We recently connected with Kelly McDowell and have shared our conversation below.

Hi Kelly, thanks for joining us today. Can you open up about a risk you’ve taken – what it was like taking that risk, why you took the risk and how it turned out?

I’ve been building events since I was a teenager. The first one I ever ran was a Battle of the Bands at a local fair — and somehow, from that moment on, organizing creative things just kept showing up in my life.

I studied business communications and public relations in school, but I cut my teeth in the event world working with major organizations like Molson Indy and Snow Jam, flying across Canada and the U.S., and later helping the (then tiny) Whistler Arts Council grow a small in-school event into a major arts and tourism draw.

But nothing — and I mean nothing — compares to starting a festival from scratch. No name, no legacy, no blueprint.

That’s exactly what I did in 2024 when I launched the Dufferin Film Festival in Orangeville, Ontario.

There was no big team. No major sponsors waiting. Just a lineup of bold Canadian short films, a tiny crew, and a vision: that this small, artistic town could become a place where filmmakers and audiences connect in meaningful ways. I wanted it to feel intimate and accessible, but still professional — the kind of festival where a new filmmaker might have their first big screening, and an audience member might walk away rethinking what Canadian film can be.

It was a massive risk.

I’ve worked in film production for years — directing, producing, running Rose Digital Media Group with my partner — so I wasn’t naïve about the work involved. But this felt different. With other events I’ve worked on, there was always some kind of infrastructure: a brand name, a budget, an audience. With this, we had to build all of it from the ground up. No one could see the vision yet. People didn’t know what the festival was going to look like, or if it would even come together.

For the first two weeks after tickets went on sale, we sold exactly zero. I had over a thousand seats to fill and no momentum. That was the moment I questioned everything. I thought, “What have I done?”

But then, the tides shifted.

Events started selling out — even as people around town were still telling me they hadn’t heard anything about it. And I remember walking out on stage at our very first screening, the host invited us up to say a few words, and I looked out at the packed house and just said, “Wow… you really came.” It was like throwing a party and being terrified no one would show up — and then suddenly, the room is full and buzzing with energy.

That’s when I knew: it was working.

Almost every event that weekend sold out. Filmmakers drove in from all over the province and across Canada. Audiences stayed after the credits rolled, asking questions, swapping insights, having real conversations. And more than once, I heard, “This doesn’t feel like a first-year festival.” That meant everything.

The biggest lesson I’ve learned? You have to let go and trust. We had a reason to believe this festival could work — this region is full of creative energy, and Canadian filmmakers need more platforms that celebrate them. But I had to keep coming back to that belief, especially when things felt shaky.

Now, in year two, we’ve doubled our programming. We’ve added special events, big-name speakers, and new venues. But the soul of it hasn’t changed. We’re still here to connect filmmakers with audiences. We’re still grassroots. And we’re still working to earn our place — because let’s be honest: there are a lot of festivals out there. It’s hard to get filmmakers to take a chance on something new.

But we’re doing the work to show them that this is a festival built for them — not just a showcase, but a space to network, grow, and build momentum. For film lovers, it’s an incredible chance to experience the talent of Canadian filmmakers up close, ask questions, and be part of something exciting and real.

Dufferin Film Festival has the vibe of a large, professional event — red carpets, sold-out screenings, live jazz under the stars — but it’s built from the ground up with heart, accessibility, and community at the core. That’s what makes it special. And that’s the kind of festival I’ll keep fighting to grow.

Taking this leap was scary. But it brought every part of my life — my creative work, my event background, my love of film and community — into focus. And if I’ve learned anything, it’s this:

You won’t feel ready. Do it anyway.

About me:
Kelly McDowell is a filmmaker, producer, and the founding Festival Director of the Dufferin Film Festival. She runs Rose Digital Media Group with her partner and has a background in film, storytelling, and large-scale event production. Based in Orangeville, Ontario, she is passionate about building platforms that amplify Canadian voices and connect audiences through authentic storytelling.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I’m a filmmaker, producer, and festival director based in Orangeville, Ontario. With my partner Nick, I run Rose Digital Media Group, a boutique video production company, and together we create cinematic, story-driven content for businesses, nonprofits, and creatives.

My path into this work started early. I’ve been building events since I was a teenager (my first was a Battle of the Bands), and I spent years working behind the scenes on large-scale productions like Molson Indy, Molson Snow Jam, and with the Whistler Arts Council. I studied business communications and public relations, but most of my education came from real-world producing — flying across the country, growing arts events from the ground up, and learning what it takes to bring big ideas to life.

I also have a background in acting — both on stage and in film — which has shaped the way I approach storytelling. I understand what it’s like to be on the creative side, and I bring that perspective into every project I produce or direct.

At Rose Digital, we focus on crafting videos that feel authentic and impactful — whether it’s a branded doc, a community story, a corporate campaign, or a live-streamed event. I’m not just a “videographer.” I’m a producer who helps clients shape the why behind their content, then delivers something beautiful and strategic.

In 2024, I launched the Dufferin Film Festival — one of the biggest risks I’ve taken and also the most rewarding. We sold out our first year, brought in filmmakers from across the country, and proved that a grassroots festival could feel both intimate and cinematic. My goal is to grow DFF into a nationally recognized platform for Canadian storytelling, while keeping it grounded, accessible, and community-focused.

What sets my work apart is heart. Whether I’m producing a client video, directing a film, or organizing a festival, I care deeply about creating space for real stories, real connections, and real opportunities.

As a mother, entrepreneur and fellow creative I try to carefully balance my work, personal and creative endeavours..

Is there a particular goal or mission driving your creative journey?

When I was in high school, I told my guidance counsellor I wanted to be an actor. Their response? “That’s great — but what do you want to do for a career?” I was steered away from creativity almost immediately. I was told it wasn’t sustainable, that it wasn’t realistic, and that I needed a backup plan. That led me to university for business communications, then a postgraduate program in public relations, and then into a career at Molson Sports & Entertainment — which, thanks to a connection, gave me the incredible opportunity to work on major events right away.

I leaned into event work because it came naturally — I’d been running events since I was a teenager. It gave me purpose and drive, but it never quite filled the creative gap I had inside. I wasn’t acting. I wasn’t painting. I wasn’t dancing. I wasn’t creating. I was just… producing.

It wasn’t until I was in my 30s that I finally had the perspective — and the courage — to realize that I could have a creative career. That acting didn’t have to mean Hollywood or Broadway. That you could work on indie films, commercials, or community stages and still be an actor. That directing and producing your own work was just as valid — maybe even more powerful — than waiting for someone else to give you permission. I realized I had been taught to undervalue the thing I loved most.

That realization changed everything. I started exploring creative work again — both in front of the camera and behind it — and it felt like coming home. All of my “non-creative” experiences, from university to corporate work to motherhood, have only made me stronger in this space. They gave me tools, perspective, and resilience. And raising two kids — including one with autism — has completely reshaped the way I see the world, and the stories I feel called to tell.

The vision that drives me now is simple: create the spaces I didn’t have. Whether it’s through Rose Digital Media Group or the Dufferin Film Festival, I want to help build a creative ecosystem where people — especially Canadian artists — feel seen, supported, and understood. I want filmmakers to know there are real opportunities out there. I want audiences to feel the power of homegrown storytelling. And I want emerging creatives to know that yes, this is a viable career. It always was.

Do you think there is something that non-creatives might struggle to understand about your journey as a creative? Maybe you can shed some light?

Absolutely. I think one of the biggest things non-creatives struggle to understand is that this is a real career — and it takes just as much work, skill, and strategy as any “traditional” job. When people hear “filmmaker” or “festival director,” they often picture red carpets or someone with endless free time making art “for fun.” They don’t see the 14-hour editing days, the midnight grant applications, the unpaid labour that goes into building a reputation from scratch. This can be true for every area of the arts.

There’s also a misconception that if you’re not famous or on a big stage, it’s not valid. I was taught that too — that acting, for example, only counts if you’re on Broadway or in Hollywood. That’s just not true. There are so many ways to be a working creative: indie film, commercials, regional theatre, storytelling events, producing your own work, building a company. That’s what I’ve done — and what I want to keep showing others is possible.

And when you’re also a parent, particularly raising a child with autism, people really don’t see how much invisible work you’re juggling behind the scenes. The emotional bandwidth it takes to raise a family, run a business, and still fight for your creative voice to be heard — that part doesn’t always get talked about.

The truth is: being a creative means wearing many hats. It means constantly proving yourself. It means being resourceful, vulnerable, and persistent — often without a roadmap. But it also means you get to make something real from nothing. That’s what keeps me going.

Contact Info:

• Website: www.dufferinfilmfest.com & www.rosedigitalmg.com
• Instagram: @kellyannemaki @dufferinfilmfest @rosedigitalmg
• Facebook: https://www.facebook.com/kellyannemcdowell/
• Linkedin: https://www.linkedin.com/in/kelly-mcdowell-b26506123
• Yelp: https://www.yelp.ca/biz/dufferin-film-festival-orangeville
• Other: I shared DFFs links and my own in a mix.. I’m not sure which you were looking for

Image Credits

Nick Rose
Remy Rozo