If you've ever read even the milder self-help/personal development texts, you've certainly come across the notion of the people-pleaser: the person who fucks himself over in the attempt to make everyone around them happy.
I'm here to disabuse you of the notion that the issue is that simple and superficial. People who consciously strive to please everyone have a very easy problem to fix, simply requiring conscious effort in the opposite direction. But that's a pretty rare situation.
The far more common case is that of the subconscious people-pleaser: someone who's always trying to please, appease or put-at-ease those around himself, and doesn't even realize that he's doing it. Let me tell you about this unfortunate character.
Our people-pleaser is someone who started out with good emotional intelligence. It may seem counterintuitive, but the people-pleaser is actually someone that can read people very well: where they fuck up is in what they do with that information.
Your typical people-pleaser grew up, whether by innate predisposition or learned skill, with a strong ability to read other people's expressions, tones of voice, gestures and so on. He could, especially, tell when people were attentive or distracted, engaged or bored, happy or angry.
Crucially, the people-pleaser learns to use this ability to adjust his own behavior in order to always elicit a happy response in his interlocutors. He doesn't do it because he's a dumb indoctrinated beta or some other catastrophic issue; he does it because we all naturally want to elicit a positive social response, and the people pleaser learned that he could do it by reading others and modifying his behavior accordingly.
The people-pleaser is not necessarily a whipped beta. In fact, strangely enough, he can also be a brash asshole. But what's important is that his behavior is constantly informed by his reading of his audience's reaction, and he modifies his behavior to elicit a positive response. The brash asshole people-pleaser will always seek to shock and entertain his audience with his asshole antics; he doesn't do it for his own amusement, and if he doesn't get the desired reaction then he's very much not happy.
The most important thing that you can understand about people-pleasers is to not expect them to be a stereotype. They come in all shapes and sizes, in all forms of behavior, and the only constants are, once again: strong ability to read others and automatic tendency to adjust their own behavior to elicit a desired positive response.
If you want to figure out whether you are a people-pleaser, ask yourself: am I constantly scanning others to see how they react to my behavior? am I very sensitive to this? do I constantly, and often without thinking, change my behavior so as to elicit a different reaction?
Of course, we all engage in this behavior to a point. The ability to read others and adjust our behavior accordingly is fundamental in a social species. But the people-pleaser overdoes it: he's constantly adapting himself to the world, to a great and self-harming excess.
There are two key things that people-pleaser doesn't realize. The first is that other people's reactions are not fully determined by what we do. If I'm telling a story and someone yawns, it might be because the story is boring (this is what the people-pleaser would automatically assume), but it might also be because that person is sleep-deprived, because he has something else on his mind, because he's a halfwit with the attention span of a goldfish, and so on.
The healthy way to handle this situation, a way that would not even occur to the people-pleaser, is to take the yawner's action as one of the inputs in your evaluation of the situation. If you judge that the story is good, if other people seem engaged, if the moment doesn't seem inappropriate, then it's likely that the yawner is yawning for their own reasons, which are none of your concern. The people-pleaser would, instead, make it his concern, and try to change his behavior accordingly.
The second thing the people-pleaser doesn't realize is that sometimes you need to make other people feel bad (or not-good). Other people aren't entitled to you laboring to always make them feel good. They simply aren't. Even when it's in your power to appease them, sometimes you just ought not to.
This thought would be completely alien to the people-pleaser, because he tries to appease others automatically, without thinking. If he sees someone that appears angry, upset or otherwise not happy, he automatically endavors to make them so. Even when he purposefully makes people mad, the people-pleaser is actually doing it to then achieve a happy state: the people-pleaser can be someone who teases, roasts, pranks, but he's only happy if the other person is a good sport and has fun with it.
The healthy way to approach this is, instead, to realize that other people's emotions aren't any more right than our own. If someone has their panties in a bunch over something, it's not your job to un-bunch them. If they are unreasonably upset with you over something, then it's their problem to deal with their unreasonableness. Always appeasing people will only teach them to be more unreasonable, if anything.
If you think you might be a people-pleaser, then Dr Derek prescribes you this therapy:
notice how you change your behavior in response to your reading of others' reactions
consciously tell yourself that you ought not to change your behavior, because the reaction is not necessarily due to your behavior, nor is it necessarily a reasonable reaction
decide if your behavior needs changing; err on the side of not changing, because your natural inclination (you're a people-pleaser after all) would be to alter it
You won't cure yourself immediately, but even in the first few days you'll make impressive, noticeable improvement. You'll feel far less burdened by the constant labor of people-pleasing, your interactions will become more genuine and, even though you might initially elicit some surprised negative reactions in people who are used to your people-pleasing, you'll then have a far more effective social and relationship life than before.
(Incidentally, this is a great part of why the "adopt a DGAF attitude" mantra works: people-pleasers take it on faith that they should stop striving to please people, which helps them overcome their natural tendencies. The problem is that they don't understand, notice nor counteract the subconscious mechanism that made them act as people-pleasers, so inevitably their people-pleasing sneaks back in somewhere. Hence why DGAF is only a stepping stone towards actually building solid frame.)