24 February 2026, by Billy Boss
Stop People-Pleasing and Start Self-Respecting (Without Guilt)
If you’re stuck in the cycle of saying yes when you mean no, then feeling drained, resentful, and frustrated afterwards, this episode will meet you right where you are. Learning to stop people-pleasing is not about becoming cold or selfish. It is about ending the automatic habit of abandoning yourself to keep the peace. It is about coming back to your truth, and learning how to hold it with calm clarity.
In Episode 80 of The Billy Boss Show, we name people-pleasing for what it really is: a learned safety strategy. A nervous system pattern that often forms when being “easy”, “helpful”, or “low maintenance” feels like the way to stay loved, safe, or connected. And the good news is this: You are not weak. You are not broken. You are not bad at boundaries. You are patterned, and patterns can be changed.
When your “yes” costs you your peace
There is a particular kind of tiredness that comes from being the reliable one. The one who answers quickly. The one who will “make it work”. The one who carries the emotional load, smooths things over, and keeps everyone comfortable, even when it means swallowing your own needs.
And what makes it so confusing is that you can genuinely love people and still be people-pleasing.
This episode is a mirror and a release. It will help you notice the moment your body says no, even as your mouth says yes. It will help you understand why it happens, and what it has been trying to protect you from. And most importantly, it will give you a simple way to start rebuilding self-respect and self-trust without guilt running your decisions.
Why this pattern feels automatic
People-pleasing often happens quickly. You feel the pressure, the awkwardness, the fear of being misunderstood, and your response comes out before you have even checked in with yourself.
You might recognise it as:
▪️ Saying “It’s fine” when it isn’t
▪️ Avoiding hard conversations, then carrying the heaviness later
▪️ Worrying that having needs makes you “too much”
▪️ Feeling relief in the moment, then regret afterwards
Stopping people-pleasing is not just about saying no. It is about learning to stay with yourself in the discomfort, and choosing boundaries that protect your energy, your wellbeing, and your self-worth.
What people-pleasing really is (and what it is not)
Here’s the definition that changes everything: people-pleasing is when you trade your truth for approval or safety.
It is not the same as being kind. It is not the same as being generous. It is not the same as being a caring woman.
People-pleasing is different because you can feel it in your body. There is tension when you answer. Relief in the moment. And then later, the emotional bill arrives: irritability, fatigue, resentment, the internal spiral of “Why did I agree to that?”
This is the cost of self-abandonment. And it is also the doorway back to yourself, because once you can name the pattern, you can change it.
The fears underneath people-pleasing
People-pleasing is rarely about the actual request. It is about what your body believes will happen if you are honest.
This episode gently unpacks the fears underneath people-pleasing:
▪️ Fear of rejection: “If I say no, they won’t like me.”
▪️ Fear of conflict: “If I speak up, it will turn into an argument.”
▪️ Fear of judgement: “If I have needs, I’m too much.”
▪️ Fear of disappointing people: “If they’re unhappy, I’ve done something wrong.”
And beneath all of these fears is often the deepest one: fear of losing connection.
For many women, connection once meant safety. So the nervous system chooses connection at any cost, even when that cost is you. This is why people-pleasing is not a personality flaw. It is often a learned nervous system strategy.
The Pause: a simple boundary practice for real life
If you have ever told yourself, “Next time I’ll speak up,” and then found yourself saying yes again, you are not failing. You are responding fast, because your nervous system is trying to avoid discomfort.
This is why the most powerful shift is not a perfect boundary speech. It is slowing down at the moment.
The Pause helps you stop people-pleasing by creating space between someone’s request and your automatic response. That space is where self-respect begins.
Your new rule (this week)
“I don’t answer on the spot.”
It might sound simple, but it is a deeply self-respecting act. It tells your body: “I am allowed to check in with myself first. I am allowed to choose.”
Words you can use without over-explaining
Try one of these boundary scripts and keep it clean:
▪️ “Thanks for asking. Let me think about it and I’ll get back to you.”
▪️ “I can’t answer right now, but I’ll let you know by tomorrow.”
▪️ “That doesn’t work for me.”
You are allowed to be warm and clear at the same time. Boundaries do not have to be loud to be powerful.
A self-respect check-in before you say yes
Here is a simple way to come back to yourself before you agree to something:
“If I say yes, will I respect myself afterwards?”
This question cuts through people-pleasing because it brings you out of fear and back into self-trust.
Instead of asking, “Will they be upset?” or “Will they still like me?”, you begin asking, “What is true for me?” and “What will it cost me if I ignore myself again?”
If you know your yes will lead to resentment, exhaustion, or the familiar inner anger later, that is not a moral failure. That is information. And information gives you choice.
When guilt appears, stay on your own side
When you start setting boundaries, guilt can rise fast. Not because you are doing something wrong, but because you are doing something different.
If you were conditioned to believe that being “good” meant being easy, helpful, and available, then choosing yourself can feel unfamiliar at first. You might feel guilty for disappointing someone, even when you are simply being honest. You might feel selfish for having limits, even when your limits are reasonable.
Here is what I want you to remember: guilt is often the emotional echo of an old version of you, the version that survived by staying small, staying agreeable, staying safe.
So when guilt appears, do not use it as a reason to abandon yourself again. Use it as a sign that you are practising something new.
Try these reminders:
▪️ “I’m allowed to have limits.”
▪️ “I’m allowed to choose.”
▪️ “I can be kind and still be clear.”
And if you need a moment of truth to hold onto, let it be this: self-abandonment always has a bill. Eventually, it is paid in exhaustion. You deserve a life where your love does not cost you your peace.
And if you’ve been carrying this quietly, the guilt, the second-guessing, the fear that you’re letting people down, I want you to hear this personally: you are not selfish, and you are not “too much” for having limits. The part of you that feels guilty is often the part that learned love had to be earned through being easy, agreeable, and available.
Let this episode be an invitation to soften the pressure, tell yourself the truth, and begin building a new relationship with you, one where you stay on your own side. One where your kindness no longer costs you your peace, and your self-respect becomes the safest place you live from.
____
Ready for deeper support?
If this episode is touching something deeper, the part where you have been holding too much, carrying emotional weight, and losing yourself in overgiving, I want you to know there is support for you.
Release & Rise is an upcoming guided experience for women who are ready to stop living from fear-based yeses and start living from grounded self-trust. It is designed to help you release what you have been carrying, rebuild self-worth, strengthen boundaries, and rise into the version of you who no longer abandons herself to keep the peace.
Join the Release & Rise Priority List
Follow me here:
Instagram
Facebook
Website
Sign up for my weekly dose of love newsletter for YOU at: billyboss.com
If you keep saying yes when you mean no, then feel drained, then feel resentful or frustrated afterwards, this episode is for you.
Today, we are naming people pleasing for what it really is, and I will give you one simple way to start breaking the pattern this week. Like literally this week.
So my friend, welcome back to The Billy Boss Show: your pathway to Healing, Confidence, and Self-love through truth, tools, and real conversations that bring you back to yourself. Now let's get straight into it.
This episode is for women who say yes quickly, even when her body is saying no. Oh I can relate so much to this. It's also for women who avoid difficult conversation, then feels heavy afterwards. It's also for women who keeps the peace but pays off in with exhaustion. And also, this is for women who worries that having needs makes her too much.
Now, if this is you, I want you to hear this from bottom of my heart with so much love and clarity. You are not weak. You are not broken. You are not “bad at boundaries.” You are patterned, and patterns can be changed.
Now, if you have been listening to my previous episodes, no doubt you have heard this before. And no doubt I will be repeating this over and over in many episodes that are coming your way: You are patterned. Nothing wrong with you. And patterns can be changed.
So, in next 15 minutes, I'm going to cover the definition of people pleasing in a way that is easily understood and what makes it obvious. We're also going to cover why people do it, and what is trying to protect you and me from. And also, what are the fears underneath it?
We are going to cover one boundary. You can practice this week with exact words. I'll give you an example what really you can say to break this pattern.
Now, I want to share a piece of my own experience because I've lived through this journey.
There was a time in my life when I was the person everyone could rely on. If someone needed support, I was there. If someone needed organising something, I handled it. If someone was upset, guess what? Somehow, I was the first person there to care for them, to be there for them, to take their emotional burden on me.
I told myself the story that, “This is just me. This is who I am. I'm helpful. I'm strong. I am reliable. I am a person who everybody needs in their life because I can take so much on.”
But if I'm honest, a lot of my yeses were not coming from love, even though I love people so much. But, most of my yeses, or lots of my yeses, were not coming from love. They were coming from fear. Fear of disappointing people. Fear of being judged. Fear of being misunderstood. Fear of someone pulling away if I didn't show up perfectly, if I did not show up when they needed me.
So, I would say yes quickly and I would make it work somehow. I would squeeze in. I would push myself through whatever I needed to push through just to do things for somebody else.
And afterwards, I would feel it in my body: The tight chest, heavy shoulders, irritation, exhaustion, anger, anxiety. Name it. I would actually feel it. And I would have that internal conversation that so many women have: “Why did you agree to that, Billy?”“Why did you speak up?”“ Why did you say yes? Now you've got to deal with it.”
No doubt you can relate to this.
And that was a turning point for me because I realised something that changed everything:People pleasing wasn't kindness. Let me say that again. People pleasing wasn't kindness. It was self-abandonment dressed up as being “nice.”
And once I saw it clearly for myself, I stopped making myself wrong…And I started learning how to choose self-respect.
And I want you to know: that if you are in this pattern, you can change it too. You can have healthy boundaries, you can have self-respect, and you can do it without guilt running your life. And let me reassure you, I will support you in this journey through breaking this toxic pattern.
So, let's define people-pleasing properly because once you can name it, you can also change it.
So here is the definition I want you to remember: That people pleasing is when you trade your truth for approval or safety. And I'll say that again because it matters:That people-pleasing is when you trade your truth for approval of safety.
And it's not the same as being kind. And it's not the same as being generous. And it's not the same as being a caring woman.
You can be kind and still be honest. You can be generous and still have limits.
People-pleasing is different because it has particular feeling in your body:When you say yes and meaning no, it has the pressure. You can actually feel the pressure when you say yes. You can feel tension as you're answering. You can feel relief in the moment, but later on you actually feel discomfort.
You also can feel drained afterwards, and people-pleasing often sounds like it's fine, when it's not. It sounds like whatever you want, when you do have preference. It sounds like don't worry, I'll handle it when, you need support. It also sounds like I don't want to make a fuss, when something matters to you.
And the reason it's a pattern is because it usually works in the short term. You avoid conflict. You avoid discomfort. You avoid that awkward moment. But long term, it costs you.
Now, if this pattern is familiar to you, you know that it costs you. It costs you your energy. It costs you your voice.It costs you your self-trust.And certainly, it costs you your peace.
If you're craving even more inspiration and real talk to fuel your confidence and success, I've got something special for you.
Make sure you join my Weekly Dose of Love. It’s a feel-good email that lands in your inbox every Tuesday, packed with motivation, mindset, tips, and tools to help you thrive in life and business.
You can sign up at billyboss.com, or simply click the link in the show notes wherever you're listening to this episode. Go on, give yourself that little boost of love each week because you deserve it.
So why do people do it? Why do we do people-pleasing?
People-pleasing is not a personality flaw. It's a learned strategy. And it often begins when somewhere, in life, you learn that being fully yourself wasn't safe.
So, your nervous system created a plan:To stay needed To stay usefulTo stay easyTo stay in control of how people feel.
And here are the most common fears underneath people-pleasing.
Now, why do I say most common fears underneath? Over a decade working with so many amazing humans, and also from our own transformational journey, this is what I sort of felt it is most common fears when we have the people-pleasing pattern.
Now, as I list some of these fears, notice which one hits you. Those fears are also not in any particular order.
Fear number one: It's fear of rejection. “If I say no, they won't like me.”“If I'm honest, they will leave me.”So, we are fearing here to be rejected.
Another fear is: fear of conflict. “If I speak up, it will turn into an argument.” If I set a boundary, things will get uncomfortable.”
Another fear is: fear of being judged. “If I have needs, I’m too much.” If I take up space, I’ll be criticised.”So to avoid that, to avoid fear of judgment, of course you will agree to whatever the person needs.
Another fear is: fear of disappointing people. “If I let them down, I’m a bad person.” If they’re unhappy, it means I’ve done something wrong.”
And here's one that sits underneath of all of these fears: Fear of losing connection.
So, all of these fears that I just mentioned: fear of rejection, conflict, judgment, disappointing people. Underneath all of these surface fears, the underneath of all of these is fear of losing connection.
Because for many of us, connection has felt like safety. So, our body chooses connection at any cost, even if the cost is ourselves.
I hope this lands for you.
And if you grew up in an environment where love felt conditional, or you felt you had to earn approval, or you were criticised for having emotions or showing your emotions, or you were punished, or you were praised for being the “easy one” or “caring one,” then people-pleasing makes perfect sense.
And this is not random. It's conditioning. But just because it was learned, that doesn't mean that it has to run your entire life.
And you know how I like to repeat the same sentences over and over again. Let me say this again. Just because this pattern has been learned doesn't mean it has to run your entire life.
So how do we break it?
I want to make this very practical for you. We are not going to talk about boundaries like they are big dramatic things. We are going to make it very simple, very useful, very simple step, simple tool.
The way you break people-pleasing, it's not by suddenly becoming that harsh or cold person, you break it by building one new skill:And that simple skill is the pause. The Pause.
Because people-pleasing usually happens very fast. You feel some type of pressure, and you answer immediately. You don't even have the time to think through.
So, you pause and your new rule is: “I don't answer on the spot.”Easy. This is self-respect. This is you giving yourself time to check in with your truth.
And here is the script or sentence that you can use. Choose one to practice this week.
When I say choose one, maybe you can also see what's coming up for you. Maybe you already have some situations that you think, oh my gosh, I can't actually avoid this. I really have to say yes.
And I want you to visualise yourself to see yourself that event coming and practice one of these sentences that you're going to use.
Well, remember to pause. And your new rule is: “I don't answer on the spot.”
And then you can say, “Thanks for asking. Let me think about it and I will get back to you.”Or you can say, “I can't answer right now, but I'll let you know by tomorrow.”Or simply, “That doesn't work for me.”
Remember to pause and remember your new rule. You don't answer on the spot.
So, practice any of these three sentences. Or maybe come up with your own one and use that one.
Now if you're thinking, “but Billy, I would feel so guilty.” Listen to me carefully.
You can have self-respect and healthy boundaries without guilt controlling you. Because guilt is not proof that you're wrong. It's often just proof. You are changing. You are doing things differently. Things that you haven't done before. Now you are doing them.
So, here's what you do in the moment you feel guilt. You don't argue with it. You don't analyse it.You simply remind yourself that: “I'm allowed to have limits.”“I'm allowed to choose.”“That I can be kind and still be here with my answers.”
Then I want you to breathe and stick with your boundary.
So give yourself permission that you are allowed to have your limits, that you are allowed to choose, and that you can be kind and still be clear, and just finalise it with a beautiful breath. Reassure yourself that you are safe. You are in control of yourself. You need to take care of your amazing self. You need to be true to yourself.
Now, one question that breaks the pattern.
Before you say yes this week, ask yourself, “If I say yes, will I respect myself afterwards?”
Now, if the answer is no, use the Pause script. Remember your new rule. That's it.
This is how confidence is built. Not by being fearless, but by being honest. Honest to your amazing self.
Now I want to close with this:
People pleasing is not who you are. It's something that you learn to stay safe and connected.And the truth will set you free: you can be loving woman and still have boundaries. You can be generous and still have limits. And you can be kind and still be very, very clear.
So, your practice this week is very, very simple:Use the pause once, just once.And ask yourself that question. If I say yes, will I respect myself afterwards?
And if you want deeper support as you let go of emotional weight and rebuild self-trust, I'm opening up guided experience called Release and Rise.
Now, if you want to be the first to know when it's really happening, join the Release and Rise Waitlist via the link in the show notes.
Now, if you love this podcast, if you love this episode and find value in this conversation we are having today, I would be so grateful if you could leave us a five-star review and rate the show. Your support helps us reach more incredible people just like you. And I'm so grateful for you being on this journey with me. Without you, I would not be here.
And before I go today, let me just remind you that self-abandonment always has a bill. Let me say that again. Self-abandonment always has a bill, and eventually it gets paid in exhaustion.
So, stay true to your amazing self because you are enough, and you are worthy of it.
Until next Tuesday, stay well and stay safe.
Why You Feel Unworthy (Even When You’re Doing Everything Right)
Coming Soon