How I’m Unlearning To People-Please

Photo by rawpixel on Unsplash

Photo by rawpixel on Unsplash

This article first appeared on Role Reboot and has been republished with permission. 

I do not remember a time in my life when I was not a people-pleaser. Maybe it’s because I am a firstborn, so, at an early age, I began overachieving. Maybe because, as an empath, I dislike absorbing anyone’s negative emotions — disappointment, resentment, worry—especially if I caused them. Or it could be because of my elaborate insecurities, which tell me that I better work (hard, harder, hardest) for any worth I hope people will find in me.

Whatever the reason, I people-please chronically.

Between my desire to make, or keep, others happy, and my desperation to avoid conflict, I say yes when I want to say no.

I apologize often, and unnecessarily. Too frequently, I feel at least a little empty until I receive affirmation. Although, finally, I have started to speak up when my feelings are hurt, I still prioritize others’ satisfaction over my own.

And yet.

A number of years ago, I learned, in some ways, to honor what I love, even if society has not prescribed it for me. For example, although it defied expectations, after college, I did not get a 9-5, or enter a graduate program; instead, in some of Baltimore’s most neglected neighborhoods, I completed a year of service through AmeriCorps. Later, when I did attend graduate school, it was in Europe. While living there, I made arrangements for my next step: another year of service; this time, in Africa.

In fact, ever since my early 20s, when it comes to things like where I live, or how I pay my bills, I have made choices for myself. Boldly. At every transition, I have opted, unapologetically, to do what feels right. Others’ opinions or expectations never interfered with that part of my path; my compass has led me to my own North.

However, in the day-to-day decisions, what I commit to, or not; what I permit people to say to me; what I set as personal aspirations for myself, I have never ceased to people-please. I still overextend myself, bite my tongue, pretend not to care. I continue to strive for standards that I believe could actually, finally, guarantee others’ love for me.

Even at the cost of my relationships.


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Although I came to know my North while pursuing the right places and professions, when it came to finding the right person, it seemed, for a long time, no North existed. On this particular path, people-pleasing maintained precedence; meeting others’ expectations seemed important enough to neglect what was best for me. Thus, for a five-and-a-half-year relationship, I was nearly frantic to marry someone I knew I shouldn’t. But because I loved him, and because apparently you’re supposed to get married in your mid-to-late twenties, I not only stayed with him, I would repeatedly persuade (read: practically beg) him to stay with me.

He, too, knew we should not be together, and periodically, would attempt to break up with me. With each “I don’t think this is working,” or “We shouldn’t do this anymore,” I learned a little more how life-breaking the demise of our relationship would be. Every time he suggested splitting up, I would plead for him to hang on; I did not want to ever need to try to remember the sound of his laugh, or smell of his cologne.

But, in addition to heartbreak, each of his efforts to end things would make me feel something else, too: the splintering of my future.

At that time, despite our incompatibilities, nothing made more sense than a life with him. We had already invested so much time into building an “us.” In the eyes of our families and friends, we had become a unit. Nothing about living solo appealed to me, especially because hardly anyone I knew was single. When everyone heard we broke up, after all this time, what would they think?

Imagining a life without him made my entire existence feel small. “Our society is designed for couples,” a stranger, not-too-long-widowed, told me at a wine tasting once. Even there, I was the guest of a friend who did not want to attend alone, so he had asked me to join him. This widow was the only person at the table without a drinking partner.

When we eventually, inevitably, unraveled, the personal loss was all I could endure; for weeks, I delayed making our break-up public. Even my parents, with whom I have always immediately shared big news, did not know for a month. Finally, sitting on the floor of their house, crying and apologizing, I disclosed my single status.

In the midst of comforting me, my mom asked, “What are you apologizing for?”

“Because your daughter is 30, and not in a relationship.” I remember thinking this was obvious, that they had valid reason to feel shame. Instead, they rubbed my back, and offered advice. They promised hope.

I needed it. At that point, I felt that my legitimacy as an adult depended on our relationship. As much as I missed him, I missed even more the validity, and value, that being with him made me feel.

Maybe sooner than I should have, I joined OkCupid, and permitted friends to introduce me to the random single coworker or acquaintance. My quest for a new relationship had specific criteria: a name to drop when people mentioned their significant others, a guest to accompany me to social events, someone with whom to spend idle time. If I could just find one person to simultaneously satisfy my emotional, mental, social, and physical needs, I would have regained the accomplishment we are all expected to attain, but what my break-up robbed me of: coupledom.

But, after a few dates with a man I found funny but with whom I (initially) did not foresee a future, I realized: My relationship does not need to mirror those around me. Our evolving dynamic revealed that relationships do not require a constant eye to what’s next, or knowledge (let alone proof) of what your partner does every night, or a quota of daily communication. Commitment does not necessitate confinement.

Well-intended loved ones encouraged me to set certain boundaries, and to request that he “define” us; out of habit, I obliged. While this may have placated them, all I felt was inauthentic. I savored the organic evolution of our relationship, and these demands were artificial. But it wasn’t until repeated tone-deaf comments from dear (married) friends — calling him “just a booty call,” or remarking about one of our photos that we look like a “real” couple — that I finally, fully understood.

The choices I make regarding my relationship, or lifestyle, or hobbies, or religion, or wardrobe, should aim to please me, no one else.

Meeting the demands of others, rather than my own, will only lead me astray from what matters most: my happiness, health, and wholeness. While I appreciate that people want what (they think) is best for me, I alone know the climate and seasons of my North, and I alone determine how I arrive there.

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