Let’s talk about the thing so many of us millennials are really good at—people-pleasing. You know the script:

• “It’s fine, really.”
• “I don’t want to make a big deal.”
• “I’ll just let it go. I don’t want to hurt their feelings.”
• smiles while dying inside

Sound familiar?

People-pleasing is often disguised as kindness, empathy, and being “a good person.” But the truth is, when you’re constantly editing yourself to avoid upsetting others, you’re not actually protecting the relationship—you’re slowly draining it. You’re not creating peace, you’re avoiding the necessary discomfort that allows for growth, honesty, and real connection.

The Real Problem with People-Pleasing

At its core, people-pleasing is an attempt to manage other people’s emotional experiences. We tiptoe, sugarcoat, over-apologize, or stay silent altogether, thinking we’re being thoughtful or protective. But here’s the reality:

When we prevent people from feeling their feelings, we prevent them from fully understanding us—and themselves.

We end up shouldering the emotional labor of everyone else. We suppress our needs, avoid setting boundaries, and try to “keep the peace” by being “nice.” But being nice and being honest are not the same thing.

What we don’t realize is that by trying to avoid “hurting feelings,” we also avoid telling the truth. And that means no one—including you—is given the chance to respond to what’s real.

Feelings Are Not the Problem

Emotions—yes, even the uncomfortable ones—are useful. They’re like notification systems. They tell us something matters. They point to what we value, what we need, and what needs to change.

But somewhere along the way, many of us learned to associate “negative” emotions with shame, being too sensitive, or being difficult. We fear being seen as “mean,” “selfish,” or “high-maintenance.” So we silence ourselves instead. And in doing so, we rob ourselves and others of the chance to connect honestly.

Being assertive is not the same as being aggressive. It’s not about making someone feel bad—it’s about sharing your experience of their behavior in a way that honors your reality.

People Need to Feel Their Feelings

When you express a boundary or share how something affected you, it’s okay if the other person feels uncomfortable. That discomfort is information. It tells them: “Oh—this matters to you.” Without it, they stay in the dark, and the behavior keeps happening.

By trying to be “nice” and hoping they “get the hint,” all we’re really doing is giving silent permission for the same dynamic to repeat. And then we wonder why nothing changes.

Clarity is kind. Ambiguity is not.

Let’s Get Clear: Assertiveness vs. People-Pleasing

People-pleasing sounds like:

• “It’s not a big deal, don’t worry about it.” (It is a big deal. You’re still thinking about it a week later.)
• “I’ll just suck it up.” (Resentment building: 89%)
• “They didn’t mean to, so I shouldn’t say anything.” (Intent isn’t the same as impact.)

Assertiveness sounds like:

• “I know that wasn’t your intention, but when that happened, I felt dismissed.”
• “It’s important to me to talk about this. I want us to be able to understand each other better.”
• “I care about our relationship, and this has been bothering me.”

See the difference?

You’re not trying to make someone feel bad. You’re just naming your experience and giving them the opportunity to show up differently.

Common People-Pleasing Scenarios (and Their Consequences)

1. Not saying something when your friend constantly cancels plans.
🧠 “I don’t want them to feel guilty.”
🎯 Consequence: You feel unimportant. The friendship becomes unbalanced.

2. Not bringing up hurtful comments your partner made.
🧠 “I don’t want to start a fight.”
🎯 Consequence: You start pulling away emotionally. Resentment simmers.

3. Taking on extra work at your job to avoid disappointing your boss.
🧠 “I want to be seen as a team player.”
🎯 Consequence: Burnout. Overwhelm. Bitterness.

4. Laughing off rude jokes from family members.
🧠 “It’s not worth it. They won’t change.”
🎯 Consequence: You dread family gatherings. You don’t feel safe being yourself.

By not letting people feel the discomfort of hearing our truth, we protect them from the very thing that might have led to understanding, change, or accountability.

Let People Feel

It’s not your job to manage other people’s emotions. It is your job to honor your own. When you speak clearly, calmly, and honestly, you give others the opportunity to respond, reflect, and repair. Without that opportunity, relationships remain superficial, unbalanced, and stuck.

We all have a right to our emotional experiences. And emotions, even the hard ones, aren’t signs of failure—they’re signs that we’re human and that something matters.

You Don’t Have to Do This Alone

Unlearning people-pleasing and building assertiveness takes time, intention, and practice. Therapy is a safe space to untangle these patterns, reconnect with your needs, and practice new ways of showing up—authentically, kindly, and honestly.

👉 Click here to schedule a session and get support in learning how to stop performing and start being real.

You don’t have to keep shrinking yourself to make others more comfortable. Your feelings, your needs, and your truth deserve space.