Celebrating 5 Years Of My Illustration Business
Image Credit: Faye Hedges
This month I’m celebrating 5 whole years since I started my business Helen Ridley Illustration. When I started my business in October 2020 I had been toying with the idea of becoming an illustrator for a few years, and had been taking some short courses to develop my portfolio, from Make Art That Sells, to An Introduction To Illustration at London Metropolitan University as well as Find Your Creative Voice by The Good Ship Illustration.
Finally, after taking a redundancy in 2020 from my role as a product technologist for a major retailer, I decided to take the plunge and become an illustrator full time. I started with designing cards and gifts to sell via my website, Etsy and in person markets, lockdowns allowing. However, I had so little confidence in my abliity as an illustrator that I couldn’t imagine doing much more than illustrating some cards.
In hindsight would not recommend going full time an illustrator if you are just starting out. I managed to support myself for the first year on savings I’d made during the first year of COVID lockdowns, but by my second year in business I decided to get a part time job at a charity. This made a huge difference in in that I could spend more time developing my portfolio whilst still having an income. Later that year I got a new part time job at the Association of Illustrators working as an Awards Coodinator which was the perfect fit to complement my freelance work as an illustrator.
Markets and Art Fairs
After the first couple of years of doing portrait commissions and selling cards, gifts and decorations, I realised that I needed to shift my business to be service based rather than product based. I had always enjoyed sketching live and working quickly so I soon discovered the world of live illustration. My first experiment with it was at Caversham Arts Trail which I took part in in the summer of 2022 and 2023. On a whim I decided to start doing live portraits of visitors and their dogs in the garden of the venue I was exhibiting at, charging per portrait. It was a huge hit, and I loved the challenge of drawing quickly, and from there I had got the bug!
Photo of me and fellow artist Sue Bridge at the Caversham Arts Trail in 2022
My next steps were to refine my live portraits to be full lenth fashion illustrations, and to start finding wedding clients. I signed up for some wedding fairs and met some lovely couples who booked me for their weddings in Spring 2023. Once I had examples of the portraits I could create at weddings, amd some lovely testimonials from clients, I was able to update my website and socials and soon started having more live illustration enquries.
Becoming a Live Ilustrator
A live portrait from my first wedding booking in Spring 2023
I illustrated at some beautiful weddings in 2023, as well as hosting workshops (including a fashion illustration workshop at Westfield London), and exhibiting at more art exhibitions and markets, but I knew that I wanted to start working with more corporate clients and retail brands alongside my wedding work.
I hosted a fashion illustration workshop at Wesfield London
In Spring of 2024, after months of emailing and following up with the events team, I was booked to do some live portraits for my local John Lewis for International Womens Day. It was really popular and I had some great feedback. I then I pitched to the events team for all John Lewis stores across the UK and they booked me for multiple events in 2024 to draw live portraits of dogs in stores in Cheltenham, Welwyn Garden City, London, Chichester, Reading and Oxford, to celebrate their stores being dog friendly.
A few of the live fashion portraits I created for International Womens Day at John Lewis in 2024
My focus on pet portraits came from the fact I had seen how popular pet portraits were at markets I had exhibited at so I booked a stall at Dogs Day Out in May 2024 and created lots of cute live dog portraits in just 10 minutes.
Since working with John Lewis I’ve gone on to do live dog portraits for lots of other brands including 1 Hotel Mayfair, Assouline, Butternut Box and more. Most recently I took part in Chelsea Dog Day 2025 creating portraits at ALO on Kings Road London.
Live Dog Portraits for the Chic Dogs book launch at Assouline in Piccadilly London
Weddings and Workshops
My live illustration work at weddings has taken me across the country to Belfast and Edinburgh as well as Suffolk, Herefordshire, London and more locally in Berkshire and Hampshire. I’ve loved all the beautiful weddings that I’ve illustrated at and have always had such wonderful testimonials from the couples who booked me.
Examples of my live wedding guest portraits
I’ve also had the opportunity to teach a range of watecolour and illustration workshops, working with local venues in Berkshire as well as with private corporate clients. I now teach regular seasonal floral watercolour workshops at Micklems Farm in Berkshire, and I have hosted the Flow and Flourish Retreat with Jodie Rose Calligraphy.
I hosted the Flow and Flourish Retreat with Jodie Rose Calligraphy in 2024 and 2025
Press and Marketing
I’ve worked hard along the way to market my work as an illustrator and I’ve built a brilliant newsletter community (you can sign up here) as well as a following on social media and I’ve managed to get a range of press features in local and national magazines, as well as being a regular guest on BBC Radio Berkshire, and last month I was a guest on BBC Radio 4 on the You and Yours Show talking about pensions as a self employed person. I also love being a podcast guest, my favourite so far is the Being Freelance Podcast. You can listen to all of my podcast episodes here.
I was featured on BBC News after being a guest on BBC Radio Berkshire talking about live illustration
Courses and Communities
Something else I’ve invested a lot of time in is taking a range of courses to learn more about how to run my business and develop my illustration portfolio. Recently I’ve enjoyed taking Fashion Illustration courses by Scott W Mason. These have really developed my illustration style and they have also given me confidence to pitch to much larger fashion clients that I would love to work with.
Other courses that I’ve taken include the Hatch Enterprise Business Incubator course this summer which has been fantastic. Hatch is a charity that supports supports underrepresented founders to grow sustainable businesses through programmes, mentoring, and community support. In particuar it has taught me how to plan and pitch for grant funding and investment in my business which I had never considered previously. Did you know that only 2% of investment in the UK is going to female founded businesses? As a graduate of the Hatch programme I’ve been able to apply for a grant fund of up to £5k to invest in my business. If I’m successful I will share more details soon.
I’ve also invested in courses that have helped me improve the marketing of my business, including Design Your Own Branding by Liz Mosley which has helped me fine tune my brand identity; the SEO Explorer Course by Mango and Wild which has really helped improve my website SEO and the Pitch Sprint by Bridie Hinson has been perfect for keeping me accountable for pitching for lots of PR and Press opportunties.
I’ve also joined some brilliant online communities that have helped me stay focused on marketing my business and I’ve also met some fantastic small businesses which has led to some collaborations and new opportunities. These include the Best 90 Days Ever by Hannah Istead, and the Hype Yourself community with Lucy Werner.
Ultimately I think this has been the thing that has kept me going in my business. Building a community of other artists and small business owners that inspire each other and reminding each other to keep going.
If you’d like to keep up to date with my illustration business and see where the next 5 years takes me you can sign up to my mailing list here.
