The Side Show: Q&A With Brand Strategist Gabriella Rackoff

By Minda Smiley 

Over the next few weeks, we’ll be showcasing side projects thanks to our ever-so-formal partnership with The Side Show, a new awards program that’s only doling out prizes to creative endeavors done outside of work.

That’s right—push your client work aside and show off the cookbook you cobbled together this summer in your studio apartment. Or your quarantine fashion blog. Whatever it may be, The Side Show wants to see it. “Best in Show” winner will receive $500. Submissions are $10 a pop and the deadline is Oct. 9.

Until then, we’re spotlighting some of this year’s entrants and their projects. Today we’re featuring an interview with Gabriella Rackoff, a freelance brand strategist. She and Zoe Share recently collaborated on a children’s book called ABC Stay Home With Me.


“ABC Stay Home with Me is a children’s alphabet book about the pandemic,” Rackoff said in her entry. “We worked with 13 Canadian illustrators who each illustrated one spread. Each letter represents a different element of our new reality in a lighthearted, fun-to-read way. Each page has its own style, and one of the illustrators defined the color palette for the rest to follow to provide cohesion.”

According to Rackoff, proceeds from the book are going to The Home Front, an organization dedicated to supporting front line healthcare workers.

What do you love most about your side hustle?

I love that I got the opportunity to work with so many amazing illustrators. I’m really into design and illustration, so doing the research to find these illustrators was really enjoyable.

How has your side hustle made you a better creative/professional?

It was really good practice in moving fast and making an idea reality without overthinking it. I was afraid someone else would do a book like this if I didn’t. It also helped me promote myself. I’m generally reserved when it comes to posting about my achievements, but this was something I really enjoyed sharing.

Has your side hustle helped you land a job? If so, how did that happen?

It has! I ended up doing a contract with Zoe Share, whom I worked with on the book. We had gotten to know each other over the years from the agency/tech community, and she brought me on to help her with some brand strategy work she was doing on her social media agency. I’ve had some amazing feedback on it in interviews.

How do you draw the line between a healthy side hustle and always-on hustle culture? How do you prevent burnout?

For me burnout comes from thinking I’m not doing enough and I need to be more successful. I think it’s about making sure you’re being served by what you put energy into and reassuring yourself that everything you do adds up and moves you forward.

If you could turn your side hustle into a career, would you? Why or why not?

Aspects of it, yes. Many people have asked me about the next children’s book I’m going to write, but I don’t think of myself as a children’s book author. For me it was about the idea and the very specific timeliness, the art direction and illustration, and making it real. Creating things that resonate with people is integral to my career in building brands.

What is your dream agency or brand-side advertising job?

I love laying down foundations for new brands. A dream job would be working at a venture studio with founders to launch new products.

To find out more about The Side Show and submit an entry, visit its website here