Learning to Say No: Why People Pleasing Doesn’t Pay (And What The Giving Tree Got Wrong)

Let me just put this out there: I used to think saying yes was the hallmark of a good human being. Turns out, it’s not. One time, I found myself agreeing to cat-sit for my neighbor—who honestly, I didn’t even like—just because I was afraid she’d think I was rude. And that’s just the tip of my overly-accommodating iceberg. After listening to an episode about The Giving Tree, boundaries, and why saying no isn’t selfish, I realized I was living the tree’s story (minus the branches). If you’ve ever felt like a stump trying to make everyone else comfortable, you might want to read on.

From Generosity to Self-Erasure: The Giving Tree as a (Terrible) Role Model

When Giving Goes Too Far

I remember the first time I read The Giving Tree. On the surface, it feels sweet—this tree loves the boy, gives him apples, shade, even her branches. But as I got older, I started to wonder: Is this really a story about love, or something else entirely?

The ending is what sticks with me. The tree, once full of life, is reduced to a stump. The boy, now an old man, sits on her. Supposedly, the tree is “happy.” But, honestly, is she? Or is that just what we’re supposed to believe?

The Cost of Endless Self-Sacrifice

• The Giving Tree’s ending makes self-sacrifice seem noble—but at what cost?
• Mothers and women are often cast into roles where endless giving is expected.
• Real fulfillment doesn’t come from being reduced to a stump for others.
• Is this nurturing or just plain unhealthy? Let’s be honest about the message.

I can’t help but see the tree as a warning, not a role model. The story has been called an allegory for maternal love. But, as discussed in the podcast, that idea is up for debate. Is it really love if it means giving until there’s nothing left of you?

‘The tree has confused giving with self-sacrifice. It almost seems like the tree is the most extreme people pleaser you could possibly imagine.’

People Pleasing: Where Do We Draw the Line?

We all want to help the people we care about. But there’s a difference between generosity and self-erasure. Sometimes, pain is a signal—telling us we’ve gone too far. Yet, the tree just keeps giving. No boundaries. No pause to ask, “What do I need?”

It’s hard not to notice how this narrative especially targets mothers and women. The expectation: give, give, and then give some more. But what happens when there’s nothing left? The tree is a stump. The boy isn’t even happy. Nobody wins.

Is This Really Nurturing?

I wonder, is this the kind of nurturing we want to model? Or is it just plain unhealthy? The story doesn’t show fulfillment—it shows depletion. Maybe it’s time we question the idea that endless giving is admirable. Maybe, sometimes, saying no is the real act of love.

Why We Can’t Stop Saying Yes (Even When It Hurts Us)

Are We Wired to Please?

Ever notice how hard it is to say no, even when every part of you is screaming not to say yes? I used to think I was just being nice. Turns out, it’s not that simple. Some of us are hardwired—or maybe just socialized—to cooperate, even if it means putting ourselves last.

It’s like there’s this invisible script running in the background: Don’t rock the boat. Don’t disappoint. Just say yes. Sometimes, I wonder if it’s biology, or if it’s just years of being told to be agreeable. Maybe both.

It’s Not About Kindness

Here’s the kicker: people-pleasing isn’t really about kindness. It’s about craving approval. I read a line once that stuck with me:

‘The root of chronic people pleasing is not concern for others. It’s concern for their approval.’

That hit hard. When I looked at my own life, I realized I wasn’t bending over backward for others because I cared so much about them. I was doing it because I wanted them to like me. To accept me. It’s a little embarrassing to admit, but it’s true.

Pressure Points: Why Women Feel It More

Let’s be real: women, especially at work, get hit with this even harder. There’s this unspoken rule that we should be helpful, agreeable, and always available. If we say no, we risk being labeled “difficult” or “uncooperative.” I’ve seen it. I’ve felt it.

When People-Pleasing Takes Over

I knew I had a problem when I started wondering if I needed to schedule calls with my friends because I was too busy helping random people. My calendar was a mess of favors, meetings, and “quick” requests. I nearly lost my mind. It wasn’t about being generous. It was about being afraid to disappoint anyone.

The Science of Saying Yes

• People say yes to strangers’ requests almost twice as often as they think they will.
• In a New York City study, nearly half of participants agreed to hand over their phones or walk someone to a destination—way more than anyone predicted.
• Across all requests, compliance was about 2x what was expected.

Why do we do this? Maybe it’s a “cooperation bias”—a fancy way of saying we’re wired to go along, even when it’s not in our best interest. Or maybe it’s just that awkward feeling of saying no and risking someone’s disapproval.

It’s Not Just You

If you find yourself saying yes when you want to say no, you’re not alone. Most of us are just trying to avoid that sinking feeling of letting someone down. But in the end, it’s our own needs that get lost in the shuffle.

The Acquaintance Trap, Gender Bias, and How Culture Loads the Deck

Why Saying No Feels Harder with Acquaintances

Ever notice how it’s weirdly easier to say no to a stranger or a close friend, but when it’s an acquaintance, you freeze? I’ve been there. The relationship is just uncertain enough that I don’t want to risk being disliked. It’s like walking a tightrope—one wrong move and, poof, there goes the connection.

This is what I call the acquaintance trap. We avoid saying no because we’re scared of rocking the boat with people we kind of know, but not well enough to trust the relationship will survive a “no.”

The Extra Weight Women Carry

Now, let’s be real. For women, especially women of color and eldest daughters, the pressure isn’t just social—it’s cultural and deeply personal. I’ve seen it, and research backs it up. We’re raised to be communal, cooperative, the “nice girl.” If we say no, we’re not just declining a request. We’re breaking a rule we’ve been taught since childhood.

• Women are asked to do more “office housework”—taking notes, planning, helping out. But we get less credit for it.
• Eldest daughters often carry extra responsibility, almost like a third parent. I’ve heard stories where eldest daughters feel their actions ripple out, affecting siblings and family reputation.

Sherry Lou, founder of the Eldest Daughter Club, put it perfectly. She grew up wanting to be liked, always saying yes. Not because she always wanted to help, but because she was scared of what would happen if she didn’t. That fear? It’s real.

Culture: The Hidden Hand Pushing Us to Say Yes

Different cultures, different rules. I grew up in a community where respecting authority and anticipating others’ needs was just what you did. In collectivist cultures, like many Asian families, the pressure to comply is even stronger. You’re not just saying yes for yourself—you’re representing your family, your community.

Sherry described it as always being aware of authority, always making sure everyone else is comfortable. It’s exhausting. And it doesn’t stop at home. In the workplace, these expectations follow us.

When Saying Yes Holds Us Back

Here’s the kicker: all this people-pleasing? It doesn’t actually help us get ahead. In fact, it often does the opposite. Sherry’s manager once told her:

For you to gain leverage in the workplace and to, like, eventually be a senior leader, you need to really carve out things of impact that you yourself lead, and that means saying no to other extraneous requests.

That hit me. Saying yes to everything means we’re always helping, but never leading. The work that gets noticed is the work you own—not the favors you do for everyone else.

Wild Card: What Would Happen If The Giving Tree Said ‘No’?

Let’s flip the script for a second. What if The Giving Tree—yes, that famous, selfless tree—had just said no? Would the boy have learned to find happiness on his own, or maybe even discovered a new way to connect with the tree? I’ve wondered about this a lot. We’re so used to fairy tales with endless giving, but what if boundaries were part of the story? It’s almost unheard of, but maybe it’s exactly what we need.

I picture the boy, a little stunned at first. No apples? No branches? No trunk to sit on? Maybe he’d stomp away, but then what? Would he realize he could plant his own seeds, or find other ways to be content? It’s a question that lingers, and honestly, it feels more real than the original ending.

Now, let’s bring this into our world. Imagine if you said no to every third request this week. Not every single one—just one out of three. Would your life fall apart? Or would you finally have time to breathe, to focus, to rest? I tried this once. It felt awkward at first, but then I noticed something: people respected my time more, and I respected myself more, too.

Of course, it’s not always easy. We’re wired to help, to please, to keep the peace. But as I learned, setting boundaries isn’t just about protecting ourselves—it’s about learning, growing, and teaching others how to treat us. Sometimes, it’s about pain, too. As one expert put it,

‘Sometimes pain is a sensor telling you to stop something. And so don’t give till it hurts, and certainly don’t give past hurting.’

That line sticks with me. It’s a reminder that giving should be sustainable, not self-destructive.

If you’re thinking about trying this—about saying no a little more—don’t go it alone. I found it helps to enlist allies. Tell your manager, your partner, your parent: “Hey, I’m working on setting boundaries. I might need your support.” Change is easier when the people around you know what you’re aiming for. Sometimes they’ll even cheer you on, or step in when you’re tempted to cave.

So, what if The Giving Tree had said no? Maybe the story would have ended with both the tree and the boy a little happier, a little wiser. Maybe our own stories can, too. Boundaries aren’t the end of kindness—they’re the beginning of real, lasting connection.

TL;DR: Saying no isn’t selfish—set boundaries, save your sanity, and don’t live your life as someone else’s stump.