://www.elizafilby.com/books) Want to hear more from Eliza? Check out her *It’s All Relative* Newsletter: [https://www.elizafilby.com/newsletter](https://www.elizafilby.com/newsletter) \+ + + ### Chapters - **00:00:00** Rethinking the Generational Divide at Work - **00:01:35** How Dr. Filby Became a Generations Expert - **00:04:33** Defining Generations: Why They're Getting Shorter - **00:08:42** The Fragmentation of Shared Experience - **00:14:29** Conspiracy Culture Infiltrates the Workplace - **00:16:16** The End of Job Security and the Rise of the Solopreneur - **00:18:02** What Leaders Must Offer in the Age of Uncertainty - **00:20:31** The Bank of Mom and Dad: Living in an Inheritocracy - **00:28:23** Why Young People Don't Have 'The Hunger' for Work - **00:31:35** The Changing Life Cycle: Delayed Adulthood and Pressured Midlife - **00:41:45** Rising Individualism and the Loss of 'We' at Work - **00:47:02** Gen AI: The Next Generation in the Workplace - **00:50:44** The Solution: Let Humans Do What Can't Be Counted - **01:00:42** Disrupting the Path to Mastery and Nurturing Human Skills - **01:03:02** How the Generations Can Come Together \+ + + Simon is an unshakable optimist. He believes in a bright future and our ability to build it together. Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do. Simon is the author of multiple best-selling books including *Start With Why*, *Leaders Eat Last*, *Together is Better*, and *The Infinite Game*. \+ + + Website: [http://simonsinek.com/](http://simonsinek.com/) Live Online Classes: [https://simonsinek.com/classes/](https://simonsinek.com/classes/) Podcast: [http://apple.co/simonsinek](http://apple.co/simonsinek) Instagram: [https://instagram.com/simonsinek/](https://instagram.com/simonsinek/) Linkedin: [https://linkedin.com/in/simonsinek/](https://linkedin.com/in/simonsinek/) Twitter: [https://twitter.com/simonsinek](https://twitter.com/simonsinek) Facebook: [https://www.facebook.com/simonsinek](https://www.facebook.com/simonsinek)

April 28, 2026 1 hr 25 min

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Episode 221

The Leadership Advice Nobody Follows (But Everyone Should) with Top Leadership Expert Don Yaeger

The most successful leaders, coaches, and teams in history share one counterintuitive secret: their main focus wasn’t winning. And yet… they won more than everyone else. My guest, Don Yaeger, learned this lesson from his mentor: legendary college basketball coach John Wooden. Don is one of my favorite master storytellers, a top business leadership coach, author of 44 books, 13 of them New York Times bestsellers, and a former Associate Editor at *Sports Illustrated*. Don has worked alongside the greatest athletes of our generation: Michael Jordan, Serena Williams, Michael Phelps. But no relationship shaped him more than the 12 years he spent as Coach Wooden's mentee. Whether or not you're a sports fan, I promise you: the lessons Don shares are as universal as it gets. We explore what it *really* means to win in business and in life. The greatest leaders in history already figured this out. The question is why the rest of us aren't following their lead. In this episode you'll learn: ➡️ Why the winningest coach in college basketball history never talked about winning (and what he focused on instead) ➡️ The Bill Walton story that reveals how great leaders hold standards without exceptions (even for their best people) ➡️ How one conversation with John Wooden transformed Don's marriage & the weekly habit he's kept for 16+ years ➡️ What Delta CEO Ed Bastian's "virtuous cycle" can teach any leader about putting people before results ➡️ What a great mentor actually look like and how to know when you’ve found one If you've ever chased the short-term win at the cost of the long game… this episode is the reset you didn't know you needed. This… is A Bit of Optimism. \+ + + If you want to read a free chapter from Don's upcoming book *The Business of Storytelling,* head to: [https://www.donyaeger.com/chapter](https://www.donyaeger.com/chapter/) \+ + + Chapters ### Chapters - **00:00:00** The Power of Appreciation: What You Look For, You Find - **00:02:02** From Delivering Newspapers to Sports Illustrated: Don's Journey to Journalism - **00:04:21** Don’s 12-Year Mentorship with Coach John Wooden - **00:06:50** Coach Wooden's Philosophy: Pyramid of Success - **00:09:00** The Bill Walton Haircut Story: How Wooden Managed Ego and Held Everyone to the Same Standards - **00:10:33** Building Better Humans, Not Just Better Players - **00:14:36** The Love Letters That Changed Don's Marriage - **00:19:35** Looking for Things to Love: The Mindset That Changes Everything - **00:22:23** Leading with Employee Care Over Customer-First Mentality - **00:33:55** What True Mentorship Really Means: It's Not Transactional - **00:47:07** Why Aren't More Leaders Following Coach Wooden's Example? - **00:53:17** The Best Storytelling Advice: Know Your Audience \+ + + Simon is an unshakable optimist. He believes in a bright future and our ability to build it together. Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do. Simon is the author of multiple best-selling books including Start With Why, Leaders Eat Last, Together is Better, and The Infinite Game. \+ + + Website: [http://simonsinek.com/](http://simonsinek.com/) Live Online Classes: [https://simonsinek.com/classes/](https://simonsinek.com/classes/) Podcast: [http://apple.co/simonsinek](http://apple.co/simonsinek) Instagram: [https://instagram.com/simonsinek/](https://instagram.com/simonsinek/) Linkedin: [https://linkedin.com/in/simonsinek/](https://linkedin.com/in/simonsinek/) Twitter: [https://twitter.com/simonsinek](https://twitter.com/simonsinek) Facebook: [https://www.facebook.com/simonsinek](https://www.facebook.com/simonsinek) \+ + + Photo/Video credits for this episode: [https://tinyurl.com/ycxdw52s](https://tinyurl.com/ycxdw52s)

April 21, 2026 55 min

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