Strategic Planning and The Castle

It’s the start of a new year, which is traditionally a good time to reflect upon what we do by looking backwards, cogitating on what we’d like to achieve in the year ahead and drawing some kind of pathway between the two. It’s not an area that I’m traditionally strong in, but something that I’d like to improve.

I was sitting in a board evaluation session the other day, and collectively we talked about the most impactful piece of writing or creative content for corporate and personal planning. I refer, of course, to that classic Australian work, The Castle.

This will surprise precisely nobody who knows me. When faced with a serious question, I tend to reach for an appropriate quote or line and hope that nobody notices I am mostly bluffing. In this case, however, The Castle genuinely earns its place in the planning canon. It is a film about aspiration, effort, values and time wasting, which is pretty much the entire planning lifecycle if we are honest.

Take Darryl Kerrigan’s approach to productivity. His son is in the backyard digging holes. “Dad, I dug another hole” he says with the kind of pride usually reserved for Nobel laureates and people who finish the Tour de France. Darryl nods approvingly. No judgement. No KPIs. Just a quiet affirmation that work has been done. The hole serves no purpose. There is no destination. But time has been filled and effort expended, and somehow that seems enough.

I have had months like that. Busy. Industrious. Genuinely exhausted. At the end of it all, I have metaphorically stood in the backyard, pointing at a collection of holes and hoping someone would pat me on the head and say “well done”. Planning, if we are not careful, becomes an exercise in sanctioned hole-digging. Strategy documents that are beautifully formatted, timelines that stretch into the distance, workshops where everyone nods a lot and uses words like alignment and cadence. Activity everywhere. Direction, less so.

Which brings me to success measures and the other immortal line from The Castle. It’s Mabo. It’s the Constitution. It’s the vibe. This is how Darryl explains his legal strategy, and if you have ever been in a planning meeting, you will recognise it immediately. We talk about purpose and vision and North Stars. We gesture broadly at culture and values. We know what good looks like, but struggle to pin it down without killing it. The vibe matters, even if it makes the finance people twitch.

In planning, we often over-fixate on what is measurable and undercook what is meaningful. We choose the things that fit neatly in a spreadsheet because they behave themselves. Revenue. Growth. Milestones hit. Meanwhile, the harder stuff like trust, reputation, resilience and whether people actually want to work here gets relegated to the appendix. The Castle reminds us that sometimes the vibe is the point. The house is not just bricks and mortar. It is where memories live. Planning that ignores this risks optimising for the wrong thing.

There is also the small matter of wasted time. The Kerrigans are not efficient people. They linger. They tinker. They talk rubbish at the dinner table. On paper, it looks like a masterclass in inefficiency. And yet there is a richness there that many of us have engineered out of our lives in the name of productivity. We plan every minute and then wonder why we are burnt out and strangely unfulfilled.

I am not suggesting that organisations should replace strategy with backyard hole digging. Although I would attend that offsite out of pure curiosity. What I am suggesting is that good planning leaves space for humanity. It recognises that not all effort will be directly linked to outcomes and that some of the most important work looks like nothing much at the time. Relationships. Curiosity. Learning. Sitting with ambiguity without immediately trying to resolve it.

The Castle also circles around fairness. The Kerrigans are not fighting because the airport expansion is objectively wrong. They are fighting because it feels unjust. Planning often stumbles when it ignores this emotional dimension. People will forgive a lot if they believe the process is fair and the intent is sound. They will resist even the smartest plan if it tramples on what they hold dear. Again, it is the vibe.

As the year winds up and I look back at my own collection of holes, I am trying to be kinder to myself. Some of them were necessary. Some were accidental. A few were probably avoidable. The trick for the year ahead is to be more deliberate about which ones I dig and why. To balance the need for clear outcomes with an acceptance that not everything that counts can be counted.

Which brings me back to that boardroom and the question about impactful planning content. We laughed, of course. Then we nodded. Because beneath the jokes The Castle offers a surprisingly robust planning framework. Know what matters. Don’t confuse activity with progress. Measure success in ways that reflect your values. And remember that at the end of the day you are planning for people, not PowerPoint slides.

I suspect that a year from now I will still be digging the occasional unnecessary hole. Old habits die hard. But if I can keep an eye on the vibe while I do it, and remember why I started digging in the first place, I might just call that progress. After all, it’s not just a plan. It’s our plan. And that’s going straight to the pool room.