A Bit of Optimism

Simon Sinek
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My career is an accident. It started when I set out to rediscover my passion and reignite a spark I’d lost — and that journey led me to the work I do now. If you know me from my books or my speaking, you know I’m fascinated by why people do what they do. What makes someone find joy and meaning in their life, or pursue something far greater than themselves? I started A Bit of Optimism to explore those ideas and expand my own perspective. This podcast is a trove of honest conversations, with people who challenge me, teach me, or simply help me see things in a different way. Some guests are household names, and others you may be meeting for the first time. But each one of them has something to share that can help all of us grow. So if you’re looking for a spark — some insight, inspiration, or just a reminder that good things are possible — join me on A Bit of Optimism! Let’s grow together.

  1. 2 DAYS AGO

    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/ Want to learn more people skills from Vanessa? Check out The Science of People: 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/ Leaderful: https://simonsinek.com/leaderful Podcast: http://apple.co/simonsinek Instagram: https://instagram.com/simonsinek/ Linkedin: https://linkedin.com/in/simonsinek/ Twitter: https://twitter.com/simonsinek Facebook: https://www.facebook.com/simonsinek

    59 min

  2. 5 MAY

    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 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/ Live Online Classes: https://simonsinek.com/classes/ Podcast: http://apple.co/simonsinek Instagram: https://instagram.com/simonsinek/ Linkedin: https://linkedin.com/in/simonsinek/ Twitter: https://twitter.com/simonsinek Facebook: https://www.facebook.com/simonsinek

    53 min

  3. 28 APR

    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  Want to hear more from Eliza? Check out her It’s All Relative 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/ Live Online Classes: https://simonsinek.com/classes/ Podcast: http://apple.co/simonsinek Instagram: https://instagram.com/simonsinek/ Linkedin: https://linkedin.com/in/simonsinek/ Twitter: https://twitter.com/simonsinek Facebook: https://www.facebook.com/simonsinek

    1hr 25min

  4. 21 APR

    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/ Join the Leaderful app! Listeners can use promo code: STORY30 when you download the app or sign up at simonsinek.com. + + + 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/ Live Online Classes: https://simonsinek.com/classes/ Podcast: http://apple.co/simonsinek Instagram: https://instagram.com/simonsinek/ Linkedin: https://linkedin.com/in/simonsinek/ Twitter: https://twitter.com/simonsinek Facebook: https://www.facebook.com/simonsinek + + + Photo/Video credits for this episode: https://tinyurl.com/ycxdw52s

    55 min

  5. 14 APR

    Why This Baseball Team Has a 4.2 Million Person Waitlist With Savannah Bananas Founder Jesse Cole

    We talk a lot about building successful things. But what does it actually take to build something people love? Jesse Cole has built an entirely new genre of entertainment: The Savannah Bananas and the Banana Ball League. They’re a viral sensation, selling out stadiums across the country, and have over 4.2 million fans on their  ticket waitlist. On the surface, Banana Ball looks like a wild and entertaining version of baseball. But underneath it all is something much more disciplined: an obsession with the fan experience.  Jesse calls his approach Fans First and it’s more than a slogan and the title of his book… It’s a standard. Every minute of the two-hour games are crammed with attention grabbing spectacle. It’s a full-blown live experience designed for every seat in the stadium: players dance, fans are part of the show, trick plays defy the laws of physics, there are multiple sing-alongs… all during an actual baseball game.  In this conversation, we talk about building something new for others, from embracing years of failure (including selling just two tickets in the first three months), to creating experiences that make people feel included, joyful, and valued. We also discuss how he took inspiration from Disney and PT Barnum, the importance of affordable in-person experiences, and how his team reviews every single detail after every show to get better the next day. Because what Jesse’s building goes beyond just entertainment. It’s a place where people can feel seen for generations to come. And in a world that often moves too fast to build things with care… Those human details might be what matter most. This… is A Bit of Optimism. --------------------------- To learn more about the Banana Ball League or sign up for the ticket waitlist, check out: https://bananaball.com/  Or if you want all things Savannah Bananas, head to: https://thesavannahbananas.com/  ---------------------------

    1hr 6min

  6. 7 APR

    Ken Burns and the Art of Telling the Whole Story

    We live in a world that pushes us to simplify everything: right or wrong, good or bad, this or that. It makes things and our place in the world easier to understand. But the truth is rarely simple… in fact, it’s often messy and deeply human. For 50 years, Ken Burns has mastered his craft, becoming one of the most prolific and respected documentary filmmakers. His documentaries notably resist easy answers. From The Civil War to The Vietnam War to Baseball, Ken has shaped how we understand American identity, political memory, and our shared history. His latest project, The American Revolution, is a six-part PBS series that tells the story of America’s founding. He revisits the revolution through multiple human perspectives, which reveals new complexity to a familiar story. Ken’s guiding principle is simple: “it’s complicated.” And that philosophy shows up in everything he does. Because the most honest stories hold opposing truths at the same time. In this conversation, Ken and I explore why storytelling matters more than arguments, how simplifying the world can help us understand it—but also distort it—and why empathy lives in the space between what’s included in a story and what’s left out. We also dive into why human behavior hasn’t changed much over time, what mistakes humans keep repeating, how embracing complexity might help us better understand each other, and what history can teach us about who we are and who we’re still becoming. If you’ve ever struggled to make sense of a complicated world, or felt frustrated by how quickly we reduce people to labels, this episode is a powerful reminder: understanding lives in our ability to see the whole story. This… is A Bit of Optimism. --------------------------- If you want to watch “American Revolution” the six-part, 12-hour documentary directed by Ken Burns, Sarah Botstein, and David Schmidt on PBS, head to: https://www.pbs.org/kenburns/the-american-revolution ---------------------------

    54 min

  7. 31 MAR

    What Happens When You’re Naive Enough to Try with KIND Founder Daniel Lubetzky

    Naiveté is one of the most powerful assets an entrepreneur can have. In fact, I think some of the most meaningful things in the world only exist because someone was naive enough to try. Daniel Lubetzky would know. In a crowded category and cutthroat industry, Daniel dared to build a company called KIND. He started with a simple question: how can we help people snack healthily without compromising their values? KIND Bars are now a household name and Daniel achieved his dream of building the culture behind the brand. A culture rooted in trust, long-term thinking, and social good. Essentially, a place where people loved to work and a company that thrived as a result. In this conversation, Daniel and I explore why entrepreneurship is less about ego and more about problem-solving, why brands are promises that must be kept, and how thinking in the short-term erodes trust in both business and society. Daniel’s story doesn’t stop at the wildly successful business he founded. The son of a Holocaust survivor, he grew up with a deep sense of responsibility to prevent hatred and division from taking root again. That calling first led him to create PeaceWorks, bringing people together through commerce, and now fuels his work with the Builders Movement. Builders is an effort to channel curiosity, compassion, and courage to reduce polarization and rebuild trust… together. Some important context, because this episode touches on peace building and polarization, is that it was recorded back in December 2025 and before recent developments in the Middle East. But this episode is about how kindness can be a competitive advantage, how optimism can be strategic, and how each of us has a role to play in building a future that’s more connected than divided. This… is A Bit of Optimism. --------------------------- If you want to learn more about the Daniel’s work with The Builders Movement, head to: https://buildersmovement.org Check out the products and work being done at KIND: https://www.kindsnacks.com ---------------------------

    55 min

  8. 24 MAR

    AI Can Do Everything… Except This (Why Humans Still Win) With Restaurateur Will Guidara

    As businesses race toward faster systems, smarter tools, and total automation, something critical is getting lost: human connection. And ironically, the rise of AI is making that gap impossible to ignore. In this episode, I sit down with returning guest and close friend Will Guidara, former co-owner of Eleven Madison Park, to explore why humanity is becoming the ultimate competitive advantage in the age of AI. Will helped transform a restaurant into the best in the world, not by reinventing the food being served, but by reinventing the experience around it. He calls this philosophy "Unreasonable Hospitality," which is the practice of going beyond what’s expected or required to make someone feel genuinely seen, valued, and cared for to create a memorable human experience. He argues that in a world where people expect excellence, the real differentiator is care. And Will isn’t alone in this belief. His book Unreasonable Hospitality, which I’m the proud publisher of, is a global bestseller. And his follow up book, Unreasonable Hospitality: The Field Guide, comes out April 28, 2026. In this conversation, Will and I unpack why human value will continue to rise in an automated world, how the smallest moments of care can create lasting loyalty, how we can turn automation’s efficiency into better experiences, and why the things that matter most in our lives are the hardest to measure. And fair warning, Will and I do giggle our way through some of this conversation about why technology can’t replace human connection, the hidden cost of achievement, and a story about how a single piece of Basque cheesecake delivered to a hotel room is a gesture thoughtful enough to make someone feel seen. That’s just the kind of friendship we have. So if you’re wondering how to stand out and live a more meaningful life in a world increasingly shaped by AI… and share a laugh with us… this is a conversation for you. This… is A Bit of Optimism. --------------------------- To stay in the loop with Will or purchase his best-selling book Unreasonable Hospitality, head to: https://www.unreasonablehospitality.com/ If you’d like to pre-order Unreasonable Hospitality: The Field Guide, out April 28, 2026, check out: https://uhthefieldguide.com/ ---------------------------

    1hr 6min
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About

My career is an accident. It started when I set out to rediscover my passion and reignite a spark I’d lost — and that journey led me to the work I do now. If you know me from my books or my speaking, you know I’m fascinated by why people do what they do. What makes someone find joy and meaning in their life, or pursue something far greater than themselves? I started A Bit of Optimism to explore those ideas and expand my own perspective. This podcast is a trove of honest conversations, with people who challenge me, teach me, or simply help me see things in a different way. Some guests are household names, and others you may be meeting for the first time. But each one of them has something to share that can help all of us grow. So if you’re looking for a spark — some insight, inspiration, or just a reminder that good things are possible — join me on A Bit of Optimism! Let’s grow together.

Information

  • Creator
    Simon Sinek
  • Years Active
    2020 - 2026
  • Episodes
    223
  • Rating
    Clean
  • Show Website
    A Bit of Optimism

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