Jack O'Sullivan: Design Deliberately

Founder and Principal Designer @ Side By Side

by Elizabeth Lavis


07 Jun 2023

Gold Winner in Branding for Graphic Design 2021
 "The solutions we provide can potentially take them to heights they never thought were possible."

For Jack O'Sullivan, Founder and Principal Designer of Side By Side, designing with a goal in mind is one of the critical components to his success. "Three pieces of the best advice I've ever heard are, focus on what you can control, small improvements over a long time lead to a great result, and be deliberate," he says.

Tasmania-born O'Sullivan built a loyal base of clients by fusing creativity and strategy, helping businesses scale and creating meaningful brands that accurately and impactfully tell a cohesive story. His studio, Side By Side, is based in Melbourne, Australia, and has one primary objective; to provide his clients with high-quality designs that make a difference.


A love of design came early to O'Sullivan, who first discovered his knack for and appreciation of design in school. "The course I did in high school was very different from that of my first year of university," O'Sullivan says. "My high school course was more about creating and having fun; essentially just using the computer to create art or complete projects like album covers and magazines. It was at university where I learned that things like kerning existed." 

Despite the learning curve and his self-doubts, O'Sullivan quickly realized he was on the right path. "I'm so glad I chose to pursue design as a career," he says. Although O'Sullivan doesn't deal with much tough client critique, thanks to his policy of setting clear expectations upfront, he suspects that he'd see it as a misunderstanding about the project. "If a client did have harsh feedback, I'd listen to what they're saying and why they might be saying it," he says. "Criticism usually arises if people are not on the same page due to a communication breakdown. Communication is crucial when defining the direction, deliverables, and desired outcome of the process."

Ultimately O'Sullivan's process breaks down into four basic steps; discover, distill, design, and deliver. He starts by thoroughly understanding the clients' needs in their truest form, then develops a strategy to bring the design to fruition. "Each project is different, but those four steps are consistent," O'Sullivan says.  

He also makes ample time to play, experimenting with humor and creativity in his personal projects and giving his all to exceed client expectations. "Designers can make a significant difference in their clients' lives," O'Sullivan says. "The solutions we provide can potentially take them to heights they never thought were possible."

O'Sullivan uses pressure as a catalyst to spark his creativity, noting that "decisions happen faster, which results in momentum for the project." He also stresses the importance of balancing pressure and a creative outcome, straddling the line between productivity and anxiety. For O'Sullivan, some reliable tools of the trade are also vital for keeping him focused. "I can't live without the Adobe Suite for most jobs," he says. "I'm slowly learning Figma for digital and web projects, and I use Notion for project management and Spar for email." Noise-canceling headphones give him uninterrupted mental space to concentrate and work.

When O'Sullivan isn't busily creating epic designs for his clients, he's indulging in great food, boxing, photography, music, or a round of pints with his mates.

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