A Bit of Optimism

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.

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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

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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

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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.

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.
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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

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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 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.

Maybe this sounds familiar: you fall hard for someone, and over a year later you're fighting about the very things that drew you to them in the first place. And you can't figure out how the person who felt so right suddenly feels so wrong.

Dr. Harville Hendrix has spent 50 years studying love. And he’s also lived through its hardest challenges: one divorce, two near-misses in his current marriage, and a couple’s therapist who fired him and his wife, calling them "the couple from hell." That marriage is now 45 years strong.

Harville is a couples therapist, and alongside his wife and creative partner Dr. Helen LaKelly Hunt, they creator Imago Relationship Therapy. They’ve also written 10 books, including the bestseller Getting the Love You Want, the book that made him a fixture on Oprah for nearly two decades. Harville’s theory is this: we don't consciously choose who we fall for, rather our unconscious does. And it has an agenda.

In this episode you'll learn:
➡️ Why you keep falling for the same person
➡️ What your childhood has to do with who you swipe right on
➡️ Why the "power struggle" phase might mean you picked the right person
➡️ The shift that saved Harville's own marriage after divorce papers were filed
➡️ Why some of us can't receive love (even when we ask for it)
➡️ What arranged marriages understood about commitment that we forgot
➡️ The difference between equal relationships and egalitarian ones
➡️ How to reach the stage where you have no needs left… only wants

In this conversation, Harville makes the case that real romantic love is what gets built after the fantasy collapses, when two people commit to the work of meeting each other's needs instead of demanding their own. And the engine of that transformation goes beyond compatibility and chemistry—it's gratitude and service.

This… is A Bit of Optimism.

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Want to keep up with Harville’s work? Check out: https://harvilleandhelen.com/

If you’d like to buy Harville & Helen’s latest book, How to Talk with Anyone about Anything, head to: https://harvilleandhelen.com/books/how-to-talk-with-anyone-about-anything/

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Chapters
Chapters

00:00:00 Nature's Agenda: Why We Fall for the Wrong Person
00:02:02 From Sharecropper's Farm to Oprah: Harville's Unexpected Journey
00:06:07 The 30-Second Encounters That Changed Everything
00:10:17 We Almost Divorced Twice: The Couple From Hell
00:13:21 Child Consciousness vs Adult Consciousness: The Critical Shift
00:15:57 The Gratitude That Ends the Yearning
00:18:45 Why Both People Don't Need to Change at Once
00:20:28 The Unconscious Imago: Your Brain Picks Who You Fall For
00:26:34 The 18-Month Fantasy: When the Real Person Shows Up
00:30:40 Arranged Marriages vs Choice: The Paradox of Commitment
00:34:47 The No Exit Decision: Why You'll Want to Quit When It's Working
00:36:34 The Transparency Trap: Afraid of Losing What You Found
00:38:35 Receiving Love: The Dinner Story That Changes Everything
00:45:49 Equal vs Egalitarian: The Recipe for Partnership
00:47:23 Dating IRL: Why Technology Can't Replace Face-to-Face
00:50:54 When Needs Become Wants: Life After Gratitude

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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

We tell ourselves the reason we never chase the big dream is that we're not ready, not brave enough, doomed to fail.

Nelly Attar would tell you she felt all of that too… but she chased them anyway.

Nelly is a psychologist turned extreme athlete and mountaineer. She built Saudi Arabia's first dance studio, MOVE, at a time when women couldn't train publicly by sneaking classes into a warehouse and office building after hours. She's the first Lebanese person to climb the five highest peaks in the world, like Everest. And she also became the first Arab to summit K2, the world’s second highest peak that’s so dangerous that one in four people who attempt it survive.

But what makes Nelly remarkable aren’t the summits and heights she reaches. It's that she's found a way to turn individual acts of accomplishment into acts of service: for the women she shows what's possible and for the team that climbs beside her.

In this episode you'll learn:
➡️ The difference between fear that protects you and fear that holds you back
➡️ How preparing and working hard can lighten the load for others
➡️ What small, daily kindness practices become the best investment you can make
➡️ Why there's no such thing as "self-made" and what actually de-risks courage
➡️ The art of “strategic retreat” + why quitting and retreating aren't the same thing
➡️ Why your title and achievements aren’t your identity (and what is)
➡️ How movement is medicine, and why the mind leads the body
➡️ What it really means to live a life of service to the people right in front of you

In this conversation, Nelly shows that the size of what you accomplish matters far less than the spirit you bring to it. She faces her fear for herself, but she does the hard work for everyone else. 

This… is A Bit of Optimism.

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Want to keep up with Nelly’s adventures? Check out: https://www.nellyattar.com/ 

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Chapters
Chapters

00:00:00 If You Don't Try, You'll Never Know: Nellie's Philosophy on Fear
00:02:20 Building Saudi Arabia's First Dance Studio
00:07:45 The Real Risk Worth Taking: Purpose Over Fear
00:12:07 The Support System Behind Every Bold Move
00:14:11 From Dance Floor to Everest: Training in the Desert for Sub-Zero Summits
00:20:13 Climbing for Others: The Service Mindset on the Mountain
00:21:19 Preparing So You Don't Burden Your Team
00:26:11 The Practice of Kindness: Small Acts That Change Everything
00:33:02 Leading Hikes to Help Others Climb Their Mountains
00:36:17 K2: Climbing Through Grief After Losing Her Father
00:39:24 One in Four Don't Come Back: The Reality of K2
00:41:00 Strategic Retreat: Knowing When to Turn Around
00:43:59 The Infinite Mindset: You Are Not Your Accomplishments
00:45:44 Creating Safe Spaces for Others to Discover Their Boundaries
00:48:39 Fear That Protects vs Fear That Holds You Back

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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

Sixteen years ago, an unknown CEO running a manufacturing company in the Midwest saw my TED Talk and recognized something in it. He sent me a letter and we made plans to meet. What started as a one-hour lunch turned into three, then four days touring factories together across the Midwest, and an idea I had only imagined turned out to already exist in reality.
That CEO was Bob Chapman. Over five decades, Bob grew an unassuming manufacturing company in the Midwest into a global proof point that leadership grounded in humanity can scale and outperform. Bob saw the people in his company as human beings in his care, people he felt responsible to help become healthy, fulfilled, and whole. His belief was simple and profound: when people are cared for at work, they build happier families, stronger communities, and a better world. He called it Truly Human Leadership.
In the years that followed, Bob became something more: a mentor, a close friend, the central figure in my book Leaders Eat Last, and one of the people who shaped how I think about leadership itself.
In September 2025, I returned to one of Bob's factories in Phillips, Wisconsin, with a camera crew, to capture Bob's incredible legacy in his own words. Six months later, Bob passed away.
As a tribute to this great man, we're releasing the full conversation, in its entirety, for the first time.
In this episode you'll learn:
➡️ Why Bob believed in seeing every person as someone’s precious child
➡️ How Barry-Wehmiller rewrote the rules and
➡️ The university Bob built to teach his employees skills they were never taught
➡️ What impact a caring workplace can have on an employees life
➡️ The real difference between a prosperous company and a healthy one
➡️ Why Bob believed layoffs meant your business has failed
➡️ Why the greatest act of charity has nothing to do with the checks you write
➡️ What changed in Bob over the fifteen years Simon knew him
➡️ The letter Simon sent Bob years ago that ended up framed on his office wall
As Bob said, "You can retire from a job, but you can't retire from a calling." He never did. This conversation is a chance to hear why, in his own words.
This… is A Bit of Optimism.
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To buy Bob’s book, Everybody Matters, head to: https://simonsinek.com/optimism-press/everybody-matters
To read about Bob in my book, Leaders Eat Last, head to: https://simonsinek.com/books/leaders-eat-last
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Chapters
Chapters

00:00:00 The Letter That Changed Everything: Meeting Bob Chapman
00:05:23 Bob's Revelation: Seeing People as Somebody's Precious Child
00:08:05 Building a University to Teach Caring: The Three Transformative Classes
00:09:32 The Healing Power of Listening: Why 95% of Feedback Was About Marriage and Kids
00:16:42 Recognition Done Right: Catching People Doing Good
00:20:55 The 2008 Recession Test: Shared Sacrifice Over Layoffs
00:23:07 "Layoffs Means Your Business Has Failed"
00:26:02 You Don't Need to Justify Caring: Safety of the Soul
00:27:53 12% Compound Growth for 25 Years: The Business Case for Humanity
00:29:53 "Our Product Is Our People"
00:34:55 From Selfish to Servant: Simon's Challenge That Sparked a Movement
00:36:26 People's Universal Truth: They Want to Know They Matter
00:38:00 Bob Has Gotten Softer: The Personal Evolution of a Leader
00:40:00 You Cannot Retire From a Calling: Carrying a Message That Heals
00:43:10 Heart Counts, Not Head Counts: The Language of Humanization
00:46:01 The Greatest Act of Charity: How You Treat People You Lead
00:49:38 The Promise: Carrying the Torch for Generations to Come

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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