Stop Labelling Yourself As A People Pleaser With Imposter Syndrome - Start By Acknowledging How Uncomfortable You Feel

There are two phrases I hear often when people are describing what prevents them from being themselves or saying something that they feel, but think will disrupt the status quo: “I’m a people pleaser.” “I’ve got imposter syndrome.”

I hear them so often that I have to believe that they have become shorthand for something many of us carry. I also encounter them in Instagram posts and LinkedIn reflections - and they are said like we all hold the same definition, and that we all know what they are supposed to mean.

They are phrases that have spawned self help books, podcast series and “10 Celebrities who have experienced…” lists. And so I assume that they are meant to help — to name something, make sense of a way of being, to help us feel less alone. I have also been wondering: what if they are blocking self reflection and critique of our working environments?

What if these short hand, pop psychology phrases are pathologising something that’s actually understandable — even wise? What if they’re individualising a problem that might actually be political?

Because here’s what I keep noticing: that the people pleasing I hear about is often not described as pleasing for fun. And it also rarely sounds altruistic - it never sounds like some desire for everyone to be happy, rooted in nothing but wishing for the best.

When described to me, people pleasing sounds more like adapting. I hear people calculating what will keep them in the room. What will get them through the meeting, or the meal, or the week.

And when people say they feel like imposters, often they’re not being irrational or ungrateful. They’re picking up on something that I think is very real: a set of messages — subtle or loud — that say you’re not really one of us. Or you might be one of us now, but you didn’t get here the same way.

Maybe what these phrases are pointing to is not some personal failing in confidence or assertiveness, but a very old truth: many of us don’t feel claimed, welcomed, considered or accepted in the places that we find ourselves.

And perhaps we’re not speaking up because we don’t trust what will happen if we do. Because we’ve been punished for doing it before. Because the rooms we’re in reward comfort and compliance, not disruption. Because while we might be tolerated, we’re not actually incentivised to be real.

I think that word — incentivised — matters.

In high-risk industries like nuclear power, aviation, and medicine, there are whole systems designed to encourage people to speak up when something’s not right. Not just because it’s the ethical thing to do, but because silence is dangerous. Employees are trained to interrupt, to challenge, to halt an operation if they think it’s unsafe. And there are anti-retaliation policies to back that up — not just warm words, but enforceable protections. The message is clear: the cost of not speaking is higher than the cost of being uncomfortable.

So I have arrived at a new set of questions that I think can help push us beyond settling for descriptions of ‘people pleasing’ and ‘imposter' syndrome’ to describe situations where we don’t feel welcome or aren’t willing to risk upsetting the status quo; When was the last time you were incentivised to be yourself? When was the last time someone made it easier, not harder, to say your truth? In what ways do you think it is in the other person's interests for you to keep how you're feeling and what you're thinking to yourself?

What I’m describing is something deeper than psychological safety. It’s like a cultural permission. It’s having spaces and relationships that expect you to disrupt the story when it doesn’t fit — and that thank you when you do.

Until then, I’m not sure I want to keep encouraging people to “work on their imposter syndrome” without also working on the systems that tell people they don’t belong. I want us to stop asking people to build their confidence when they’ve never been met with curiosity. And I want us to be honest that what gets called “people pleasing” is often just someone trying to protect the very thing they weren’t sure was welcome in the first place.

So maybe the next time someone tells you they’re a people pleaser, try asking them this: “How would that change, if you knew that your truth and your opinion was wanted?”