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Dream Teams: Owen Bryson and Anna Paine Work Hard, Play Hard, and Laugh Hard

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The Dig Agency Creative Directors speak to LBB’s Delmar Terblanche about friendship and finding truth in their work.

Dream Teams: Owen Bryson and Anna Paine Work Hard, Play Hard, and Laugh Hard


There was a dog in the room when I spoke to Anna and Owen, and they were only too keen to show her off. As they kept reacquainting me with their four-legged co-worker, the three of us found the interview collapsing more than once into laughter and coos of adoration. There was joy in the room, and, when we drilled down into the pair’s working relationship, there was joy there too.

“I sometimes refer to Anna as my work wife because, honestly, it is like being a married couple sometimes,” remarked Owen, to which his professional partner replied: “You get to go into a meeting with someone who’s got your back all day every day. I think that’s pretty cool.”

Anna Paine and Owen Bryson have been a team for 10 years now. Having met at Media Design School in Auckland, the two made a name for themselves at DDB Sydney, where they spent seven years (in Anna’s words) “working our arses off”.

They’ve recently joined Dig Agency, where they’re relishing what Owen describes as “the freedom and autonomy an independent gives you.” Anna elaborates, explaining “We like to be involved in the building of a great agency… We loved our time at DDB, and we learnt so much, but we’re excited by the new.”

Before signing on as creative directors with Dig, Anna worked as an art director and Owen as a copywriter. Together, they developed a system for wringing the unusual and the unexpected out of every brief.

“The first person you need to sell it to is yourself,” says Anna. Owen adds that they try to “treat the audience like they’re humans,” before asking “What are the obvious ideas? What first comes to mind? Then find fresher ground.” 

This ties into what both describe as a “shotgun” approach; exploring as many ideas as possible in as quick a space as possible, before zeroing in on the odder standouts. As Owen puts it, “do what’s expected. Then don’t.”

The two literally finish each others’ sentences as they describe their process. It’s clear they’re a duo who operate on a unique level of creative harmony. Both have their theories as to why.

Owen claims “I’m a big kid. And Anna is the voice of reason. Like if you don’t tether a helium balloon it floats away, and that’s no fun for anyone.” True to her partner’s description of her, Anna’s answer is more pragmatic. “Owen is a far better copywriter than I could ever be, and they always say you should surround yourself with people who are better than you. Also, we’re both no-bullshit.”

Asked to summarise their teamwork, the pair give a simple answer. “Our greatest strength is giving each other strength.”

Elaborating, Owen claims that with every big, challenging brief he “usually goes through the 7 stages of brief grief (denial, anger, acceptance etc),” while “Anna’s raw confidence in our abilities always gets us through it.”

“I think both Anna and I are natural problem solvers,” he says. “There honestly is no better feeling than cracking a brief - it’s quite an addictive high.”

This gets to the heart of what it is the pair love about their work. They see working in advertising as, essentially, an act of creative problem solving - identifying a human need, and then serving it in the most creative way possible.

“What I love about advertising,” Anna explains, “is how much of it is a study of people. How you have to understand the psychology behind any brief.”

The creativity helps too.

“Anna can get excited about typography on a beer coaster,” Owen laughs. Anna laughs too. We all laugh. It’s beyond clear just how in sync this creative pair is - how they admire one another’s strengths; how they bolster one another’s weaknesses; and how they’ve spent a decade bringing out the best in each other.

Any advice for budding creative partnerships?

“Stick with it.” Anna says. “It gets better.” Owen laughs, recalling long hours and grinding work schedules, and then adds something taught to them over 10 years ago at Media Design School. “Follow the work, not the money.”

The pair’s loyalty to each other, and to honest creativity above all, shines through. Dig, and indeed Sydney itself, is lucky to have them.


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Dig Agency, Wed, 07 Dec 2022 04:57:51 GMT