When People Pleasing Becomes a Business Problem.
It looks like care… but it feels like exhaustion.
James is amazing at what he does.
He has more clients than he’ll ever need, a strong reputation, known as the trustworthy one, the go-to person in his industry. If you need help, he’s there. If something goes wrong, he steps in. He treats all his clients the same, shows up, delivers, cares.
And he’s exhausted…
He told me how much he’s been struggling with one particular client he’s had for years. How much he’s given, how much he’s tried, how much he’s bent himself to make it work.
And still… it never feels like he’s enough.
No matter what he does, it doesn’t suffice, it doesn’t land, it doesn’t satisfy.
And here’s the thing. He doesn’t even need the client. There’s no financial pressure, no real reason to stay. And quite frankly, a part of him feels done.
But another part… just won’t let go.
How does someone with a thriving business and a reputation to envy, not know how to say no?
At one point, James started looking for a strategy, a tool, something he could change in his business so clients wouldn’t ask so much of him. He was convinced there was something he was doing wrong. Something strategic he hadn’t quite got right yet.
But no strategy in the world will fix this.
Because this isn’t a business strategy problem, it’s a people-pleasing problem…
People pleasing is sneaky. On the outside, it looks like care, generosity, being a good human, someone people can trust. But underneath, it’s exhausting. It drains you and keeps you stuck in a quiet, relentless feeling of never being enough. Because there’s always someone else to please. It’s an endless supply.
And the moment you start thinking about changing it, about setting boundaries, pulling back, protecting your energy, you feel guilty. So you go back. Back into overgiving, overextending, overriding yourself. Same cycle, different day.
And for someone wired like that, it’s a hard pattern to break. Why? Because it doesn’t feel like a flaw. It feels like the most important part of who you are.
As a recovering people pleaser myself, I know how hard it is to change. There’s something almost addictive about it. The overdelivering. The helping. The feeling of being needed.
But there’s a line.
A line between supporting and helping someone… and overdelivering.
When we overdeliver we take over their experience. We try to fix it, carry it, soften it, make it easier for them.
When we actually support however, we stay beside them. We trust their capacity. We don’t rush in, force an outcome, or assume we know what’s best.
And here’s the uncomfortable truth:
If you want to recover from people pleasing, you’re going to have to stretch beyond what feels “good”. And that stretch often feels like becoming someone you don’t want to be.
Cold.
Self-centred.
Even a bit… egocentric?! 🫣
If you’ve built your identity around being the one who gives, who helps, who holds, then anything outside of that will feel wrong at first.
Of course it will, but that doesn’t mean it is.
When you’ve been using people pleasing as a way to be liked, to be needed, to feel valued, then stepping outside of it will shake something.
But what if being more self-focused is actually what will allow you to give more powerfully, not less?
What if that discomfort of setting boundaries is not you becoming less caring… but more able?
Yes, you may overshoot and lean too far into self-centredness at times.
You may pull back too much at other times and fall back into overgiving.
But if you can stay with that unease instead of immediately trying to correct it, you start to recalibrate. You start to recognise that your inner capacity matters far more than you may have thought.
Success is a magnifying glass. 🔎
What shows up in our personal patterns will show up in our professional life.
We can’t out-strategise it. We can’t hide it behind achievements, reputation, or how good we are at what we do.
People don’t meet the version of us we’ve carefully constructed on the outside,
they meet who we actually are.
Love, Madelaine
… Writing this, I am aware this will not resonate with everyone. There are parts that are messy, imperfect, parts that can be scrutinised. Some of you will prick big holes in it, some will think it’s not original enough, some will be triggered, others will look for insights and deep meaning… and there is nothing I can do about that.
I will not be able to please you all. And I am practising to be ok with that. Truly.
Because I am not here to make you comfortable. And I am not here to be approved and liked by everyone. I am here to speak and live as close to my current truth as possible. And if that’s you too, I’ll meet you there.
x M
When you are ready to go deeper into this work, there are currently a 3 ways to play:
1. 1:1 Coaching
For those ready to dive directly into the work:
https://www.madelainevallin.com/coaching-with-madelaine-vallin/
2. Integrated Leadership Intensive (June)
A small, focused group experience for leaders and people of influence ready to deepen their impact:
https://www.madelainevallin.com/leadership-intensive/
3. 7-Day Soul Tuning Journey (Free)
A place to begin, in your own time.
https://www.madelainevallin.com/experience/