Hamilton artist turns doodling hobby into a business

You may not have heard of Jenna Gregory, but you’ve probably seen Jenna’s Doodles. Hamilton artist Jenna has been drawing guests’ portraits for the Mike on Much Podcast for the past four years, and her work can be found in shops across Hamilton and beyond. She also has an exhibition on display at Mulberry Coffee House on James North until June 10.

I met up with Jenna recently to find out more about her business journey from a doodling dream to small business owner.

What’s the story behind how you started your business?

After graduating from Graphic Design I figured I would work in a design agency, but instead took off to travel New Zealand for 8 months. It was one of my two best life decisions, and New Zealand has become a huge inspiration for a lot of my work. When I returned I struggled to find work in my field and fell into a couple administrative jobs while also working at a pub. For administrative work it was pretty awesome. I worked for a comedy agency, followed by a music agency. Both things I loved, but deep down I was brokenhearted that I wasn’t in a creative role. To stay in tune with my creativity I started a self-project “Jenna’s Doodle-a-Day”. I’d use my lunch break or time at the front desk of the pub to draw and then I’d post it online. Interest started to grow and people started asking for custom work. It was through these jobs that I met many incredibly talented people who were running against the grain and chasing these “dream jobs” that most think are impossible. I was inspired by their off-the-beaten path ways and it gave me the courage to eventually try it myself.

A friend recommended moving to Hamilton to start my business. He said the arts community was very supportive and living was affordable. So that was that, in September of 2014 I quit my job, loaded up the U-haul and moved here to try to build a business from practically nothing. I didn’t know anything about Hamilton. For the first couple of months I was really excited, then realized I didn’t know what I was doing and thought I had made a huge mistake and started to get really depressed. But I knew I had to keep trying to put the pieces together, so I chipped away and pushed myself to get more involved with the arts community. After taking a part-time job at the Art Gallery of Hamilton my social network expanded at a surprising rate and all of the pieces started falling into place. That was May of 2015, and since then the wheels have continued turning and now being an Artist is my full-time job. I am so thankful that I took the leap, and moving to Hamilton to do it was the second of the two best decisions I have ever made.


What are some of the pieces that fell together that helped launch your business?

I’ve had some wonderful opportunities designing artwork with some great Canadian musicians, including former Great Big Sea member Séan McCann, Pat Maloney, Shawn Kerr, My Father’s Son, and Tragedy Ann. All lovely and amazing people. Collaborating with musicians has been one of my favourite areas of custom work. One of the first larger projects to come my way which has become an ongoing project for about four years now, has been working with fellow Hamiltonians Mike Veerman, Max Kerman and Shane Cunningham on the “Mike On Much Podcast“. I have had the wonderful opportunity working with them from the get-go drawing the portraits of their guests. If you haven’t listened to it, I highly recommend it.

What advice do you have for someone wanting to start a business?

Find people who are doing what you want to do and ask questions. Whenever I meet someone who says they would like to do what I am doing, I always encourage them to email me and ask questions. I am more than happy to share what I’ve learnt or where I get supplies to help them save time researching. I think if I had of done that, maybe I wouldn’t have felt so overwhelmed in the beginning when I was starting out. Another piece of advice that a friend gave me years ago, when you are meeting someone new and making small chat, try to find a smooth way to mention what you are working on or goals you are trying to reach. People generally want to help others, but if they don’t know what you are doing, they won’t know how to help.

What business tool could you not live without?

Though it seems obvious, the internet. It was the first place I really saw strangers connect with my work and started thinking that maybe people would buy my work. Also, as an introvert I find it difficult to knock on doors asking people to wholesale my work, and having access to find stores online and contact them through email makes it much easier.


What do you love most about Hamilton?

I love how much nature surrounds the city. I love hiking, and nature is a huge inspiration for my work. There is a wonderful balance having all of the amenities of a city, but also the ability to escape into a peaceful place. And, my friend was absolutely right in saying that there is an incredibly supportive arts community here. In all of the places that I go to do shows, there is something extra special about Hamilton.


You can find Jenna’s greeting cards and prints on her website at JennasDoodles.com and in select retail locations across Ontario, including The Hamilton Store, Art Gallery of Hamilton, Mixed Media, Cake & Loaf, Pretty Grit and True Hamiltonian.

Check out Jenna’s current exhibition at Mulberry Coffee House, in conjunction with fellow artist Jenna Shamoon. On til June 10!


Instagram: JennasAdventureTime

Facebook: Jenna’s Doodles

Website: JennasDoodles.com




-Suzanne, The Generator

Share Article:

Hamilton artist turns doodling hobby into a business


Keep Reading

Today's Leaders for Tomorrow's Future

The Human Touch of Social Platforms

In a recent episode of Today’s Leaders for Tomorrow’s Future with Amanda Calzolaio, Suzanne Zandbergen shares her passion for social media platforms as a medium

The Generator turns 10!

It’s officially 10 years in the books for The Generator! On March 28, 2024 we marked our 10 year anniversary, and celebrated with a tea