Twenty Years Ago this month I made one of the biggest decisions of my life! I officially started my art business. It was October 2006 and I was stressed leading a team as the Fleet Supervisor of a trucking division for a chemical company. I was driving part time, supervising, and my blood pressure was through the roof! Although I was successful at my job I was not enjoying it anymore. It had been a long road to that point and due to an incident at the office I made a decision on the fly to quit my job. I had had enough! I was 43 years old and hated fighting with a team that I was trying to support! On a Friday afternoon I finally threw in the towel and sent an email to my Boss and his Boss that I was giving them my two months notice and would be done at the end of that year. The next question you’re going to ask is, “What did your Wife say?”

My Wife had been blind copied on that email, we worked at the same company and she knew the stress I was under, it was a nightly conversation. That night I decided to work for myself and promised her that if I wasn’t successful in my business I would go back to driving trucks. So how did I start an art business from nothing? I had technically started it three years earlier as a part time venture. I was doing commissions for friends, neighbours and had my very first art show at the Oakville Art Society in 2003. I joined a couple art groups and built a small studio in the basement of our home. I didn’t know it but I had been working up to a full time business for three solid years. Until now an art business had been just a dream, a dream that started back when I began drawing at 10 years old. But here’s the problem!

I was doing fine pen and ink landscapes at the time and the art world was going digital. I also needed to pay the bills at home, I was five years into a new marriage and new home. My mindset is as long as you are working in the arts you can say your a professional artist. To bring in money I started teaching art classes at the same art group where I had been taking classes. I taught beginner classes in painting and drawing, teaching almost eight hours per day at all hours. I also went back to adult night school learning web design, photoshop, digital cameras, business, and more. I joined art boards, attended workshops, and learned social media. Not only was I upgrading my skills but I was meeting people at the same time, many of those hiring me for gifts and small projects. It wasn’t really a plan but a race to build my art business as fast as I could, with the help of my Wife we got started!




Then 3 years later something changed, I created a comic book series for kids. In Oakville Ontario there are many talented landscape artists but very few comic book artists. I used my trucking background and philosophy of life lessons from the road to create the PRIDE JUNKIE Comic Series. The Pride stands for PASSION, RESPECT, INTEGRITY, DIGNITY, and EXCELLENCE! All of these elements have been important in my life and I wanted them to be the lessons behind the stories. Each issue took 6 months to create as I was doing all the writing, artwork, production, and marketing and only able to create one issue per year. I created three issues which you can now read online before it became too much to continue, but it did teach me some valuable lessons. It taught me how to create a comic series and what it takes to market one. It gave me credibility in my art classes and I even switched to cartooning classes for kids and stopped doing landscapes. The classes also brought in private lessons for students, one private student I taught weekly for two years. The real benefit was it launched my caricature career!









I had always admired caricature artists but didn’t really think of that as a career. Heck when I started my business I didn’t know it would be a career at all! In my art classes I began getting asked to draw for birthday parties and because I didn’t know that was a thing I turned them down. Finally one day I said, “Yes” and began practising like crazy at home and learning from every book I could get my hands on. I did a couple of events and then found ISCA (International Society of Caricature Artists) where I am still a member to this day. The organization offers networking, conferences, and instruction for caricature artists. I attended conferences, read and learned all I could, and slowly moved my art business to caricatures only. Today I specialize in caricature entertainment for weddings, corporate events, and parties.











What’s it like to be 20 years down the road? Our business has changed and is about to change again. We have added more services through our other divisions under our corporate name Outridge Enterprises Inc but still enjoy drawing caricatures. I love meeting new people and have found our groove in the wedding market. I look forward to continuing that into my later years.

As I close I would like to say thank you to all of you that have hired me, believed in me, and supported the business. There have been a lot of great memories over the years and hopefully many more to come. If you are someone thinking of starting an art business you will only succeed if you take the step and do it! Work hard and don’t be afraid to try new things, it may just help you do what you love. It did for me!
About the Author
Bruce Outridge has been a professional artist for over 20 years. Coming from a trucking background today his art business focuses on caricature entertainment for event, gifts, and more. You can learn more about Bruce and his work at www.bruceoutridgeproductions.com