When Healing Hurts: Why Setting Boundaries Feels Like Betrayal


There’s this moment in your healing journey when you realize the people who claim to love you the most are the ones fighting hardest against your growth. It hits you like a slap — not the gentle awakening you expected, but a cold, brutal realization that saying “no” to others often means saying “yes” to being alone.

I remember when I first started working with my therapist in Milan. I thought healing would make me easier to love, not harder. Ma che ingenuità (what naivety). I thought people would celebrate the version of me that finally stopped apologizing for existing.

Instead, I became the problem.

Why Everyone Gets Mad When You Start Emotional Healing

Here’s what nobody tells you about healing: it’s not just about you getting better. It’s about disrupting an entire ecosystem of relationships that were built on your willingness to disappear.

For years, I was the one who absorbed everyone else’s emotions. The one who said “yes” when I meant “no.” The one who made myself smaller so others could feel bigger. And honestly? People got comfortable with that version of me.

When I started my restaurant business, I was still that people-pleaser. I’d say yes to every supplier meeting, every last-minute change, every “small favor” from partners. I was drowning in other people’s expectations, but at least nobody was calling me selfish.

Then therapy happened. And suddenly I was saying things like, “That timeline doesn’t work for me” or “I need to think about this before I commit.” Simple stuff. Reasonable stuff.

The reaction was swift and brutal.

“You’ve changed.” “You’re not the same person.” “That therapist is brainwashing you.”

It felt like being punished for finally learning to breathe.

The Loneliness of Growing Up

There’s a specific kind of loneliness that comes with healing. It’s not the loneliness of being abandoned — it’s the loneliness of outgrowing the roles people need you to play.

I started noticing how many of my relationships were built on my dysfunction. Friends who only called when they needed someone to vent to. Family members who expected me to absorb their chaos without complaint. Colleagues who relied on my inability to say no.

When I began setting boundaries, these relationships didn’t adjust — they broke.

And the guilt? Madonna mia (holy hell). The guilt was crushing. There were nights I’d lie awake thinking, “Maybe they’re right. Maybe I am being selfish. Maybe I was better before.”

But here’s the thing about healing — once you taste what it feels like to respect yourself, it’s impossible to go back to betraying yourself for the comfort of others.

What Emotional Healing Actually Costs

Nobody talks about the price of getting better. We think healing is all meditation and self-care smoothies. But real emotional healing means grieving the person you used to be and the relationships that only worked because you were broken.

I remember a conversation with Luciana during this period. I was crying because I felt like I was losing everyone.

Forse le persone che se ne vanno quando cresci non erano mai davvero tue,” she said softly. (Maybe the people who leave when you grow were never really yours to begin with.)

Ma fa male lo stesso,” I replied. (But it still hurts.)

Certo che fa male. Ma il dolore di crescere è diverso dal dolore di restare piccoli.” (Of course it hurts. But the pain of growing is different from the pain of staying small.)

She was right, but knowing something intellectually and feeling it in your bones are two different things.

The People Who Stay (And the Ones Who Don’t)

Here’s what I learned about relationships during my healing journey: the people who get angry when you set boundaries are the same people who were benefiting from your lack of them.

The friends who called me “dramatic” for asking to be treated with respect? They disappeared when I stopped being their emotional dumping ground.

The family members who said I was “brainwashed” for not accepting their criticism? They went quiet when I stopped seeking their approval.

But some people stayed. And those relationships? They got deeper, more real, more honest. They had to be rebuilt on a foundation of mutual respect instead of my compulsive need to please.

It’s like renovating a house — you have to tear down the old structure before you can build something solid. The dust and debris are part of the process, not evidence that you’re doing it wrong.

The Truth About Boundaries and Love

I used to think boundaries would make me unlovable. What I discovered is that boundaries make you lovable to the right people — and unlovable to the wrong ones.

And honestly? That’s exactly how it should be.

The people who love the boundaried version of you are the ones who were waiting for you to show up as yourself all along. They’re not threatened by your growth because they’re secure enough in themselves to want you to be secure too.

The people who loved the boundaryless version of you? They loved what you could do for them, not who you actually were.

Che differenza (what a difference).

What Nobody Tells You About Getting Better

Healing isn’t a straight line from broken to whole. It’s a messy, non-linear process of discovering who you are when you’re not busy being who everyone else needs you to be.

Some days you’ll feel strong and centered. Other days you’ll question everything and wonder if it was easier when you just said yes to everything.

Both feelings are valid. Both are part of the process.

The goal isn’t to become someone who never feels guilty about boundaries or never misses the simplicity of people-pleasing. The goal is to become someone who chooses their own well-being even when it’s uncomfortable for others.

Even when it costs you relationships you thought were permanent.

Even when people call you selfish for finally learning to love yourself.

Anche quando fa paura (even when it’s scary).

Because here’s what I know now that I didn’t know then: the right people will love you more for having boundaries, not less. They’ll respect your “no” because they understand it makes your “yes” meaningful.

And the people who don’t? They were never really yours to lose.

🌿 If this reflection found you in the middle of your own growing pains, know that you’re not alone in this. The newsletter’s here when you need a reminder that healing is worth it, even when it hurts — quiet wisdom for the messy middle of becoming yourself.


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