Confessions From A Recovering People-Pleaser
Updated: Sep 23
I used to live life like it was a ✨Miss Congeniality✨ contest. Well, a contest I wanted to maybe be a runner-up in but wouldn’t have felt comfortable winning. What if I actually won and someone was mad…at ME?!🥺
I spent too many years believing that if I could be the easygoing one, dependable one, the one to say, “It’s ok!” (even when it was very much not okay), then no one would think I was difficult, selfish, or be disappointed.
Yeah…no. You cannot please everyone. It's true and trying is exhausting as hell. The problem wasn’t that I cared about others. The problem was some of my “generosity” was me being terrified of disappointing people. Some of my “I don’t care” was actually “I care so much that I've decided your feelings are now my responsibility.” And, some of my “understanding” was me disregarding my own feelings so nobody else had to feel uncomfortable. Turns out, that's not a happy or healthy way to live this one precious, short life.
Someone is going to misunderstand you.
Someone is going to be disappointed.
Someone is going to think you’re difficult.
People may make you out to be a villain.
And someone might even call you a bitch!😂
You’ll survive! I promise;)
I’ve had a number of people-pleasing interventions over the years. Many years ago, a mentor invited me to coffee and handed me copies of, “The Power of a Positive No" and "Nice Girls Don't Get the Corner Office." Apparently, that’s how obvious it was. When I started a job on a radio morning show, my mom called one day after the show. She said, “You’re not being your authentic self on air. You’re holding back. Be you. You’re not going to please everyone, sweetheart.”
I wish I could tell you that those moments were enough for an instant epiphany and that I magically became a woman who could confidently express her true feelings without a 10-minute explanation, follow-up text, email, and phone call making sure everyone was okay. Not so. It took a “friend” embarrassing me publicly (not for the first or even a fifth time) to push me into therapy. I had to learn that what I thought was loyalty, empathy, and compassion, were often exhausting attempts to manage other people’s feelings so I could control what they thought of me.
Learning the role I played, why, and that I was the only one with the power to change it was a huge turning point. Here are some of my confessions and the lessons I’m still practicing every day.
Confession: I made being the “nice girl” 🙋🏻♀️ part of my identity.
Loyalty kept me in relationships, environments, and situations that common sense and my intuition should have taken me out of long before I actually left. I thought commitment meant enduring. I thought being the person who stayed said something good about my character. Sometimes it did, but often it was just fear: fear of being the bad guy, fear of being selfish, and fear of losing approval.
Lesson: Being liked is not the same as being valued.
Confession: I thought I was responsible for the emotional temperature of the room.
If someone was sad or disappointed, my instinct was to fix it. If someone was angry, I often wondered if I contributed somehow. If someone misunderstood me, I needed to explain myself over and over until they gave me some sort of implication that they understood or weren’t upset.
Here’s the deal…
Other people's feelings belong to them. Their reactions belong to them. Their discomfort belongs to them. You can care about how someone feels without taking responsibility for making them feel better.
I know! Who knew? 🤷🏻♀️ Not us people-pleasers, apparently.
Lesson: Other people’s feelings and reactions belong to them.
Confession: I confused compassion with obligation.
I used to think compassion meant giving people endless chances. I should have a PhD in giving the benefit of the doubt. I could explain away almost anything:
“They’re just insecure.”
“They had a hard childhood.”
“They’re dealing with a lot.”
“That’s just how they are.”
“They don’t know any better.”
Understanding someone’s past or stress explains their behavior, but it doesn’t require you to endure it. You can have genuine compassion for someone and still set firm boundaries.
Lesson: Understanding someone’s behavior doesn’t obligate you to tolerate it.
Confession: I doubted my own judgment to keep the peace.
For years, when someone crossed a line, my first instinct wasn’t, “That wasn’t okay.”
It was: Just let it go. Maybe I misunderstood. That’s probably not how they meant it. I’m sure it was just a joke.
When you hear enough versions of “I didn’t mean it like that, or “I was only joking!” or “Oh, that’s just how he/she is,” you start doubting your own perception. You don’t just question what happened, you question whether you’re even allowed to be bothered by what happened.
Lesson: Someone else doesn’t have to gaslight you, it’s entirely possible to gaslight yourself.
Confession: I was terrified of being cast as the villain.
I was so afraid of being labeled the bad guy that I allowed mistreatment, stayed quiet, and tolerated situations I should have separated myself from just to avoid being misunderstood. Manipulators will play on that fear.
Here’s an important note: Not all manipulation is calculated or malicious. People learn patterns for getting their needs met, protecting themselves, or avoiding rejection, just like people-pleasers try to control the environment or situation to attempt to keep from looking difficult. But whether it’s conscious or not, you do not have to tolerate it. Setting a boundary will almost always make you look like a villain to someone who was benefiting from you having no limits.
You can’t control their narrative. You can’t. You can’t. You can’t. Been there done that! Still do sometimes. You don’t need to explain or defend yourself like you’re on trial to anyone. The people who genuinely know your heart won't be fooled anyway and as for the rest? Let them think what they want. Most of the time, they're either benefiting from the relationship or narrative, or only seeing the side that was carefully staged for them.
Lesson: Sometimes you have to be willing to look like the villain in a story where you were actually just protecting yourself.
Confession: I said yes before my brain had time to process there were other options.
I used to say yes to or caved into situations so often that I sometimes felt resentful. Most of the time resentment isn’t signaling that someone asked too much, it's telling us that we said yes when we really wanted to say no. I learned that if I don't communicate my limits, I can't expect other people to know what they are. People aren’t mind readers.
I avoided boundaries for years out of fear of being perceived as rude, difficult, or selfish, but the alternative was worse. I’d be a doormat, hide my discomfort, and let resentment build until I finally snapped. Because I didn't know how to communicate a boundary calmly when it was small, I’d end up overcorrecting and taking things way too far. I went straight from passive to aggressive, missing the middle ground entirely.
Lesson: Resentment is a sign you’re giving out of obligation
instead of genuine willingness.
Confession: I was scared of boundaries and didn’t really understand them either.
Boundaries aren't punishments, threats, or walls we build to make people behave. They're limits around our own time, energy, body, emotions, responsibilities, and relationships. It's a decision about our own participation. You can tell someone you’re not available for something or that you disagree with them, but you can't control whether they're disappointed. You can decide what you’re willing to tolerate in a relationship, but you can't control whether someone thinks your need is reasonable.
Even now, when I tell someone I’m unavailable, my brain starts drafting a five-paragraph justification. The difference today is that I force myself to pause before hitting send. I don’t have to build a legal case for why I said no. People who benefit from your people-pleasing will often experience your boundaries as a loss, call it selfishness, or complain that you've changed.
I don't have to abandon the boundary because someone is unhappy about it. Their disappointment doesn't automatically mean I've done something wrong. Their anger doesn't automatically mean I've been unfair. Their discomfort doesn't automatically mean I need to fix it.
Lesson: If a boundary only works when the other person agrees with it,
it's not a boundary.
It's a negotiation for their approval.
I also learned what healthy boundaries can feel like from a supervisor who modeled them at work. Before asking staff to pick up a shift or taking on an additional role, she would say, “I respect your no.” She made it safe to decline before she even asked the question.
Lesson: Boundaries aren't about making other people comfortable with your limits. They're about getting comfortable with your own.
Confession: Guilt trips were a major trigger.
For a long time, guilt was the lever people could pull to get me to move. It didn’t even have to be overt. A heavy sigh, a shift in tone, or passive comment like, "You’re probably too busy to make it,” “You wouldn’t know because you never call," or “Lindsay doesn’t have kids to pick up so she should be free to do it,” was enough to change my plans, feel obligated to participate in one-sided conversations, or do whatever to keep the peace. Not because I had actually changed my mind, but because I felt guilty.
A guilt trip is simply someone using discomfort to get what they want. Once I learned to name guilt trips for what they were (manipulation), they lost their power. A guilt trip is simply someone using discomfort to get what they want. It works on people-pleasers because we’ve been conditioned to view anyone else’s discomfort as our emergency.
While there are definitely people who know exactly what they’re doing, it’s been enlightening to realize that people-pleasers aren't automatically the victim, and guilt-trippers aren't automatically the villain. Both are just learned behaviors interacting with each other.
Lesson: A guilt trip is not evidence you’ve done something wrong.
The Grief of Changing
When you stop being the person who always says yes, always accommodates, or plays the game, there will be people who don’t know what to do with you. You might lose relationships, or at least the version of the relationship you thought you had. It’s a painful realization to learn that certain people liked the version of you who never said no more than they liked the authentic you.
☝🏼BUT, there’s something liberating about that realization, too. Now you know. You know who can respect your no, who can handle disappointment without creating a scene, and who values you for who you are rather than what you can do for them. You don’t have to chase the people who only want the “yes girl.” You can let them go and make room for relationships where you don’t have to abandon yourself to earn your place. 👏🏼
The Shift
I would love to tell you I’ve fully mastered all of this and stroll through life completely immune to the fear of disappointing people. The reality is that I’m a recovering people-pleaser, not a recovered one. It takes a long time to build muscle memory so trying unlearn something is challenging. Knowing better doesn’t mean patterns magically disappear, but I do recognize them faster. I still notice when I’m explaining myself for the fifth time hoping for approval. I notice when I’m about to do or say something because I’m afraid of someone’s disappointment rather than genuine desire. And when that familiar wave of guilt sets in, I stop and ask myself if I actually did something wrong, or if I’m just uncomfortable because I didn’t do what someone wanted me to do?
The irony of this work is that once you learn the why, you start noticing it in other people, too. It’s eye-opening and a little humbling. You notice the person immediately apologizing for everything, saying yes to everything, the one altering their opinion to match the room, the one making excuses for someone’s toxic behavior so they’ll be perceived as understanding instead of judgmental (when you know it’s really just fear masked as good intentions). Watching someone work that hard in an invisible popularity contest is uncomfortable and exhausting, not because I’m above it, but because I’ve been there and I still fall off the wagon sometimes.
Another truth is that people-pleasing can actually feel exhausting on both sides of relationships because one person is trying to be what they think everyone else wants while the other person never quite knows what is real. Are they just telling you what you want to hear? Do they seem like a completely different person in various settings? Do their actions match their words? Connection is truly so much better when people just show up as themselves.
While I’ll always be someone who cares deeply about others, I’m done living life like I’m trying to win the title of Miss Congeniality. I don’t need to be the easiest person in the room, I don’t need to be universally understood, and I definitely don’t need to be universally liked. I just want to be honest about who I am, what I can give, what I can’t, and what I’m willing to tolerate.
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