Disappointing Others vs. Disappointing Yourself

The Permission Slip Every Female Entrepreneur Needs to Read

There is a version of you that has been saying yes for a very long time.

Yes to the project that wasn’t right for you. Yes to the coach’s advice you knew in your gut was off. Yes to the volunteer commitment, the favor, the last-minute ask, and no to yourself. To your time. To your priorities. To the business you were actually trying to build.

This episode of the Serendipitous Rebel Podcast is the one where Wendy and Krystal name it directly: you are allowed to disappoint other people. And more than that. Sometimes, disappointing them is the only way to stop disappointing yourself.

People Pleasing Is Not a Virtue. It’s a Survival Strategy.

For a lot of women — especially those of us who grew up as the responsible one, the oldest daughter, the default fixer in the family — saying yes became a way to feel safe and valued. Being needed felt like being worthy. And that strategy worked, for a while. It got us through early careers, through difficult family dynamics, through situations where our value really did depend on our output.

But we carried it past its expiration date.

And now, as female entrepreneurs trying to build businesses that actually reflect our values and our lives, we’re still running the old code. Still saying yes to coaches who tell us to pivot the thing that was working. Still overcommitting to communities we want to be liked by. Still shrinking our own priorities to avoid the discomfort of someone else’s disappointment.

As Krystal put it on the retreat that sparked this conversation: you have to be willing to disappoint others if it means you don’t have to disappoint yourself.

The Real Reason It’s Hard to Say No

Here’s what the research actually says, and what Adam Grant and Kristen Bell’s viral conversation surfaced so clearly: people pleasing isn’t really about your need to please others. It’s about your inability to tolerate the negative emotions that might come up when you don’t.

Kristen Bell tells a story about ordering coffee on a plane with too much cream, deciding she’d ask for less next time. Then, when the flight attendant came back around, saying “That’s fine” anyway and drinking the coffee she didn’t want. Not because she wanted to please the flight attendant. Because she couldn’t tolerate the micro-discomfort of the exchange.

Sound familiar? That’s not a character flaw. It’s a muscle that hasn’t been trained yet.

The Vicious Cycle No One Talks About

Here’s the pattern that plays out when we default to yes:

• Overcommit — you say yes to protect someone else from disappointment

  Overload — you take on more than you have bandwidth for

• •Under-prepare — there’s simply not enough of you to go around

• Hide — you pull back, go quiet, stop showing up

• Shame — you feel disappointed in yourself for not following through

• Resentment — you start feeling angry at the person you said yes to in the first place

That last one is the tell. When you feel resentment watching someone else set a boundary, prioritize themselves, or simply do something you wish you were doing — that’s not judgment. That’s information. It’s your internal compass pointing at something you need.

Krystal tells the story of watching Wendy show up consistently for rowing, and her first reaction being “Well, that must be nice.” That flash of resentment wasn’t about Wendy. It was about Krystal and what she actually wanted for herself. Once she saw it for what it was, she stopped watching and started doing. Now she’s in the Pilates social club and hasn’t looked back.

Every Yes to Someone Else Is a No to Something in You

Your time is not infinite. Your energy is not infinite. Your bandwidth is not infinite. Every yes you give away has a cost on the other side — and that cost is almost always paid by you.

Wendy shares one of her deepest regrets: missing her childhood best friend’s wedding — a wedding she was in the wedding party for — because she didn’t set a boundary with her employer about not working a dinner. She didn’t just disappoint herself that night. She disappointed her friend. The very person she was trying to protect by saying yes in the first place.

This is what chronic people pleasing actually produces: not protection, but damage. And not just to you.

Building the Disappointment Muscle

You don’t start with the hard ones. You start small. This week, find one low-stakes, low-consequence opportunity to disappoint someone on purpose. Order the pizza from the place you want. Say no to the second-grade stage decoration committee. Skip the thing you said you’d attend but don’t actually want to.

And then notice: what happened? Did the relationship survive? Did the world end? Wendy calls this checking the survival rate. Most of the time, the answer is that everyone is fine. Because, as her son says: it’s not that deep.

The people who genuinely love you for you (and not just for what you do for them) are the ones who will stick around when you start saying no. And how someone responds when you set a boundary? That tells you everything about whether they belong on your square squad.

What the SAVOUR Method™️ Has to Do With It

This isn’t just a mindset conversation. It maps directly onto how you build a business — and a life — that actually fits you.

S — Step Out of Your Comfort Zone: Saying no when yes is your default is one of the hardest things you’ll do. It is also, without question, stepping out of your comfort zone.

A — Align with Purpose: Every time you say yes to something misaligned, you drift further from the life and business you’re building. Choosing yourself is an act of alignment.

V — Venture Under Your Own Power: Prioritizing yourself — your time, your health, your goals — is venturing under your own power. Literally and metaphorically.

O — Open to Community: The right community supports you in this. They don’t drain you. They don’t guilt you. They cheer when you protect your priorities.

U — Unwind with Self-Care: Choosing yourself is the ultimate form of self-care. Not the spa version — the structural, ongoing, daily version.

R — Ritualize and Celebrate: When you successfully disappoint someone and live to tell the tale? Celebrate it. You just built the muscle.

You Don’t Need Permission. But Here It Is Anyway.

No one is coming to hand you a permission slip. No one is going to tell you it’s okay to put yourself first, to say no, to disappoint someone in service of your own life.

So Wendy and Krystal are saying it: it’s okay. In fact, it’s necessary. Not just for you — but for the people watching you. Your children. Your clients. The women in your community who are waiting for someone to model what it looks like to choose yourself without apology.

You only get one life. Disappointing yourself for the entirety of it is not the way.

Continue this conversation in the free SAVOUR™️ Community at serendipitousrebel.com/community — a space where female entrepreneurs come to do business and life on their own terms.