The Beginning of the Journey of a Reformed People Pleaser

I realized something odd a couple weeks ago. It’s been on my mind and not going away–so that means…a blog post! It’s about standing up for what is right, setting boundaries, and maybe even being assertive.

Before I get into some details, it’s probably important to understand that I’m a people pleaser. Well, let me revise that sentence a bit. I’m a reformed people pleaser who is at the beginning of a journey to listen to what feels right for me versus what will make other people happy. And sometimes, it keeps me up at night.

A couple weeks ago, I was in a strange situation at an elementary-aged basketball game, where my daughter plays on one of the teams and I coach. Without too many boring and unimportant details, winning was extremely important to the other coach, who hadn’t won a game all season. To be fair, it wasn’t that important to me because we had been winning all season. But holy cow, it seemed crucial to a couple of my girls, too, including my daughter (ugh–where does this scoreboard watching come from?) who also is a strong-willed girl who seems to feel every emotion twofold.

Anyway, this other coach was doing some things to win that seemed a little “sneaky”, and my daughter was in tears most of the game. Part of it was she was being a sore loser (just trying to keep it real), but a lot of it was frustration at the injustice of what was happening. And finally, before the last quarter, I went out in front of the players, the referees, the fans, and the other coach and said: “This is enough. My daughter has been in tears this whole game. What is happening in this game is not worth it. This is the way we are doing things this last quarter.”

Then I turned around and walked away, sat down on my bench, and felt AWFUL. I kept second guessing myself: was I upset because we were losing? Was I being fair to the other coach and team? Did I just make that “scene” because there were shenanigans going on that were not fair? Why did I feel awful?

After talking about it with friends later that night and literally being awake a few hours in the middle of the night, I realized why I felt so awful–because I hadn’t done exactly what that other coach had wanted me to do. I had been assertive, which is pretty foreign to me, and I stuck up for what I believed was right and tried to put an end to “let the other team win for once no matter what.” I thought about how the other coach had asked me before the game to have an unfair match-up that gave his team a definite advantage, and I said no. I didn’t think it was fair to that player of mine. It was not in the spirit of this learning league. But then the unfair match-up happened in the game anyway. And I let it.

I struggle with this boundary-setting/people pleasing/assertiveness so much almost every day of my life. Every time I set a boundary, (which let me tell you guys I have overthought all sides of the boundary about as much as a person can) and then someone crosses it and I have to be assertive and stick up for myself, I’m full of conflicted emotions, doubts, and sometimes even–guilt and regret. Most of the time, it’s because the feeling of sticking to the boundary is completely foreign to the 47 years of people pleasing in my history.

But I’m working on it. I’m working on NOT being a people pleaser. I believe it is possible to be a nice, considerate person and still stick up for yourself. So get ready for some more blog posts like this in the future because I know I’m not alone, and I’m on a journey…


Margo Dill (luvboxerdogs)

Luvboxerdogs is just my Wordpress name, but these posts are put up by me, Margo L. Dill. I'm a writer and an editor, and this is my site--welcome! I hope you like it and stick around to read what I have to say or even better, some of my amazing guest posters. :)

4 thoughts to “The Beginning of the Journey of a Reformed People Pleaser”

    1. Well, let’s hope that I handle it somewhat well on this journey. Although I always like to say that I’m making imperfect progress in most things that I try to do.

  1. Margo, I relate to this a lot! Especially the feelings of doubt and guilt when you finally do stick up for yourself. It’s like I can never trust my own decision to take a stand, and I think it all comes down to self worth, and yes, people pleasing. I find it hard to stick up for myself, but easy to stick up for someone else. At least I have that going for me. Lol. I just need to step outside my body and pretend I’m someone else when I have to stick up for myself. The other thing is confrontation, at times, makes me feel ill. I’m looking forward to more of your posts on this topic. You are not alone on this journey! And I applaud you for standing up for your team and what’s right. 🙂

    1. Ang:
      I think maybe I am the same way! I am not so bad at sticking up for other people–especially Katie. 🙂 And I think sometimes I am fairly outspoken at injustices that happen to me too–but it’s dealing with the guilt afterwards that is so hard for me. I also plan to cover good traits of people pleasers because we do have some!

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