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Diary of a Recovering People Pleaser · Oct 10, 2025

People pleaser? Me?

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Teresa Wilson · Diary of a Recovering People Pleaser

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-5:45

For the purposes of beginning somewhere, this story begins on Christmas Eve, 2024.

I woke up feeling off. I couldn’t quite locate what particular flavour of off it was, so I tried some journaling. Then I sat in quiet meditation. But the off persisted and the root cause wouldn’t reveal itself.

To call in some extra insight, I reached for my deck of trusty archetype cards and pulled The Shapeshifter. And the thing that jumped out at me – positively grabbed me by the ears, spat in my face yelling LOOK AT ME – was that the shadow side of Shapeshifter was people pleasing.

And I responded with a huh.

A huh that gently morphed into an oh.

Oh. People pleasing? Me?

We all know that fish don’t know they’re swimming in water. Silly fish. And yet here I was confronted with my own swirling ocean. Could this off-ness be connected to people pleasing? And, if so, was I about to sink, swim or drown?

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For the purposes of beginning somewhere else, let’s travel back to 1977. I am 5 years old, and it’s the start of a recurring nightmare that travelled with me throughout childhood.

In the dream, I am in the playground at school. The bell rings and the other children start going back into the classroom. However, I realise that I’m not wearing any knickers and go and stand by the wall, burying my head in my arms and crying, waiting for someone to come and comfort me. Nobody comes, and I’m alone in the playground now. I step away from the wall and realise that I have a mask on my face. I take the mask off but there is another mask underneath. I rip this off but there is another mask and I wake up, terrified: I cannot find my face.

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It has been my experience that the subconscious operates with an inherent elegance. It doesn’t work on clock time, but on divine time. It doesn’t care for logic, instead enjoying imagery and poetry. It knows the motifs and metaphors that matter to us and will mark these as important. Like cookies on a computer, it will code certain fragments of experience as significant and be sure that we will find them, when needed, at a point in our lives when we will have the capacity for the meaning to open and reveal itself, like a beautiful lotus flower.

I take great comfort from this; as though the sub-conscious views our lives as one great scavenger hunt. The memory of that dream is an example of a fragment that was bookmarked as important and lay waiting for me to rediscover it.

I thought of that dream, as I sat and held the Shapeshifter card in my hands that Christmas Eve morning, and of what it meant to not be able to find my face. This sepia toned memory travelled from the 1970s and landed as an ‘oh’ in the present. Here it was then. The realisation. I was about to drive and see my family and this off-ness was heralding the realisation that I Shapeshift with my family. I people please. I mask.

And quite possibly, at 53, two weeks out from the end of my marriage, maybe I was done with that. Maybe I was ready to call time on the reflexive behaviour that had been my M.O my whole life.

Merry Christmas to me.

I am happy you are here. I am working this out in real time and using this diary as a way to sense-make as I go. Too many thoughts swirling does no one any good, so I am using this diary as a butterfly net, swooping my ideas into order on the page. I am sharing in the hopes that, whether people pleasing is loud or quiet in your life, you might find some solace in the companionship as you travel alongside me.

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