Why Setting Boundaries Feels So Awkward (and Why It Gets Easier)

The emotional discomfort of boundary work, especially for people-pleasers.

Setting boundaries can be one of the most challenging parts of emotional health, especially for those who have spent years trying to please others or avoid conflict. If you’ve ever felt guilty or uncomfortable setting limits with others, you’re not alone. The discomfort often feels overwhelming, but there is hope—setting boundaries gets easier with time and practice.

What Are Boundaries, Really?

Boundaries are essentially limits we set to protect our emotional, mental, and physical well-being. They define where one person ends, and another begins.

Boundaries can be

• physical (such as how close someone can stand to you),

• emotional (how much emotional labor you’re willing to take on for others), or

• mental (the thoughts, ideas, or beliefs you choose to adopt).

They are not about building walls or shutting others out—they are about healthy self-care and ensuring that your needs are respected.

Why Does It Feel So Awkward?

For many people, especially those with people-pleasing tendencies, setting boundaries can feel unnatural or uncomfortable.

This discomfort usually stems from:

1. Fear of Conflict: People-pleasers often go out of their way to avoid conflict or upsetting others. Setting a boundary can feel like you’re creating a potential conflict, even if it’s necessary for your own well-being.

2. Guilt: There’s often a deep-seated belief that saying “no” or setting a limit means you’re being selfish, unkind, or unhelpful. This is especially true for individuals who’ve learned to value others' needs over their own.

3. Unfamiliarity: If you haven’t been taught to set healthy boundaries or if you’re not used to them, they can feel foreign. You might not know how to communicate your needs clearly or confidently.

4. Fear of Rejection: Setting boundaries can trigger a fear of abandonment or rejection, especially if you’ve experienced situations in the past where setting limits led to negative consequences.

Have You Felt This Way?

• “I feel guilty saying no to someone, even when it’s for my own well-being.”

• “I worry that setting boundaries will make people mad at me or stop liking me.”

• “Why does saying no feel so uncomfortable, even when I know it’s the right thing to do?”

These feelings are a sign that boundary work may be something worth exploring in a deeper way. It’s completely normal to feel awkward at first, but these feelings don’t have to control your ability to set healthy boundaries.

How Can We Work With It?

Here are a few tools to help you get more comfortable with setting boundaries:

• Start Small: Begin by setting small, low-stakes boundaries. For example, you can set limits on your time by saying no to a social invitation or letting someone know when you need space. Start practicing on easier situations, and build up to more difficult ones.

• Use “I” Statements: When communicating your boundaries, try using “I” statements to avoid sounding accusatory or confrontational. For example, “I need some time alone to recharge” or “I’m not available for that request right now.”

• Practice Self-Compassion: Remind yourself that setting boundaries is an act of self-care, not selfishness. You’re allowed to take care of your own needs without feeling guilty or ashamed.

• Role - Playing: Role-playing with a trusted friend, partner, or psychologist can help you practice how to say no or express a boundary in a way that feels comfortable to you.

• Visualize Your Boundaries: Sometimes, it’s helpful to imagine yourself setting boundaries in a calm and confident way. Visualization can help ease the discomfort and make it feel more achievable.

How Sessions Can Help

A session can provide a supportive and safe space to explore your feelings about boundaries.

A psychologist can help you:

• Understand the root of your discomfort with setting boundaries, often tracing it back to past experiences or learned behaviors.

• Develop healthy communication skills, so you can express your needs with confidence and without guilt.

• Explore people-pleasing behaviors and identify patterns that may be keeping you stuck in unhealthy relational dynamics.

• Work on self-worth and self-compassion, so you feel empowered to prioritize your needs without fear of judgment or rejection.

Sessions are not just about addressing crisis moments it’s about building the emotional tools you need to thrive in your relationships and your personal life, including the ability to set and maintain boundaries with confidence.