“Lose Yourself” to Find Connection: Why People Pleasing Holds Us Back

“People-pleasing actually prevents connection.”

This truth hit me like a ton of bricks. Growing up knowing I was different from most people, I craved acceptance. No, I needed it. As I started noticing those differences, hiding them became a full-time job. I thought, If only I could be more like them, they won’t know I’m different, and then they’ll accept me.

It started there—pretending to be someone else to fit in. But it didn’t stop. It became how I interacted with everyone. Whenever I met new people, I’d stay quiet, telling myself I was just shy or introverted. Only recently did I realize what was really going on: I was studying them. I observed group dynamics and individuals closely, trying to figure out how to engage in ways that would make me more likable.

I made myself easygoing to avoid conflict, constantly saying, “Whatever you all want to do.” It became my battle cry. I thought that if I kept adapting, people would eventually like me, accept me, and never suspect I was different. But what I didn’t realize was that people-pleasing actually prevents connection.

The Invisible Wall of People Pleasing

When you people-please, you don’t allow others to see the real you. It creates a barrier, not a bridge. Instead of fostering connection, it builds relationships based on performance and pretense. For years, I poured so much energy into being what I thought others wanted, only to feel even more isolated and rejected.

When I first came out as gay, this habit deepened. I was determined to prove that being gay didn’t change who I was. I had worked so hard to be the best son, student, friend, and employee that I couldn’t let all that collapse over one word. While many people accepted me, coming out still didn’t feel safe in every space.

At work, I hid my partner’s pronouns and avoided sharing my identity with students, fearing backlash. One principal refused to let our GSA advertise publicly, signaling to me that being out wasn’t safe. In another instance, a parent weaponized my marriage during a school board meeting. Each of these experiences reinforced the idea that hiding parts of myself was the only way to survive.

But here’s the thing: Survival isn’t connection. And if connection is the goal, people-pleasing won’t get us there.

The Cost of People Pleasing

People-pleasing comes at a cost, both to ourselves and to those around us:

1. Emotional Exhaustion

Constantly adapting to others’ expectations is draining. It disconnects you from your own feelings, needs, and desires.

2. Resentment

Suppressing your true self builds frustration, especially when it feels like others take your kindness for granted.

3. Missed Opportunities

By prioritizing others’ preferences, you may miss out on experiences or relationships that align with your authentic self.

Moving Toward Authenticity

If you want true connection, you have to let go of people-pleasing. Here’s how:

1. Recognize the Pattern

Notice when you’re people-pleasing and ask yourself why. Are you avoiding conflict? Seeking approval? Identifying your triggers is the first step. 

2. Set Boundaries

Boundaries aren’t about shutting people out; they’re about inviting healthier interactions. Practice saying no when something doesn’t align with your values or energy.

3. Embrace Vulnerability

Real connection requires showing up as your whole self. Share your thoughts, feelings, and preferences, even when it feels scary. The scared feeling is your body trying to protect you from being hurt, however if we don’t disrupt old patterns, we can’t grow. 

4. Prioritize Your Values

Know what matters most to you. When you act in alignment with your values, you naturally attract people who accept and celebrate the real you.

5. Reframe Rejection

Not everyone will accept your authentic self—and that’s okay. Rejection isn’t a failure; it’s redirection toward the people and spaces where you truly belong. Not everyone is for you, so how can you be for everyone. You can’t miss the people and things that are made for you. 

A Journey Toward True Connection

As I’ve worked to let go of people-pleasing, I’ve learned that authenticity isn’t just liberating—it’s transformative. It’s the foundation of genuine relationships, where you can be seen, heard, and celebrated for who you are.

To those still caught in the cycle of people-pleasing: You are enough, exactly as you are. (Read that again.) The connections you’re searching for are waiting on the other side of vulnerability.

So ask yourself: What small step can you take today to show up as your most authentic self?

Because when you let go of people-pleasing, you make room for something far more valuable: real, meaningful connection.