This is easily the hardest lesson I have to learn, and I'm not even there yet. Consistently I find myself, as you might as well, basing my decisions and opinions of myself and situations on how everyone else will feel about them.
This is not a way to live your life.
You could be the most selfless person on this planet and still fail at making everyone happy. It's nearly impossible to make everyone happy. Everyone has different ideas, wants, thoughts, and stipulations. Allowing everyone to have exactly what they want to make them happy just doesn't happen.
Now let's say it's some people that deeply care about you. Yes, they have ideas for you, plans, hopes, and dreams for you. They want the absolute best for you and as people who love you, they know you pretty well, well enough to believe they know what's best for you. But at the same time, they want you to be happy. What happens when what makes you happy isn't what they think is best for you?
I still don't know what to do with that. I've seen that and how it hurts people over and over again. And I don't wish it upon anyone. It's a terrible burden deciding who's happiness you give. Do you do what they say and be unhappy? Do you do what you want and upset them? Do you fake happiness for them?
I'm no expert, but as someone who has these thoughts and has watched as it tears people apart, even the most selfless and people pleasers of all, I think there is a very important lesson to learn here.
If you have to make anyone happy, make you happy. Sometimes that will be by making others happy, a beautiful selfless quality, but you are also an important person who deserves happiness. You deserve to be happy just as anyone else does. If you can create mutual happiness, making others happy as well as yourself, then well, you've won it all. If you can't, and it's there happiness or yours, this is the advice I give:
1: How important is it?
Is this issue more important to them or you? Who's life does it affect? Is this as big as college or as small as going out one night? How much does it mater to you?
2: Can you live with it or can they?
Can you live with it? Can they? How hard does it affect you and them? Is it that big of a deal? Can you accept it? Should they?
3: Accept and become happy with whatever the answer is
Whether you decide to do what makes them happy or what makes you happy, accept it. Be happy with the decision and do not (DO NOT) be upset with yourself for it. You obviously went through deliberate decision making to come to the decision you came to, so you know deep down that it's the best decision. And let's not forget the most important thing to consider, you are a human and you are worthy of happiness just as much as they are.
Whatever you decided, be happy with it even if no one else is. You are human, you do deserve happiness, and you do have choices. It's okay to make them. It's okay to be happy.
Every people pleaser needs to learn that.
It's okay to make yourself happy.