The Billy Boss Show
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The Billy Boss Show is your weekly dose of healing, empowerment, and transformation. If you’re ready to release old wounds, rebuild your self-worth, and step into a life filled with love, joy, and confidence — this is your space.
I’m Billy Boss, and I know what it’s like to feel stuck, overwhelmed, and disconnected from yourself. From surviving childhood trauma, depression, anxiety, toxic relationships, addiction, and a long journey of healing… I rebuilt my life into one of health, happiness, and emotional freedom.
Now, my mission is to guide women to heal deeply, rise powerfully, and love themselves unconditionally.
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The Billy Boss Show
#80 Stop People-Pleasing and Start Self-Respecting (Without Guilt)
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Have you ever heard yourself say yes before you’ve even felt what you actually want to say, and then later you feel it in your body: the tension, the heaviness, the irritation, the quiet resentment?
That is not you being “too nice”. That is people-pleasing, and it is costing you more than you realise.
In Episode 80 of The Billy Boss Show, Stop People-Pleasing and Start Self-Respecting (Without Guilt), Billy unpacks why women fall into this pattern, what sits underneath it, and how to start changing it this week with one simple tool: The Pause.
In this episode, you’ll learn:
- How to spot people-pleasing in the moment
- The real fears underneath it: rejection, conflict, judgement, disappointing others, and losing connection
- A simple boundary practice to create breathing space before you respond, without over-explaining
- The self-respect check-in that changes your decisions: “If I say yes, will I respect myself afterwards?”
- Why guilt often shows up when you start healing, and how to stay on your own side anyway
Tune in and give yourself a deep exhale. This episode will help you catch the moment you say yes out of fear, not truth, and practise one simple pause that brings you back to self-respect, clarity, and choice.
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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
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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.
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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 useful
To stay easy
To 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.