I'm frequently told to be more assertive (by parents, multiple teachers, and even random strangers)
I have weak boundaries and I'm practically a doormat. So naturally people tend to take advantage of me or walk all over me.
The thing is, I recognize that persistence and assertiveness are key elements to success. My dad always told me to "never let things go" in business. He told me that many employees requested raises over the years, and the only successful candidates were those who KEPT asking him and would not drop the subject.
Last week I went to guy buy a new hair curler. The girl at the counter must have misheard me and she started ringing up TWO hair curlers. Idk what's wrong with me, but I did not say anything. i paid a total of almost 400 dollars and purchased TWO of the same product just because I didn't want to be an inconvenience. The girl seemed annoyed already and I didn't want to be a nuisance. See how absurd and out of control my behavior is. And I ended up not even liking the hair curler! So now I spent 400 dollars on two items I will never use. I'm not even planning to return them either.
The one time in my life I was actually persistent and assertive, it really paid off. I registered for a summer course at school, forgot about it, and never participated. The school eventually gave me a failing grade and charged me 3000 dollars for the class. Once I realized, I immedicately apperalled the grade and wrote several essays arguing why I deserved to have the grade removed and a full refund for the class. I KEPT persisting and contacting the school until they eventually acquiesced. I received a full refund and the grade was omitted from my transcript.
I also over-tip service people out of guilt and people-pleasing tendencies. I spend 42 dollars at a restaurant recently and tipped them 35 dollars for some reason. The food wasn't even that good, but I kind of felt sorry for the lady. And I can't stop myself. Even if I receive bad service, I tip them extremely high out of guilt or something. I don't know why I'm so "nice" and so desperate to avoid conflict, when many of these people would have zero issues stealing from me or tipping me zero dollars. I can't even bring myself to report bad service or theft. I end up feeling too bad and sorry for the person. So I just let it go.