Learning How to Confront Someone When You’re a People-Pleaser

“The more room you give yourself to express your true thoughts and feelings, the more room there is for your wisdom to emerge.” ~Marianne Williamson

I have always been a people-pleaser, a trait that on the surface seems positive. Like many of us, I want people to like me, and I do my best to make them feel loved. But when someone is angry with me or feels I’ve hurt them in some way, no matter how insignificant or fleeting that anger or pain is, it crushes me.

Over the years, I learned to value other people’s happiness and expectations over my own. To be honest, I didn’t know how to speak up for myself, I’d been trying to be “likable” for so long. This was especially true at work. If my boss criticized me, I felt I was letting her down, and worked diligently to earn praise.

I became dependent on accolades to feel worthy, but this meant I also plummeted into despair when I didn’t measure up to expectations.

A couple of years ago, I was working at a non-profit with a group of people I truly respected and admired. It was my dream job—I was a publicist for a company that was doing good things in the world, not just trying to make money. I loved this job, and worked hard.

Eventually, I was offered a promotion—a management position, overseeing staff and developing strategy. I was thrilled! This was a tangible acknowledgement of how hard I’d worked, how valuable I’d become.

There were strings attached. The department heads wanted me to continue doing my old job since they didn’t have the budget to hire another person.

I was flattered that my bosses wanted to give me more responsibilities (proving my worth). But I also knew the organization was taking advantage of me by not hiring someone to help, and this was difficult for me to accept and address directly. If they really liked and respected me, how could they think this was a fair offer? I was asked to do two jobs for the price of one.

It gutted me. After all my hard work, I knew I deserved more.

But these are good people, I reminded myself. Surely there’s something I’m overlooking. Am I unworthy of more?

I felt my self-esteem plummet.

It took a few days for me to realize I had to stand up for myself. Nobody else was going to do it. My bosses, who I’d come to see as friends, were taking advantage of me and my people-pleasing approach.

To make things worse, this job was my livelihood. I didn’t know how quickly I could get another job, so it was frightening to think about confronting them. How would it end? Would they fire me if I turned them down? How could I support myself?

I was terrified, but I knew I had to say something. Even if I struggled to find another job, I knew this was a test of my self-esteem. I couldn’t live with myself if I’d just gone along with their plans, pretending it was okay. I had to rise to the occasion no matter how uncomfortable I felt.

I was trembling as I met with my supervisors, the four of us sitting around a table in a sterile conference room. I thought these familiar faces were my advocates, but now I saw that I had to advocate for myself.

I talked about my responsibilities, how hard I’d worked, how much I loved the organization and the people. I asked that they hire another person and offer me a decent raise, or I wouldn’t accept the new position.

“I suggest you reconsider,” one of them said. “It’s a great opportunity for you.”

I was shocked. An opportunity?

“I need more help if you want me to stay,” I insisted.

“We’re offering you a great career move. Are you saying you don’t want a promotion?”

I felt numb. They were trying to wear me down, to make me feel like this was a positive. But I knew better. I didn’t want to work two jobs when the hours were long enough, and they refused to negotiate.

When I realized I’d have to accept their terms or quit, the fear kicked into high gear. Would I be able to get another job in this economy? How would I support myself? It was my ego shouting, trying to take control and remind me that I needed this job, and this paycheck. But my gut knew better. I didn’t “need” to stay, and a paycheck wasn’t worth my sense of self. I knew that it might take a while, but I could find another job.

When our meeting ended, I walked back to my desk and typed up my resignation. Nobody stopped me or tried to convince me to stay when I announced my departure.

Strangely, I was relieved. By deciding to confront the situation and my supervisors directly, I’d let go of my burning desire to live up to their unreasonable expectations. Instead, I saw myself and the situation more clearly.

If they weren’t willing to see my value, I had to honor it myself, even if it meant confronting people I liked and admired. I learned that confrontation, though still difficult for me to do, was just as healthy as being kind.

Soon after I quit, I was able to find work. In fact, leaving that job opened up opportunities I wasn’t aware of, because I hadn’t been looking. I now have a steady stream of freelance assignments, as well as more time to dedicate to other passions of mine, like traveling, hiking, and writing a novel.

Here’s what I’ve learned about dealing with conflict:

Asserting myself is a healthy practice.

We all deserve an equal playing field. When I speak up for myself, it means I’m honoring my needs, too. When I’m going to extremes trying to please others, I get resentful, whether I realize it in the moment or not. Over time, this resentment interferes with my relationships. When I create healthy boundaries with someone in my life, I’m doing both of us a favor.

It might be uncomfortable in the moment.

Confronting someone is never easy, especially a friend, family member, or someone in a position of power over you (like a boss). It might make me squirm and feel terrible in the moment, but in the long run, I have felt such relief. I’ve taken the silent burden off of me, so I can feel more peaceful. The positives outweigh the negatives.

I must look past my fear.

When we face big risks in life like potential unemployment or the end of a relationship, fear kicks into high gear. When fear overwhelms me, I like to step back and look at the situation from an outsider’s perspective.

If a good friend told me she was going through the same experience, what would I say? No doubt I’d support her in advocating for herself, so I should take my own advice. No matter the result, it’s worth the risk to honor ourselves.

It is impossible to please everyone anyway.

This is a hard lesson for me. I have a deep desire for people to understand who I am; that what I do and say comes from a good place. However, this isn’t realistic. There are always going to be people who don’t like me, who misunderstand me. It is not my job to make them feel differently about me; that is completely up to them. What I can do is treat people with respect and kindness, and let go of the outcome.

Confrontation isn’t about hurting someone else; it’s about standing in my power.

The ability to confront ultimately comes down to an issue of self-esteem. Because I was trying to gain acceptance and love, I was at the mercy of external circumstances to feel worthy. Now I see that I have to accept my own worthiness no matter what.

We are all worthy. We are all lovable. And we are all responsible for creating boundaries to honor our worth. This I know is true.

About Kelly Seal

Kelly Seal is a writer, publicist, and author of the book Date Expectations: A Guide to Changing Your Dating Life and Finding Real Love. She lives in L.A. and spends her free time hiking in the Santa Monica mountains, obsessively reading news, and blogging at She is currently at work on her second novel.

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  • Debbie


    You are “spot on” regarding confrontation and being a people pleaser. After reading your article, I felt your story was exactly mine (too)! You are so right about confronting someone being about standing in your own “power.” Also, it’s not about being unkind, either.
    Keep up your good work and wise insights….thank you for helping (anyone) reading your article to grow.

    Debbie B.
    Rochester, Mi.

  • Perfect attitude!

    Everytime you accept what you don’t like, you lower your own self-esteem and program your brain that you accept what unacceptable for you, thus you feel terrible!

    I’ve done the same with one of my contractors.

    That kind of work was terrible,
    so I reached out to him and said I’m terminating the contract
    and want to talk about it.

    He was so shocked and amazed at the same when
    he heard my reasons for doing so, that he sent me
    another offer right the next day.

    Actually he offered me almost 2x the money for the same
    amount of deliverables just to have me in his team.

    I felt the same back then. I was afraid how I was
    gonna replace the client with another one,
    but his new offer was pretty good, so I accepted
    and it was a win-win.

    If I didn’t do it,
    I would feel terrible every single day
    for accepting what was absolutely unacceptable for me.


  • Kelly Seal

    Thank you Debbie!! It was hard to admit this about myself, because I want to seem independent and in control, but I think ultimately it helps other people-pleasers to stand in their own power, too. It’s not about being unkind at all! It’s about owning your own worth. XO

  • Kelly Seal

    Fantastic! Thanks for sharing. I think this fear is especially true with our jobs when others have power over us. It’s important to recognize this and to hold out for what you deserve. Well done!!!

  • Sloppy_dreams

    Right now I’m suffering from the same issue. But I think my problem is more serious since I’m working with psychologist. People who don’t try to please others are the healthiest people on earth. Believe me or not, the more you try to get a praise from other people, the more you become nervous and unhappy. I wish one day I’ll be able to solve this problem too. It’s ruin my life like nothing else.
    Thank you for sharing.

  • Kelly, thank you so much for sharing this! I can relate. You’ve managed to put into words something I was struggling to articulate myself for so many years – “It took a few days for me to realize I had to stand up for myself. Nobody else was going to do it. My bosses, who I’d come to see as friends, were taking advantage of me and my people-pleasing approach.” – It’s so hard to realize that no one will show up unless you choose to show up and stand up for yourself… xo

  • Kelly Seal

    Thank you LesyaLi – yes, this was a hard lesson for me to learn, and hard to do. But worth it. Thank you for your comment! XO

  • Kelly Seal

    I’m sorry to hear this, and yes, I know how being a people-pleaser works against you, because you can never make everyone happy. It’s impossible, we know it’s impossible, and yet we still try and make it happen! I get it. It’s a process, so don’t beat yourself up. You have to practice giving yourself the same kindness and reverence you give to others, and this takes thoughtful action. Thank you so much for your comment – keep striving. Your life is moving forward, whether you realize it or not. XO

  • lv2terp

    BEAUTIFUL!!!! 🙂

  • It’s all about the lessons, isn’t it, Kelly? No matter how hard those are, when we get to learn something valuable, we emerge transformed, and, hopefully, stronger than before… XO 🙂

  • Kelly Seal

    Exactly! Hard in the moment, freeing after. 🙂

  • Kelly Seal

    Thank you! 🙂

  • Al Package

    Yes, this is me, too. Thanks for the article.

  • Adam

    Great article! I’m having a problem with my manager not letting me manage my team the way that I want to. I’m going to speak up and let him know how I feel. Thank you!

  • Mandy

    Hi Kelly, thanks so much for this.

    I feel that I’ve been put down quite a few times in my jobs that it’s starting to affect my self esteem. Right now I always censor my thoughts and opinions to my superiors because I don’t want to seem too controversial or uncooperative for their liking. Sometimes I even “act dumb” so that I wouldn’t be seen like a threat or a nuisance.

    I’m dying to do my own thing so that I can finally act as myself again.

  • Alison Hilaire

    I struggle with people-pleasing too and it’s really difficult. However, I realized 3 things lately:
    1/ The people that do not seem to appreciate me are often people that I don’t actually like that much (when I really take time to analyze what kind of person they are). So why bother this much, desperately trying to please them?
    2/ My people-pleasing is the result of my lack of self-esteem/self-love. To compensate this, I look for “self-love” in others’ attention, love, praises, but it will never be enough: they will never be able to fill this inner void.
    3/ My lack of self esteem which lead to people-pleasing created for me some sort of strange vicious circle of everlasting disapointment and frustration: I expect others to give me the exact love/attention/praise that I crave but because these are very high and unrealistic expectations, they are never met. And since it’s very difficult for me to stand up for myself, I can’t even let them know that I’m disappointed by their attitude anyway.
    In conclusion, put yourself first, because no one else: will they are too busy putting themselves first already!

  • Kelly Seal

    Well-said! It is an issue of self-esteem, which can be hard to admit. It’s a void ultimately that we need to fill ourselves.

  • Kelly Seal

    Don’t ever dumb yourself down for anyone. It doesn’t work in the long run, and it only hurts you. I totally get it – you want to be accepted. But you feel more freedom in being yourself, and ultimately, being yourself leads you down a more fulfilling career path.

  • Kelly Seal

    And thank you for your comment – I totally appreciate it! Hang in there – it gets better! XO

  • Kelly Seal

    Awww, that’s great! Thanks for your comment, and good luck…we are routing for you and your team!

  • SoCalSurfer

    Excellent article! Great example and glad you were able to assert yourself and move on… Life is a tricky balance between being too aggressive, too passive and ideally assertive as needed! As an introverted/analytical engineer I avoid confrontation and often end up a people pleaser. This has led to less daily stress and often a more harmonious existence but in the business/work world it has created problems for me. I was a manager for years and too often I let employees get away with too much and in the end it created problems for me.

    At middle age I have learned to pick my battles better – being assertive when needed yet avoiding unnecessary confrontations. As the Serenity Prayer goes:
    “God grant me the serenity to accept the things I cannot change, courage to change the things I can, and wisdom to know the difference.”

  • Leidee Rose

    I completely understand your position. After two failed marriages, I’m finally standing up for myself in most areas of my life. I know during this process several people decided that I was of no value and cut me out of their lives. Normally, I would be devastated and attempt to create a “compromise” so that I was still in their good graces. But I had to step back and “pause” because I could see me falling back into those old people-pleasing habits. I’m stronger now and these days I remind myself that at the very least I need to value who I am. I happier and enjoying life to the fullest.

  • Kelly Seal

    Congratulations Leidee, how incredibly rough. I do know the feeling of trying to “compromise” and be someone I’m not so that others will accept and like me, especially family. It’s a difficult lesson. I’m so glad you have grown from this experience to stand in your power! XO

  • Unassuming Obelisk

    I’m a teen, going into senior year, and I’m just now realizing that I’m a total people-pleaser. I don’t know how to stop. I don’t think I’ve ever stood up for myself. My mom, as much as i love her, keeps dragging me into things that I would rather not do. (no, not the usual “do the dishes”, that’s fine) I’m like this in all areas of life. Even little kids can pressure me into doing things for them, without much effort. I wish i knew how to stop it, but I don’t. I’m currently just waiting for my chance, but I think you’re right, nobody is going to advocate for me. I’m going to waste my summer on depression if I don’t do something soon. Any tips on where to start?

  • Great article, but it doesn’t address what happened with that people in her old job, you said you love the people of that organization, do you still love them? Are you still in contact?
    I think this is important because I can challenge people I don’t care about but if I’m a friend pleaser and I stand up my fear is that we’ll never be friends again, maybe I’m too radical but saying these kind of things can harm people. Any suggestions? Thanks