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27 April 2023 5 min read

Finding the Russian on the internet was the breakthrough Oliver Shepherd had been waiting for.

Lawyer by day, painter by night, Oli didn’t have any formal training in fine art. Yet, he was undoubtedly in love with it.

He had bought his first set of oil paints after watching Girl with a Pearl Earring. The 2003 film starring Scarlett Johansson as Griet, a young maidservant in the household of the Dutch painter Johannes Vermeer. Oli still remembers being mesmerised by the grinding of the raw pigments, the mixing of the oil and a conversation in the film about how to really see a cloud. Was it just white? Or was it yellow, blue and grey?

Coming home, Oli tried to recreate that magic on his canvas, to mixed results.

Oli has spent years studying the techniques of painters he admires such as Caravaggio, Vermeer and Da Vinci.

“It was all crap. I loved it but it was pedestrian at best,” he admitted.

Meanwhile, Oli still wanted to pursue a career as a lawyer. This would eventually lead him to his day job with us as a Legal Counsel in Enterprise Legal, within our Governance business unit. Landing the role meant he could enjoy painting as a passion rather than a profession.

Still, Oli was ambitious. He wanted to paint like Caravaggio, Vermeer, Da Vinci and Bosch, the great masters he so admired. He just didn’t know how. Then he found Alexei Antonov, AKA Artpapa.

A Russian master painter, Antonov had a lot of advice to offer his audience – don’t listen to modern music when you paint, don’t look at bright colours and try the Flemish technique.

Oli took on one of those suggestions and dropped the rest.

Seven-layers deep

Cut to 2023, and Oli is on the shortlist for the Archibald Prize. Judged by the trustees of the Art Gallery of New South Wales, it is the most prestigious portraiture art prize for painting in Australia.


The subject of his entry is Jessica Cottis, artistic director and chief conductor of the Canberra Symphony Orchestra. She is the first woman to hold both posts.

Oli created the portrait using the Flemish technique which involves working across seven layers. Each brings a new detail to the painting beginning with a plain white background, and adding shapes, then forms, light and shadows, and finally colours. The result is painting with texture, depth and an intense, almost luminous quality.

There is a science to creating an artwork so striking and detailed. Oli uses his paint to trick the eye more than once, giving us a sense of dimension and movement.

An example is in Jessica’s jumper, where he adapted pointillist and divisionist techniques, using small areas or points of pure colour next to each other to be blended optically rather than physically.

“I started messing around on the jumper with the colours I liked, just placing the different blue and green shades together. I used a thick glaze, not mixing them, just laying them side-by-side in tiny, little squares. When you stand back, the eye just blends them together.”

Oli’s portrait of Jessica Cottis is rich with symbolism and meaning.

It was like looking at the clouds again, and really seeing what was there and not just what the mind expected to find.

“My first paintings were flat; they were colourful but ridiculous. It’s taken me 15 years of work to understand how to paint. The biggest thing I’ve learned along the way is how to look at things.

“You have to switch off your seeing brain and get into the analytical side of things. Ask yourself what you are really looking at, then paint it as it is,” Oli said.

A conductor and a synaesthete

Technique aside, it is his subject who makes this painting.


“Jessica is fascinating. She’s very, very idiosyncratic with her movements when she’s conducting. She’s dramatic and exciting to watch but she’s also very contemplative,” he said.

In conversation with her, Oli discovered that Jessica also experiences a form of synaesthesia where she hears sounds as colour. When listening to music that particularly appeals to her, she sometimes sees shades of electric blue and green that pulse. Coincidentally, Oli too loved those colours. It’s how they settled on the look of her jumper.

There are other symbols and meaning embedded in the portrait.

Jessica is an avid amateur lepidopterist, hence the Ulysses butterfly (Papilio ulysses) perched on one side of the bench. She was thrilled when Oli sent her images of butterflies from various displays around our Black Mountain site, where he works.

In the painting, she also holds the musical score and the baton she conducts the orchestra with. It was a pose familiar to Oli – he had watched her plant the baton just so every time she was grappling with something during rehearsals.

Jessica was happy with Oli’s focus on her face, the baton and the score.

She saw them as the things the conductor uses to direct her orchestra: facial expressions and vocal directions, the baton and the music itself.

In the running for the Archibald Prize

This is Oli’s first time on the Archibald Prize shortlist, and it is a huge milestone in his career as an artist. But it doesn’t mean he’s ready to hang up his hat at CSIRO. Here, he deals with information law, governance, general statutory interpretation and really novel questions of law.


“The great thing about having this career in law and that side career as an artist is that they complement each other. They don’t clash but each makes the other more enjoyable. I couldn’t paint what I want to paint if I didn’t have my CSIRO career to keep me going.”

Curious to know more? You can catch Oli at the opening of the Archibald Prize Exhibition at the Art Gallery of New South Wales, which will run from 6 May – 3 September 2023. The winner of the $100,000 prize will be announced on 5 May. And don’t forget to cast your vote by 6 August for your favourite portrait in the ANZ People’s Choice award.

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