The Productivity Sweet Spot ~ Episode 85
The Hidden Cost of People-Pleasing on Your Entrepreneur Mindset

You plan your week. You protect your calendar. You have the productive habits in place.
And then someone asks you for something — and even though every part of you wants to say no, you say yes. And you carry the weight of it in silence.
That pattern has a name. And it is quietly costing you more than you realise — in your business, in your relationships, and in your energy.
In this deeply honest conversation, I sat down with Lisa Haydon-Bennett, a therapist who works with women navigating the invisible weight of who they’ve been told to be. What started as a conversation about sustainable energy in work and building an entrepreneur mindset that actually lasts… turned into something much more real. Because we followed the thread all the way back to good girl conditioning — the deep-rooted pattern that teaches women to earn their place through accommodation, compliance, and over-giving. And what that pattern costs us, not just emotionally, but structurally, in how we work and lead.
We explore the parts of us that are still trying to earn approval — the teenage version that comes out when we feel unheard, the compliant self that says yes to avoid conflict, and the shame spiral that happens when we dare to want something different.
We also talk about intent versus impact — why the people around us may not mean to dismiss our needs, but why the impact still lands hard. And what it means to come back to yourself before you respond, rather than either reacting or going quiet.
This conversation will feel familiar if you’ve ever questioned whether you’re allowed to want what you want. It is not a quick fix. But it is an honest, compassionate look at what’s underneath the busy loop and why sustainable productivity has to start inside.
- Good girl conditioning and why it gets harder to unpick as we get older
- How people-pleasing shows up in your business just as much as in your relationships
- The intent vs. impact gap — and why it still hurts even when it wasn’t on purpose
- What it means to come back to yourself before you respond
“When we give more than we’re willing or able to give, it breeds resentment. Willing and able — both matter.”
“It wasn’t about the run. It was about the regard for you and your time and your needs.”
“The good girl conditioning is so deeply embedded by the time we reach our 40s that it’s not you failing to recognize it — it’s just that deeply ingrained.”
“Sometimes you’re not able to say it to him in that moment. But you can say it to yourself: I’m having a really hard time with this.”
“It’s not your fault that that happened. But it is your responsibility now to change it.”
EXCERPT
What does it really cost you to say yes when you mean no? In this episode, Anne Rajoo sits down with Lisa Haydon-Bennett, a therapist who works with women navigating the invisible weight of who they’ve been told to be, to explore how good girl conditioning quietly shapes our productive habits, our entrepreneur mindset, and our ability to protect our energy. Together they trace the roots of people-pleasing from childhood praise and emotional suppression all the way into business — into how we price, how we communicate, and how we over-give until resentment takes hold. They explore the intent vs. impact gap in relationships, the teenage part that comes out when we feel unheard, and the small, grounding practice of naming what’s happening inside before you respond. This is a conversation about sustainable energy in work and in life — and why that work has to start with self-trust.
INTRO
I had planned to go for a run. I had it in the calendar. I knew I needed it.
And then someone asked me to give it up — for a good reason, a real reason. And I said yes.
But I was angry. Not just annoyed. Angry. And then I felt guilty for being angry. And then I kept going.
If you’ve ever caught yourself saying yes when every part of you wanted to say no — and then carrying the weight of that in silence — this conversation is going to feel very familiar.
My guest today is Lisa Haydon-Bennett — a therapist who works with women navigating the invisible weight of who they’ve been told to be. And the conversation we had… honestly, I didn’t expect it to go where it went.
Because we started talking about productivity and sustainability — about how to make your work and life feel enriching, not just functional. But what we actually got into was the deeper pattern underneath all of it. The good girl conditioning. The parts of us still trying to earn approval. The teenage version of us that comes out when we feel unheard.
And the way it all collides — in our relationships, in our businesses, in our bodies.
This one went somewhere real.
TRANSCRIPT
Anne:
Something that’s been on my mind and that is impacting my work — and has for many years — is the fact that my work, I can structure. I can prepare, I can plan, I have technical tools. I can set this all up to feel beautiful, sustainable, and peacefully productive. But then there are elements in my life where I don’t have that control, and it’s difficult. The emotional elements.
Lisa Haydon-Bennett:
Yes, exactly. And once you’re in that emotional space, it affects your work because you carry it with you — even if you try all the tools and tricks they tell you to manage your emotions. They’re still there.
Anne:
And I believe they build up over time. There’s a lot of accumulation. Like, “Oh, it’s this again. We’re doing this again. Now he’s going to behave like that again.” And so a lot comes up in my mind and it all goes somewhere really fast. It definitely affects how I show up at work.
Lisa:
There’s a Buddhist principle that says: when we give more than we’re willing or able to give, it breeds resentment. “Willing” means I don’t want to do it. “Able” means I literally don’t have the space or the hours. That tension builds a sense of resentment — and then the emotional charge that comes with it.
And that’s where we talk about boundaries — understanding what our boundaries actually are. But we don’t always understand what they are. Or maybe they’ve shifted along the way.
For you, it sounds like perhaps those limits have always been there internally. But for your husband, it’s always just been that way — you’ve always done those things, and that’s how it’s been set up. So it might be quite confronting for him that you’re now choosing to prioritise your sustainability. It may feel to him like he’s being deprioritised.
Lisa (cont.):
And the way we make work sustainable is to organise our days in a way that feels enriching. Women don’t tend to start with, “What feels enriching for me today?” They tend to start with, “What needs to get done? What’s expected of me?”
Anne:
That’s exactly it. The run that I had planned — that was mine. That was what felt enriching for me.
[Note: Brief connection disruption occurred here. Conversation resumed seamlessly from this point.]
Lisa:
It’s really interesting because I’m sitting in my therapy chair, and something struck me — how these conversations about power dynamics come up even in spaces where we work really hard not to have them. And what I’ve learned is that there are different parts of ourselves that switch in and out, and that’s shaped by how we grew up as well as by societal conditioning.
Going back to what we were talking about: the good girl. Where does that come from? How can we relax that in our work so that we don’t undervalue ourselves and we don’t over-compromise?
That’s so difficult for women. And it’s extra difficult for mothers. I have so much empathy and regard for mothers trying to juggle this — the complexity of it, and the tenacity it takes to say, “Something has to change.”
Anne:
Yes. And I think at the end of the day, I do want to be a good wife. I want to be a good mother. I want to be a good person. But all of these different identities or areas of my life seem to have their own definition of what “good” looks like. And very often they clash.
Good entrepreneur, good wife — sometimes they don’t work together. Good wife, good mum. How do you actually bring it all together when it genuinely doesn’t feel like it can all work at once?
Lisa:
That’s such a powerful point. Being a good person at work means thriving. But because women have been discounted in so many ways — implicitly and explicitly, for so long — it’s hard for women to detect what’s actually happening. And equally for men, because they haven’t lived the same experience. They may not recognise the implicit messages they’ve unconsciously sent.
But coming back to the good girl at work, the good wife, the good mother — those expectations do overlap. That’s where the question of “good enough” comes in, isn’t it? And it sounds like your version of good enough may clash with your husband’s. His “good enough” might look like you being more deeply in service to the family.
Anne:
Yes, it’s so interesting. And I think it sounds like you’ve identified that I inherently know what I need to be well throughout my day — and that there’s an internal dialogue that goes: “Am I okay to want this?”
Even earlier, with that Buddhist phrase you brought up — I reflected on that moment. I wanted something. I also agreed to support my husband because he needed me. But it didn’t go well. We both had emotions around it and ended up in a situation that could have been nicer.
What I noticed is this pattern: I say yes because I want to be the good wife, the good mother, the good person who supports her family. But if I’m honest, deep down, I shouldn’t have said yes. Because what I really wanted was to hold my plan and do my run.
I do this often. Do you have any insights around that pattern?
Lisa:
I wonder if parts theory might help here. What you could say to yourself is: there’s a part of me that wants to support him, and there’s a part of me that wants to go on the run. You’re in internal conflict.
The pattern you’re describing is an either/or: if you go on the run, it means you’re not a good mother, not doing what’s expected of you. That either/or creates discomfort that’s hard to sit with.
What might help is being able to say “part of me wants to do that, but part of me feels conflicted” — and then asking your partner: “Can you help me with that internal conflict?” It gives them shared responsibility and helps them see what that conflict actually looks like.
It sounds like you’re trying to process that conflict by yourself. But you’re in partnership. You don’t have to carry this alone.
Anne:
Yes — and the reason I gave in was that my husband had been supporting me in certain ways recently, so I felt like it was my turn to reciprocate. But I also really needed that run. I had a race on Sunday, and it was my last proper training window. It was all neatly scheduled. So there was definitely some rigidity for me there too — in terms of protecting my plan.
Lisa:
So there’s some discomfort in not sticking to the plan?
Anne:
Definitely. I generally don’t like it when things mess with my plans. He’s incredibly spontaneous. I’m a planner. It’s very much the opposites-attract dynamic that we’re dealing with.
Lisa:
Something really significant here is that our bodies carry the memory of unmet needs from childhood. When a current situation touches one of those old unmet needs, the emotional charge that gets stirred up in the body can be much bigger than the situation seems to warrant.
What I sense might be happening is an emotional mismatch — something deep in the dynamic between you and your husband that neither of you is fully aware of. And communication, while it sounds simple, is not easy.
What struck me as you were speaking is how much you were processing internally. You were carrying a lot of feelings — and they weren’t coming out. It sounds like there wasn’t space for that in the moment either.
Anne:
Exactly. He called me at the end of the day when I was in the middle of making dinner. “Tomorrow, this is happening — can you do the kids?” And I just said okay. Then he came home late, I was dealing with bedtime, and the next morning came so fast. There was literally no time to process any of it.
That’s a bit of a theme in our relationship right now. We’re both trying to build something business-related, and we have two children who get a lot of our attention. The result is that processing emotions with each other gets the very short end of the day.
Lisa:
That’s very real for so many people. And something that came to me as you were speaking was that sense of regard — of having regard for each other. What might have got lost in that exchange was not about the run. It was about regard for your time and your needs.
His intention wasn’t to dismiss you. But the impact was that something old got activated — a feeling that was difficult to locate in the moment, other than as frustration or anger. That’s often the default emotion in that “family of anger” territory.
What’s helpful in those moments — when you can’t have the conversation right away — is to pause, reflect, and come back later and say: “When you did that, I felt this. This is what I’d like to happen instead.” Not, “You made me feel this way.” Just: this is what came up for me.
Anne:
That’s really true. The morning after, we had a bit of a fallout. And when I reflected, I realised two things. One: I had said yes to something I didn’t really want to say yes to. And two: what I was actually looking for was acknowledgement. Just a “thank you — I know Wednesdays are your run day, I know you have your race coming up, I appreciate you doing this for me.” That was all I needed.
Instead what I got was: “You don’t want to do this for me. You’re not supporting me.” That’s when I reacted in anger — because I felt unseen, unappreciated. And that’s how it spirals.
And something that came up for me while we were talking is that this connects back to how I was raised. In my family, we didn’t express much emotion — nothing too great, nothing too bad. I was the “cry baby.” When I was upset and cried, it was shut down. “You’re a strong woman, stop crying.” And I still feel tears coming when I’m frustrated or angry — and I hold them back. Because that little girl inside me still hears: good girls don’t cry.
Lisa:
That took my breath away a little. This idea of being labelled a “cry baby” — of having your emotions not just unacknowledged but actually ridiculed. That’s a significant thing to grow up with.
This isn’t about criticising your parents. We’re looking at the past through a much more sophisticated lens now than what was available to them. But what it means is that you learned: big feelings aren’t okay.
One thing that can help is learning to say, “I notice that I’m feeling really angry.” Or: “I notice I’m feeling really emotional.” Just naming it — not to sweep it away, but to lessen the intensity enough that you can come back to your adult self. In that moment, you’re not in the present. You’re in an emotional memory. And that’s very difficult to communicate from.
And when you described your husband’s response — that defensive reaction — that was his defence coming up. He wasn’t able to stay with your feelings in that moment, because something was activated for him too. That is so common in relationships. It’s not about shaming either of you. It’s about recognising that you both have your own story, your own childhood wounds, and those wounds will tap each other — especially when there’s no time or space to slow down.
Anne:
That really lands. And there’s another thread that kept coming up for me while we were talking: I see the same patterns showing up in my work. In entrepreneurship, you don’t always have control over the money coming in. You have the responsibility to support your family, to deliver for your clients — and at the same time you feel guilty that you’re not there for your children, or guilty that you’re not doing enough work. When you were speaking, I had about 500 thoughts at once. This is my daily world.
Lisa:
And that’s so much for anyone to carry. People are struggling with this and doing it alone, feeling like something is wrong with them — which activates shame. And then it’s hard to talk about.
What I want to say about your children: what’s different about your generation compared to older generations is that you’re able to say: “Mum had a lot of big feelings there. That was a lot.” You’re teaching them that big feelings are allowed, that they don’t have to bury how they feel. Some of what they’re witnessing is healthy, if you can help them name it: “Sometimes we have big feelings, sometimes we don’t understand each other. That’s normal.”
Anne:
Thank you for that. I sometimes get caught up in this perfectionist “good mum” image and I’m really hard on myself. But actually, I do naturally share with my children how I feel and why things are happening. Because I grew up not knowing any of my parents’ inner world — and as an adult woman looking back, I wanted to understand. I want my kids to have a better understanding of me: why I go for a run, why I make the choices I make — not because I don’t want to be with them, but because I’m choosing to look after myself and show them what that looks like.
Lisa:
Absolutely. You’re teaching them what dysregulation looks like and what repair looks like and what big feelings look like. That is life. And when they encounter those things in the world, they’ll have a framework for it.
And coming back to the good girl and the self-compassion piece — when something activates that old shame spiral, the practice is not to push that part of you away. The opposite is needed. It’s to say: “That must have been really hard for me at that time. I want to take care of that part of myself.”
In therapy, we often say: “I’m learning to believe this about myself.” And on the harder days: “I’m having a really hard time with this.” And another phrase I love: “I don’t say that about myself these days.” If someone calls you difficult, you don’t have to accept that. “We don’t say that about ourselves.”
Anne:
I love that. And what stands out for me is how this keeps showing up — I’ve worked through certain things before. Motherhood triggered a lot of this, and I dug into it through therapy and coaching. And then I thought I’d solved it. But then it shows up differently in different areas of my life — as the mum, as the wife, as the entrepreneur — always from the same root pattern. That used to feel crazy to me. Like, didn’t I already fix this?
Lisa:
What happens is this: you could have done the work on your part. But you’re relying on other people not to trigger what was activated in you. The trigger is what’s going on for them. The activation is what comes up for you.
So you might go into a meeting feeling rooted and regulated — but the other person is presenting something from their own unresolved material. It can be contagious in a way. Your wound might be “I’m not good enough.” Their wound might be “I have to be the best.” And those two wounds will find each other.
The practice is: you might not catch it in the moment. But afterwards, you can say, “I noticed what happened there. How can I come back to myself? How can I return to what’s actually true for me?” And then — rather than trying to push away the angry teenager that came out — the more useful thing is to turn toward her and say: “That must have been really hard. There’s a reason I respond this way. Let me take care of that part of myself.” It’s not letting yourself off the hook. It’s your responsibility now to work with it. But from compassion, not from shame.
Anne:
This is how I really feel about it — there’s no blame toward whatever happened in childhood. But there is responsibility to find a way to work with it. And what I’ll take from this is that phrase: “I’m learning to believe that.” When it feels uncomfortable to have compassion for myself, to allow this part of me to exist — to be able to say, I’m learning to do that. Yeah.
Lisa:
And when it’s really hard: “I’m having a hard time.” And another: “I don’t say that about myself these days.” I’ve been doing this work for fifteen years, I have a master’s degree, and I am still a human being with complicated conversations and complicated feelings. We’re all just trying to do our best.
Anne:
I love that. And I think that’s a beautiful way to wrap this up. It’s given me things I didn’t have before. I appreciate it so much.
Lisa:
Thank you for turning the conversation around on me, too. That gave me a lot to think about. And maybe we have an off-camera conversation again sometime soon.
OUTRO
What I keep coming back to from this conversation is something Lisa said about intent versus impact.
Your partner’s intention wasn’t to dismiss you. But the impact was that something old got activated — something that had nothing to do with Wednesday morning and everything to do with years of learning that your needs come last.
And that’s the thing about good girl conditioning. It doesn’t announce itself. It just quietly runs in the background, shaping what you say yes to, what you swallow, and what eventually comes out sideways.
So two things you can take away from today:
First — when you feel that spike of frustration, before you react or go quiet, try naming it internally. Not for anyone else. Just: I’m having a really hard time with this right now. That small act of acknowledgement can bring you back to yourself before you respond.
Second — notice where you’re giving from resentment rather than willingness. That’s not a character flaw. That’s information. It’s telling you where a limit needs to exist — or where you’ve been saying yes without really meaning it.
And if this episode made you think about how much you’re carrying — in your relationships, in your business, in the roles you hold — I want you to take two minutes and do the CEO time quiz.
Because how you spend your time as a CEO tells you everything about where your energy is actually going — and where it’s leaking. It’s a quick, clear lens on how you’re really working, not just how you think you are.
If this one landed for you — share it with someone who needs to hear it. Or screenshot and tag me on Instagram @annerajoo. I’d love to know what it stirred up.
Next week, I’m sitting down with Laziena Hodge — and this conversation is for anyone who considers themselves a self-aware, growth-oriented person… who has also quietly started to wonder why certain relationships still don’t work, no matter how much inner work they do. Because Laziena brings something most people haven’t thought about: repair. Not just the intention to do better — but the actual language and practice of coming back to someone after things break down. She calls it the repair table. Don’t miss this one.
I’m Anne Rajoo and this is The Productivity Sweet Spot — I’ll catch you next time. Until then, stay peacefully productive.
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