TzeLin, you really opened up a fruitful discussion here and offer both the good an bad aspects of people-pleasing. I generally want to please the people around me, family, friends, online acquaintances even. However, not to my own detriment. If something will clearly disadvantage me in a big way, or make me regret the decision then I won’t do it.
I don’t see people-pleasing as a bad thing as long as it is done for the right reasons and to show you genuinely care for someone. If it is crawling to purely get something you want or to advance yourself, than I think it is wrong.