The person setting boundaries can be heartbroken, too.
I’m Hailey, and I help people outgrowing identities built on approval, achievement, and others’ expectations step into a more vital and self-trusting life. You can subscribe to my newsletter and get my articles delivered directly to your inbox here.
People outgrowing a chapter of life—whether it’s a relationship, a career, a community, or a or a belief system—tend to share a common thread:
painstakingly, they’re learning to listen for their own needs and boundaries after years of prioritizing approval and others' expectations.
Resentment. Burnout. Hollowness. Invisibility. The costs of self-suppression have grown too loud to ignore, so slowly, they begin saying no to honor their limits; taking space from people and environments that drain them; and leaving unhealthy relationships.
Over the years, I’ve had hundreds of conversations with my clients in this position about how to cope with boundary-setting guilt: how to cope with the fact that, sometimes, setting boundaries hurts the people that we love.
But often, they’re struggle with an even more painful experience: the fact that they—the person setting the boundary—are heartbroken, too.
By heartbroken, I don’t mean “feeling guilty” or “feeling sympathy for others’ pain.” I mean personally heartbroken: mourning the familiarity, wishful hope for change, or idealized future the relationship offered before we surrendered to our need for self-protection.
Self-help culture depicts boundary-setting as a cathartic victory: an empowering rush that comes from refusing to put up with an unlikeable person’s behavior any longer. But truthfully, the majority of boundaries are subtler, far more nuanced, and occur in our relationships with beloved partners, family members, and friends: people from whom the thought of disconnection (no matter how necessary) sparks everything from mild unease to full-blown grief.
We tend to arrive at these boundaries after years of unsuccessfully trying to make the relationship work: overlooking mismatches in needs, downplaying hurtful behaviors, and ignoring signs that this connection, in its current form, negatively impacts our mental health.
Eventually, we’re forced to accept the fact that sometimes, boundaries are necessary to protect our well-being, even when it really hurts.
In this article, we’ll discuss how to cope with this boundary-setting heartbreak as you outgrow chapters built on approval and others’ expectations. We’ll unpack how we can simultaneously need a boundary without wanting it; explore how one part of us can want self-protection, while another part wants to maintain connection at any cost; and demystify how to find peace of mind when coping with the grief of severed connection.
I Want to Be Close, But Not Like This
Maybe you recognize that your family member’s hurtful behavior stems from childhood trauma. You know that they’re trying their best; you know they don’t mean to hurt you.
But when you’re with them, you’re hyper-vigilant, on high alert, walking on eggshells. The relationship, in its current form, doesn’t feel safe enough—so you visit them a bit less. Speak to them a bit less. Create enough distance so that you’re not constantly in fight-or-flight as the result of difficult interactions. (I teach you how to set boundaries like this with difficult family members in my on-demand workshop, Using Boundaries to Sustain Complicated Relationships).
What do you want? You want them to treat you calmly and respectfully. You want free-flowing safety, love, and trust. You want to connect with your family member; you want to spend time together doing things you both love.
But you know, from experience, that what you want isn’t possible—nor is it within your control. What you need is a boundary to be okay. This boundary might feel heartbreaking for them, but it’s heartbreaking for you, too.
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Perhaps you love your romantic partner more than you’ve ever loved anyone—but your needs, capacities, or long-term goals simply aren’t aligned. You know these misalignments would eventually sew seeds of resentment between you, so you decide to call it off now.
What do you want? You want a deep, rich connection with the person you love. You want to willpower away your incompatibilities and let your heart rest in the beautiful moments you’ve been creating.
But what you want is only possible if you both change your essential selves for the other—and that’s not happening, nor should it. What you need is a boundary, to give you both a chance to find more compatible love.
No doubt, this boundary will be heartbreaking for them. But it’s heartbreaking for you, too.
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Perhaps you struggle with chronic illness, family obligations, or financial commitments that force you to set boundaries around your time and energy—even though you really want to connect more with your loved ones. But you don’t have the bandwidth, and if you push yourself past your limits, you won’t be physically or emotionally okay.
What do you want? You want to drive in your sister’s car with the windows down and gossip about your family. You want to help your neighbor with her yard sale, be a regular at your friend’s book club, and attend the weddings of your childhood best friends. But if you pursue your wants, you’ll neglect your need to rest and recoup.
This boundary might feel heartbreaking or frustrating for them, but it’s heartbreaking for you, too.
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When we set these boundaries, we’re make the radical choice to accept reality as it is instead of staying suspended in wishful thinking that others—or our own capacity—will suddenly change.
Before, perhaps we spent years wishing, hoping, or begging that others would take our needs seriously and meet us in the middle.
Or perhaps we tried to maintain the relationship by willpower-ing away the incompatibilities; by trying to change aspects of ourselves that, in truth, were immutable: our core needs, limits, or capacity.
Only when it became clear that self-abandonment wasn’t a sustainable solution did we surrender—and our boundaries are that surrender manifest.
When Part of Us Wants Protection, but Another Part Wants Connection
Boundary-setting heartbreak arises from the painful experience of being internally divided: yearning for connection, and yearning for protection from that connection, at the same time.
One part of us truly wants to set boundaries in order to be well. This part understands how mismatches in needs, unhealthy patterns, and chronic misattunements in the relationship have eroded our well-being. More than anything else, this part wants us to be safe and at peace.
But another part of us doesn’t want to set boundaries because the loss of connection feels excruciating, even if the relationship isn’t perfect or healthy. This part is willing to pay for connection at any cost—even if the cost is loss of self.
Whether we’re setting limits around time, space, or privacy; taking distance and reducing the intimacy of a connection; or breaking up, divorcing, or becoming estranged from a loved one; this part of us feels crushing heartbreak at the severance of connection. It grieves the future it had hoped for: the future where connection can go on, and everything magically works out.
In my work with clients, it’s not unusual to spend multiple sessions negotiating the conflicting emotions of these parts.
Our healing lies in making room for all of it: the wistful desire for a healthy closeness—the urgent need for space or distance—the grief of setting a boundary—the relief of setting a boundary—the pride that self-abandonment is no longer a solution we’re willing to entertain—and the heartbreak of loss.
The Boundary-Setter’s Heartbreak is Invisible
Part of what makes the boundary-setter’s heartbreak so devastating is its invisibility. Because we’re the ones inserting space or distance into the connection, our grief goes unacknowledged.
The assumption, by the boundary recipient, is: “You set this boundary, so you must want this. You don’t want to be close to me. You don’t care about my feelings. You’re not hurting at all.”
But I can assure you, after thousands of coaching sessions with aspiring boundary-setters, that the truth usually sounds more like this:
I care for you deeply, and I wish we could stay closely connected, but I don’t feel safe, seen, or respected enough to do so.
If there was a way to be close to you without sacrificing my mental and emotional health, I’d choose it in a heartbeat.
I’m grieving the relationship I wish we could have had, and I’m devastated.
I’m mourning the loss of the future I’d imagined with you. It’s more painful than you could imagine.
I don’t want this space, but I need space this to be okay. I wish it didn’t have to be this way.
Your Heartbreak Needs Attention, Too
A chosen loss of connection is still a loss of connection. When we set boundaries with those we love, the part of us that craves closeness may suffer immensely—and it’s important that we show that part understanding, gentleness, and compassion.
We might assume that the “solution” is to focus on the positive by reminding ourselves of all the reasons for our boundary, celebrating ourselves for our courage, and imagining a happier future ahead.
But in the same way we’d never tell a grieving loved one to “look on the bright side” after the death of a cherished connection, we shouldn’t gloss over our hurt. Rationally reminding ourselves that our boundary was necessary doesn’t override the emotional reality that part of us is grieving and suffering. Our healing lies in holding the complexity of our many emotions, grief and all.
Watch my on-demand workshop, Using Boundaries to Sustain Complicated Relationships, for step-by-step guidance identifying and setting the boundaries that will protect your needs in difficult interactions with friends, family, and colleagues.
Even the healthiest relationships include differences, disagreements, and mismatches in needs. Using Boundaries to Sustain Complicated Relationships will teach you how you can sustain difficult relationships by learning how to disengage from interactions that don’t feel good; how to stop over-giving and feigning comfort when something’s bothering you; how to differentiate and get clear on where you end and others begin; and how to be discerning when deciding when a connection needs to end for good.
This workshop includes:
💻 A Zoom recording and PDF slide deck.
Workshop purchases include a 90- to 120-minute, pre-recorded Zoom session and a downloadable PDF slide deck. You can watch the Zoom workshop any time, anywhere, as many times as you’d like.
🌱 Education, reflection, and community discussion.
Workshops combine step-by-step education with reflection questions and high-impact coaching exercises. The sessions have been pre-recorded with a live audience, so you get the benefit of past participants’ discussion and Q&A.
🧭 Action steps, not just education.
My workshops are designed not just to teach and inspire, but to leave you with a concrete, real-life plan that you can start putting into action as soon as the session ends.
✨ Non-stop access for 2 years.
The Zoom session will be available to you for 2 years after your purchase—and the PDF slide deck is yours to keep forever.