I invite you to disappoint someone

When your daughter inherits your people-pleasing

Nov 20, 2025

My cousin, an executive coach, closed our phone call with a line I’ll never forget.

“Today, I invite you to disappoint someone.”

I laughed. To buy myself time so my brain could catch up.

My stomach tightened. My heart started pounding. My body understood what it meant before my mind did.

My whole life, I’d been taught that disappointing people was the worst thing you could do. The mom guilt. The people pleasing. The inability to say no. It had all been baked in since childhood.

“I’m disappointed in you” — aren’t those the words you never want to hear from a parent?

My cousin didn’t elaborate on her invitation. She just left it hanging there.

Within days, I started hearing the word everywhere.

A mother in leadership, sobbing on a coaching call: “I feel like I’m disappointing everyone. My boss. My team. My kids. I’m trying so hard! But I feel like I’m failing everywhere.”

Then my own daughter, calling from boarding school, heaving with sobs: “I feel like I’m disappointing everyone! You. Dad. My teachers. My friends. I’m trying so hard. And I just feel like I’m failing.”

That one hit me in the gut.

Here was my child, carrying the same weight that my adult clients were carrying. The same weight I’d carried my whole life.

I wanted to tell her it was okay. That she didn’t have to please everyone. That disappointing people doesn’t mean you’re failing.

But she’s a smart kid. She wasn’t learning from what I said. She was learning from what I did.

I was passing down my people pleasing like an heirloom.

Someone in one of my coaching groups shared a quote from Glennon Doyle’s book Untamed:

“Every time you’re given a choice between disappointing someone else and disappointing yourself, your duty is to disappoint that someone else.”

Your duty. Not a character flaw. Not a failure. A duty.

The older I get, the clearer it becomes: it’s impossible to move through life as a mother and a leader without disappointing people. The real question is who we’re willing to disappoint. And in service of what?

When I worked as a lower school head, I knew what my colleagues wanted: an always-available listener. Someone who would drop everything to help.

And I wanted to be that person. But I also needed time to think. To do the strategic work that only I could do.

So I started closing my door.

I knew it would disappoint people. I held a faculty meeting and explained why. I hung a wreath on my door as a signal: I’m here. I’m working. But I’m not available right now.

Some were no doubt disappointed. Some probably thought I was being “distant” or “removed.”

But the school ran better. My decisions improved. And I had energy left for my own children at the end of the day.

That same wreath now hangs on my home office door. It sends the same message to my husband and kids when I’m working: I’m here. But I’m not available.

They’ve learned to respect it. And I’ve learned that disappointing people in small moments prevents disappointing them, and myself, in bigger ones.

This remains a practice for me. I can disappoint my children when I need to, and even my colleagues, but disappointing my parents? My siblings? I feel that old clench in my gut.

A few weeks ago, Thanksgiving plans were coming together. My older kids would be home from boarding school. One was finishing college applications. I realized I wasn’t going to be able to host my whole family like last year.

I had to tell them I couldn’t host.

I felt the gut clench. I’m the oldest child. Isn’t that my job?

And yet, my own kids needed me. And my energy was finite.

So I took a breath.

I called my mom.

I called my sister.

The world didn’t end.

I’m learning.