• 1 hour 1 minute
    What Mentally Strong People Do on Their Worst Days with Psychotherapist Amy Morin

    Be honest: you've taken a mental health day that made you feel worse. You stayed in bed, you avoided the thing, and by evening it was still waiting for you—with less of the day left to face it.

    Amy Morin thinks the problem starts with the word. We treat mental health as something you either have or you don't… and framed that way, there's nothing to actually do on a bad day. Her work runs on the opposite premise: mental strength is a practice, and you build it like you'd build anything else.

    Amy is a psychotherapist, a clinical social worker, and the author of the bestseller 13 Things Mentally Strong People Don't Do and the new The Mental Strength Playbook. She became a therapist at 22 and lost her mother at 23. Three years later—to the day—her husband died, and the mental health agency where she worked gave her three days of bereavement leave. She built the practices that became her book in real time, from there.

    In this conversation, Amy walks through exactly what she did to get mentally fit. Not as theory, but as the small, unglamorous things that got her out of bed. And I press her on the question nobody in her field says out loud: whether an industry built to help us has any incentive to finish the job.

    In this episode you'll learn:
    ➡️ Why the mental health day you take to feel better isn’t helping
    ➡️ How to tell whether to solve the problem or solve the feeling (most of us pick wrong)
    ➡️ The 15-minute daily exercise Amy's clients say lifts the weight of the world
    ➡️ Why "I am anxious" and "I have anxiety sometimes" build two different lives
    ➡️ How to compromise with yourself on a bad day instead of going all-or-nothing
    ➡️ Why "I'm just staying busy" is avoidance we've learned to compliment
    ➡️ What playing the victim actually gives you (+ why it's so hard to give up)
    ➡️ Simon's rule for hard days: no crying alone

    Amy's argument is a hopeful one: the feeling follows the action. Do one small, ordinary thing today, and you've already started.

    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

    + + +

    If you’d like to buy Amy’s new book, The Mental Strength Playbook, head to: https://amymorinlcsw.com/books/ 

    + + +

    Chapters

    + + +

    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

    22 September 2026, 7:00 am
  • 50 minutes 17 seconds
    The Dating Advice Making Us Worse at Love with Relationship Expert Amy Chan

    The internet is flooded with advice for dating in the smartphone age: know your type, trust the spark, watch for red flags, protect your peace, never settle.

    It sounds like self-respect, but relationship expert Amy Chan thinks it’s a big reason dating feels impossible right now.

    Her argument: we need to correct the lessons we’ve learned when it comes to dating. The person who’s great on a first date isn’t necessarily great at a relationship. Instant chemistry isn’t always a good sign. A red flag could just be an imperfection. And keeping our options open has made a lot of us genuinely bad at choosing someone.

    Amy is the founder of Renew Breakup Bootcamp and the author of Unsingle: How to Date Smarter and Create Love That Lasts. For nearly two decades she’s looked at dating through psychology and neuroscience — why we’re drawn to certain people, why relationships fall apart, and what actually predicts whether one lasts. She started her career helping people end relationships… Now, she teaches them how to build one.

    In this episode you'll learn:
    ➡️ Why “instant chemistry” is one of the worst predictors of a lasting relationship
    ➡️ The quiet qualities research says actually predict a happy partnership
    ➡️ Why dating skills and relationship skills are two completely different skill sets
    ➡️ How the algorithm rewards red-flag advice 10X over green-flag advice (and what that’s doing to you)
    ➡️ Situationships: why the breakup hurts more when there was never a breakup
    ➡️ “Leaky energy,” micro-cheating, and the honest test for both
    ➡️ The 9-date experiment Amy gives clients who are stuck dating the same person
    ➡️ How the right relationship shrinks old wounds 

    ➡️ Why discomfort is a critical skill dating requires

    Amy’s advice isn’t about finding a better person. It’s about becoming someone better at love. And that’s advice all of us could use! 

    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

    + + +

    To get a copy of Amy's book, Unsingle: How to Date Smarter and Create Love That Lasts, head to: https://missamychan.com/#books 

    + + +

    Chapters

    Chapters

    • 00:00:00 Why Modern Dating Advice Is Making Us Worse at Love
    • 00:02:26 From Broken Heart to Breakup Bootcamp
    • 00:09:50 Why Dating Feels Harder Than Ever
    • 00:11:35 The Two Different Skill Sets: Dating vs. Relationship
    • 00:12:26 Online Dating and the Imagination Problem
    • 00:14:17 The Coffee Date Defense and the "Five Out of Ten Rule"
    • 00:15:53 The Cure for Avoidant Attachment
    • 00:18:13 The ADHD Love Bomb Confession
    • 00:24:49 What Self-Care Culture Gets Wrong About Commitment
    • 00:30:31 Situationships: The Safe Space That Keeps You Stuck
    • 00:33:07 Leaky Energy and Micro-Cheating
    • 00:35:08 Amy's Seven-Year Relationship and Emotionally Corrective Experiences
    • 00:39:28 The Instant Chemistry Trap
    • 00:40:59 The Nine-Person Dating Experiment
    • 00:44:37 Why Young People Aren't Dating Anymore
    • 00:45:49 Bad Feelings Don't Mean It's Bad
    • 00:48:02 The Single Skill That Saves Relationships

    + + +

    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

    15 September 2026, 7:00 am
  • 47 minutes 13 seconds
    Why Trying to “Sound Smart” is Losing You the Room with Strategic Story Producer Rob Willis

    Have you ever sat through a presentation and felt your attention just start to…drift? Chances are, it wasn't the content. It was the delivery.

    A year ago, Rob Willis was a corporate trainer with years of experience and a sharp eye for what makes people listen. He wondered if what he taught in workshops would resonate with a larger audience. So he started making short videos that break down what makes great speakers great: from their word choice, to structure, to the energy they brought to any room or conversation. 

    Rob even made a video breaking down my method of public speaking. In his video,  Rob dissects my signature opening line, and my friends couldn't stop sending it to me. One hundred videos in one hundred days later, Rob's videos are going viral on a regular basis, and a whole new audience is eager to learn from him.

    But what I find most interesting about Rob is where he actually learned all of this. Not in a classroom. He learned it by giving free walking tours in Berlin, where nobody pays up front and anyone can leave at any moment. If you're boring, people simply walk away — no tip, no small talk, just people voting with their feet.

    Rob and I discuss what that taught him about holding a room, why the smartest person in the room is rarely the most persuasive one, and the handful of simple, almost mechanical shifts that separate a forgettable pitch from one people actually remember.

    In this episode you'll learn:

    ➡️ Why "if I just explain it better" is the most common, and most inaccurate, assumption speakers make

    ➡️ Rob's trick for holding anyone's attention, whether it's a boardroom or a crowd on a street corner

    ➡️ What real charisma is made of (hint: it's not confidence, it's belief)

    ➡️ Why so many people suddenly sound fake the moment they step on stage

    ➡️ 5 things you can do in your next meeting to immediately present better 

    You don't need a TED Talk on your calendar to get something out of this one. Any of us who wants to be understood — in a meeting, a pitch, a hard conversation — will find something worth stealing.

    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

    + + +

    Want to keep up with Rob and his video breakdowns? Check out: https://robdwillis.carrd.co/

    + + +

    Chapters

    Chapters

    • 00:00:00 The Former Tour Guide Who Cracked the Code
    • 00:03:12 Why Trying to Sound Smart is Losing You the Room
    • 00:03:48 100 Videos in 100 Days
    • 00:06:16 Breaking Down the Patterns: What Makes Simon Sinek Work
    • 00:07:33 Learning to Speak Without a Plan
    • 00:11:41 The Knowledge Deficit Trap: Why More Information Doesn't Always Work
    • 00:12:33 The Tour Guide Philosophy and Tracking What Actually Works
    • 00:16:20 Simon's Book Writing Journey
    • 00:23:10 The Art of the Distilled Message
    • 00:25:53 The Bolt of Lightning Myth: How Great Ideas Really Happen
    • 00:26:55 Let Them Get There First: The Power of the Aha Moment
    • 00:29:10 Hans Rosling and What is True Charisma
    • 00:31:47 Speaking With Conviction, Not Questions
    • 00:34:30 The Speaking Voice Trap: Why You Sound Weird on Stage
    • 00:36:42 Five Things You Can Do Tomorrow to Become a Better Speaker
    • 00:44:14 The Five-Minute Rule: Why Less is Always More

    + + +

    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

    + + +

    8 September 2026, 7:00 am
  • 50 minutes 37 seconds
    Your Limits Are Learned (And They Can Be Unlearned) with Brain Coach Jim Kwik

    This might sound familiar: you read a full page, get to the bottom, and realize you absorbed none of it. There's a stack of books beside your bed you fully intend to finish. And the only phone number you can remember is your own.

    Jim Kwik says none of that means something is wrong with our brains. It’s that we were taught what to learn, but rarely ever taught how to learn.

    Jim would know. A well-meaning teacher called him "the boy with the broken brain" when he was nine, and for years he believed it. He's spent the three decades since proving otherwise — as a top brain coach, a leading expert on memory and accelerated learning, and the bestselling author of Limitless. His new book, Limitless Daily, offers 366 daily upgrades to help you focus, remember, and think better.

    In this episode you'll learn:
    ➡️ Why reading faster can actually improve comprehension
    ➡️ The free technique that stops your mind wandering mid-page
    ➡️ How to prompt your own brain the way you prompt AI
    ➡️ What your "dominant question" reveals about your personality
    ➡️ Why school teaches us what to learn but never how to learn
    ➡️ What digital dementia is + how to spot it in yourself
    ➡️ Why focus is a muscle, not a personality trait
    ➡️ The one thing AI will never be able to do for you

    I asked Jim an entirely selfish question about how to actually get through the unread books next to my bed, and got an answer that goes far beyond discipline. Jim explains why the technology making us more capable is quietly making us less able. 

    And by the end, we landed somewhere neither of us expected: AI could have given Jim every piece of advice that changed his life, word for word. But it wasn't the advice that changed him. It was that a living, breathing person cared enough to give it.

    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

    + + +

    If you want to buy Jim’s new book, Limitless Daily, head to: https://limitlessdaily.com 

    Want to check out Jim’s other work like his best-selling book Limitless? Go to: https://jimkwik.com 

    + + +

    Chapters

    Chapters

    • 00:00:00 The Boy With the Broken Brain: When Labels Become Limits
    • 00:00:25 The Power of Adult Words on Children
    • 00:06:51 The Freshman English Failure: Rock Bottom Before the Breakthrough
    • 00:09:54 The Breaking Point: Collapsing in the Library
    • 00:14:26 The Intervention: A Mentor Who Saw Potential, Not Limits
    • 00:15:16 Accidental Careers: When Your Work Becomes Service to Others
    • 00:20:48 110 People Showed Up: The Accidental Beginning of a Career
    • 00:25:02 30 Books in 30 Days: The Student Who Saved Her Mother's Life
    • 00:26:19 Service Over Success: Why Purpose Matters More Than Profit
    • 00:31:31 Grow Givers vs Go Getters: Growing So You Have More to Give
    • 00:32:23 Why Smart People Can't Finish Books
    • 00:34:24 Your Brain Is Bored, Not Broken
    • 00:38:49 The Visual Pacer Hack That Changes Everything
    • 00:40:23 Ask Better Questions: How to Prime Your Brain for Learning
    • 00:44:55 Focus Is a Muscle: Training Attention in the Age of AI
    • 00:46:00 Why AI Will Never Replace Bedside Manner
    • 00:49:11 It Was Never About the Information, It Was The Power of Being Seen

    + + +

    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

    + + +

    1 September 2026, 7:00 am
  • 58 minutes 7 seconds
    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 title

    Mary 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

    Chapters

    • 00:00:00 From Wall Street to Reality TV: Using Fame as a Tool for Good
    • 00:02:57 Growing Up in the Bayou: Four Sisters and a Pet Alligator
    • 00:07:19 Why Finance? Growing Up With Money Anxiety
    • 00:08:25 Meeting Jimmy Kimmel's Agent: The Accidental Origin Story
    • 00:10:29 Quitting Wall Street for Reality TV
    • 00:12:58 Why Finance Makes Everyone Feel Stupid
    • 00:14:14 Mary and Pip: Translating Finance for Real People
    • 00:17:23 Becoming Confident on Camera: From Mortified to Vulnerable
    • 00:25:22 The Power of Positive Self-Talk: Mirror Affirmations That Actually Work
    • 00:28:31 Trust Your Gut: When Smart People Give You Bad Advice
    • 00:30:09 What Does A Mentor Actually Look Like?
    • 00:33:27 Gazelles Get Eaten: Why Hypergrowth Isn't Always Good
    • 00:42:24 Spears: The Feedback Technique That Changed Everything
    • 00:45:32 Correcting Language That Creates False Narratives
    • 00:54:02 The Reluctant Sellout: When Freelancers Are Forced to Compromise
    • 00:56:02 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/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

    25 August 2026, 7:00 am
  • 1 hour 1 minute
    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 4

    We 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

    Chapters

    • 00:00:00 Plans vs. Imagination: The Risk of Staying Safe
    • 00:02:43 From Chicago to Amsterdam: The Audition That Changed Everything
    • 00:07:02 The Boom Chicago Pitch: When Amsterdam Became Irresistible
    • 00:11:58 The Beatles in Hamburg: Getting Your 10,000 Hours
    • 00:16:18 The Joy of the Thing: Why Not Thinking About Your Career Makes You Better
    • 00:20:01 Real Opportunity vs. Your Imagination: Why People Stay Put
    • 00:20:58 Strong Opinions, Loosely Held: The Art of the Flexible Plan
    • 00:21:28 Curiosity as Currency: The Jack of All Trades Philosophy
    • 00:22:51 The Ted Lasso Origin Story: A Pool, Some Bits, and a Name
    • 00:25:45 The Soccer Missionary: How Amsterdam Made Brendan the Beard to Ted's Lasso
    • 00:27:31 Everything Contributes to Everything: The Payoff of Wasted Time
    • 00:30:31 Midwestern Chipperness Meets British Stiff Upper Lip: The Culture Clash of Ted Lasso
    • 00:32:57 Diagnosed as Ted Lasso: When Your Company Is the Character
    • 00:33:46 Bringing Yourself to the Character: Acting as Being, Not Becoming
    • 00:37:23 Coach Beard Was a Placeholder: How a Play Gave Him a Name
    • 00:44:06 The Art Couple: The Play Brendan Wishes He Could Do Forever
    • 00:46:33 The 1986 NFC Championship: A Pure Childhood Memory
    • 00:54:07 When Comedy Became a Need: Making Mom Laugh
    • 00:55:59 Season Four: Belief, Trust, and Starting Over
    • 00:57:28 Don't Pick Sides: The Gift of Knowing Your Own Mistakes
    • 00:59:04 The Purity of Art: Why Brendan Keeps Writing

    + + +

    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

    + + +

    18 August 2026, 7:00 am
  • 45 minutes 53 seconds
    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.

    + + +

    CHAPTERS

    Chapters

    • 00:00:00 When Conflict Turns People Into Monsters
    • 00:02:16 Reframing Tension: It's a Sign, Not a Problem
    • 00:02:43 The Resentment Gremlin: How Waiting Makes It Worse
    • 00:03:50 Oh No, Let's Just Skip It: Why Hard Conversations Feel Impossible
    • 00:08:01 The Passive Aggressive Company: When Tens of Thousands Avoid Feedback
    • 00:10:02 When Passive Aggression Is The Solution to Conflict
    • 00:11:15 What Actually Stops Us: Fear, Narrative Building, and Self-Righteousness
    • 00:20:38 Conflict Is a Team Sport for Mutual Understanding
    • 00:23:04 You're Not the Problem, I'm Not the Problem: The Problem Is the Problem
    • 00:25:21 The Interruption Technique That Stops Character Assassination
    • 00:26:27 Timing Matters: Not Too Hot, Not Too Cold
    • 00:28:31 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 Sandwiches
    • 00:40:25 Breaking the Fourth Wall: Pause, Reset, and Start Again
    • 00:43:41 The Scaffolding Philosophy: Messy Humans Need Support Structures

    + + +

    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

    + + +

    About Alex Simon

    Alex 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.

    11 August 2026, 7:00 am
  • 52 minutes 36 seconds
    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 you

    Whether 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.

    + + +

    CHAPTERS

    Chapters

    • 00:00:00 Why Nobody Thinks They Need to Learn How to Apologize
    • 00:05:49 The Wheelie Bag Philosophy: What Saying Sorry Actually Means
    • 00:08:52 Why People Who Take Too Much Credit Can't Handle Blame
    • 00:10:15 Blame Culture: Why Our First Instinct Is Always to Point Fingers
    • 00:13:37 The Difference Between Being Wrong and Taking Accountability
    • 00:17:34 The Catharsis of Apologizing: Relief for Both Sides
    • 00:24:04 The Leader Who Gives All Credit and Takes All Blame
    • 00:27:55 The Anatomy of a Real Apology: Recognition Plus Impact
    • 00:30:19 When Guessing the Impact Goes Wrong
    • 00:33:46 Repair In Real-Time With Micro-Accountability
    • 00:35:17 The Three-Part Apology That Finally Landed
    • 00:41:06 How to Receive an Apology Without Twisting the Knife
    • 00:43:18 When Sorry Isn't Enough Without Behavioral Change
    • 00:46:16 When You Can't Just Fix It: Asking for Help With Repair
    • 00:49:57 Why We All Think We Already Know How to Apologize
    • 00:51:10 Accountability Is the Gateway to Trust

    + + +

    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

    + + +


    About Alex Simon

    Alex 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.

    4 August 2026, 7:00 am
  • 57 minutes 47 seconds
    What Is Your Team Afraid to Tell You? | A Bit of Optimism: Feelings at Work | PART 3

    Giving and receiving feedback is one of the hardest things we do at work and most of us just... avoid it.

    But avoiding feedback has a cost. Everything you need to grow is already in the room and it's just sitting in your blind spot. Your colleagues can see it. Your boss can see it. And nobody will tell you, unless you learn to ask.

    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, Alex and Simon take on feedback: how to give it, how to take it, and how to ask for it. 

    You’ll discover ways to give feedback people can actually hear, receive criticism without taking it personally, and build a feedback culture on any team. Alex and Simon share practical techniques like the one-word ritual Simon borrowed from the Air Force that made his whole company crave critiques, the “FBI” method for delivering hard feedback without blowing up relationships, and questions Alex asks her team to surface everything left unsaid, like "What are you afraid to tell me?"

    In this episode you'll learn:

    ➡️ Why we avoid giving feedback + what that avoidance quietly costs our teams 

    ➡️ "Spears": the Air Force ritual that turns criticism into something people actually want 

    ➡️ The “FBI” (Feelings, Behavior, Impact) method for giving feedback people can actually hear 

    ➡️ The Army Rangers' peer assessment’s "foxhole question" + what it reveals about character 

    ➡️ How to think of feedback as preventative care and build that muscle

    ➡️ Why everyone receives feedback differently (+ how to give people what they need)

    ➡️ When to give feedback (hint: never the moment you think of it) 

    ➡️ The four-word habit that builds a thick skin: "What can I do better?"

    Whether you're leading a team, managing up, or just tired of side-texting about a problem no one will name out loud, feedback is one of the most valuable skills you can build. 

    And remember: feedback is kind, even when it’s not nice.

    This... is A Bit of Optimism.

    + + +

    Chapters

    • 00:00:00 The Spinach in Your Teeth Problem: Why Nobody Tells You
    • 00:03:48 The Story of Two Failed Feedback Sessions
    • 00:06:37 Why Feedback Obsession Changes Everything
    • 00:08:05 The Company That Was Too Nice to Give Feedback
    • 00:10:35 Army Rangers and the Three-Level Evaluation System
    • 00:14:24 Why Giving Feedback Feels So Hard
    • 00:17:16 Spears: The Air Force Technique That Changed Everything
    • 00:20:08 All the Information You Need Is in Your Blind Spot
    • 00:22:28 FBI: The Three-Part Formula for Feedback That Lands
    • 00:25:37 Why Vague Praise Doesn't Help Anyone
    • 00:27:16 Credit Is Free: Recognition Languages at Work
    • 00:31:05 The Collaboration Meeting: Preventing Problems Before They Start
    • 00:42:34 The Air Force Commander Who Cried Every Night for Six Months
    • 00:45:08 When to Give Feedback: Not When You Think of It
    • 00:47:24 The Virtuous Cycle: What Happens When You Get Feedback Right
    • 00:49:08 How to Build the Muscle of Receiving Feedback
    • 00:51:43 Generational Difference For Feedback
    • 00:52:57 One Simple Question: What Can I Do Better?
    • 00:55:49 Feedback Is Kind Even When It's Not Nice

    + + +

    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

    + + +

    About Alex Simon

    Alex 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.

    28 July 2026, 7:00 am
  • 48 minutes 40 seconds
    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 involved

    Whether 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.

    + + +

    Chapters

    • 00:00:00 Listening to Understand vs Listening to Be Right
    • 00:00:38 Why Most of Us Are Bad Listeners
    • 00:02:08 What People Ask For vs What They Actually Want
    • 00:02:53 The Four-Second Rule for Better Listening
    • 00:04:05 Defining What Listening Is NOT
    • 00:05:42 Listening Beyond Words: Tone, Volume, and Subtext
    • 00:06:33 The Problem With Knee-Jerk Problem Solving
    • 00:07:14 The Real Story: When We Failed to Listen and Lost an Employee
    • 00:10:56 Needs vs Strategies: Understanding What's Really Being Asked
    • 00:12:28 Being Present: The Social Benefit of Meditation
    • 00:15:48 Body Language: Squaring Up and Putting Phones Away
    • 00:18:26 Listening With Warm Eyes That Believe in Them
    • 00:21:50 When Defensiveness Gets in the Way
    • 00:26:46 The Four-Second Rule in Action
    • 00:29:28 Is There More? The Buddhist Question That Peels Back Layers
    • 00:31:11 Creating Self-Reliance Through Listening
    • 00:34:26 Listening and Power Dynamics at Work
    • 00:35:16 Creating Safety So People Don't Withhold Information
    • 00:36:08 Why People Repeat Themselves Over and Over
    • 00:37:45 Reflective Listening: When to Mirror Back What You Hear
    • 00:40:11 Be As You Wish to Seem: Authenticity in Listening
    • 00:41:42 Listening Up: Understanding What Your Boss Actually Needs
    • 00:42:49 The One Degree Off Problem
    • 00:45:18 Asking Questions Depersonalizes Criticism
    • 00:47:02 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/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

    + + +

    About Alex Simon

    Alex 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.

    21 July 2026, 7:00 am
  • 58 minutes 5 seconds
    The Hidden Cost of Always Saying Yes | A Bit of Optimism: Feelings at Work | PART 1

    Welcome to Feelings at Work, a special series from A Bit of Optimism with Simon Sinek. 

    Work isn't just about deadlines, meetings, and getting things done. It's also where we experience frustration, excitement, trust, anxiety, belonging, conflict, and joy. If we want to build healthier teams and better workplaces, we have to get better at understanding the emotions that shape how we work together.

    That's what this series is about.

    In each episode, Simon Sinek sits down with Yale professor and Lifeshop founder Alex Simon to explore one emotional challenge that affects how we work, lead, and relate to one another. Together, they unpack the emotional skills most of us were never taught—but use every single day.

    This episode is about saying yes.

    Have you ever agreed to something... and immediately regretted it?

    Maybe you didn't want to disappoint someone. Maybe you thought, I'll figure it out somehow. Maybe your calendar is packed, your to-do list never gets shorter, and somehow you're still worried you're letting people down.

    Most of us don't think of ourselves as "people pleasers."

    We just want to be helpful. We want to be dependable. We want to be someone others can count on.

    But what if constantly saying yes is actually making things harder—for you and everyone around you?

    Together, Simon and Alex explore why so many thoughtful, capable people take on more than they can realistically handle. They unpack the hidden patterns that lead to overwhelm, resentment, and burnout—and why trying to keep everyone happy can quietly make us less reliable.

    The good news? This is a skill we can learn.

    In this conversation, you'll discover practical ways to communicate more honestly, set healthier boundaries, and build stronger relationships—without feeling selfish or letting people down.

    In this episode you'll learn: 

    ➡️ Why saying yes too often can actually make you less reliable

    ➡️ The hidden connection between overwhelm, burnout, and self-betrayal

    ➡️ The simple phrase that creates space before committing 

    ➡️ A better alternative to saying yes or no: how to "share the dilemma"

    ➡️ What leaders can do to create teams where people feel safe telling the truth

    ➡️ Why healthy boundaries strengthen relationships instead of hurting them

    Whether you call it people pleasing or simply trying to keep up with everyone else's expectations, this conversation is a reminder that taking care of yourself isn't selfish.

    It's one of the best ways to show up for the people who matter.

    This... is A Bit of Optimism.

    + + +

    Chapters

    Chapters

    • 00:00:00 Why We Need to Talk About Feelings at Work
    • 00:02:00 What People Pleasing Actually Looks Like
    • 00:04:20 Why People Pleasing Hurts You and Your Team
    • 00:07:00 Why We Say Yes When We Mean No
    • 00:10:00 Different Types of People Pleasing
    • 00:13:00 Why Approval Can Become Addictive
    • 00:15:00 How People Pleasing Leads to Burnout
    • 00:18:00 The Hidden Cost of Being "Hyper Competent"
    • 00:21:00 Why People Pleasing Doesn't Actually Help People
    • 00:27:30 Simon's Experience With Saying Yes to Too Much
    • 00:31:00 How Leaders Can Help People Pleasers
    • 00:38:20 The Power of "Let Me Get Back to You"
    • 00:40:00 How to "Share the Dilemma"
    • 00:44:00 The Difference Between Being Reliable and Being Available
    • 00:47:00 Building Healthier Boundaries at Work

    + + +

    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

    + + +

    About Alex Simon

    Alex Simon is a Yale professor and the founder of Lifeshop, a school for adult emotional education. 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.

    14 July 2026, 7:00 am
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