How Do I Set Boundaries Without Feeling Guilty?

If you struggle with people pleasing, perfectionism, or overachievement, you’ve probably noticed that setting a healthy boundary doesn’t always feel good. In fact, it might feel downright wrong and make you avoid setting the boundary in the first place.

The good news is: This is normal!

The bad news is: This is very frustrating!

That’s because even when a boundary is appropriate, guilt can still show up, especially if you’re setting boundaries where you haven’t before.

Let’s break this down. In this piece, I’ll:

1. Define what guilt is and how it can be useful
2. Talk about why guilt isn’t always a reliable guide
3. Offer a values-based approach to help you tell the difference between helpful and misplaced guilt

What Is Guilt, and When Is It Helpful?

I like Brené Brown’s definition from The Gifts of Imperfection:

“We feel guilty when we hold up something we’ve done or failure to go against the kind of person we want to be. It’s an uncomfortable feeling, but one that’s helpful. When we apologize for something we’ve done, make amends to others, or change a behavior that we don’t feel good about, guilt is often the motivator.”

In other words, guilt (like all emotions) can be a signal. It shows up when our actions (or inactions) are out of step with our beliefs or values. It’s uncomfortable, but often useful, motivating us to apologize, repair, or make a better choice next time – like that time you yelled at your kids and felt guilty, so you apologized to them and repaired. That’s helpful guilt and once you apologized, you were able to move forward and be better. 

But what about that time you told your demanding boss you couldn’t stay late because you had a doctor’s appointment, but then you felt so guilty about disappointing your boss that you cancelled your appointment and stayed late? 

That’s not helpful guilt. That’s misplaced guilt.

I know, because that was me.

A Personal Story: When Misplaced Guilt Took Over

About 13 years ago, I was a newly licensed psychologist working for a boss who was highly critical and perfectionistic. I had scheduled my doctor’s appointment weeks in advance, and I knew it would take weeks to get back on the doctor’s schedule, but I canceled it anyway when she told me we needed to work late. I told myself, “It’s just a physical. Nothing urgent.” But I didn’t realize that this was part of a bigger pattern in which my guilt was calibrated to my boss’s standards, not my own.

According to Brené Brown’s definition, guilt is about falling short of the kind of person you want to be. I had defined this based on my boss’s approval so any time I didn’t meet her expectations, I felt guilty, even when her expectations were unreasonable.

The moment I knew something had to change came on a Saturday, when my husband and I were moving into a new apartment. I checked my email and saw a long message from my boss, criticizing me for involving an external group in a project. She said I had overstepped and that it “needed to be fixed ASAP.” I also noticed she cc’d some of the other supervisors where I worked.

My body froze. My mind raced. The tears started flowing. I knew that the “mistake” was minor but the feeling that I had done something “wrong” was so powerful I couldn’t think clearly.

I spent the entire weekend spiraling, convinced I had ruined everything. By Monday morning, I was a bundle of frayed nerves and telling myself I’d have to apply for a barista job at Starbucks after packing up my desk.

Using Values to Sort Out Your Guilt

I didn’t get fired. But I did realize I needed to rethink how I related to my boss and to myself.

I started talking to colleagues who helped me see some of the problematic dynamics with my boss, and I started to see the red flags I had missed in myself: Trouble sleeping, irritability, spontaneous bouts of tearfulness, exhaustion, low self-worth. 

I also realized that my own perfectionism and self-critical beliefs prevented me from recognizing how problematic my boss’ expectations were, so I started asking myself:

What kind of boss do I want to be someday?

That question helped me clarify my values, like integrity, kindness, and trust. These values then became a litmus test by which I could differentiate helpful guilt from misplaced guilt:

• If my guilt came from violating my chosen values, it was likely helpful. 
• But if it came from disappointing someone else’s arbitrary or unrealistic standard, it was probably misplaced.

Here’s the thing, though…I still felt guilt when I set healthy boundaries with my boss. Even when I started making more values-aligned choices, the guilt was still there. And I also noticed she was treating me differently, which hurt, even though I was gaining confidence in my boundary decisions.

Knowing that this disconnect between my feelings and behaviors was normal helped me weather the rough parts of this change process. When you’re engaged in a realignment or transformational process, your feelings need time to catch up to your beliefs because they are still operating on the old set of beliefs.

Why Boundary Work Includes Emotional Tolerance

This is why, when I work with people on boundary setting, we don’t just talk about scripts and communication tools, we also work on building the capacity to tolerate uncomfortable feelings like guilt, fear, and doubt.

With time and practice, you’ll see the results of your new behaviors and this will help you validate or adapt your behavior accordingly. The reward on the other side of the struggle is that eventually, when you do feel guilt, like when you’ve genuinely done something misaligned, it’ll be easier to recognize and respond to it constructively:

• Your apologies will come from a place of clarity, not panic.
• Your boundaries will come from self-respect, not self-doubt.
• And the choices you make will feel more like you.

Final Thoughts

You don’t have to wait for guilt to go away in order to do what’s right for you. Anchor to your values and give your actions some time to retrain your emotions. When guilt shows up, pause and ask:

• Is this guilt pointing me toward a deeper alignment with who I want to be?
• Or is it a misleading signal based on someone else’s unreasonable or arbitrary standards?

If you’re navigating this kind of growth—especially if you’re unlearning people-pleasing or perfectionism—know that you’re not alone.

I share tools like this every week in my newsletter, designed to help you take values-based action even when it feels hard: