Self employed life? The confidence crusher that is ‘what to wear’

Self employed life? The confidence crusher that is ‘what to wear’


In 1993/4 I was 11/12. I was also just about to hit 6ft 2 with a mop of unruly curly hair and size 9 feet. I felt like Godzilla.

Buying clothes was tough, what I could get was extremely expensive and way too grown up for my tender age to feel comfortable in. I lived in mens clothes that were as baggy as possible and my Reebok classics. My school uniform consisted of a sweatshirt my nan knitted and black mens joggers. 

During my teens and particularly as I started working and flirting 😉 I began to hate going to clothes shops. I wore cropped trousers (full length regular) and nearly always tied a jumper around my waist to hide the gap in my midriff. I had no idea how to dress that would make me look the way other girls did. 

I either felt like a boy or like a frump. There was never an in-between.

Did I always feel that way? 

Around 15 I remember being told that I should dress for the job I want and so, off we went to Long Tall Sally. We bought a pair of black figure hugging bootleg trousers, a minty green button up blouse and a black blazer. It was my first experience of feeling professional, smart and womanly (I thought my bum looked pretty ok in those trousers).

I got the job I wanted and I remember having my ID photo taken wearing that very same mint green blouse. I was the epitome of dressed to impress in my eyes.

Whenever I wore that outfit I felt smart, professional and capable of anything. It was like putting on a costume or a suit of armour – wearing it filled me with confidence in my ability to do my job, just like wonder womans bracelets or Batmans suit.

I got older, life changed, I stayed in the offices and worked my way up to senior management. On my best days I felt good in my clothes, smart and like I was taken seriously. 

I wasn’t smarter because of my clothes, I was more confident because of the way I presented myself. My confidence meant that I was able to better manage whatever the day threw at me and better management made me more confident. It was a self-fulfilling circle.

Then and now

Since then I have traded boardrooms, call centres, building sites and corporate offices for a little home office that is just off of my bedroom. I am decidedly heavier and my tummy can be really sensitive what with being full of benign tumours and cysts. 

Whilst brainstorming my content earlier this week (video will feature quite substantially) as well as planning in some in person 1-1 sessions, a full day event and some other real life connections I realised that I feel like that schoolgirl again, the one with the knitted school jumper and mens jogging bottoms. 

My mind wanders relentlessly to the ‘how to dress myself saga’ that I have created in my mind. If I’m honest it’s not just been recently it’s been for a long long time.

It seems like such a small thing but expressing yourself with your appearance is exactly what we all do, whether it be our hairstyle, our sense of fashion or whether we wear make-up or not. For me, it’s about the outside reflecting my personality and professionalism in perfect synergy but since I work from home and rarely see other people in real life I’m not sure what that looks like anymore. 

If I take that old advice and I dress for the job I want then I would live in my pj’s because my business is exactly what I want and I work from home, mostly unseen. 

Taking action, almost any action, will help get you through a confidence issue or emotional barrier <Click to tweet!

I don’t plan on worrying about it for too long, like with anything the way to move through it is to take action. So I have a make up lesson to book (Thanks to a Christmas gift voucher) and I can sort through my clothes but I do ask myself how much of this is because of the way I want to present myself and how much of this is because I want other people to like the way I present myself?

Struggling with figuring out who you want to be in your business? If you want to chat about anything feel free to email me amy@theamyjohnson.com

Catch you later, Amy x