Every Painting Has a Story: January 2024 – My Childhood Art

Hello friends, welcome to the first blog post of 2024! In previous years, I shared backstories to paintings featured in my calendars but this year will be a little different. Throughout 2024, I will be featuring some of my past work that will never make it into calendars and maybe not even onto social media. (Gasp!) Consider it a backstage pass to my artist life. I hope you enjoy what I have in store!

When I was planning the blog topics for this year, I thought why not start from the beginning? My mom had kept a folder with some of my earlier work so I have a few examples I can share. When I look back at my early art, I wouldn’t suspect that I would become an artist later. But I do recall always enjoying drawing and painting ever since I was young.

The earliest drawing I have: my family. (Drawn in crayon at 5 years old)

The earliest drawing I have is this crayon drawing. My mom noted who the people in the picture were. I have included my cousin (who was a young adult living with us at the time), my dad, my mom, and me, all wearing what appear to be party hats. In the top left corner I have included a yellow sun with radiating rays, some blue to indicate the sky at the very top of the page, and five rather large birds. On the ground is a flower and we are standing next to a yellow house. I’m guessing I drew this when I was around 5 years old.

6 year old Olive pointing to her painting on display.

I also have this photo of me standing proudly pointing at a painting on display. Judging by my buck teeth and pigtails, I would say I was around 6 years old here. I can’t tell what my painting is about but there are quite a lot of details. I also know that rainbows were a recurring theme in my art around that time.

Watercolour Rainbow 1 by Olive (6 years old)
Watercolour Rainbow 2 by Olive (6 years old)

These next two paintings were from Grade One (6 years old) and they also feature rainbows. It’s interesting to see how some 35+ years later, I’m still painting rainbows! Grade One was also when I got my earliest positive response and affirmation of artistic talent. Unbeknownst to me, my teacher had submitted one of my drawings to a contest for the Ontario Dental Association and it had been chosen as a cover for one of their brochures. I used to have a copy of that brochure but it has since been lost. Along with my drawing being chosen as cover art, I received a prize of $500 – which in 1987 was a big deal! (I think my parents donated the money back to the school.)

Watercolour Tulips by Olive (10 years old)

By Grade 5, I can start to see a more refined sense of aesthetics come out in my work, as this tulip painting shows. I have a couple workbooks from that year and in my drawings I started to include elements of shading.

Funny monster drawn in marker and watercolour by Olive (12 years old)

By Grade 7, I definitely knew that I enjoyed art. This is one remaining drawing I have from that year – a fantastical monster that is both silly and colourful. I had the same art teacher for Grades 7 and 8 and when I told her I wanted to audition for a fine arts high school, she spent extra time at lunch and after school to help me prepare for that. (Thanks, Mrs. Shadrach!) She had no idea that getting into that school would pave the way for my future career.

There you have it. How my art journey started.

I don’t have any reflection questions this month but if any of my art from childhood connects with you, feel free to spend some time with it. Also, I would love to hear what you might see in my earliest work. Thanks for reading along. I look forward to sharing some of my high school work with you next month!


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As always, I love to hear from you! If something in this story resonated with you, if you’re interested in commissioning a painting, or if you have other thoughts, feel free to email, or connect with me on Facebook or Instagram. Thanks for being part of my journey and for letting me be a part of yours!