When Your People Pleasing Isn't Pleasing Anyone

What Social Media Gets Wrong & How to Actually Stop

Hi friends! This week’s episode is all about people pleasing… we actually had so much to share about the topic we split it up into two parts. We explore the layers of people pleasing behavior—where it comes from, how it manifests, our personal stories and why it affects not just the person doing it, but everyone around them.

The internet is full of quick fixes and viral mental health trends. But when it comes to people pleasing, most social media posts offer the same simplified narrative: it's just a trauma response. While that can certainly be true for many, the reality is much more nuanced.

Below we are going to dive into the highlights from the episode. For the full experience, including homework, journal prompts, and our best tips that go beyond what we shared in the episode, upgrade your subscription.

The Hidden Sides of People Pleasing

Something I've noticed as a therapist (and in my own recovery journey) is that people pleasing often comes with strings attached. Here's my personal confession that might shock you: my people pleasing was sometimes manipulative.

Years ago, I had an epiphany in therapy when I realized I wasn't doing nice things for others purely out of kindness. Instead, I was:

• Saying yes when I wanted to say no to avoid discomfort

• Over-apologizing excessively when I made mistakes

• Buying people elaborate gifts when I messed up (like that time I ate someone's special Williams-Sonoma monkey bread mix and then spent hundreds of dollars on random kitchen items to "make up for it")

What I was actually doing wasn't pleasing people at all—I was trying to control how they felt about me and avoiding facing real consequences for my actions.

The Many Faces of People Pleasing

People pleasing can stem from many different roots:

• A trauma response from difficult childhood experiences

• Modeling from parents who demonstrated similar behaviors

• Agreeableness is a personality trait

• Adaptation strategies from frequently moving or changing environments

• Avoidance of conflict or uncomfortable emotions

• Chameleon-like behavior to fit in and be accepted

On the other hand, Sam shared how her people pleasing developed as the oldest child caring for a brother with a disability. She became exceptionally skilled at soothing others, diffusing situations, and taking on discomfort to make situations better. These skills that served a purpose, but led to resentment later.

From the episode:

"Assertiveness will feel like aggression when you are used to people pleasing. You may feel as though you are being rude when really you're just operating as an emotionally stable human being."- Sam

The Price We Pay (And Others Pay Too)

There's something crucial that gets missed in most discussions about people pleasing: it doesn't just hurt you—it affects everyone around you too.

When we people please, we:

• Build resentment that leaks out as passive-aggressive behavior

• Prevent others from truly knowing us

• Don't give people the chance to adapt to our actual needs

• Set everyone up for relationship failure through mind-reading expectations

"You cannot hold people accountable for things they didn't know they did," Sam says. When someone doesn't communicate their needs or boundaries clearly but feels upset when those needs aren't met, they create a self-fulfilling prophecy of disappointment.

Keep reading below to get access to the rest of this article including: signs your people pleasing isn’t working for you anymore (we go way beyond the basic “signs you’re a people pleaser” trend, journal prompts, and homework for how to change this pattern.