We’re back for Episode 3 of Season 2 of The Future With Friends, and this time Simon Waller (or should we say Bigsy) is joined by his long-time friend Anthony “Richo” Richardson, one of the first people he met when he relocated to Melbourne. This isn’t a professional connection, more a camping and degustation buddy from years gone by. It’s a friendship that’s stretched across decades, which gives the conversation a very different kind of honesty and ease.

The theme of this episode is The Future of Regret, based on a scenario Richo has written, set 42 years into the future. It’s a deeply reflective exploration of what life, meaning, and responsibility might look like in a future shaped by radically extended lifespans, AI-driven education, and accelerating technological change.

Richo brings a grounded, human lens to the conversation, imagining everyday moments that make the future feel tangible, like a 94-year-old still cycling with friends, while also surfacing the emotional weight of what gets lost or left unresolved across such long lives.

The conversation moves beyond fascination with technology and into more uncomfortable territory. They explore how extended lifespans might reshape our relationship with purpose, regret, and legacy, and whether having “more time” actually makes us more fulfilled or simply delays the things we avoid confronting today.

Underneath it all is a quieter, more confronting question about inequality, opportunity, and what kind of future we are actually building for each other.

As always, the conversation is rooted in lived experience as much as it is in future thinking. Simon and Richo reflect on the choices we make now as parents, citizens, and professionals, and how those choices quietly shape the emotional and cultural inheritance we pass on to future generations.

We’re back for Episode 2 of Season 2 of The Future With Friends, and this time we’re exploring The Future of Analogue with Simon’s good friend, Colin D Ellis.

Colin shares a beautifully imagined future where society has consciously stepped away from smart technology and re-embraced the analogue world, from dumb phones and vinyl to simply noticing what’s happening around us.

His scenario paints a calm, intentional future, but the conversation quickly moves beyond the vision itself. Simon leans in to explore what would actually need to happen for such a significant cultural shift to take place, and whether a movement back to analogue living is truly possible in a hyper-connected world.

Together, they explore the impact of digital technology on our mental health, the growing appetite for disconnection, and the conditions required for meaningful societal change. They even begin to toy with the idea of creating their own social movement, grounded in simplicity, presence and human connection.

As two dads, they also don’t shy away from the role parents play in shaping the next generation’s relationship with technology, reflecting on the habits we model and the environments we create for our kids.

It’s a thoughtful, warm and quietly provocative conversation that feels like it’s only just getting started, and will leave you questioning your own relationship with technology and what kind of future you actually want to live in.

We’re back for Season 2 of The Future With Friends, and we’re kicking things off by exploring the future of protest with special guest, journalist and soon-to-be author Kath Walters.

Kath brings decades of experience to the conversation. From her early days in the protest movements of the 1970s, to a career in journalism holding power to account, to now experimenting with AI and writing fiction about the future, she has spent a lifetime thinking about how stories shape the world we live in.

She shares a future scenario set in March 2035 in The Rocks, Sydney, where she stands among 500,000 people protesting for climate action alongside her daughter. But the real conversation goes far deeper than the scenario itself. Kath reflects on what would actually need to change between now and 2035 for a moment like that to happen, and why hopeful visions of the future can be just as powerful as dystopian ones in driving action.

Together, Kath and Simon explore the evolution of activism, the forgotten history of successful protest movements, and the role of writers, artists and storytellers in shaping what people believe is possible. They discuss strategy, community, joy, and why protest isn’t just about anger. It’s also about connection, creativity and reclaiming a sense of collective agency.

It’s an enlightening, engaging and energising conversation that will leave you thinking differently about protest and feeling far less powerless about the future.