Setting Boundaries for People Pleasers: Why You Feel Guilty & What to Do Instead

Setting Boundaries for People Pleasers: Why You Feel Guilty & What to Do Instead

If you've tried setting boundaries before but they crumbled the moment someone pushed back, this episode is for you. Psychologist Dr. Therese Mascardo explains the 4 reasons boundaries feel impossible and exactly what to do instead.

You'll learn how to set boundaries that protect your peace without destroying your relationships, how to sit with guilt without letting it make your decisions, and how to enforce boundaries consistently without being cruel. If you're tired of saying yes when you mean no, or feeling like protecting your energy makes you selfish, this conversation will change how you think about boundaries forever.

Listen now:

Apple Podcasts: https://podcasts.apple.com/us/podcast/checking-in-with-dr-therese-mascardo/id1847993697

Spotify: https://open.spotify.com/show/0JYJn4AqCeUU67dKcmhnyg

YouTube: https://youtube.com/@exploringtherapy

In This Episode:

The 4 Barriers to Healthy Boundaries:

Confusing boundaries with ultimatums - You're trying to control what they do instead of deciding what you'll do

Thinking guilt means you're wrong - Your brain hates new things and floods you with guilt to pull you back to what's familiar

Setting boundaries without changing beliefs about worth - You can't set sustainable boundaries while believing your value comes from never disappointing anyone

No plan for enforcement - A boundary without enforcement is just a suggestion

The Solutions That Actually Work:

How to shift from ultimatums to commitments (the "When/Then" structure)

The 24-Hour Guilt Rule for sitting with discomfort

Making boundaries about capacity, not worthiness

The Broken Record Technique for consistent enforcement

Key Quotes:

"Boundaries aren't walls you build around other people—they're choices you make about your own behavior and energy."

"A boundary is not a rule for someone else—it's a commitment you make to yourself about how you'll respond."

"Boundary guilt isn't a sign you're being mean—it's a sign you're breaking old patterns that weren't serving you."

"You can't set sustainable boundaries on top of a foundation that says your worth comes from never disappointing anyone."

"The question isn't whether someone deserves your help—it's whether you have the capacity to help without depleting yourself."

Why This Episode Matters:

Here's what I've learned from working with hundreds of people who struggle with boundaries: The reason boundaries feel so complicated isn't because you're doing something wrong. It's because most of us were never taught how to have them in a healthy way.

We learned either to have no boundaries at all—saying yes to everything, taking responsibility for everyone's feelings—or to put up walls that keep people out entirely.

But you don't have to choose between being kind and protecting your peace. You don't have to become a different person to have healthy boundaries. You just need to understand what boundaries actually are and learn some specific skills for implementing them.

This episode walks you through exactly how to do that, with strategies you can start using today.

What boundary do you most need to set right now?

Is it with family, friends, work, or maybe with yourself? Sometimes just naming it is the first step. Reply to this email and let me know—I read every single response.

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About Checking In:

This podcast is for high-achievers, perfectionists, and eldest daughters who look like they have it all together but are silently struggling. Think of me like a big sister with a doctorate who's been there too and knows what actually helps.

No confusing academic jargon or pretending I have all the answers. Just real conversations about building a life you don't need to escape from.

New episodes every Thursday.

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