“As a designer, you always have to evolve. It’s not the kind of job that once you’re in, you can sit back and say, ‘Okay, I made it’ – because technology’s always changing and there’s always new trends you need to stay on top of.”
For Greenwood, the journey from “artsy kid” to successful graphic designer wasn’t the most linear of paths.
“I look back at it now and I kick myself. I couldn’t make that connection between pursuing something I loved, something that fulfilled that creative muscle in me, and equating it with how I could pursue it as a career,” he explained.
“It was always there, but I didn’t see it as a possible job.”
It wasn’t until after earning his Bachelor of Arts in English and trying his hand at becoming a writer – a pursuit he ultimately found too “loose” for his practical sensibilities – that Greenwood found a niche for himself in non-profit communications work.
While working at the Writers’ Trust of Canada from 2004-2008, Greenwood was tasked with designing various print and digital marketing pieces on behalf of the not-for-profit champion of Canadian writers.
“I found other ways of storytelling by working with images and typography and illustrations and all those other things design encompasses,” he said of the experience.
After leaving the Writers’ Trust, Greenwood moved into a communications role at the AIDS Committee of Toronto. There, he designed annual reports, campaign materials, and “key pieces” for high-profile events like the annual AIDS Walk and Fashion Cares.
“Fashion Cares was a huge event and the work I did on it – including a video that premiered at the last event with Elton John – was really visible,” Greenwood said, noting that, following the event, he began to pursue freelance work with other organizations like CAMH and CATIE.
After winning a Social Good Design Award in 2012, Greenwood become involved with the Association of Registered Graphic Designers – an organization he credits with giving legitimacy to his work as a “quote-unquote self-taught designer.”
“It was a bit of a long haul for me and certainly it was a challenge not having a formal art background…but the support of RGD helped push my career forward,” Greenwood said, noting that he joined as an affiliate member in 2012 and then became a certified member of the association in 2017.
In 2014 Greenwood began work as the lead designer for the National Ballet of Canada.
“It was really high profile work – work on side of streetcars and on billboards in the middle of downtown Toronto,” he said, admitting his Ballet experience was both rewarding and terrifying at the same time.
“The reward of a designer is to have the opportunity to collaborate with amazing people like art directors and photographers – to take their work and make it fit within the brand of an established brand. To be responsible for all of that and then put the results on the side of a building – it was really satisfying to see.”
After two years at the Ballet, Greenwood was ready to tackle his next challenge – teaching.
While speaking with a friend who taught video editing at Toronto Film School, Greenwood was intrigued to learn the school was looking for graphic designers to help develop and teach some brand new online courses that were just being rolled out at the time.
“That was really exciting to me, because I thought there was a real opportunity there to be involved in something that was new and would help shape the school as it moved forward,” he said of joining TFS in 2016.
In the Drawing I & II courses, Greenwood leads online students on an exploration of the fundamentals of Adobe Illustrator, then oversees them as they apply their newfound Illustrator skills to real-world applications – such as packaging design, infographics and 3D art.
During the Portfolio course, meanwhile, Greenwood works one-on-one with final-term students to help them learn how to market themselves as designers.
“I work closely with the students to understand what kind of design they’re interested in doing and what kind of jobs they’re interested in pursuing,” he said.
“Then we work to put a portfolio together that best represents who they are as a designer. It’s very much personalized and each portfolio is unique to each student.”
For Greenwood, perhaps the most rewarding facet of his teaching job at TFS is being able to personally relate to his students’ struggles and offer them the hard-earned advice he picked up along his own road to success.
“I’ve already been through a lot of what they’re going to go through – I’ve embarrassed myself at interviews and I’ve done really amazing interviews; I’ve fought for a lot of jobs, and I’ve not gotten some jobs and gotten other jobs,” he said.
“So as much as I can, I try to give them advice – but for the most part, I’m really just trying to be a cheerleader for what they want to do. It’s a very competitive field, so you have to be scrappy, embrace every opportunity, and fight for your place at the table.”