Most people know me as a CMO in Web3, but here’s something you might not know: I also run a coaching practice.
And this morning, I spent three hours coaching a communications executive who was completely stuck—not because she lacked skills, drive, or opportunities, but because she was terrified of disappointing people.
She’s in a job she wants to leave, but she keeps turning down better offers because she feels ashamed to quit on her team. She’s caught in a loop of guilt, obligation, and regret, making decisions that work for everyone… except herself.
And honestly? I get it.
Let’s Be Real—We’ve All Done This
- ✅ Gone out when we really wanted to stay home
- ✅ Said yes to another meeting in an already-overbooked day
- ✅ Taken on an extra project even though our calendar was already screaming for mercy
- ✅ Agreed to something we absolutely didn’t want to do because saying no felt worse
We’ve been conditioned to believe that disappointing others is a terrible thing. We avoid it like the plague—tiptoeing around difficult conversations, stretching ourselves thin, and prioritizing everyone else’s comfort over our own.
But here’s what I’ve learned:
Disappointing people is sometimes necessary for your sanity.
No, seriously. Someone else’s disappointment doesn’t mean you’ve failed them. It doesn’t mean you’re a bad person. It just means you’re no longer making choices based on keeping everyone else happy at your own expense.
Sounds radical? Stay with me.
4 Myths About Disappointing People (And the Truth That Will Set You Free)
Myth #1: If You Disappoint Someone, It Means You’re Letting Them Down
We equate disappointment with failure, as if someone else’s unhappiness is proof we did something wrong.
Truth: Disappointment is about unmet expectations—not actual harm.
People expect us to always be available, to never change, to do what’s convenient for them. When we don’t meet those expectations, they feel disappointed. That’s their reaction—it doesn’t mean we owe them anything.
Myth #2: You Should Avoid Disappointing People at All Costs
Somewhere along the way, we got the message that “nice” people don’t rock the boat. That self-sacrifice = love.
Truth: If you never disappoint anyone, you’re probably doing something wrong.
If every decision you make is based on keeping others comfortable, you’re not living your life—you’re living theirs. And let’s be honest: no one hands out awards for being the most agreeable person in the room.
Myth #3: People Will Be Mad at You Forever if You Let Them Down
This is the fear that keeps so many of us stuck. What if they resent me? What if they cut me off?
Truth: Most people get over it. And if they don’t? That’s their problem, not yours.
Sure, some people might sulk. Some might guilt-trip you. Some might send a passive-aggressive “no worries” text. But most people—if they actually care about you—will adjust. And if they don’t? That’s valuable information.
Myth #4: Never Disappointing Anyone Means You’re a Good Person
Ah, the classic. If I keep everyone happy, it means I’m kind, generous, selfless… right?
Truth: You can be a great person and still say no.
Kindness doesn’t mean being a doormat. It doesn’t mean abandoning your own needs so others don’t feel inconvenienced. True kindness includes honesty—even when it’s uncomfortable.
The Reality? Disappointment Is Inevitable.
If you’re evolving, growing, and making choices that align with your future, you will disappoint some people along the way. And that’s okay.
In Kabbalah, there’s a concept that anything we receive without true effort feels like “the bread of shame”—something unearned, something that doesn’t sit right. When we give or say yes out of fear rather than genuine generosity, it drains us.
So the next time you feel guilty for setting a boundary, saying no, or prioritizing your needs, remind yourself of this:
- 💡 The people who truly love and respect you will survive their disappointment.
- 💡 And so will you.
Ever struggled with the fear of disappointing others? What’s the hardest “no” you’ve ever had to say? Drop your thoughts in the comments—or DM me if this hit home.
If you want to go deeper, check out my website esther-katz.com. Drop me a note: estermlacha@gmail.com And if you’re still running in circles trying to make everyone happy, maybe it’s time we had a chat.
