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Cassa Grant

Cassa Grant

Executive coach and director of Chalkbox, a workplace skills training company. I write about leadership, capability, and building teams that actually work.

People pleasing will kill your dreams

3 min readJun 10, 2026
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Dun dun dun…

Ok, that’s a pretty dramatic intro to this article, but I really do believe it’s true.

Pretty much everyone I know struggles with people pleasing to some degree or another. As a recovering people-pleaser myself, this really hits home for me, and has for a long time.

Fundamentally, we have a need as humans to be liked and accepted (if we are, it will up our chances of survival, after all!) so it makes sense that we would want to please others so that we can hopefully… be more liked and accepted.

To add to this tendency, I read recently that 50% of people cite Words of Affirmation as their Love Language (from Gary Chapman’s excellent book ‘The Five Love Languages’).

I tend to think of these more as “appreciation languages”- the ways that we feel important and affirmed when we interact with others.

A lot of people would say that people-pleasing is caused by insecurity or low-self esteem.

When you don’t trust yourself, you can’t trust others, either. That’s why you’re always needing THEM to affirm you.

And when you can’t trust them to accept you even if they don’t agree with you or you don’t do everything that you THINK that they want…

…you’ll try to please them.

Even if it means sacrificing what you really want (AKA your hopes and dreams)…

Other than approval-seeking because of lack of self-trust, there are a couple of reasons we might try to people-please:

If we don’t fulfill others’ requests or expectations, we’ll be rejected or criticized.

Low self-esteem sabotages us and makes us believe that our own needs and desires are not as important as those of others.

Some people may engage in people-pleasing behavior as a way to alleviate feelings of guilt or to make up for past (perceived or real) mistakes.

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Some cultures or social groups may place a strong emphasis on pleasing others and prioritizing the needs of the group over the individual.

And all of us need some affirmation to a certain degree, even if we don’t identify it as our primary love language.

So, start noticing: I encourage you to start to notice where you’re people-pleasing just to get those sweet sweet words of affirmation.

When you know the circumstances that you’re most likely to fall into people-pleasing in, you can start to be a lot more discerning with where you REALLY need to be affirmed, and where you really DON’T need to.

And then it’s just about practicing not doing it (which I talk about in other articles).

But the first step is noticing.

When you get this right, you’ll start to see that people basically don’t even notice that you didn’t bend over backward to try to please them.

And meanwhile, you’re doing the things that really satisfy YOU.

When we constantly prioritize the needs and desires of others over our own, we can lose touch with our OWN passions, values, and goals.

Not only that, but people-pleasing can also lead to feelings of burnout, resentment, and even depression.

It’s impossible to please everyone all the time, and constantly trying to do it can leave us feeling drained and unhappy (ask me how I know!)

So if you’re ready to start living better, start to bust out of the people-pleasing cycle.

Say no, set boundaries, and prioritize your own needs and desires.

You’ll find that you have more energy, more joy, and more fulfillment… and if you’re like me, you just might like having those things more than having the perceived approval of someone else.

If you enjoyed this article, please forward it to your friends.

Originally published at https://www.linkedin.com.

Cassa Grant is an executive coach and facilitator based in Nelson, New Zealand. She works with leaders navigating career transitions, identity changes, and the practical realities of managing people well. She publishes The Better Leadership Blueprint on LinkedIn and is the director of Chalkbox, a New Zealand workplace skills training company.

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Cassa Grant
Cassa Grant

Written by Cassa Grant

Executive coach and director of Chalkbox, a workplace skills training company. I write about leadership, capability, and building teams that actually work.