Do You Have What It Takes To Be Your Own Boss?

Are you ready to set up your own brand? CEO of Fashion-Enter Ltd & www.fashioncapital.co.uk Jenny Holloway discusses why and how she made the bold step to work for herself…

As we are now in 2025 many creatives reflect on their career to date and wonder if they should take that bold step to work for themselves and have their own brand. No one can make that decision for you it’s really only up to you, I remember when I was a senior buyer at Principles for Women on a big fat salary package with a car and bonuses it was one of the most daunting moments of my life.

The truth is I couldn’t make up my mind! I had a mortgage to pay, bills, wanted to go out, have holidays – I am sure you get the drift. So what made my mind up for me in 1999? Frustration!

I was at that point where I couldn’t take the politics anymore. I couldn’t work any more hours than I was doing (well, I thought it was a lot until I started to work for myself) and I just didn’t feel happy. I wanted to be my own person and take my own responsibilities. 

It was easier for me because I had a husband working full time, so I need to point that out, but I started my own business at weekend’s and at the end of the day after work so I eased my way into being self employed and that certainly made a difference. 

Do not be under the illusion that working for yourself is easier. It certainly is not because you have your own personal pressures of wanting to succeed and you have to pay the bills. It’s not for everyone. You have times of a crushing sense of anxiety, and just not knowing what to do next. You doubt your ability and wonder why on earth you ever left the security of being an employee. 

You experience failures, and then more failures and you need the resilience to get up and dust yourself down! And you learn. I mean this – you really learn what went wrong and why and then don’t make the same mistakes again. 

Is Self Employment for Me

This Power Point (click the link above) logically reviews how to work for yourself and if this is right for you…it’s a thought provoker really and it provides some guidance on what the legalities are too – remember these change every year especially with budgets and in April when Minimum Pay Increases occur.    

I often get asked if I made the right decision to leave the multinational corporate world of retail buying to be a CEO of my own companies. Truthfully, it depends on the day! On bad days when I see the bills mount up and there are curve balls that take me off my feet I wonder what am I doing. I could have had a much easier life with money guaranteed. However, overall, I would say yes, for me and my personality it’s right for me to be master of my own destiny. 

I am highly motivated and I want to excel in whatever I do. I like to be independent and accountable. I really enjoy problem solving and running a social enterprise, where I know I am making a difference to people and their lives, makes me find a level of contentment that I know my old job would never have given me. I am by nature a positive person and though this sounds over the top I love meeting people that I can help with skills, their business, or even just personally. 

One thing is for sure however. You only live once so don’t waste your precious time and for me I could not have a life of regret.  Sometimes you just have to feel that fear and go for it! There really is nothing to fear but fear itself and that’s not how I want to live. 

So Good Luck. We are  hosting a Masterclass this month to support you further: Breaking into Fashion: Myths, Realities, and Roadmaps, this is a 1-hour, free session held via Zoom with a live Q&A session at the end. Register for your free place and a Zoom link will be emailed to you closer to the date.