As she climbs the stairs at Jacksons on George, Brenna Hobson has flashbacks.

Although she’s lived in Glasgow for seven years working as executive director of the National Theatre of Scotland, Sydney-born and raised Hobson has been here before in a different life.

As someone involved in the theatre for over two decades, first at the Australian Theatre for Young People rising to executive director at Belvoir St Theatre before leaving for Scotland in 2017, Hobson is still familiar with Sydney’s after-hours venues as post-performance gathering places.

I’d had flashbacks, too, when I landed at this Circular Quay staple that was once a grungy but reliable late-night watering hole, where we meet for lunch.

Gone are the sticky carpets and fully tanked clientele, replaced by waiters decked out in white in the high-end Bistro George, run by Maurice Terzini, the founder of Bondi’s upmarket Icebergs Dining Room. We both laugh about it being so Sydney – constantly reinventing itself.

Rebranded as Sydney Place by developers Lend Lease, the new building’s white curved form evokes sailing boats and, according to its architects, is influenced by its “history of the site as a former boatyard, and celebrates its unique location close to the ‘sails’ of the Sydney Opera House.”

Coincidentally enough, that’s where Hobson now spends much of her time as the recently appointed director of programming at the World Heritage-listed building at Bennelong Point. She took over in July from beloved arts and theatre veteran Fiona Winning, who has left the Opera House after six years in the role.

Hobson now oversees the arm of the organisation that presents over 700 performances each year in the areas of contemporary music, performance, First Nations, talks and ideas, children, families and creative learning, classical music and screen. She has a lot on her plate – unlike the sparse servings at Terzini’s upmarket establishment.

She’s familiar with the ins and outs of the nation’s best-known building after serving as a member of the Sydney Opera House Trust from 2014 until 2017. Among other things, she was on the audit committee which oversaw the early stages of the $300 million decade of renewal works at the Jørn Utzon-designed space.

“There are two dedicated arts roles among the trusteeship,” Hobson explains over our entrées in Bistro George’s birdcage-like dining room – she’s chosen yellowfin crostini, while I’ve gone for the heritage beetroot, goat’s curd and walnut salad with fermented honey dressing.

“Deborah Mailman and I were those two representatives ... it is also one of the ways the trust facilitates having younger trustees,” says Hobson, who was in her late 30s when she joined the trust as an independent industry voice.

“I really enjoyed it because as a production person at both Bangarra and at Belvoir [St Theatre], I’d worked on the shop floor, and that was something the other trustees found interesting.”

Hobson wasn’t expecting to return to Sydney so soon from Scotland, where she spearheaded the creation of a year-long festival featuring world-leading contemporary performance companies and Scotland’s young people. But the job was the drawcard.

“I’ve got a long history with the Sydney Opera House, working backstage for resident companies and then serving on the Trust, but I’ve never been a staff member before, so when I saw that the role had come up, I jumped at it,” she explains.

She was appointed to this role by Louise Herron before the Opera House chief executive took six months of long-service leave in July. The two have known each other for over two decades since both were at Belvoir with artistic director Neil Armfield, and Hobson was a staff representative on the Belvoir board. With speculation still rife as to who will replace Herron when her current 12-year tenure comes to an end, Hobson, at 48, and the face of generational change, could be a candidate.

When I ask her outright about the top job, she laughs out loud.

“That’s a huge job. Louise set herself the task of sorting out the building, and she’s most of the way there. She’s already talking about the next phase of renewal. Louise has still got enthusiasm for the Opera House,” Hobson says.

Hobson has loved the Opera House, and theatre in general, most of her life. An only child, she was raised in Sydney’s inner west and attended Glenaeon, the Rudolf Steiner School in Middle Cove, from kindergarten until year 12. It took her an hour and a half each way to get to and from school, she explains over our mains, the special tagliolini, eastern rock lobster, cherry tomato, bisque and cognac.

“At Glenaeon, they very much believed in teaching the whole child as opposed to just isolated parts, which is pretty mainstream educational philosophy now, but back in 1980, when I was starting, was pretty radical,” she says.

When school was up, she intended to go to the National Institute of Dramatic Art, but NIDA had a very strict rule at the time that you had to take a year off. By the time the year was up, she was already working backstage at Belvoir and started to attend TAFE one day a week to study production management.

“Like a lot of people who work in the theatre, I started off doing acting classes and loved that ... but I stopped acting when I was about 12. I realised that I loved the shows. I loved everything about making the work. I loved the social aspect of it. But actually acting wasn’t my passion. I loved being backstage, making it all happen.”

While working as a production manager at Belvoir, she studied arts administration at UTS, leaving for a stint as executive director of Canberra’s Jigsaw Theatre Company before returning to Belvoir.

“I wasn’t the sort of production manager who was going to end up managing the Olympic Games. Theatre has always been the first love for me,” she says.

“It’s a tough life as an actor, and for many actors, there’s not that much self-determination and I think I was probably always going to want to have a bit more control of my own destiny.”

She was lured to the National Theatre of Scotland, which was formed in 2006, because of the energy of the company, as well as Scotland’s lively cultural scene.

“The Edinburgh Festival is one of the biggest arts marketplaces in the world. To be in Edinburgh in August is always extraordinary,” she says.

At the National Theatre, she did everything from payroll to driving the van on tour to remote village halls all over Scotland, from Shetland to Skye. As the company had no home theatre, its goal was to bring theatre to the people. They commissioned a host of different works, like Thank You Very Much by choreographer Claire Cunningham, which involved actors with disabilities performing as Elvis tribute artists.

“The company culture was a bit like Belvoir – a bit familial with all the good and bad that comes with that, but it’s been a lovely company to work with. And everyone wants a chat in Glasgow to know why you left the lovely weather of Sydney.”

She loves Scotland and, having wanted a dog all her life, has just got a border collie, Eoin, (note the Gaelic spelling), whom she walks everywhere, even to her office in Glasgow from the home she owns. So after our lunch, when I later hear she’s confirmed in this role, I need to ask about her dog.

“Eoin is indeed coming. We can get an import licence for him once he’s been producing rabies antibodies for six months following his vaccination, and then he’s in quarantine for 30 days. So it will be the end of the year before he joins me. I now know more about Australia’s quarantine laws than I’d been expecting to,” she explains.

Until the paperwork is sorted, Eoin remains in Scotland while Hobson looks for a canine-friendly Sydney rental. Weaving has become a new hobby, but there will be little time for that in the Opera House job. Does she ever wonder if she made the wrong decision not to become an actor?

“To be completely honest, I wasn’t good enough. The thing that I really love is being close to the art and having that role in programming. But also, I love how organisations work. I’m currently looking at potentially setting up a separate vehicle for commercial work and how that could work in terms of tax law and all sorts of kind of pointy-headed things. So I definitely picked the right job.”

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