21. The People-Pleasing Myths That Keep You Stuck
What’s new: Five people-pleasing myths are holding leaders back — and busting them can change the way you work.
Why it matters: People-pleasing often masquerades as achievement, but it drains your energy, erodes boundaries, and keeps you from leading authentically.
In this episode, you’ll learn:
How “being nice” can be fear in disguise
Why adaptability without boundaries leads to burnout
The personality patterns that fuel approval-seeking
Why disappointing others can be a sign of growth
How to shift from being liked to being trusted
Transcript
Hi friends, welcome back to Upleveling Work. This season, we’re decoding personal growth: how to overcome fear, navigate uncertainty, and build the habits that lead to lasting success. I’m Michelle Kay Anderson—executive coach, systems thinker, and your guide to making work more human.
Today we’re talking about a topic I know so many of you have felt the pull of: people-pleasing.
Ever found yourself staying late to fix someone else’s mess? Biting your tongue in meetings so you won’t be seen as “difficult”? Saying yes when your gut says no—because you worry about being labeled uncooperative, or worry even more about risking connection, safety, or belonging?
For many managers—especially those whose identities haven’t always fit the traditional leadership mold—people-pleasing can feel like survival.
Early in my career, I thought being the “good girl,” the helpful one, the one who never made waves, was the key to belonging and success. And for a while—sure, it worked. Praise, positive reviews, invitations to exclusive happy hours and bigger projects. I knew the expectations, I knew the models of success, and I conformed to them. That’s how you climbed the ladder—by working harder than anyone else, filling in the gaps no one else noticed, and never letting a ball drop. I didn’t think of it as over-functioning or people-pleasing—it felt like achievement. It felt like doing what needed to be done.
In practice, that meant firing most of my coworkers when the job required it, working 12- to 15-hour days to launch big projects while my husband was home fixing up our first house, and constantly scanning for what was needed next so nothing—and no one—fell through the cracks. And it wasn’t just at work. At home, I anticipated the needs of my family before they asked, avoided saying things that might upset someone, and kept my days jam-packed with commitments I had agreed to because I couldn’t imagine saying no. Looking back, I can see how much of it came from this deep sense of hyper-responsibility—maybe eldest daughter energy, maybe my Enneagram One wiring, maybe just this belief that if something had to get done, it was on me to do it.
If this resonates, you’re not alone. Today, we’ll bust five myths about people-pleasing, show how these myths connect to your identity and leadership style, and share some tools so you can start unhooking from that constant drive for approval.
And if you’ve been following this season, you’ll notice connections to how mental models, imposter syndrome, and narrative identity shape us—because people-pleasing isn’t just about “being nice.” It’s a systemic adaptation, especially for marginalized folks in dominant workplaces.
Myth 1: People-Pleasing Is Just Being Nice
“I’m not people-pleasing, I’m just being nice. I like making people happy.”
Here’s the truth: people-pleasing isn’t about kindness—it’s about fear of disconnection. It’s a unconsciou strategy to control how others see us so we can avoid rejection, criticism, or disappointment.
Tara Mohr, in her book “Playing Big,” talks about how many of us have been “hooked” by praise and criticism since childhood. When we’re hooked, we’re not led by our inner compass. We’re led by imagined reactions.
Reflection: Where in your life do you feel responsible for others’ emotional states? How does that shape your decisions?
Myth 2: Adaptability Means Always Saying Yes
Companies love adaptability. But are you praised for being “easy”—even when you’re exhausted behind the scenes? Adaptability is flexible. People-pleasing is rigid.
Real adaptability is grounded in your values and boundaries—people-pleasing often erases them.
Especially for new-ish managers, women and marginalized folks: You’re seen as easy to work with, but that constant yes can breed resentment, burnout, and a loss of clarity.
So, I want you to think about: Can you be adaptable without abandoning yourself? Where is that line for you?
Myth 3: People-Pleasing Is a Personality Thing
Every personality style can people-please—but for different reasons.
The Enneagram is powerful here:
Type 2: If I’m not helpful, will I still be loved?
Type 3: If I’m not impressive, will I be valued?
Type 9: If I create tension, will I belong?
Each type has its own version—these are strategies to meet core needs, not flaws.
Reflection: What’s the need you’re trying to meet when you say yes? What’s the fear you’re trying to avoid?
Myth 4: Disappointing People Means You’re Doing Something Wrong
Do you have an identity story like “I’m reliable; I never let people down”?
If you never disappoint anyone, you’re probably not living your own life. Growth—especially growth out of people-pleasing—means you’ll sometimes need to disrupt expectations or let someone down in order to honor your truth. Are you willing to be misunderstood? Yikes -that’s hard for a lot of people!
This ties to our episode on mental models—sometimes the mental model of a “good leader” or “good team player” is so narrow it leaves no room for authenticity.
Reflection: What would it mean to trust that disappointing someone doesn’t mean you’ve failed?
Myth 5: Being Liked = Being Effective
Especially for women and marginalized folks, you’re told to be agreeable, selfless, conflict-free. Yes, relational intelligence matters, but being liked is not the same as being trusted—or respected.
Sometimes the most effective leadership moment is the one where you make an unpopular decision, but your clarity and integrity build trust.
Reflection: What would shift if you cared more about being trusted than about being liked?
We’ve talked about five big myths that keep us stuck in people-pleasing. But knowing the myths doesn’t always mean you’ll catch yourself in the moment. So let’s talk about some bite-size habits you can practice this week — ways to create just enough space to make a choice that’s yours, not just automatic.
Bite-Size Habits: Creating Flexibility When People-Pleasing Shows Up
Practice the Pause: Next time you feel the urge to please, take one breath and ask: “Is this about my values or my fear?”
Micro-boundaries: Start small — maybe you say no to one meeting, or ask for clarity before you take on a project. Small acts grow big confidence.
Self-compassion ritual: It’s okay to disappoint people. That’s leadership, not failure. Often the first step is simply creating safety in your body so you can weather that discomfort.
And I want to acknowledge: for those of you who are the “first,” “only,” or “different” in your workplace, these habits can feel like higher-stakes risks. You may be navigating real systemic pressures where rocking the boat has consequences. That’s why part of the work here is developing discernment — to see the difference between a perceived risk and a real one, and to decide from a place of self-loyalty, not fear.
If you want to dig into this more, I’ve made a free worksheet with the reflection questions from today’s episode. It’s designed so you can copy it into your Google Drive, spend 15–20 minutes journaling, and see what patterns emerge. (You can download it at the top of this page.)
Coaching Makes the Difference
And if you try these experiments and keep finding yourself back in the same cycle, that’s not a lack of willpower — it’s just a sign you might need a thought partner.
You’ve been told to be adaptable, but never taught how to protect your boundaries. You want to lead with care and inclusion, but wonder if speaking up could make you a target. Let’s name the real costs: exhaustion, chronic resentment, stalling your growth—and feeling unclear about what you want, versus what others demand.
People-pleasing is often rooted in years of conditioning, attachment patterns, and real workplace dynamics. Coaching gives you a place to slow it down, see the pattern clearly, and practice new moves in a space where it’s safe to try. If that’s what you need right now, you can learn more at michellekayanderson.com.
People-pleasing is deeply human — it’s not something to beat yourself up about. Get curious. Experiment. And remember: every time you choose integrity over approval, you’re building a healthier way of working, for yourself and for the people who look to you for leadership.
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