At night, the Sydney Opera House worker lies awake thinking about the war in Gaza, the rapid development of artificial intelligence and the private life of Magda Szubanski.
He's curated the Curious Festival and booked speakers, Szubanski included, to investigate what he and others lose sleep over.
"We've been living in an age of information overload for a long time now," Mr Rolley told AAP.
"What we're trying to do with this festival in particular is to sort of press pause.
"To take all the stuff coming our way, through our (social media) feed or just through our life and dig into some of the meatiest and impactful questions of our time."
The rapid rise in AI is dominating public debate and one of those ideas - or fears - is the technology superseding human intelligence and somehow gaining consciousness.
"It just begs the question," Mr Rolley said.
"What is human consciousness in the first place?"
Author Michael Pollan knows a thing or two after he took a mind-altering journey to the frontiers of human consciousness with psychedelics and wrote the New York Times bestseller, How to Change Your Mind.
He'll give his insights at the Opera House and explore radical perspectives on how humans might begin to navigate this complex idea.
Kath & Kim star Szubanski will open up about her private battles with grief while publicly leading the marriage equality fight for the LGBTQI community.
Palestinian chef Sami Tamimi will talk about the ongoing conflict in the Middle East because, in Mr Rolley's mind, food is the greatest avenue to explore a touchy topic.
The talks at Curious Festival are vastly different but the Opera House hired Mr Rolley because of how he reads the culture.
"To go from something about Palestinian food straight into something about AI, it generates something in you," he said.
"You start to see connections."
Other events include the son of the FBI's most wanted woman discussing his childhood on the run and Vanity Fair journalist Gabriel Sherman's take on the Murdoch empire story after decades of reporting on the family.
The Curious Festival runs from Saturday until November 4.
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