Entrepreneur Caroline Winn’s Eye-opening Journey Towards Self-Employment

If you’ve ever wondered what skills you need to be self-employed, or how you can move from your 9-5 to self-employment, what better way than to hear it from someone who has done just that?

We got in contact with entrepreneur Caroline Winn, who took up a varied and diverse journey towards self-employment to discuss her experiences and how the skills she has learned in her roles have benefitted her employment practices.

Meet Entrepreneur Caroline Winn:

‘’Hi, my name is Caroline Winn. I am 59 years old and live in Begbroke, Oxfordshire with my partner Mark. I enjoy being out in nature, walking by the sea, listening to music, reading and have been interested in all things Mind, Body, Spirit for many years: in particular crystals.”

entrepreneur Caroline Winn
Caroline Winn holding a Green Calcite Crystal. Photo by Caroline Winn.

Employment History:

”I have been working since I left college and have done a wide range of jobs. I started my career as an Apprentice on the Youth Opportunities Programme at Cherwell District Council in Banbury doing Admin work.  When my apprenticeship finished I was lucky to secure a job as Secretary to the Head of Personnel.  I then moved to Pontin Holidays where I was responsible for recruiting all the seasonal staff for 26 holiday centres in the UK. 

After being made redundant I temped for a while before getting a job at the Horton General Hospital in Banbury as Secretary to the Assistant General Manager.  During my time at the Horton I got promoted to PA to the Chief Executive, edited the hospital newsletter and ran several training courses for Admin staff.  In 1996 I won Employee of the Year in Banbury in recognition of my work at the hospital but also in the community.  

I left the hospital in the late 1990’s and went to Oxford Brookes University where I got a CELTA qualification. I taught English as a Second Language in Brazil and Turin in Italy before coming back to the UK where I taught Basic I.T. skills to a wide variety of clients. I then returned to Local Government and worked as PA to the Head of Transport Development at Oxfordshire County Council and trained as a volunteer career coach.

I coached staff and mentored young members of staff wanting to get into the County Council.  I left the County Council in 2013 and joined Restore as an Employment and Recovery Coach.  I coached clients with a wide range of mental health issues who wanted to get back into training/education, volunteering and employment.  

I took a brief career break and moved to Bournemouth but I was unable to find work so applied for a job with Aspire back in Oxfordshire and was offered the job. I have now been at Aspire over 4 years working as an Employment Development Worker. During my time with Aspire I worked on a project supporting military veterans and their families and latterly clients with drug and alcohol addiction enabling them to get back into structured activity, training/education, volunteering and employment.”

Self Employment:

”I decided to set up my own Spiritual Life Coaching business in 2021 after studying with BSY for several years.  I have always had an interest in Mind Body Spirit and in particular crystals.  I completed the Starting your Own Business Course with Aspire which I found invaluable in terms of preparing me for self-employment.  I worked closely with Sophie Kilminster and Simon Brooker at Aspire who helped and encouraged me to set up my business. 

I was able to draw on my experience of coaching clients in my day job and knowledge I had gained from doing my professional courses to launch the business.  You need to be passionate, driven and patient when setting up your own business.  You need to do your research with regards to markets and get honest feedback from family and friends about your products.

My biggest piece of advice to anyone wanting to set up their own business is not to rush things.  Take your time and don’t be afraid to change things if something doesn’t work.  It is a continuous learning process.  Don’t give up your day job as you need to have an income coming in whilst you are setting up your business.

I have run several online crystal workshops which my clients have found really informative.  I have introduced them to seven basic crystal tumblestones that are easily obtainable, inexpensive and have multiple healing properties. I tell clients what to look for when buying crystals, how to care for them and do a simple crystal meditation that can be done anywhere at any time. In addition I have made several crystal gift boxes for clients for their birthdays or a special occasion.

The gift boxes contain a bespoke crystal, tealights, organic tea, chocolate, cotton tote bag and an oracle card picked by me.  There is information about how to use the crystal and card in the box.  The boxes have gone down really well with clients and they have appreciated the thought that has gone into them.”

Advice to New Self Employed Entrepreneurs:

”I am very supportive of any of my clients from disadvantaged backgrounds wanting to go into self-employment.  I actively encourage them to go on the “Getting into Business” course run by Aspire as this is a great starting point for anyone who is thinking of going into business.  Having been through the process myself I know that it works and therefore I can give clients an insight into what is involved.  It has been lovely to see some of my clients at Turning Point go down this path and to be able to realise their dreams.’’

Entrepreneur Caroline Winn’s impressive journey towards self-employment  is not one unheard of before. Many entrepreneurs start their journeys after a period of ‘regular 9-5 employment, while others are entrepreneurs straight out of school. The important thing is not to feel uncapable of self-employment simply because of the stage of your career or the stage of your life you are currently in.

Employment is rarely ever linear, and many would argue that the range of experiences developed by working in many roles or organisations, or simply learning how to run a business yourself is invaluable. That could explain why The University of Nottingham states “Medical schools want to find the best candidates and believe they can come from any background’’. Each experience, whether you consider it to be a success or a failure is worth the time, because there is always growth and development to come out of it. 

So why not go ahead and start that project you wanted to do, or develop that business idea you had thought of? The best and only time is now!

If you’d like to read more about entrepreneurship in Oxford, why not read up about SkinBeautyOxford, a local beauty business run by Tess, or head over to our ‘entrepreneurship’ articles?