Why You Should Stop Being A People Pleaser

One of my greatest strengths in the world of connection is that I’m not a people pleaser. That sounds like an odd strength, doesn’t it? Some would say that it’s not a strength at all, and, in fact, it’s a weakness. I can hear the criticism as I type this. 

     “Vincent,” I can hear them say, “you preach about generosity but you believe that it’s a strength that you aren’t a people pleaser? Isn’t generosity about the idea of giving, and giving abundantly?”

     That is exactly what generosity is about. But I would argue that being a people pleaser is not being generous. Often, it’s being an enabler. 

     People pleasers are some of the nicest people that you will ever meet. They will say yes to just about anything to help people. They don’t want to let people down. They will stay on the phone longer, they will move things around to accommodate you and they will repress their own feelings to allow you to express yours. But they might also be the first to be taken advantage of. And often they will be the last ones to know it. 

     So how do we be helpful, generous, and supportive without being taken advantage of? It begins with a phrase that might be hard to understand and can seem contradictory at first. 

     Generosity is on your terms. 

     Wait, what? That might sound like the most selfish statement related to generosity that you may have ever heard! But think about it a little bit longer. Shouldn’t your generosity be on your terms? If not, who’s terms should it be on? The person or organization asking for something? 

     Have you ever been in a situation where your generosity was on someone else’s terms? If you have, I’m going to guess that it didn’t end well. The chances are, either you eventually became burnt out, felt taken advantage of or got resentful. The odds also point to the possibility that they continued to ask for too much, didn’t respect your time, and got annoyed with you when you became burnt out, felt taken advantage of or became resentful. 

     This is a recipe for damaged relationships. 

     It’s their fault for taking it too far. But it’s our fault for not setting up the one thing needed that would have kept all of the checks and balances in place. 


     Dr. Henry Cloud wrote the book on this- appropriately titled Boundaries. Seventeen years ago, that book helped reframe a difficult family situation where I had not set proper boundaries. A lack of good boundaries in relationships is like a lack of a good fence around your property. It’s easy for someone who doesn’t respect boundaries to step over the line. In fairness, they might not have even known where the line was. That’s why communicating those boundaries is important. But often, it takes someone abusing it for it to be addressed. 

     So when I said that I wasn’t a people pleaser, I guess I lied. There have been people who have used guilt, fear and drama to push me in that direction. I’d worry that they would get mad at me for standing up to them, for expressing my feelings and for me saying no. So, instead of facing the discomfort head on, I would choose to lay down my boundaries. I’d allow their boldness to trample over my fence, making them believe that my yard was their yard. Over time, they started to believe it to be true. 

     Have you ever had guests over to your home that didn’t respect your boundaries? That is exactly what the people pleaser is up against in certain relationships. They have not protected their boundaries for so long that there is a desperate need for a re-zoning. The first thing to understand is, if someone is bold enough to step over your boundaries without worrying about how you feel about it, it may be a challenge to reestablish a healthy boundary. But it’s a necessary challenge. If you don’t, either you will remain resentful or a doormat. It’s your choice.

      When you decide to reestablish that boundary- put up that fence-

prepare for resistance. These people who have been hanging out on your lawn, drinking your drinks and enjoying your space are going to be in for a bit of a surprise. They got used to your stuff being their stuff. 

     When you put that fence up- you most likely will find out if they truly were your friend or if they were just taking advantage of you. If they bristle at the thought of having to be on the other side of the fence until they are invited back, you have a fair indication of how they felt about your friendship. Your generosity was on their terms, they believed. 

     If they understand and thank you for letting them know, you also have an indication of the strength of the friendship. Because why would any true friend want to take advantage of another friend? Disclaimer- if you don’t like confrontation- this will be tougher for you. Or maybe it’s the perfect time to step up and improve your debate skills. You know you need to get better at it, it’s just been too comfortable to avoid it. 

     I’d argue that you won’t lose true friends. You will lose people that you thought were friends. But once you understand boundaries, your relationships will become healthier, you will see clearly who is trying to hop over your fence, and your life will have less drama and more happiness. But people pleasers of the world, remember. 

Generosity is on your terms.


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