Why Boundaries Can Hurt as Much as They Help
Written by Kirstey KAE, Founder and Resilience Educator
Kirstey KAE is the founder of Embrace Head & Heart Inc., where she specializes in translating the science of resilience into everyday practice. Drawing on neuroscience, behavioural science, and trauma-informed practice, she helps people understand the patterns behind stress, behaviour, and resilience so they can create meaningful, lasting change
Setting a healthy boundary doesn't always feel healthy. Sometimes it feels like guilt, grief, anxiety, or lying awake replaying a conversation we know needed to happen. Resilience educator and behaviour change specialist Kirstey KAE explores what happens beneath the surface when setting a necessary boundary leaves us questioning ourselves. She highlights the lessons those feelings can teach us about our patterns, relationships, self-trust, and resilience. Some of the deepest work of boundaries happens after we assert ourselves, when saying no is behind us, but learning to trust ourselves is just beginning.
What a boundary is and what it isn’t
A boundary is simply an understanding of where one person ends and another begins. It helps define what we're comfortable with, what we're responsible for, what we're available for, and what we will do when those limits aren't respected.
A boundary isn't a way to control what another person does. It's a decision about what we will do in response. For example, “You can't yell at me” attempts to control another person's behaviour. “If yelling starts, I'm going to step away from the conversation, and we can try again later” communicates a boundary.
Boundaries allow us to stay in relationships without continually abandoning ourselves to maintain them. They help protect our time, energy, values, emotional capacity, physical space, and overall well-being. They can also help preserve relationships by giving resentment less opportunity to quietly accumulate.
The emotional cost of setting boundaries
Boundaries have become an increasingly familiar part of the way we talk about healthy relationships and personal well-being. They are often associated with confidence and self-respect. We learn that saying no is important, that our needs matter, and that protecting our time, energy, and well-being is something we shouldn't feel guilty for doing. Yet knowing all of that doesn't necessarily change what happens when we actually begin setting them.
Often, boundaries don't initially feel empowering. They feel uncomfortable. Setting boundaries can be accompanied by feelings of guilt, anxiety, self-doubt, and, most often, a surprising amount of grief. The decision itself may have taken months to make, only for the aftermath to leave us questioning whether we should have made it at all.
The boundary we set may have hurt someone we love. They could respond with anger. At times, nothing dramatic happens at all, but we still spend the next three days replaying the conversation, wondering whether we were selfish, unkind, or unreasonable.
A boundary can be healthy and still hurt. Understanding why may be one of the most important parts of learning to set them.
Why a healthy boundary can feel so uncomfortable
When saying yes, keeping quiet, smoothing things over, or taking responsibility for other people's emotions has repeatedly helped us maintain connection or avoid conflict, those responses become familiar. Our brains are continually learning from our experiences and applying that knowledge in our daily lives. When a particular response repeatedly helps us avoid conflict, maintain connection, or bring relief to an uncomfortable situation, the brain takes notice. Over time, what began as a conscious choice can become a familiar response. We may find ourselves automatically saying yes, apologizing, overexplaining ourselves, or trying to make someone else feel better before we've even had time to process the situation or fully express ourselves.
Then, one day, we do something different. We say “no,” we don’t explain ourselves, and someone else winds up disappointed.
Intellectually, we may understand why the boundary was necessary, but our brains pay attention to patterns, predictability, previous experiences, and strategies we’ve used to successfully stay safe, secure, and connected.
This is one of the reasons changing a pattern can feel so uncomfortable. The brain isn't necessarily asking whether the new response is better for us. It's comparing what is happening now with what it has learned from the past. Suddenly, we're behaving differently, and the other person is responding differently. Different can feel uncertain. Our brain will automatically begin to question us. This is different. Different might not be safe. That's where guilt, anxiety, rumination, and the urge to immediately undo the boundary can appear.
Discomfort isn't always a warning that we're doing something wrong. Sometimes it's evidence that we're doing something differently.
A deeply relational experience
Something deeply relational is happening here. Human beings are wired for connection, and throughout our lives, we learn what helps us maintain closeness, approval, belonging, and predictability within our relationships.
For some, that may have meant being agreeable or avoiding conflict. For others, it may have meant taking care of everyone else, keeping the peace, or learning to anticipate what other people needed before considering their own needs.
When a boundary interrupts one of those patterns, the discomfort isn't always just about saying no. It can also be about what that no might mean for the relationship.
“Will they be angry?” “Will they think differently of me?” “Will this change things between us?”
Suddenly, setting a boundary can feel as though we're being asked to choose between honouring ourselves and maintaining connection with someone we care about.
The grief that comes with boundaries
Setting a boundary can bring a surprising sense of loss. We may find ourselves grieving the relationship we hoped we could have, the version of ourselves who could keep everyone happy, an old role within our family, the belief that if we just explained ourselves well enough, the other person would understand, or even the realization that a relationship only worked when we were willing to continually overextend ourselves.
Sometimes the grief isn't about the boundary at all. It's about what another person's response to it reveals. Perhaps we hoped they would understand. Perhaps we believed the relationship could accommodate our needs as easily as it had accommodated theirs. Sometimes setting a boundary shows us something about a relationship that we weren't prepared to see. Understanding that the boundary was necessary doesn't make that realization hurt any less. It can be heartbreaking, but grief doesn't mean the boundary was wrong. Two things can be true at once, I needed this boundary, and I am sad that I needed it.
What to do with grief and guilt
So, what can we do with the guilt and grief that can show up after setting a boundary? We can change our internal dialogue by asking ourselves different questions.
Instead of immediately asking, “Why do I feel so guilty?” or “Did I do something wrong?” we might ask ourselves:
“What am I afraid will happen because I set this boundary?”
“Did I do something wrong, or does this just feel wrong?”
“Would I believe this boundary was unreasonable if the other person wasn't upset by it?”
“Do I regret the boundary, or do I just wish it didn't hurt?”
“What am I trying to protect by taking the boundary back?”
These distinctions matter. Our brains can interpret unfamiliarity, conflict, or another person's disapproval as a sign that something is wrong, particularly when old patterns have taught us that maintaining connection means keeping the peace. Feeling uncomfortable after setting a boundary doesn't necessarily tell us whether the boundary itself was healthy or unhealthy. This feeling tells us that we're doing something unfamiliar.
Guilt and grief don’t need to be dismissed or overlooked. They can offer useful information. Perhaps we were unnecessarily harsh, communicated poorly, or there is something that needs to be acknowledged or repaired. Other times, guilt shows up simply because someone is disappointed, and we may have spent years learning to interpret someone else's disappointment as evidence that we've done something wrong.
Changing your inner dialogue with these questions creates space to look beneath the guilt rather than immediately treating it as evidence that something has gone wrong. We may discover that we're afraid of losing someone's approval, changing a relationship, or being seen differently. We may realize that the boundary itself isn't what we're questioning at all. We're questioning it because of how someone else responded. At times, what feels like regret is actually grief. We don't necessarily want to take the boundary back, we simply wish setting it hadn't changed something we cared about. Understanding what's underneath the discomfort helps us recognize whether something needs to be repaired or we're simply being pulled back toward what feels familiar.
Boundaries don’t have to feel good to be healthy
Learning to set boundaries isn't about becoming comfortable with disappointing people. It's about becoming more able to tolerate the discomfort that can come with being honest about what we need.
There may be guilt. There may be grief. There may be moments when we desperately want to take the boundary back just so everything can feel familiar again. That doesn't automatically mean the boundary was wrong. Resilience can look like staying with that discomfort long enough to discover that we can survive someone else's disappointment without abandoning ourselves. We then learn one of the quieter lessons that boundaries teach us, we can maintain our sense of self and care deeply about other people without continually leaving ourselves out of the equation.
We can care that someone is hurt by a boundary and still need the boundary. We can understand another person's reaction without making ourselves responsible for causing it or fixing it. We can love someone and say no. We can grieve what changes and still recognize that the change was necessary.
The deeper work behind boundaries
Understanding why we respond the way we do is one thing. Learning to respond differently takes practice, and sometimes it's easier when we don't have to do it alone.
Setting boundaries is about more than saying no, it’s about trusting ourselves enough to honour our needs, even in discomfort. It involves recognizing long-held patterns, questioning the beliefs that sustain them, and embracing the fact that we can choose new ways to respond to life.
True transformation takes place not just by finding the right advice, but by slowing down, delving deeper into understanding ourselves and our life experiences, practising new responses, and experiencing support instead of judgment along the way.
This is the essence of what Calling the Circle embodies.
This fall, I invite you to join a small group for a 12-week virtual journey centred on self-discovery, building confidence and self-trust, reconnecting with our strengths and values, and beginning to shift the patterns that no longer serve us.
Maybe this article brought a particular relationship to mind, maybe it made sense of guilt you've been carrying after finally saying no, or maybe boundaries are only one of several places in life where you've started to realize, “I don't want to keep doing this the same way anymore.” Calling the Circle is a place to begin exploring what comes next.
If joining a group isn't what you're looking for right now, you can continue these conversations with me through Embrace Head & Heart Inc. on Facebook and Instagram, where I share practical tools and insights to help make the science behind resilience, stress, behaviour, and our everyday patterns a little easier to understand, and a lot easier to use.
Read more from Kirstey KAE
Kirstey KAE, Founder and Resilience Educator
Kirstey KAE is the founder of Embrace Head & Heart Inc. and a resilience educator, speaker, and coach passionate about making the science of resilience understandable and practical. With more than 14 years of experience, she draws on neuroscience, behavioural science, and trauma-informed practice to help people understand why they think, feel, and respond the way they do. She believes resilience isn't about pushing harder, it's about understanding ourselves more deeply so we can respond to life's challenges with greater awareness, confidence, and choice
