A Bit of Optimism

A Bit of Optimism

By Simon Sinek

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,... more
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  1. Number 1: What Happens When You Bet on Yourself with Ted Lasso’s Brendan Hunt

    Maybe you know the feeling: everyone around you seems to be getting ahead, and every hour you spend on something "frivolous" — the hobby, the detour, the game on a Sunday afternoon — feels like falling behind. Brendan Hunt's career is proof those hours are never wasted. The detour turned out to be the path all along. Most of us know Brendan as Coach Beard and as the Emmy Award-winning co-creator of Ted Lasso. But before any of that, he was an unknown Chicago improv actor when the Amsterdam comedy institution Boom Chicago offered him something different. He moved to Amsterdam for a year… that turned into five… and he joined an alumni roster that now includes comedians like Seth Meyers, Jordan Peele, Amber Ruffin, and Jason Sudeikis. Brendan performed every night, fell head over heels for soccer ("a soccer missionary for all Americans," as he puts it), and struck up a friendship with Jason Sudeikis. Years later, all of it collided into one of the most beloved shows on television, Ted Lasso, which is back for Season 4 on Apple TV+. Brendan has also returned to his first love, the stage, with his solo show The Movement You Need.In this conversation, Brendan and I trace the wildly unplanned path from Chicago to Amsterdam to AFC Richmond… and land on a different way to think about ambition: master the craft in front of you, and let the plan catch up later.In this episode you'll learn:➡️ The real origin story of Ted Lasso (it began as a YouTube-only commercial written by a pool) ➡️ Why Coach Beard barely talks + the improv rule that explains everything he does ➡️ The "Beatles in Hamburg" secret to mastering any craft ➡️ Why stepping away won't put you behind (everything will be exactly where you left it) ➡️ How "wasting" Sundays watching Dutch soccer created the Lasso–Beard dynamic ➡️ The surprising origin of the BELIEVE sign + who it was designed to annoy ➡️ Why the flip side of belief is trust + and how it shapes Season 4We spend so much of our lives protecting the plan. Brendan's story is a reminder that the things worth protecting are usually the ones we never planned for at all. This… is A Bit of Optimism.+ + +This episode is brought to you by SAP. Bring it with SAP GROW. The AI Cloud ERP for any size business. Learn more at https://SAP.com/GROW + + + Check out Brendan as Coach Beard on season 4 of Ted Lasso on Apple TV+: https://tv.apple.com/us/show/ted-lasso If you want to learn more about Brendan’s solo show, The Movement You Need, head to: https://themovementyouneed.com + + +Chapters Chapters00:00:00 Plans vs. Imagination: The Risk of Staying Safe00:02:43 From Chicago to Amsterdam: The Audition That Changed Everything00:07:02 The Boom Chicago Pitch: When Amsterdam Became Irresistible00:11:58 The Beatles in Hamburg: Getting Your 10,000 Hours00:16:18 The Joy of the Thing: Why Not Thinking About Your Career Makes You Better00:20:01 Real Opportunity vs. Your Imagination: Why People Stay Put00:20:58 Strong Opinions, Loosely Held: The Art of the Flexible Plan00:21:28 Curiosity as Currency: The Jack of All Trades Philosophy00:22:51 The Ted Lasso Origin Story: A Pool, Some Bits, and a Name00:25:45 The Soccer Missionary: How Amsterdam Made Brendan the Beard to Ted's Lasso00:27:31 Everything Contributes to Everything: The Payoff of Wasted Time00:30:31 Midwestern Chipperness Meets British Stiff Upper Lip: The Culture Clash of Ted Lasso00:32:57 Diagnosed as Ted Lasso: When Your Company Is the Character00:33:46 Bringing Yourself to the Character: Acting as Being, Not Becoming00:37:23 Coach Beard Was a Placeholder: How a Play Gave Him a Name00:44:06 The Art Couple: The Play Brendan Wishes He Could Do Forever00:46:33 The 1986 NFC Championship: A Pure Childhood Memory00:54:07 When Comedy Became a Need: Making Mom Laugh00:55:59 Season Four: Belief, Trust, and Starting Over00:57:28 Don't Pick Sides: The Gift of Knowing Your Own Mistakes00:59:04 The Purity of Art: Why Brendan Keeps Writing + + +Website: http://simonsinek.comLeaderful: https://simonsinek.com/leaderfulPodcast: http://apple.co/simonsinekInstagram: https://instagram.com/simonsinekLinkedin: https://linkedin.com/in/simonsinekTwitter: https://twitter.com/simonsinekFacebook: https://www.facebook.com/simonsinek+ + +

    1h 2min
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  2. Number 2: How to Say the Hard Thing and Keep the Relationship | A Bit of Optimism: Feelings at Work | PART 5

    Every lasting relationship has survived at least a few hard conversations. But most of us would still rather not have them... So we put them off and tell ourselves the tension will fade on its own. Instead it goes underground: into the stories we build about people, the resentments we quietly collect, and the side-texts we send about a colleague we won't talk to directly.But a hard conversation is a short burst of discomfort in exchange for something better on the other side: trust, collaboration, and a relationship strong enough to survive the next one. Feelings at Work is a special five-part series from A Bit of Optimism, where Simon Sinek and Alex Simon, founder of LifeShop, explore the human skills that shape how we work, lead, and build relationships. Together, they unpack the emotional challenges most of us face every day—from people pleasing and listening to giving feedback, taking accountability, and having difficult conversations.In this final episode, Simon and Alex take on hard conversations: why tension is telling us something useful, why the story we build about someone gets harder to undo the longer we wait, and what to actually say when it's time to have the hard conversation.Simon and Alex share tools like how to know when to bring something up so you don't show up hot, how to break the fourth wall and reset a conversation that's already going sideways, and the practice of “Watering Someone’s Flowers.” In this episode you'll learn:➡️ Why tension is a smoke signal telling you to address something ➡️ How conflict is a team sport for mutual understanding➡️ How to move from "you're the problem" to both of you facing it together ➡️ The "resentment gremlin" + why feeding it feels so satisfying ➡️ When to initiate a hard conversation ➡️ Why it’s important to start with a request for grace➡️ “Watering someone's flowers”: the practice that softens any tension➡️ What to do instead of “feedback sandwiches”➡️ How to interrupt, reset, and take something back during a conversation Whether you're leading a team, dreading a review, or rehearsing the same speech in your car for the third week running, learning how to have hard conversations is an essential skill to build. And remember: a hard conversation isn't a sign that something has gone wrong. It's a sign that something matters enough to fix.This... is A Bit of Optimism.+ + +CHAPTERSChapters00:00:00 When Conflict Turns People Into Monsters00:02:16 Reframing Tension: It's a Sign, Not a Problem00:02:43 The Resentment Gremlin: How Waiting Makes It Worse00:03:50 Oh No, Let's Just Skip It: Why Hard Conversations Feel Impossible00:08:01 The Passive Aggressive Company: When Tens of Thousands Avoid Feedback00:10:02 When Passive Aggression Is The Solution to Conflict00:11:15 What Actually Stops Us: Fear, Narrative Building, and Self-Righteousness00:20:38 Conflict Is a Team Sport for Mutual Understanding00:23:04 You're Not the Problem, I'm Not the Problem: The Problem Is the Problem00:25:21 The Interruption Technique That Stops Character Assassination00:26:27 Timing Matters: Not Too Hot, Not Too Cold00:28:31 Setting a Goal: What Do You Actually Want From This?00:29:44 Asking for Grace Grace: "I'm Going to Get This Wrong"00:33:07 How to "Water Someone's Flowers"00:38:02 Try This Instead of Feedback Sandwiches00:40:25 Breaking the Fourth Wall: Pause, Reset, and Start Again00:43:41 The Scaffolding Philosophy: Messy Humans Need Support Structures+ + + Website: http://simonsinek.com/Leaderful: https://simonsinek.com/leaderfulPodcast: http://apple.co/simonsinekInstagram: https://instagram.com/simonsinek/Linkedin: https://linkedin.com/in/simonsinek/Twitter: https://twitter.com/simonsinekFacebook: https://www.facebook.com/simonsinek + + +About Alex SimonAlex Simon is the founder of Lifeshop, a school for adult emotional education and teaches emotional intelligence at Yale University. She teaches the emotional and communication skills we all should've learned in school—but didn't.She facilitates experiential workshops on how to have hard conversations, stop people pleasing, listen better, navigate major life transitions, and build healthier relationships. Her sessions are practical, deeply connective, and somehow shockingly fun.When she was 27, Alex created The Self & Other: In Theory and Practice, one of Yale's most sought-after courses.In 2025, she founded Lifeshop in New York to bring emotional education beyond the classroom and into everyday life. She also launched The School of Life in New York and leads workshops for organizations around the world.Before dedicating her career to emotional education, Alex worked as a management consultant at Bain and held strategy and operations roles across industries. She has also lived and trained at Plum Village and Esalen and completed dozens of programs in mindfulness, communication, and personal development.

    46min
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  3. Number 3: How to Trust Yourself When Everyone Has an Opinion with Love Thy Nader's Mary Holland Nader

    Maybe this sounds familiar: you finally get the opportunity you've been waiting for, and the voice in your head says, "I'm not ready, I don't belong here." Now imagine hearing that voice with millions of people watching.Mary Holland Nader has lived it. She never dreamed of fame, but when Hulu's reality series Love Thy Nader came knocking, she traded her secure Wall Street job for the spotlight and put her new platform to work. It allowed her to launch Mary & Pip, a purpose-driven fintech company that takes a wellness approach to money, demystifying finance for those of us it usually makes feel dumb. She also brings that expertise to her new podcast, Growing Interest (where I was lucky to be among her first guests). On the show, Mary Holland lets us join every step of her founder’s journey… even when it’s messy. Because she never wanted to be famous, but now that she is, she’s realized fame is leverage. And Mary Holland's committed to using hers to help and inspire others. In this episode you'll learn:➡️ How to survive a 180-degree life pivot➡️ Why your gut doesn't tell you what to do — it checks your values ➡️ The "corny" morning ritual that transformed Mary Holland's confidence ➡️ How to stop making your doubts your identity (with one simple grammar change) ➡️ The difference between being nice and being kind — and why feedback is kind ➡️ The 2 questions every founder should ask before raising money ➡️ Why Simon gives his time to supporters instead of critics ➡️ The "reluctant sellout" + how financial stability protects your values ➡️ How to introduce yourself when you're more than one job titleMary Holland is a new breed of entrepreneur — proof of what happens when you use your platform for something bigger than yourself. She stopped waiting for confidence to arrive and decided to build it… in front of everyone. This… is A Bit of Optimism.+ + +This episode is brought to you by SAP. Bring it with SAP GROW. The AI Cloud ERP for any size business. Learn more at https://SAP.com/GROW+ + +Tune in to Mary Holland’s new podcast, Growing Interest, and you might just see Simon as a guest.Improve your financial wellness with Mary & Pip. Head to: https://www.maryandpip.com Want to keep up with Mary Holland and her sisters? Check out Love Thy Nader on Hulu: https://www.hulu.com/series/love-thy-nader + + +Chapters Chapters00:00:00 From Wall Street to Reality TV: Using Fame as a Tool for Good00:02:57 Growing Up in the Bayou: Four Sisters and a Pet Alligator00:07:19 Why Finance? Growing Up With Money Anxiety00:08:25 Meeting Jimmy Kimmel's Agent: The Accidental Origin Story00:10:29 Quitting Wall Street for Reality TV00:12:58 Why Finance Makes Everyone Feel Stupid00:14:14 Mary and Pip: Translating Finance for Real People00:17:23 Becoming Confident on Camera: From Mortified to Vulnerable00:25:22 The Power of Positive Self-Talk: Mirror Affirmations That Actually Work00:28:31 Trust Your Gut: When Smart People Give You Bad Advice00:30:09 What Does A Mentor Actually Look Like? 00:33:27 Gazelles Get Eaten: Why Hypergrowth Isn't Always Good00:42:24 Spears: The Feedback Technique That Changed Everything00:45:32 Correcting Language That Creates False Narratives00:54:02 The Reluctant Sellout: When Freelancers Are Forced to Compromise00:56:02 You're Not a Founder, You're an Inviter: Finding Your True Identity + + +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/leaderfulPodcast: http://apple.co/simonsinekInstagram: https://instagram.com/simonsinek/Linkedin: https://linkedin.com/in/simonsinek/Twitter: https://twitter.com/simonsinekFacebook: https://www.facebook.com/simonsinek

    59min
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  4. Number 4: Why Being Right Is Costing You Trust | A Bit of Optimism: Feelings at Work | PART 4

    Everyone says they want more accountability at work… yet few of us think we're the ones who need to learn how to be more accountable.Most of us believe we already know how to own a mistake. We've all said sorry and truly meant it. But meaning it and doing it well are two very different things. And when we’re the first to apologize, we model to everyone around us how cathartic accountability can be.Feelings at Work is a special five-part series from A Bit of Optimism, where Simon Sinek and Alex Simon, founder of LifeShop, explore the human skills that shape how we work, lead, and build relationships. Together, they unpack the emotional challenges most of us face every day—from people pleasing and listening to giving feedback, taking accountability, and having difficult conversations.In this episode, Simon and Alex take on accountability: why owning a mistake can feel like losing, why taking credit and dodging blame come from the same place, and what a real repair actually looks like. You'll discover why owning your part doesn't mean admitting you were wrong, why the confidence to say, "I got that wrong," is what actually makes people follow you, and how to repair something in a way that genuinely clears a pathway forward. Simon and Alex share practical tools like the "wheelie bag" rule for separating intent from impact, the two-part formula that turns an empty gesture into apologies people can actually feel, Alex's practice of "micro-accountability" for owning small things before they accumulate, and the one word that quietly cancels everything you said before it. In this episode you'll learn:➡️ Why saying you're sorry doesn't mean you're wrong➡️ The two-part apology formula: what you actually did + the impact it had ➡️ How to name someone's hurt + leave room to be corrected ➡️ "Micro-accountability": owning the small stuff before it turns into the big stuff ➡️ Why people who take too much credit are the same people who dodge blame ➡️ What real confidence actually looks like ➡️ How to receive an apology and why refusing it is its own kind of failure ➡️ Why being uncoachable is the biggest problem at work➡️ How to ask people to build the fix with youWhether you're leading a team, rebuilding trust with a colleague, or still quietly replaying an argument from three years ago, accountability is one of the most healing skills you can develop. And remember: owning your part is a gift you give the other person AND you give yourself.This... is A Bit of Optimism.+ + +CHAPTERSChapters00:00:00 Why Nobody Thinks They Need to Learn How to Apologize00:05:49 The Wheelie Bag Philosophy: What Saying Sorry Actually Means00:08:52 Why People Who Take Too Much Credit Can't Handle Blame00:10:15 Blame Culture: Why Our First Instinct Is Always to Point Fingers00:13:37 The Difference Between Being Wrong and Taking Accountability00:17:34 The Catharsis of Apologizing: Relief for Both Sides00:24:04 The Leader Who Gives All Credit and Takes All Blame00:27:55 The Anatomy of a Real Apology: Recognition Plus Impact00:30:19 When Guessing the Impact Goes Wrong00:33:46 Repair In Real-Time With Micro-Accountability 00:35:17 The Three-Part Apology That Finally Landed00:41:06 How to Receive an Apology Without Twisting the Knife00:43:18 When Sorry Isn't Enough Without Behavioral Change00:46:16 When You Can't Just Fix It: Asking for Help With Repair00:49:57 Why We All Think We Already Know How to Apologize00:51:10 Accountability Is the Gateway to Trust+ + +Website: http://simonsinek.com/Leaderful: https://simonsinek.com/leaderfulPodcast: http://apple.co/simonsinekInstagram: https://instagram.com/simonsinek/Linkedin: https://linkedin.com/in/simonsinek/Twitter: https://twitter.com/simonsinekFacebook: https://www.facebook.com/simonsinek+ + + About Alex SimonAlex Simon is the founder of Lifeshop, a school for adult emotional education and teaches emotional intelligence at Yale University. She teaches the emotional and communication skills we all should've learned in school—but didn't.She facilitates experiential workshops on how to have hard conversations, stop people pleasing, listen better, navigate major life transitions, and build healthier relationships. Her sessions are practical, deeply connective, and somehow shockingly fun.When she was 27, Alex created The Self & Other: In Theory and Practice, one of Yale's most sought-after courses.In 2025, she founded Lifeshop in New York to bring emotional education beyond the classroom and into everyday life. She also launched The School of Life in New York and leads workshops for organizations around the world.Before dedicating her career to emotional education, Alex worked as a management consultant at Bain and held strategy and operations roles across industries. She has also lived and trained at Plum Village and Esalen and completed dozens of programs in mindfulness, communication, and personal development.

    53min
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  5. Number 5: The Secret to Better Conversations Isn't Talking | A Bit of Optimism: Feelings at Work | PART 2

    The fastest way to improve your relationships isn't talking. It's listening.Most of us hear what's being said. Very few of us know how to make someone feel heard.Feelings at Work is a special five-part series from A Bit of Optimism, where Simon Sinek and Alex Simon, founder of LifeShop, explore the human skills that shape how we work, lead, and build relationships. Together, they unpack the emotional challenges most of us face every day—from people pleasing and listening to giving feedback, taking accountability, and having difficult conversations.In this episode, they explore one of the most important communication skills we can develop: listening.Together, they share practical techniques to improve your listening skills, build trust, navigate difficult conversations, and create better outcomes at work and at home. You'll learn why people often ask for one thing but actually need another, how to stop jumping into fix-it mode, and Alex's simple Four-Second Rule for becoming a better listener.When people feel heard, relationships grow stronger, conflicts become easier to navigate, and conversations become more meaningful.Because better conversations don't require everyone to be a great listener.They only require one.In this episode you'll learn:➡️ Why hearing someone isn't the same as making them feel heard➡️ How to stop jumping into "fix-it mode" and start listening with curiosity➡️ Alex Simon's simple Four-Second Rule for becoming a better listener➡️ Why people often ask for one thing but actually need something else➡️ How better listening builds trust, strengthens relationships, and improves teamwork➡️ How to navigate conversations when power dynamics are involvedWhether you're leading a team, supporting a friend, or navigating a difficult conversation, listening is one of the most valuable skills you can develop.Because when people feel heard, relationships grow stronger, conflict becomes easier to navigate, and better conversations follow.This... is A Bit of Optimism. + + +Chapters00:00:00 Listening to Understand vs Listening to Be Right00:00:38 Why Most of Us Are Bad Listeners00:02:08 What People Ask For vs What They Actually Want00:02:53 The Four-Second Rule for Better Listening00:04:05 Defining What Listening Is NOT00:05:42 Listening Beyond Words: Tone, Volume, and Subtext00:06:33 The Problem With Knee-Jerk Problem Solving00:07:14 The Real Story: When We Failed to Listen and Lost an Employee00:10:56 Needs vs Strategies: Understanding What's Really Being Asked00:12:28 Being Present: The Social Benefit of Meditation00:15:48 Body Language: Squaring Up and Putting Phones Away00:18:26 Listening With Warm Eyes That Believe in Them00:21:50 When Defensiveness Gets in the Way00:26:46 The Four-Second Rule in Action00:29:28 Is There More? The Buddhist Question That Peels Back Layers00:31:11 Creating Self-Reliance Through Listening00:34:26 Listening and Power Dynamics at Work00:35:16 Creating Safety So People Don't Withhold Information00:36:08 Why People Repeat Themselves Over and Over00:37:45 Reflective Listening: When to Mirror Back What You Hear00:40:11 Be As You Wish to Seem: Authenticity in Listening00:41:42 Listening Up: Understanding What Your Boss Actually Needs00:42:49 The One Degree Off Problem00:45:18 Asking Questions Depersonalizes Criticism00:47:02 Listening Is a Muscle You Can Build+ + +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/leaderfulPodcast: http://apple.co/simonsinekInstagram: https://instagram.com/simonsinek/Linkedin: https://linkedin.com/in/simonsinek/Twitter: https://twitter.com/simonsinekFacebook: https://www.facebook.com/simonsinek + + +About Alex SimonAlex Simon is the founder of Lifeshop, a school for adult emotional education and teaches emotional intelligence at Yale University. She teaches the emotional and communication skills we all should've learned in school—but didn't.She facilitates experiential workshops on how to have hard conversations, stop people pleasing, listen better, navigate major life transitions, and build healthier relationships. Her sessions are practical, deeply connective, and somehow shockingly fun.When she was 27, Alex created The Self & Other: In Theory and Practice, one of Yale's most sought-after courses.In 2025, she founded Lifeshop in New York to bring emotional education beyond the classroom and into everyday life. She also launched The School of Life in New York and leads workshops for organizations around the world.Before dedicating her career to emotional education, Alex worked as a management consultant at Bain and held strategy and operations roles across industries. She has also lived and trained at Plum Village and Esalen and completed dozens of programs in mindfulness, communication, and personal development.

    49min
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