Four months. 14,000 kilometres. One Basalt Black 997.2 Turbo Cabriolet. From the Scottish Highlands to the Stelvio Pass, Le Mans Classic to the Hockenheimring, Kerry and I spent the better part of 2025 discovering what happens when you hand back your lanyard, drop the roof, and just drive.

Across four autumn days in Victoria, 95 crews set out on a journey defined not by speed, but by precision. What regularity rallying taught us about patience, communication and the particular pleasure of driving with intent.

I wrote these principles in 2019. I thought I was writing about digital strategy. Reading them back now, I realise I was writing about AI strategy — six years before most organisations began trying to build one.

Twenty-five years ago, four of us made it to the top of Kilimanjaro. None of us would have without our sherpas. The same is true of digital transformation — and the mountain has only gotten taller.

The pandemic proved that single-threaded supply chain thinking was a liability. The years since have kept making the same argument. The organisations navigating it well are the ones that built a genuine Plan B — and a Plan C.

Construction builds the physical world everyone else depends on. It is also one of the least digitally sophisticated industries in the Australian economy. That is not an accident — it is the product of five specific, well-understood barriers.

The hardest moment is not generating the ideas. Most organisations are surprisingly good at that part. The hard part is the morning after — when everyone returns to a job whose priorities have nothing to do with what was just discussed.

You probably have a different name for them now. A decade ago I warned that organisations were hugely unprepared for the next wave of automation. I was right about all of it. I just underestimated the scale and the speed by an order of magnitude.

My proposition is simple: leaders need unstructured time in genuinely uncertain environments to renew themselves. The case for getting lost has never been stronger — and the latest reason is sitting in your browser right now.

I wrote the first version of this argument in 2014. I wasn't thinking about artificial intelligence. Reading it back now, I might as well have been. The central warning — that technology without cultural intelligence is an expensive sideshow — has become the defining question of the AI moment.

Every senior executive I speak to is navigating the same sensation: asked to lead into unknown territory, with an incomplete map and no guarantee of safe return. That sensation has a name. It's called an expedition.

Imagine your mind is a supermarket — aisles arranged for the world you grew up in, promotional ends stocked with your most-used ideas. When did you last drive a bulldozer through it? The latest reason to do the remodel is sitting in your browser right now.

Shackleton has been on every leadership reading list for thirty years. That doesn't make him any less right. And one specific insight from his model describes the AI adoption challenge in 2025 more precisely than anything written this decade.