Why Am I Always Trying to Please People?

The difference between being warm and being run by the need to be liked, and how to start telling them apart.

In a recent live Q&A session of my Healing Insecure Attachment course, someone asked me a question that clearly struck a chord with others in the group. She finds herself always trying to please people, she said, even people she barely knows, and even people she’s hiring and paying. With a contractor working on her house, or the teacher at the front of her yoga class, the same low hum is there: a wish for them to be pleased with her, and a quiet discomfort at the thought that they might not be. By the end of some days, a good deal of her energy had gone into managing how other people felt about her, often without her quite deciding to.

If you recognize yourself in any of that, you’re in good company. And it’s worth saying at the outset that not all of this is a problem. There’s a normal, healthy kind of pleasing in which we’re simply there to like and be liked, prepared to find what’s good in other people. There’s also an ordinary, sensible warmth in being a positive presence, like when you want to deepen a friendship or get along with the person fixing your sink. Some of us are also just more amiable by temperament than others; people vary in this the way they vary in height. None of that needs fixing.

The question is whether the pleasing has started to run you, rather than the other way around.

Notice What You’re Seeking and Avoiding

A useful place to begin is with a plain question: what experience am I seeking through pleasing this person, and what experience am I trying to avoid? Often there are two things underneath at once. There’s something we’re reaching for: to be approved of, included, seen as good, perhaps an old wish to be noticed and cherished that goes back a long way. And there’s something we’re trying to head off, usually the discomfort of someone being displeased with us, which for many people can feel out of proportion to the actual stakes.

When pleasing is being driven by that second thing, by the need to avoid anyone’s displeasure, it tends to cost us. We drop our own preferences, agree to things we don’t want, and lose track of what we think, all to keep the other person’s face friendly. For many people this is an old strategy, learned early, when keeping the people around us pleased may have felt necessary for staying connected and safe.

Can You Tolerate Someone Not Being Pleased With You?

If the engine is avoiding displeasure, then the work is learning, gradually, to tolerate it. This doesn’t mean becoming careless about other people’s feelings, or going looking for conflict. It means letting yourself find out that someone can be a little disappointed in you, or mildly put out, and that you remain intact. The world does not end. You are still here.

It helps to start small. You might decline an invitation you’d normally have accepted out of obligation, voice a mild preference that differs from the group’s, or let a small silence sit instead of rushing to smooth it. As you do, notice the feelings that come up, and notice, too, that they pass, and that you’re still standing. There’s a great deal to be gained from practicing this in low-stakes ways, because the capacity you build in small moments becomes available in the larger ones.

When Someone Is Pleased, Let It In

There’s another half to this, and it’s the part people tend to skip. When someone is pleased with you, when warmth or appreciation actually comes your way, are you taking it in? Many of us don’t. The good moment arrives and slides off, or we discount it and move on. So the hunger underneath never gets fed, and we go looking for more approval to fill a cup that has a hole in the bottom.

So when appreciation comes, slow down for a few seconds and let it register. Feel it in your body. Let it reach the part of you that has wanted to be liked and valued. This is what turns a passing moment of being appreciated into something that gradually settles in and steadies you, so that over time you need the next person’s approval a little less.

Find Someone to Model

It can also help to bring to mind someone you like and respect who gets along with people perfectly well, someone who can manage the contractor, the colleague, or the difficult relative, but who doesn’t seem hijacked by the need to please, and doesn’t crumble when someone is briefly unhappy with them. Watch, in your mind, how that person carries themselves. You’re not trying to become them. You’re using them as a kind of reference point, a living reminder that it’s possible to be warm and well-liked and still have firm ground under your feet. You can be amiable and have good boundaries; the two go together more easily than we tend to assume.

A Small Experiment

For the next week, try holding both halves of this at once. Pick one small place to risk someone not being fully pleased with you, and let yourself feel what comes up without rushing to repair it. And when someone is warm toward you, whether it’s a thank-you, a real smile, or a word of appreciation, pause for a breath and take it in rather than brushing past it. Risking the displeasure loosens the grip of the fear. Taking in the approval feeds the part of you that has been hungry for it. Worked together, over time, they slowly return the steering wheel to you.

A Quieter Kind of Warmth

Being liked is a good thing, and wanting it is human. The trouble comes only when the wish to be liked is in the driver’s seat, quietly steering your choices and dimming your own preferences. As you become more able to tolerate someone’s passing displeasure, and more able to receive the warmth that’s genuinely offered, the pleasing tends to settle back into its rightful, smaller place. You can still be kind, still a warm presence. You’re simply no longer paying for it with yourself.

This kind of pleasing is one of the threads that often runs through insecure attachment, where the wish to keep other people’s approval can have deep and tender roots. If you’d like to understand where it comes from and work with it directly, my Healing Insecure Attachment course explores these patterns in depth, and you can use the code SUBSTACK10 for 10% off.

The content in this article has been adapted from my spoken word.