The Hard But Necessary Work of Disappointing Others

Most of us go through life trying to avoid one thing: disappointing the people we care about. We soften our "no," overextend ourselves, and push down our own needs, all in the hope that if we give enough, we’ll be loved enough. 

But here’s the hard truth: You cannot have healthy, whole relationships if you aren’t willing to be a disappointment sometimes.

I recently worked with a client who spent her life walking on eggshells, doing everything she could to avoid upsetting others. She picked up after everyone in the house, said yes to every additional work request, and rearranged her schedule to accommodate other people’s needs. She thought this was what it meant to be a good friend, a good daughter, a good partner. But underneath, she felt exhausted, unseen, and quietly resentful.

The more we talked about it, she realized that her exhaustion wasn’t just from doing too much—it was from abandoning herself over and over again. She had never let herself be a whole person in her relationships because she had been so afraid of what might happen if she disappointed someone. Would they be angry? Would they leave? Would they stop loving her? 

One of the first times she set a real boundary—telling her parent she couldn’t drop everything to help—it felt unbearable. The guilt. The anxiety. The nagging voice inside saying, You’re being selfish. And yes, her parent was frustrated. But something else happened: she didn’t disappear. The relationship didn’t end. It led to a further conversation that resulted in more respect and her feeling more like an adult. For the first time in a long time, she felt solid and centered, like she was standing on her own two feet instead of contorting herself to keep everyone else happy. 

Because here’s the thing: Being willing to disappoint others doesn’t make you unkind. It makes you real. It makes you someone who can be known, not just for what you do for others, but for who you actually are.

Yes, sometimes boundaries create tension. Sometimes people will feel hurt, surprised, or unhappy. But that moment of discomfort is also a moment of truth. A moment when a relationship can shift into something more honest, more reciprocal, more whole.

The relationships that can withstand your no—those are the ones worth holding onto.

So if you’ve been avoiding setting a boundary because you’re afraid of disappointing someone, or if you aren’t even aware that you might need some boundaries, I invite you to ask yourself: What if my job isn’t to be endlessly available and acceptable for others? What if my job is to be whole?

If this work feels difficult, you don’t have to do it alone. I’d love to walk with you as you learn to build relationships that make room for all of you—not just the parts that say “yes.”