Why Holding a Boundary Can Feel Worse Before It Feels Better

photo credit: Bankim Desai

This is part of The Hidden Mechanics of Boundaries, a limited series about what happens under the surface before, during, and after a boundary. Article 9 of 10.

When you start saving money, you can feel broke. The money you used to spend is now being set aside, so you’re experiencing less freedom to spend even as you’re building more financial freedom.

Working out can leave you feeling weak while you’re getting stronger. Learning something new can make you feel dumb because suddenly you’re aware of everything you don’t know. Building a business can involve feeling like a failure over and over as you work toward creating success.

The same contradiction can show up in emotional healing. Working through old trauma can bring painful feelings to the surface, leaving you feeling more broken even as you begin to heal. And setting boundaries can leave you feeling alone while you’re creating the conditions for healthier relationships.

These experiences aren’t identical, and feeling worse doesn’t automatically mean something’s helping. But they illustrate something many of us have experienced: the beginning of a change can feel like the opposite of what we’re trying to create.

Boundaries are no different. I know because when I first started even thinking about setting them, I felt like I was going to die.

What I wanted was more authentic connection with other human beings. Yet the thought of doing something that might upset someone brought up a feeling of absolute terror. Death is the ultimate disconnection, and that’s what it felt like I was facing as I tried to learn a healthier way to connect.

I couldn’t simply wait for that feeling to go away before moving forward. I had to learn that someone could be upset with me and it could still be okay for me to have a boundary. And I had to consider more than what I was feeling in that moment.

The discomfort I’d gotten used to

When I got into recovery, I did a relationship inventory. Initially, I focused on romantic relationships, and there were 28 men on that list. That included everyone from people I’d dated a handful of times to people I’d lived with for years, and everything in between.

None of those relationships had been healthy. As I looked at the pattern, I could see that my codependence had gotten worse over time. In the vast majority of those relationships, both of us were deeply involved in substance abuse. We were numbing ourselves and spending so much time inebriated that we weren’t building an honest, present connection with each other.

And the problems extended well beyond romance. I was dissatisfied with friendships, family relationships, volunteer relationships, and relationships with colleagues.

I knew I didn’t feel good in my life. I knew I didn’t feel good in my relationships. But much of the time, that discomfort was a low hum of continual dissatisfaction, numbed with drugs, alcohol and food. It usually didn’t become excruciating until a relationship had gotten so intolerable that it was ending.

That low hum of dissatisfaction was familiar. I’d lived with it for years. The terror that came up when I considered setting a boundary was much louder, so it was easy to experience the boundary as the bigger problem.

But I was comparing one intense moment of discomfort with a familiar lifelong pattern without accounting for what that pattern had cost me over time.

I needed to weigh the discomfort of changing against the years of dissatisfaction I’d already lived through.

When I considered all of it, the discomfort of setting a boundary began to pale in comparison. That didn’t make the fear disappear. It gave me a reason to move forward while I was still afraid.

Seeing my patterns didn’t feel good either

Learning boundaries also meant learning things about myself that I didn’t particularly want to know.

I’d thought I was an honest person. Then I started noticing the ways I wasn’t being honest. I said yes when I really wanted to say no. I went along with things that didn’t work for me. I let people believe I was okay with something when I wasn’t. I also lied about cigarettes, drugs, alcohol and relationships.

Recognizing my dishonesty didn’t feel good. Becoming more honest eventually did.

I’d also thought I was simply a nice, kind, thoughtful person. I didn’t understand how much of my people pleasing was an attempt to influence how other people felt about me. I was accommodating them partly because I wanted their approval, to avoid their disappointment and to keep them connected to me.

Coming to see the dishonesty and manipulation in my own behavior was painful. Those weren’t words I would’ve used to describe myself. But once I could recognize what I was doing, I could begin to change it. And as I stopped doing it, I started feeling better about how I showed up in my relationships.

The same thing happened with my expectations. I had wildly unrealistic expectations of myself, other people, and the world. I thought that if people would just do things my way, everything would be okay.

Discovering how unrealistic those expectations were didn’t feel good. Gradually bringing them into alignment with reality did. Accepting life as it was gave me a kind of relief I couldn’t get from continually insisting that it should be different. I started to feel comfortable in my own skin, which was new.

I also had to reckon with how convinced I’d been that I knew what other people should do, even while I was struggling to manage so many areas of my own life. Why was I so sure I had the answers for everyone else?

That was humbling. It also helped me start bringing my attention back to my own choices, where I could actually make a difference.

There’s a gap between recognizing a pattern and changing it

At first, I could see behaviors I hadn’t known were there, but I hadn’t yet developed another way of responding. I was more aware of my dishonesty, my people pleasing, and my unrealistic expectations while I was still learning how to change them.

That awareness was uncomfortable. Something I’d previously done automatically was now something I could see myself doing.

The same thing can happen after you set a boundary. You’ve said what works for you, but you may still feel the urge to take it back. You may want to explain it one more time, offer something you don’t want to offer, or make sure the other person isn’t upset.

If accommodating people has been how you’ve relieved that discomfort, holding your boundary means you’re practicing another response before that response feels familiar.

You’re learning to let someone have their feelings while you stay connected to yourself. You’re learning to be honest even when honesty doesn’t immediately bring approval. You’re learning that you can care about a relationship and take your own experience seriously within it.

Those are substantial changes. It makes sense that they take practice.

What’s happening under the surface

When holding a boundary feels worse before it feels better, several things may be happening underneath that discomfort:

1. You’re interrupting a familiar source of relief. Saying yes, smoothing things over, or taking responsibility for someone else’s feelings may have helped you feel better in the moment. Holding your boundary means you’re learning to handle that discomfort without returning to the behavior that kept the larger pattern going.

2. You’re questioning what you used to believe was keeping you connected. If you believe that people will stay connected to you only when you accommodate them, a boundary can feel like a threat to the relationship. You’re beginning to make room for connection that includes your needs and your honesty, even while that possibility still feels unfamiliar.

3. You’re noticing what you used to overlook. Once you can recognize your people pleasing, dishonesty, or unrealistic expectations, it can seem as though you’re doing everything wrong. Some of what feels worse is the discomfort of seeing a pattern clearly enough to begin changing it.

4. You’re changing your understanding of yourself. It can hurt to discover that behavior you understood as kindness also involved fear, approval seeking, or attempts to influence someone’s response. You’re learning to take responsibility for those behaviors without making them the whole truth about who you are, and without using them as ammo to beat yourself up.

5. You’re feeling the immediate cost before the longer benefits. The guilt or fear may arrive as soon as you hold a boundary. Greater trust in yourself and healthier ways of relating take repeated practice. There can be a gap between doing something that supports you and feeling the benefits of doing it.

6. You’re giving familiar pain less authority over your choices. The low hum of dissatisfaction may feel easier to live with because you know it so well. As you account for what it’s cost you, you can begin choosing based on the life you want to build, even when the next step feels uncomfortable.

Look at more than how you feel right now

If you’re holding a boundary and feeling worse than you expected, consider the larger picture.

What led you to need this boundary? What’s happened when you’ve repeatedly ignored that need? How have you felt after saying yes when you really wanted to say no? What has the familiar way of doing things cost you?

Your feelings in this moment deserve care. So does the part of you that’s been dissatisfied, exhausted, resentful, or unheard for years.

Building Internal Safety includes learning how to stay with yourself through uncomfortable feelings. You can acknowledge that you’re scared, seek support, and give yourself time without immediately undoing the choice you made.

Over time, I began to experience the benefits of the changes I was making. Being honest felt better than pretending. Having expectations grounded in reality felt better than continually being disappointed that life wasn’t following my instructions. Participating in relationships more authentically felt better than trying to secure connection by accommodating everyone.

I couldn’t experience those benefits fully before I started practicing the behaviors that made them possible.

Think back to those examples at the beginning. Feeling broke while you save doesn’t tell the whole story of what’s happening with your money. Feeling weak after a workout doesn’t tell the whole story of what’s happening with your strength. Feeling lost while you learn doesn’t mean you’re learning nothing. And feeling like a failure while you build a business doesn’t mean you can’t create something successful.

The same can be true when you work through old wounds or learn to hold boundaries. You may feel more exposed as you begin to heal. You may feel alone as you stop trying to secure connection by abandoning yourself. What you’re feeling in that moment can be the opposite of what you’re working toward.

For me, the path toward more authentic connection included feeling terrified of disconnection. The path toward feeling good about my honesty included facing the ways I’d been dishonest. The path toward greater peace included seeing how much I’d been fighting reality. I had to begin making those changes before I could experience the relief they eventually brought.

That’s why it matters to look beyond how a boundary feels in its first uncomfortable moments. Ask whether it allows you to be more honest, take your needs seriously, and change a pattern that’s been hurting you. Those things count, even before they feel good.

You don’t have to feel the way you hope to feel in order to begin building the life you want. Sometimes, you’ll feel the opposite first. You can be afraid of losing connection while learning how to connect more honestly. You can feel uncertain while building trust in yourself. The feeling you’re seeking may grow from the very practice that feels so uncomfortable today.

That’s the work we make room for in Boundaries That Hold: learning to support yourself through what happens after you set a boundary, so the discomfort of changing doesn’t keep returning you to the patterns you’re ready to leave behind. If you recognize yourself here, I invite you to explore the course.