Why do you have to win?

A catalyst of a question

This question made me curious enough to change my entire perspective.

Every once in a while, someone asks you a question that changes your life, your perspective and maybe even your picture of yourself. That happened to me in 2019. The questioner was

Karon

, a close friend and someone whose opinion I greatly respect. You’ll find that I mention her pretty often in my articles.

Anyway…

I’d called Karon to rant about a person in my life whom I felt wasn’t being respectful of me. I don’t mean a stranger in a store or in traffic. I knew this person well, and saw her often.

After listening to me list all of my issues with the person, I blurted out, “I feel like just can’t win with her.” Silence.

Then, Karon asked me,

Epiphany. Eureka! That moment when something simple, and probably a bit obvious to Karon, punched me in the gut. I don’t recall my exact response, but by the end of the conversation, I’d calmed down and I was asking myself, “Why do I have to win?”

What did I even mean by that statement? I don’t see myself as overly competitive by nature, but that question triggered a vision of me that I may have previously disregarded. And it led to me looking into my mind and heart, exploring if I really did feel the need to win over someone else.

Road to Discovery

Some of my initial education into exploring myself involved a small group experience learning about Enneagram. I discovered pretty quickly that I was a 2, with my greatest fear being that I wouldn’t be loved and my greatest motivation being my desire to please others in order to earn that love. There’s a reason they call E2 “The Helper.” By nature, I am empathetic, compassionate and a people pleaser. But my motivations, as a human, were not always be pure. I often overextended myself, became the primary problem solver, and worked diligently to assist others while neglecting my personal self-care, physically and mentally. At that time, I had a tendency, to become who I thought others wanted me to be. That way, they loved me because I became someone they could love. Sadly, I lost myself along the way.

Some real friends, including Karon, helped me see not only the falseness of this behavior and thinking, but also the harm it could cause to me and others. I saw my mother, who has passed, in myself, but back in her day, they called her an enabler. She married two alcoholics, and I believe she either thought she wasn’t worth more or she believed she could be the person they needed to bring about changing themselves. I will never know, but I understand her behavior so much better now. Sadly, that did not work well for her, and it felt as I was moving in the same direction.

Through work with my therapist, my friends, and my now husband, I learned to love without having to transform myself into someone else. I discovered that caring for myself equipped me to better care for others. One of my most dramatic insights came when I realized that in most of my childhood memories, my mother was invisible despite me knowing that she had been there. I feared that if I did not change my thinking, my feelings and my actions, I would become invisible myself.

Wait, what about that question?

Back to the “Why do you have to win?” question: over time, I discovered that my statement, “I just can’t win with her” had nothing to do with a competitive personality. What it really expressed was my frustration at not being able to please her, to win her over, even as I tried to be the person I thought she needed or wanted. I eventually learned that it’s absolutely okay not to win someone over, or transform myself to their liking. In fact, it’s not only okay, it’s better for both of us. She didn’t need a false me, and I didn’t need a “friend” who desired a false friend.

Even on Substack

At times, on Substack Notes, I find myself occasionally falling back into my people pleaser mode - responding to people’s notes in ways that will make them feel good, even if I am not passionate about what they’re posting. I often leave note responses for a time before posting them to make sure I’m legitimately believing in what I write. It’s funny because one person recently mentioned how nice I am, and I froze. It caused me to go back and reexamine every message and post I’d sent to her. Then I breathed deeply because I realized I meant every word of it, and I hadn’t done it to seek love.

I also struggled when I first began commenting on Notes expressing my strong feelings and thoughts about the current U.S. administration. I didn’t want to hurt anyone’s feelings (imagine that) and I also didn’t want to comment just to be part of a group. As an exercise, I spent a week writing down my thoughts, concerns and emotions without posting any of it. During that process, I realized my thoughts expressed how I really perceived the situation, and I’m much more confident in sharing them now, knowing that they’re mine own and not just shared to make others feel good or accept me.

I don’t see pleasing others as a negative. I enjoy helping and supporting my fellow humans. It gives me joy to encourage and love on other people. My motivation for doing so is just different now, and I know that I don’t have to win others over. I don’t even have to try.

Are you a people pleaser or have you overcome the struggle of desiring to win people over? I’d love to hear from you.

Curiously yours,

©Beth the Baker 2025

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