The art of disappointing others: 8 skills people-pleasers must learn in order to survive

For years in finance, I said yes to everything. Extra projects? Sure. Weekend work? No problem. Taking on a colleague's workload when they were swamped? Absolutely.

I thought I was being a team player. What I was actually doing was slowly eroding my sense of self.

Research shows that excessive people-pleasing manifests as neuroticism, social withdrawal, and diminished self-worth, with serious consequences for mental health.

The paradox is this: the more you try to please everyone, the less authentic you become. And without authenticity, you can't build the genuine connections you're actually seeking.

Here are eight essential skills every people-pleaser needs to develop.

1. Recognize that your worth isn't tied to others' approval

This one hit me hard during my last year in finance.

I'd been passed over for promotion twice, despite outperforming most of my male colleagues. I'd worked seventy-hour weeks, said yes to every request, bent over backward to make everyone happy.

And it still wasn't enough.

That's when I realized: people-pleasers often have unmet psychological needs that they try to satisfy through external validation.

Your value as a person exists independent of what you do for others. Full stop.

This doesn't mean you shouldn't be helpful or kind. It means your self-worth can't hinge on constant approval.

2. Learn the difference between kindness and people-pleasing

Here's what most people don't understand: kindness and people-pleasing aren't the same thing.

Kindness comes from a place of genuine care. It's freely given, without strings attached.

People-pleasing comes from fear. Fear of rejection, fear of conflict, fear of being disliked.

When we pretend to be something we're not to influence others' perceptions, it depletes our self-control and makes us more stressed.

Real kindness maintains your boundaries while still caring about others. People-pleasing sacrifices your boundaries to avoid discomfort.

3. Get comfortable with discomfort

Saying no feels terrible at first, especially if you've spent years saying yes.

Your body will protest. You'll feel guilty. You'll worry you've damaged the relationship.

This is normal.

Setting healthy boundaries requires self-awareness about what you are and aren't comfortable with, and that self-awareness only comes through practice.

The discomfort doesn't mean you're doing something wrong. It means you're doing something different.

And different always feels uncomfortable before it feels normal.

4. Practice saying no without over-explaining

People-pleasers love to over-explain. We think if we just give enough reasons, the other person won't be disappointed.

But here's what I learned: the more you explain, the more negotiable your boundary becomes.

A simple "I can't take that on right now" is complete. You don't owe anyone an elaborate justification.

When I finally learned this, I started with small things. "No, I can't make that meeting." "I'm not available this weekend."

Each time got slightly easier.

The goal isn't to be rude. It's to be clear.

5. Distinguish between realistic and unrealistic expectations

Not all disappointment is created equal.

Sometimes you disappoint people because you've genuinely let them down. Sometimes you disappoint them because their expectations were unreasonable to begin with.

Learning to tell the difference is crucial.

My partner Marcus helped me with this. When I'd spiral about disappointing someone, he'd ask: "Was their expectation reasonable given your actual capacity?"

Often, the answer was no.

You're not responsible for meeting impossible standards.

6. Build tolerance for others' negative emotions

This might be the hardest one.

People-pleasers often conceal their true emotions to avoid disappointing others, but the reverse is also true: we can't handle when others are disappointed in us.

Someone's disappointment won't kill you. I promise.

They might be frustrated. They might be upset. They might even be angry.

And they'll survive. So will you.

You can be empathetic without taking responsibility for fixing their feelings.

7. Reframe "disappointing" as "being honest"

Language matters.

When you tell someone you can't do something, you're not "disappointing" them. You're being honest about your capacity.

When you set a boundary, you're not "letting someone down." You're communicating your limits clearly.

This reframe helped me enormously. Instead of seeing myself as constantly failing people, I started seeing myself as respecting them enough to be truthful.

Honesty might feel disappointing in the moment, but it builds trust over time.

8. Surround yourself with people who respect boundaries

Pay attention to how people respond when you set boundaries.

Some people will respect them immediately. Others will push back, but ultimately accept them.

And some people will consistently disregard your boundaries no matter how clearly you state them.

That last group? They're showing you who they are.

Healthy relationships can handle disappointment. They might not like it, but they respect your right to make decisions about your own life.

The people who can't tolerate any disappointment aren't looking for a relationship with you. They're looking for compliance.

Final thoughts

Learning to disappoint people doesn't make you selfish or difficult. It makes you human.

I spent years believing that if I just tried harder, did more, gave more, I'd finally feel secure in my relationships and career. Instead, I felt resentful, exhausted, and disconnected from myself.

The irony is that once I started disappointing people occasionally, my relationships actually improved. The ones worth keeping, anyway.

Because when you show up authentically, even if it's disappointing sometimes, people know they're getting the real you.

And that's worth more than perfect compliance ever could be.