Why Setting Boundaries Feels So Uncomfortable (Especially If You’re Anxious or a People-Pleaser)

If you’ve ever said yes when you meant no, replayed the conversation for hours afterward, or felt a knot in your stomach just thinking about setting a boundary — you’re not alone.

For many people, boundaries don’t feel empowering at first. They feel uncomfortable. Anxiety-provoking. Sometimes even shame-inducing. Especially if you’re someone who cares deeply about other people’s feelings, harmony, or being seen as “easygoing” or “good.”

Let’s talk about why boundaries can feel so hard, and why that discomfort doesn’t mean you’re doing something wrong.

Why boundaries trigger anxiety

On the surface, a boundary can look simple: “I can’t do that.” But internally, it often brings up a lot more.

You might notice thoughts like:

• What if they’re upset with me?

• What if I disappoint them?

• What if I’m being selfish?

• What if they think I’m being difficult? 

• 
  

For anxious or people-pleasing individuals, boundaries can feel risky because they threaten something that once felt essential: approval, safety, or connection.

Many of us learned — early on — that being accommodating, agreeable, or self-sacrificing helped us:

• avoid conflict

• keep the peace

• feel accepted or loved

• stay emotionally safe
  

So when you start setting limits, your nervous system may react as if something dangerous is happening — even if, logically, you know you’re allowed to have needs.

That discomfort isn’t a sign you’re doing it wrong. It’s a sign you’re doing something new.

The people-pleasing loop

People-pleasing often begins as a strength: empathy, generosity, responsiveness. But over time, it can turn into a loop that looks something like this:

You say yes → you feel overwhelmed or resentful → you criticize yourself for feeling that way → you keep pushing yourself anyway.

This cycle can be exhausting.

And when anxiety is involved, it can feel easier to just keep accommodating others than to sit with the discomfort of saying no — even if that discomfort shows up later as burnout, resentment, or emotional fatigue.

Boundaries interrupt this loop. But interruption is rarely comfortable at first.

Boundaries aren’t ultimatums or punishments

One reason boundaries feel so charged is that they’re often misunderstood.

Boundaries are not:

• ultimatums

• punishments

• demands that someone else change

  
  

At their core, boundaries are simply information.

They communicate:

• what you’re able to do

• what you’re not able to do

• how you’ll take care of yourself if something continues

  
  

Setting a boundary involves saying something out loud. Enforcing that boundary or maintaining that boundary involves action - changing your behavior. 

You don’t need permission to have limits. And you don’t need to justify them endlessly for them to be valid.

A values-based reframe

One of the most helpful shifts I see in therapy is moving from the question:

“How do I make this not uncomfortable?”

to:

“What kind of person do I want to be while I’m uncomfortable?”

When boundaries are guided by your values — rather than by fear or guilt — they tend to feel more grounded, even when they’re hard.

You might ask yourself:

• What matters to me here?

• What am I trying to move toward — not just away from?

• What would it look like to be honest, kind, and self-respecting in this moment?
  

Discomfort doesn’t mean you’re being unkind. Discomfort shows up when we do something new. That’s normal and natural. 

You’re allowed to practice

If setting boundaries feels awkward, clumsy, or emotionally loaded — that’s okay.

This is a skill. And like most skills, it gets easier with practice, reflection, and support.

You don’t have to overhaul your relationships overnight. You don’t have to get it “right” every time.

Small shifts count.

If you’d like a simple tool to help you clarify your limits and respond without over-explaining or spiraling, I’ve created a short worksheet to guide you through that process. You can download it here:

Boundary Setting Worksheet

Want support navigating boundaries, anxiety, or people-pleasing patterns? Therapy can be a space to slow this down, understand where these patterns came from, and practice new ways of relating — at your own pace. Reach out today to schedule a free consultation call.

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