Deb Blum thought she was being a good friend.
For two years, she’d shown up for this friendship in every way she knew how. She said yes to the bike rides even though she couldn’t keep up on the hills. She went to her friend’s house every time instead of alternating. She chose the hiking trails her friend preferred. She carefully monitored what she said, making sure she was always accepting, always supportive, always there.
She was being the friend she thought this person needed.
And then one day, she sat down and wrote an email. An email where she took full responsibility. An email in which she tried to repair the damage she felt building. An email where she listed out ten things (TEN THINGS) she’d been dishonest about over the course of their friendship.
“I basically told her I’d been lying to her for two years,” Deb told me. “I mean, I didn’t quite say it that way, but I kind of said that.”
Her friend’s response? “Who are you? How can I ever trust you again?”
And just like that, a two-year friendship exploded.
Here’s what Deb realized too late: People-pleasing isn’t kindness. It’s not selflessness. It’s not being a good friend.
It’s betrayal. First of yourself, and eventually, of the friendship itself.
Where It All Started: The 10th Grade Story That Changed Everything
To understand how Deb ended up in that painful place (writing that devastating email) we need to rewind about 30 years.
Deb was in 10th grade. She stood up for herself in a situation with a friend. That friend didn’t like it. And that friend got a group of other girls to gang up on Deb.
“I spent an entire year being physically bullied in every way you can imagine,” Deb shared. “And the story I told myself was that I cannot be me. That woman couldn’t handle me being my true self.”
Think about that for a second. One year. One experience. One message that got seared into her brain:
Being yourself is dangerous.
Other women can’t handle the real you.
You need to be who they need you to be.
And from that moment forward, Deb became hypervigilant. She watched for signals and cues. She checked in with herself constantly to make sure she wasn’t doing anything that might upset someone. She became a careful listener who rarely shared about herself.
She learned to people-please as a survival strategy.
And here’s the thing that absolutely breaks my heart about this: Deb isn’t alone.
So many women have a story like this. Maybe not bullying exactly, but some moment (or many moments) where being yourself resulted in rejection, disapproval, or conflict. And from that experience, we learn to dim ourselves. To be careful. To become who we think others need us to be.
We think we’re protecting ourselves. We think we’re protecting our friendships.
But we’re actually setting ourselves up for something much more painful down the line.
The Pattern That Follows You Into Adulthood
Here’s what’s wild about these early experiences: They don’t just affect us in the moment. They create patterns that follow us for decades.
For Deb, that 10th-grade experience created a pattern that looked like this:
- ▪️ Never fully revealing herself
- ▪️ Always being the listener, rarely the sharer
- ▪️ Saying yes to things she didn’t want to do
- ▪️ Monitoring everyone else’s reactions constantly
- ▪️ Trying to be who she imagined they needed her to be
And you know what? It kind of worked. She had lots of friends. She was well-liked. People enjoyed spending time with her.
But she was exhausted. And underneath it all, she felt disconnected. How can you feel truly known when you’re constantly performing a version of yourself?
“I used to brag about being the friend who could drop everything for anyone,” she told me. “When something went wrong in somebody’s life, I could just drop everything and do anything they needed. I said that with pride.”
(Sidebar: I used to say the EXACT same thing. I thought it made me a good friend. Turns out, it was actually creating a hole in my friendships where I was playing Superwoman and never letting anyone give back to me without betraying herself.)
But here’s where it gets really interesting, and really complicated.
Deb noticed something about her own mother. Her mom was beloved for being a great listener. She prided herself on the fact that nobody really knew her: they would just talk and talk, and she would listen and give advice, but she never shared anything about herself.
And Deb watched that. She absorbed that model of friendship.
Except in Deb’s own friendships, she became her mother. She was the listener. She was the advice-giver. She was the one who never shared.
It felt safer that way. If she didn’t reveal herself, she couldn’t be rejected for who she really was.
But it was also deeply unfulfilling.
In the full episode, Deb shares more about how that 10th grade experience shaped the way she showed up in friendships for the next 30 years. If you’ve ever traced a current pattern back to something that happened when you were young, her story will hit close to home.
The Moment Everything Came to a Head
Fast forward to that friendship that exploded. The one with the bike rides and the hiking trails and all those tiny moments of self-abandonment that seemed so small at the time.
Deb described a specific moment that perfectly captures what was happening:
“She was a really good bike rider and could ride up hills really well, and I couldn’t. So I would usually have excuses about it, or I would go, but then not really want to go, and then I would not tell her I didn’t really want to go.”
Can you feel the exhaustion in that? The constant internal negotiation?
And it wasn’t just the bike rides. It was:
- ▪️ Always going to her friend’s place instead of alternating
- ▪️ Choosing the hiking trails her friend preferred
- ▪️ Not speaking up about what she actually wanted
- ▪️ Dancing around topics instead of being direct
- ▪️ Performing acceptance instead of being honest
“I thought I was doing this kind service by not telling my whole truth,” Deb said. “But I could feel it in my body: how painful it was for me to abandon myself so deeply.”
And then came the moment that broke everything open.
They were on a bike ride. Deb spoke her truth about something. And her friend said exactly what Deb had been afraid she would say: “I don’t know if I can trust you if you don’t accept that in me.”
Deb realized she was in a no-win situation. If she stood up for herself, her friend couldn’t accept her. If she didn’t stand up for herself, she was betraying herself.
So she went home and wrote that email. Ten things she’d been dishonest about. Taking full responsibility. Trying to repair.
But here’s what she didn’t realize: You can’t repair a foundation that was never built on truth in the first place.
Why People-Pleasing Is Actually About Control
This is the part that’s going to sting a little, but stay with me.
Deb said something that completely shifted my perspective: “We believe we’re people-pleasing because we want to make other people happy. But deep down inside, what we don’t want is to feel their disappointment, their disapproval, or them being upset with us. We don’t want the conflict. We’re trying to control the outcome.”
Read that again.
People-pleasing isn’t actually about being nice or kind or selfless. It’s about trying to control how other people feel about us.
We’re so afraid of rejection, conflict, or disapproval that we’d rather perform a version of ourselves than risk showing up as who we really are.
And in doing so, we’re not actually building real friendships. We’re building relationships on a foundation of… what? Performance? Fear? Control?
Here’s how I think about it using my Roots framework (where friendships are like trees with roots made up of shared experiences, emotional intimacy, and stories):
When you’re people-pleasing, you’re planting fake roots. Your friend thinks you love biking together: that’s a root. Your friend thinks you prefer going to their house: that’s a root. Your friend thinks you share certain beliefs or preferences: more roots.
But then one day, you reveal that actually, none of those roots were real. You didn’t love biking. You didn’t prefer their house. You were just saying what you thought they wanted to hear.
It’s like you just dug up the soil and detonated a bomb under the entire tree.
Your friend is left thinking: What roots are real? Which parts of you were true? How can I trust anything about this friendship?
And honestly? That’s a fair question.
The Incremental Work of Unlearning These Patterns
So how do you change this? How do you stop people-pleasing after decades of it being your default setting?
Deb’s answer might surprise you: Very, very slowly.
“It took me about 10 years to shift this pattern,” she told me. “I shifted it in tiny, incremental steps with every interaction.”
Here’s what that actually looked like:
She started sharing small things about herself. In conversations where she would normally just listen and give advice, she’d share one tiny thing about her own life. Just one. And then maybe next time, two things.
She held her tongue on advice. This was huge. Instead of immediately jumping into fix-it mode, she practiced just… listening. Without the advice. Without trying to solve.
She started being honest about her capacity. Instead of always saying yes, she began admitting when she didn’t have the bandwidth for something.
She picked one small thing to be honest about. Maybe it was suggesting a restaurant instead of always deferring. Maybe it was saying “actually, I’m not really into that” instead of going along.
And here’s what’s important: In an hour-long conversation, she might only do these things once or twice. The other 95% of the time, she was still falling into her old patterns.
But over time (over YEARS) those tiny shifts added up.
“The same thing I did in my relationship with my mother,” Deb explained. “I stopped sharing so much and started asking her more questions. She would deflect, and I’d get sucked back in, and then I’d go back and ask her again.”
It’s not a straight line. It’s not even a gentle curve. It’s a messy, back-and-forth process of catching yourself, trying something different, falling back into old habits, and trying again.
But eventually? The new pattern becomes more natural than the old one.
In the full episode, Deb and I talk through the difference between fitting in and belonging in much more depth, and what it actually felt like for her to start choosing belonging over fitting in. If you’re someone who has spent years adjusting yourself to match the room, this conversation is for you.
Fitting In vs. Belonging: The Framework That Changes Everything
There’s a concept that Deb and I kept coming back to throughout our conversation: the difference between fitting in and belonging.
When you’re people-pleasing, you’re trying to fit in. You’re morphing yourself into whoever you think you need to be to be accepted by a particular group or person.
But belonging? Belonging is different.
“When you’re looking at belonging, you be you, and you be your true you, and then you see where you belong,” Deb explained. “If someone doesn’t really like you, you realize it’s not personal; not everybody is going to jive with everybody.”
Here’s what that means practically:
Fitting in: Walking into a room, assessing what people seem to value, and adjusting yourself to match that.
Belonging: Walking into a room knowing who you are, what you value, what you enjoy, and looking for people who share those things.
Fitting in: Meeting someone who loves biking and pretending you love it too, even though you really don’t.
Belonging: Meeting someone who loves biking, being honest that it’s not your thing, and seeing if there are other activities you’d both genuinely enjoy.
Fitting in: Saying yes to everything because you’re afraid saying no will make people not like you.
Belonging: Being honest about your capacity and trusting that the right people will respect your boundaries.
The scary part? Belonging requires you to be willing to let some friendships fall away.
Not everyone is going to be your person. Not everyone is going to like the real you. And that has to be okay.
What Deb Wishes She’d Known Earlier
When I asked Deb what she would tell her younger self (or anyone currently stuck in these patterns): here’s what she said:
“Be brave enough to be you, and risk early enough in the relationship to allow some relationships not to work.”
Let that sink in.
The way to avoid the “10 things I’ve been lying about” email isn’t to get better at people-pleasing. It’s to be more yourself from the beginning, even if it means some friendships don’t develop.
Because here’s the truth: Those friendships that would have ended anyway if you’d been yourself? They’re going to end eventually. Either they’ll fizzle out because you’re exhausted from performing, or they’ll explode when the truth finally comes out, or you’ll just drift apart because there was never a real foundation there.
But if you’re more yourself from the start?
Yes, some people won’t click with you. Some friendships won’t develop. Some people will decide you’re not their person.
And that’s actually good news.
Because the friendships that DO develop? They’ll be built on truth. On who you actually are. On real shared experiences and genuine connection.
You won’t have to wonder if they’d still like you if they knew the “real” you. Because they already know the real you. That’s who they became friends with in the first place.
The Work Starts With You
Before we wrap up, I want to address something Deb said that really struck me:
“We need to belong to ourselves first. When we belong to ourselves and become our own best friend and connect internally to ourselves, it cultivates enough safety internally to be able to risk being yourself in the world.”
This isn’t just about changing your behavior in friendships. It’s about doing the internal work to:
- ▪️ Notice your patterns (When do you people-please? With whom? In what situations?)
- ▪️ Understand where they came from (What early experiences taught you it wasn’t safe to be yourself?)
- ▪️ Recognize what you’re actually trying to control (Approval? Avoiding conflict? Managing others’ feelings?)
- ▪️ Build enough internal safety that you can risk being honest
That internal work? It’s not optional. You can’t skip it and just try to “act more authentic.”
Because if you don’t feel safe within yourself, if you don’t trust yourself, if you don’t genuinely believe you’re worthy of being liked for who you are… you’ll just keep performing different versions of people-pleasing.
The external changes (sharing more, setting boundaries, being honest about preferences) only stick when they’re rooted in internal shifts.
Start Here: Notice One Pattern
If you’re reading this and recognizing yourself in Deb’s story, here’s where I want you to start:
Pick one friendship pattern you want to notice this week.
Not change. Not fix. Just notice.
Maybe it’s:
- ▪️ How often you defer to what others want instead of stating your preference
- ▪️ When you give advice instead of just listening
- ▪️ How you respond when someone asks, “What do you want to do?”
- ▪️ Whether you’re honest about your capacity or always say yes
- ▪️ If you share about yourself or mostly just listen
Just notice it. Pay attention to when it happens, how it feels in your body, and what you’re afraid might happen if you did something different.
That’s it. That’s the first step.
Because you can’t change a pattern you don’t even realize you’re running.
And once you start noticing? You can begin making tiny, incremental shifts. Not all at once. Not perfectly. Just… differently than before.
One small moment of honesty. One boundary. One time, you share something real about yourself instead of deflecting.
Those tiny shifts? Over time, they add up to a completely different way of being in your friendships.
A way where you don’t have to explode the roots because they were real all along.
Want to hear the full conversation about people-pleasing patterns and how to break them? Listen to the complete episode of Friendship IRL wherever you get your podcasts. Deb goes even deeper into her mother’s influence, the specific moment on that bike ride that changed everything, and how she’s building friendships differently now. Subscribe so you don’t miss future conversations about showing up authentically in your relationships.
What friendship patterns are you noticing in yourself? I’d genuinely love to know. The more we talk about these things openly, the less alone we all feel in our struggles.
