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.

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