The problem with being a people pleaser

I came across Gary Vaynerchuk’s “Being a People Pleaser is a Strength, Not a Weakness,” during my latest crisis in being a lifelong people pleaser. I’d done it again and people-pleased my way into a corner. I was miserable, and it seemed impossible to untangle my way out.

“People pleaser” sounds innocuous enough. It sounds like a sweet person who’s trying too hard, or a normal person who’s maybe a little needy. But I was starting to sense it was darker than that. After being raised by a people pleaser, having people pleasers as close friends, and being one myself for decades, I’ve come to understand just how insidious it really is.

Don’t get me wrong—in a lot of ways, being a people pleaser was like having a superpower. It made me a star employee, indispensable. I could be counted on in the most difficult situations. It made me a great friend; even when I gave tough advice, I made you feel loved and affirmed. In relationships, being a people pleaser made me the effortless perfect girlfriend. Somehow I was a perfect match no matter who my partner was, whether they were a forest-dwelling hippie, an academic, a heroin addict, or a hedge fund manager. In every role, I was cool, just what you needed, and completely in sync. Never a doormat, never a push-over, just a version of myself that was tailor-made.

My persistent people pleasing went unnoticed — even by me — for decades. Perhaps because, for women at least, the trait is normative. Or maybe no one pointed it out because everything seemed fine. Great, even. If you’d asked, I’d have instinctively said, Me? Oh, I’m fine. Just great!

Some people pleasers are easy to spot with their overly sunny personality or cloying voice. Not this one. I had always admired people who were brash and didn’t give a damn; they seemed so free. I was never going to be them, obviously, but in true chameleon fashion I could play the part. I adopted a flippant attitude and a sardonic tone. It became my trademark. I was undetectable.

Along the way I found socially acceptable outlets where my desire to help had plenty to devote itself to. I taught in underfunded public schools, worked with refugees and indigenous groups, stuck it out in dysfunctional organizations. In fields where hardship reigned, I regularly met people like me. There are whole industries where pleasers sublimate their people pleasing into difficult work. Oftentimes it looks like striking just the right tone, choosing just the right words. Oftentimes it’s an implicit part of the job. (Try getting an emotionally volatile leader to repair the damage from their latest outburst—or try getting a classroom of 35 teenagers to do anything). I had an innate knack getting everyone to reach consensus, all while sparing people’s blushes and quietly championing the underdog. It rarely occurred to me that I was anything other than just a really good person. It was far more flattering than seeing that what made me the capable worker, the noble volunteer, the perfect partner, was my obnoxious compulsion to please.

It’s time for an example. Let me cast my mind back… when have I people-pleased? Was it the time I relocated to Mexico to hand-hold an abusive nonprofit director…? No, that was just volunteering for a cause.

Was it the year I had five courses to teach and no curricula, so I stayed up until midnight every night inventing my own materials? No, that was just teaching.

Was it the year I shaved my legs, started wearing makeup, and became a glittering conversationalist at dinner parties? No, that was almost fun. I was just being my dazzling and multi-faceted self! And one hell of a supportive girlfriend.

OK, how about all those TV shows I sat through; that trip I canceled; that “loan”; all the times I bit my tongue; that decade I rehabilitated a junkie; that time I went to a Yankees game?? Ah, that was all for love. Or, well, something close to it.

It’s hard to pick an instance because, at the time, I didn’t categorize anything as people pleasing. At the time it was Really, it’s not a big deal. I got you, don’t worry about it. Often I was just rolling up my shirtsleeves: If I don’t do this, no one else will. Usually it was “good for me”: It’s healthy to step out of my comfort zone. I am growing my capacity. I can do hard things.

A better way to locate when I have people-pleased might be to take a step back, look at the situation I was in, and ask myself how and why I ended up there in the first place. How did I agree to teach five different courses my first year when two or three would have been plenty? Why didn’t I demand books or materials, or borrow them, or fundraise to buy my own? How was it that I ended up hobnobbing with finance people? Why did I waste my time trying to become legible to someone else’s group of people? How did I have tens of thousands of dollars laying around to financially support a junkie? Why was I emotionally compelled to spend my money helping that person, and not spend it on any of the goals and plans I had originally saved up all that money for? How is it there are dozens of major situations like this in my life, and hundreds of minor ones? For someone who has such control over situations, why am I so unable to control which situations I find myself in?

And for someone who supposedly loves the underdog, how the fuck did I end up at a Yankees game?

So what. Maybe all this was great. Did it ever hurt me to be a people pleaser? If we look on the surface, no. Things always ran smoothly and were sometimes a spectacular success. I taught all those classes, my students passed their state tests, I even won an award. The ex-junkie ex is stable, sober, and has a savings account now. There’s a lot to be happy about. Even things to be proud of.

I’d love to read this as a sign of how great I am, how capable. But that would be to miss the forest for the trees. I know I was only in these situations because I had catastrophically failed to value my needs and desires as much as I valued the needs and desires of others. There were numerous points at which I could have pushed back, said no, disengaged, asked for help, or decided that whatever I’d gotten myself into was no longer my concern. It wasn’t in the dramatic moments, like relocating to Mexico, or signing a lease with an addict, where I got in over my head. It was all the little moments before that. It was every time I felt for another person more than I felt for myself. Every time I decided that the situation needed me to stretch myself, needed me to withstand it, needed me to fix it. Every time I didn’t even think to myself: You know what? I’m not sure I want this.

Under the surface, being a people pleaser has been a serious detriment to my life. If it can be quantified, I’d say I have always experienced less, emotionally, because I didn’t see things through my own eyes. I had my own judgment, yes, but it only got the final word once the jury was in, and the jury was everyone else. Even if I thought I handled something beautifully, I didn’t feel that was true until all parties agreed.

One specific loss is that I don’t know if I’ve really loved. What is love when you are using tools of emotional control on your partner all the time, even if they never notice it, even if it ostensibly made their life better? What is love if you constantly give the other person what they want—including yourself—without even being sure you want to?

I would burn out over and over again. Yet every time it took me by surprise. After temporarily breaking free from whatever claustrophobic situation I’d gotten myself into, it would become clear just how much effort I had been expending and just how little the situation had been feeding me.

This spurred me to do something I spent my entire twenties doing: jumping on a plane and traveling by myself for a year at a clip. Packing up and moving to a random city where I knew no one. Buying a car and driving away, to the desert, to be nowhere. I couldn’t meet another person without sniffing out their deepest desires and fears like a goddamn truffle pig. I would instinctively be, do, say things that, while true, were expressly designed to comfort others. I didn’t know how to be around people without letting this social tic disfigure me. After trying to be something for so long, I’d get sick of it and take the mask off. But under it I didn’t know what I really was or what I actually wanted.

I would send myself to remote places hoping to get over it, or at least get away. It was nice; travel is great. But then you realize you’re just another idiot abroad trying to run away from something. One of my favorite tautologies is everywhere you go, there you are. Eventually I’d meet someone or take on a new job and the cycle would start again.

There’s nothing wrong with being pleasant or wanting to help people. Rather, the fundamental problem with giving and helping is when people pleasing becomes compulsive — when it becomes an intrinsic function of one’s personality. I argue that people pleasing is, at its core, compulsive, disfiguring, unhealthy. One problem is that it leads to diminishing results. The other problem is in its dangerous psychology.

The mark of the people pleaser is that they meet every situation with a compulsive need to be liked or to avoid conflict.

Sure, most people would prefer to be liked and avoid conflict, but pleasers go to much greater lengths than those who are merely congenial or good-natured. Whereas the healthy, balanced individual will deal with people using a varied approach tailored to the situation, the mark of the people pleaser is that they meet every situation with a compulsive need to be liked or to avoid conflict. People pleasers are always on cue—that’s the compulsion at work.

Much of people pleasers’ actions can be seen as an elaborate dance to avoid conflict. For them, emotions that provoke — especially anger — hold a special gravity. Good natured people can still get angry. People pleasers don’t get angry. It’s not just a matter of being polite. They may become despondent, depressed or even suicidal, but they don’t get angry. They repress the full emotional range because they have a larger need that trumps everything else.

Not only do they not get angry, they go out of their way to assuage unpleasant feelings exhibited by those around them. The more adept pleasers become emotional detectives that ferret out displeasure in others before it even surfaces. They patch things up before temperatures even rise. They’ll ameliorate your worries about things you hadn’t even had a chance to think of yet. How do they do it so well? Because they’re afraid that someone might get upset — and terrified someone might get upset at them. Many enablers fit this type.

Some people pleasers operate with a deep need to be liked. Wanting approval is normal, so it’s a matter of degree. The problem is particularly insidious because the need to be liked is so strong that it gets conflated with one’s self worth. This is where codependence starts to take root.

People pleasing is one of the most socially acceptable ways to hide one’s trauma in plain sight.

Does all this sound a bit extreme? My view is that people pleasing, as an evergreen personality trait, is extreme. The unwillingness to use one’s full emotional range points to old wounds that hurt too much to be dealt with. People pleasing is one of the most socially acceptable ways to be fucked up. There you are, so clearly exhibiting your trauma, and yet it goes completely unnoticed. Constantly smoothing things over with niceness is a great way to hide in plain sight. Who’s going to complain? You’re not fucked up, you’re helping people! When you’re busy helping others, no one thinks to ask how you might need help. And if you stay busy enough, you may never have to ask yourself.

The other psychological danger of being a people pleaser is that as you get better at playing the chameleon for other people’s needs, you necessarily start to lose sight of your own. Emotional self-awareness — your interiority — behaves somewhat like a muscle; the more you rely on it, the stronger it gets. The reverse is also true: ignore it and it starts to atrophy. If you stop caring how you feel, you’ll feel less. If you stop asking yourself what you want, at some point you’ll forget to want anything. Only this isn’t some Zen Buddhist lack of want; in our culture it translates to a diminished sense of self. In its absence, it makes sense to start viewing ourselves through the one thing we’re doing really well, which is playing the chameleon. This is the insidious cycle where self worth gets conflated with how happy other people are with us. It is nothing to applaud. It is not “transcending the self.” It is denying the self, and it comes at a cost.

Materially, everything I did was subject to the law of diminishing returns.

Another way of quantifying the damage people pleasers inflict on themselves is by looking at their material lives. Much like how I felt my own experiences, even love, to be diluted because I lived mostly through the eyes of others, so too I found that materially everything I did was subject to the law of diminishing returns.

The point in Gary Vaynerchuk’s Medium post was that people pleasers need to simply ask for what they want in return. I completely agree, but found this to be nearly impossible to do. Judging by the comments on his post, other people pleasers feel the same. Asking for what you want is a necessary habit, but it stands in direct opposition to everything people pleasers stand for. You’d have to break yourself of the entire compulsion if you were to start demanding that your own needs be met. In truth, you might have to come a long way before you’d even know what you need.

The reason I didn’t notice my own people pleasing nature for so long was because I sought outlets where it was useful—nonprofit work, dysfunctional organizations, high-need communities. I didn’t have to negotiate for what I would get out of it — the work was volunteer from the get-go. Though it sucks to go years doing difficult work you’ll never be paid for, I didn’t particularly mind. What am I here for if not to help others? Anyway, it was out of my hands — nonprofit work is another tautology in that it doesn’t pay. Of course this meant I was always broke, but I assumed that was only right. After all, who am I to get a bigger piece?

Oddly enough, later in life I started a family business. I didn’t get into it because I thought I’d make a good businessperson — quite the opposite. I started the company because we had developed a solution to a health problem no one else was solving, and the moral imperative required trying to take the product to market. (Old habits die hard: even the way I describe it shows I still interpret my actions in the language of helpfulness.) Forming relationships to grow the business wasn’t the problem; the problem was that business at some point requires making deals and negotiating. I was skilled at negotiating on behalf of others, but advocating on my own behalf was a something of a logical impossibility. Seeing my personality through the more functionalist lens of business logic forced me to reckon with the fact that people pleasing wasn’t just making business impossible, it had long been making my whole life impossible.

Advocating on my own behalf became a logical impossibility.

In a culture based first and foremost on economic gain, the ability of a person to negotiate their status and pay is seen as a personal responsibility; if one doesn’t ask, they shouldn’t expect to receive. I’m not necessarily critiquing this, merely pointing out its implication that the economy of giving and pleasing is not viewed as a collective good with collective responsibility, but rather a personal matter. This is the implication behind “It’s a dog-eat-dog world,” “Good guys finish last,” and the brutalist motto, “You eat what you kill.”

The twist here, though, is that people pleasers don’t often concern themselves with their own happiness in the first place. In some way, they don’t even recognize that their needs are their responsibility, or that they have them at all. Friends have even remarked to me, “It must be so easy to be you—you never need anything.” What a perplexing notion. Even I was confused by it: I guess I don’t need anything; I have nothing and I’m fine. But what we consider “fine” is a permanent estrangement from self, and our greatest hope is to merely be around people who don’t abuse our nature. With such a mentality, one does not receive unless by accident, or by a conscientious third party going out of their way to do so. It probably goes without saying, but such people are exceedingly rare.

Those who are best at people pleasing often have
a generous attitude toward the world coupled with deep empathy.

Being a people pleaser is a complex phenomenon. Those who are best at it often have a generous attitude toward the world coupled with a deep sense of empathy. These traits are intrinsically valuable for individuals and the collective. The generous person shares even when he has little, and gives for the sake of giving. They inspire the best in others, and are the backbone of good communities. The empathetic person fosters genuine trust, forms bonds, resolves conflict. Empathy is such a rich and nuanced capacity that society, love, and morality, are hollow without it.

Much as one cannot touch a flame without feeling the burn, the empathetic cannot encounter a person without feeling that person’s inner self, and the generous cannot perceive another’s need without wanting to help. But the people pleaser, generous of spirit and understanding of heart, is almost guaranteed to get burned.

In all corners of the world are people who, by sheer dint of life experience and personality, are inclined to care for others. But being a people pleaser means taking it to an extreme, and many do so at great cost to themselves.

Thank you for reading. Care to recommend?