Clare Brennan / Creative Director / Ottawa, Canada

Clare Brennan, Creative Director and Co-Owner of FIFTY Strategy + Creative, as well the founder of Creativity in Common.

Creativity is a muscle, one that you strengthen with use, like all muscles. Flex it, stretch it and push it. It’s what we all need to do if we want our creativity to grow.”


Thanks so much Clare, for taking some time to share some insights and to answer a few questions about creativity and your career in advertising!

How long have you been a creative director and did you always feel drawn to a creative career when you were young?

I have been a Creative Director for over 20 years now, yikes. I was always drawing and looking at architecture and sculpture. It just kinda led me to a job where I could be creative and make ends meet.

As an advertising agency owner and a creative director, how do you blend creativity and entrepreneurship?

Well, what I sell is creativity. So as an entrepreneur, if the product isn’t creative it’s not selling and that’s bad for business. So I guess that’s at least how I see the two connecting.

What motivated you to start your ‘Creativity in Common’ project.

I’ve been teaching creativity as a first year course to advertising student for the last 12 years or so. After putting together all this information on methods to ignite creativity I thought I could find a way to pass it to people outside of my classes. To get more people taking the creative risks they have always wanted to.

Is everyone creative or capable of creativity?

Absolutely. A lot of people feel creativity is something you are born with, kind of an accident of birth. Or a bolt of inspiration that strikes if you are lucky. But creativity is available to us all. The first step is believing you have the capability to create and then go do it, and repeat. Creativity is a muscle, one that you strengthen with use, like all muscles. Flex it, stretch it and push it. It’s what we all need to do if we want our creativity to grow.

How helpful is collaboration to creativity or is it more of an independent process?

It’s both, but with the help of others, our creativity just has so many additional options for growth. Other people push us to reach higher and consider new possibilities. They can also be the support we need to take a creative risk or augment our skills to make things we couldn’t do on our own. My best work has always been aided with the support and creative strengths of others.

What are the similarities when marketing a person with a headshot vs marketing a company?

With either one, the audiences should feel the message is real. Whether a person or a large company, people want to believe in what they see and read. People are smart, they can tell when it doesn’t ring true. Person or company, I got to trust the image being projected.

What advice would you give to your younger self as a creative professional?

Creativity flourishes in a team. This isn’t about your ego or how good you are, it’s about how good your team is. A great team will always lift the members to produce better work. That’s what I tell my students because that’s what I wish someone had told me.

What are the qualities you look for when hiring a photographer?

Openness, creativity, a great ability to make the subject feel comfortable and at ease. Someone who sees my client to be as important as I do. And someone I want to spend a day with, so you better have some good stories.


How does empathy play in the process when mapping out the creative direction for a new campaign or marketing initiative?

You need to understand your audience and what motivates them, and your client is part of that audience. Both are people with a need to be respected and be understood. Empathy lets us do both and build a campaign that talks to someone other than yourself.


How do you kindle your inspiration and curiosity to be more creative?

As I said earlier, creativity is a muscle and you do have to work it to make it stronger and stop it from getting all flabby. So, I fill my life with creative stuff both industry related and personal. From listening to smart, seasoned creatives to working with a classes of young creative folks. Or from collage work to found object sculpture. It’s a contrast process to add creativity into my life.


How critical is mindset in your day to day as a creative director? Do you do anything specifically when starting your day to be more open to new ideas?

Carol Dweck did all this great research into having a growth mindset. She has all these great stuff about looking at creativity as something to constantly gain mastery of as opposed to becoming an expert at. I do my best to start every project thinking I can always learn more and if that is how I start my creative day it leaves me open to new thoughts and ideas and opportunities.

Lastly, in your opinion, why do headshots matter?

We are attacked by so many images every day and the ones that stand out for me are the ones that show authenticity and reality. A great headshot should just do that, so I can begin to trust the subject. Trust is what we are looking for, that’s what I hope to see in a good headshot.

Thanks so much Clare, for giving us a glimpse into your world of ads, brands and fun creativity!

Please take a moment to learn more about Clare’s work at: FIFTY Strategy + Creative

Dwayne Brown


Dwayne Brown has dedicated his adult life to professional photography. Throughout this extensive career he has had the opportunity to photograph a diverse array of people in many places, contributing to his personal and professional growth. His continued curiosity and desire to craft excellent imagery fuel his passion for headshot photography.