I used to be a doormat until a few mishaps made me realize that I was not being respected and I did not respect myself. Over time I found the courage to stick up for myself and I realized that 1 - most people are reasonable and understand when we set boundaries; and 2 - for the people who aren’t reasonable, their hurt feelings are not my problem. It takes courage to stop being a doormat but when you become more assertive, you are better positioned to influence and help others - so it’s better for everyone. Good luck!
Yes, that second point makes a lot of sense. My aversion to speaking up and having boundaries is partly that I feel bad for the other party involved. It’s like I don’t want them to feel embarrassed? Or I feel bad for them for not knowing better? Or I have this deep anxiety about making things awkward. But it’s stupid, because if I just silently carry on feeling resentment and outrage, it’s still awkward—just for me, not them.