People pleasing all the way

Or how it's a hard balance at times to get rid of the people pleasing vibes

I realised today that I have always worked for fairly assertive women. Pretty much all of my bosses were women. I worked for 20 years for two women bosses. One was more the ‘people person’ i.e. empathetic and the other the ‘business head’ (not particularly great people skills to put it mildly). I went straight from university into jobs where I was always working underneath a strong woman. And I got into the habit of always wanting to please that woman. It didn’t matter what the end client said, or what my colleagues said, one negative comment from my female boss and that would be the ONLY thing that stayed with me.

I still carry the memory of my boss (the more business headed one) telling me that I’d made a massive error with a client because I’d said their creative strategy was wrong -headed. I think about the moment whilst I’m having a shower or even when I’m putting my kids to bed. I was often told in reviews that I needed to be more opinionated, but at the same time I needed to make sure the client was happy. When I came out with me real opinion on anything (in senior meetings) then this opinion was usually dismissed, ridiculed or stolen by one of the men in the room and passed off as their own opinion.

I learned to mask my identity. The only way it came out was in doodles on my note pad (usually either smiling faces or sometimes on bad days - giant penises- to represent some of the male colleagues that got on my nerves the most).

This people pleasing is a common trait amongst women for sure, but for me it felt particularly acute. Even when I went freelance I ended up working for strong women who I battled to stay on the right side of. I tried to second guess what they wanted. I was overly subservient at times (despite having more experience than they did). The worst example of this was when I got a role in a start up and had a female boss twenty years younger than me who I tried so very hard to please.

This ended with me sitting in a room whilst she went through time sheets with me (I’ve written about this before- she wanted me to account for every minute of every day to see where my work priorities were each week). I bent over backwards for her. Quite literally. Nothing was too much. Now I’m freelance and I realise I feel most comfortable in this type of relationship. I am my own boss (in many ways) and yet the minute I start working for a woman (client) then I feel the people pleasing taking over. I recently started working with a brilliant journalist and she was commissioning work but rather than thinking about the quality of the work I was writing, I just wanted her to be pleased with what I’d done. I have paused a bit on that work now and feel exhausted. Each interaction I had to reply to. Each mail. Each message. And I was back to being a 20 year old intern again at the insights agency- hanging onto my bosses every word and making notes, always making loads of incomprehensible notes so that I could follow her direction to the letter.

It’s a hard dynamic to shrug off. We sometimes feel comfortable even when things don’t feel right. So we would rather have the relationships we’re used to rather than the ones that are authentic and bring out the best in us. I have some new projects coming up and I am finding it hard at times to course correct. I cling to other women like a life raft. What should I do? What is right? What do you want from me? Is this okay? It gets in the way of my ideas. Of feeling inspired. It’s a pain. But I also know that I NEED TO DICTATE MY NEXT MOVE and I can’t be the people pleaser forever. It’s lovely if people like my work, it’s important that I do things right, but ultimately I am working for myself and it’s myself I must please. I have my own standards and my own boundaries. And if I don’t stop people pleasing it’s an unhelpful habit that will haunt me forever.

I was talking to my mum this morning about an important meeting I had coming up. ‘It’s hard because I want to be opinionated, I want to show I have great ideas but I also don’t want to come across like I’m inflexible and rigid and can’t take direction,’ I said to her.

‘Just be yourself!’ mum replied, ‘You’ve earned that right.’

I thought about it and realised that all the times I’d thought too hard about what other people wanted, the content, or the debrief, or the output had usually suffered. I needed some direction but the best work was usually the work where I went with my own internal compass and wrote the things and created the work that I liked.

I am realising as I get older that I’m getting better at recognising the patterns that have made me the way that I am. The people pleasing is common and unhelpful. It can follow us through our entire life. I am just getting to that stage right now where it’s loosening its grips. It’s still there. It still speaks up but I’m trying hard not to listen, not to let it dominate my thoughts.

I’m getting comfortable with the idea that people are not pleased with me. Which feels revolutionary sort of.