A Bit of Optimism

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.

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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

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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 

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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

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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.

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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

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.

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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

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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 

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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

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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

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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.

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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

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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

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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.

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.

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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

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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

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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.

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.
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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

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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
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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.