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.

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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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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.