I want to stop people pleasing

I’m a people pleaser, particularly at work and particularly with my boss. This is leading to me feeling annoyed and irritated, both with my boss and myself.

I find it hard to challenge what she says and find myself agreeing to do tasks, often menial ones as she delegates EVERYTHING and in my opinion does very little herself. I have pushed back a bit more lately when I’ve been prepared but if she catches me off guard I find myself agreeing with her. I have noticed that she (perhaps cleverly?) states her opinion very confidently and as though it is absolute fact whereas I tend to sound more unsure and add fillers like ‘I think’ or ‘maybe’ before I state my own opinion. I have tried to catch this but I’m finding it hard to change consistently. I want to be more assertive with her and to stop doing everything she tells me to do.

I also feel like she laughs at me sometimes and this makes me feel uncomfortable. For example, we were talking about Jung’s personality types on Friday (part of the work we do) and a weakness of my own personality type is to be ‘unpredictably emotional’. She said Alison you are predictably emotional and laughed. I laughed as well but was actually quite upset by this comment and I don’t really know what she meant. She said it in front of others. This is an example of her catching me totally off guard with something I didn’t agree with and I simply laughed too then felt upset afterwards. Which is maybe an example of the being emotional, but this is part of who I am as a highly senstive person and I don’t think this should be poked fun at.

Another example was I had gone along to observe a training session which I will be delivering at a later date. Before the first break she asked me to go and get everyone coffees from the canteen. There were 15 people so I spent about half an hour of the session fetching the coffees and missed the most important bit I wanted to observe. I commented afterwards about it but it seemed to fall on deaf ears. I wanted to say no and could someone else go at the time but again it was in front of others and I didn’t want to seem petty or unhelpful.

I tried a model but am a bit stuck

C – Work
T- I want to stop people pleasing
F- Uncomfortable
A – I try and push back but not consistently, particularly if I’m caught off guard and often after the event
R – ?