Diplomatic Dispatches
Out-thinking Chaos: Playing the Infinite Game
The first episode of the How to Diplomat Podcast is now live! Listen to my conversation with John Constantine, US Secret Service agent, where we talk about leadership under pressure, cultural diplomacy, and how to redefine your identity when the uniform comes off. |
This week marks 19 years since I commissioned as an army officer from the Royal Military Academy Sandhurst (the UK’s equivalent of West Point).
At least I think it’s this week. The whole thing was a blur of painkillers, protein bars, shouting and no sleep.
I can still feel the weight of that moment: the thump of the regimental band’s bass drum on the parade square, pride mixing with apprehension at what lay ahead.
Those emotions have faded. The lessons stayed.
Sandhurst taught me what it really means to lead: set direction, train hard so you can fight “easy,” and accept that even the most cunning plan rarely survives first contact with the enemy.
It taught me that leadership isn’t about sticking to what you thought would happen. It’s about seeing clearly what has changed, however unexpectedly, and recalibrating fast.
You don’t succeed by clinging to rigid plans and ideology. You succeed by constantly reassessing stepping back to see the bigger picture, and adapting faster than your adversary.
That means confronting the facts on the ground as they are; not as doctrine said they should be, not as intelligence hinted they might be, and not as you wish them to be.
Even in 2006 when I commissioned, uncertainty wasn’t the exception. In the shadow of 9/11 and its aftermath, uncertainty was the rule.
Fast-forward to 2025, and uncertainty feels like it’s in overdrive.
On a recent episode of The Rest Is Politics podcast, Alastair Campbell described a live poll he ran at the Asia Power Forum in Singapore, where he asked the audience (comprising roughly half Asian and half Western participants) several questions; one of which was:
Which of the two superpowers (China or the US) is the greater threat to global stability?
The result?
USA 79%, China 21%.
It’s an extraordinary shift - and worth exploring. In trying to understand its root, I found myself returning to Simon Sinek’s concept of the infinite game:
“
Finite games have fixed rules, known players, and an end point. Someone wins, someone loses.
Infinite games have shifting rules, players who come and go, and no finish line. The goal is to keep playing.
Politics and geopolitics are infinite games. You don’t “win” at global politics; your aim is to stay in play.
The players who endure (in politics or in business) are those with a purpose beyond themselves, who build trust, and who can pivot radically when conditions change.
China and Russia tend to play the infinite game. The West too often thinks short term - in polls and election cycles - reducing complex realities to simple wins and losses.
Take China’s incredibly ambitious Belt and Road Initiative launched in 2013. A decade later, it has helped redraw infrastructure, extend soft power across continents and gain deep loyalty in return. In beneficiary countries, I heard the same line again and again:
“
“Why accept conditional funding and lectures from the West when China offers infrastructure with no strings attached?”
That’s the infinite mindset in practice: patient, persistent, purpose-driven. Caveat: none of this is an endorsement of Beijing or Moscow - on human rights, Ukraine, Hong Kong, Xinjiang and more, my view is clear. I’m observing the tactical advantage that infinite-game thinking confers, not celebrating the actors.
Why this matters
→ Leaders who refuse to step back get lost in the noise of their own plan.
→ Leaders who only look backwards fight yesterday’s battle.
→ The ones who endure are those who stop, read the ground as it is, and adapt their plan - while keeping the greater mission in sight.
This is as true in business and politics as it is in war.
The country - or company - that thinks only in quarters has already lost. Infinite players outpace finite ones not by sheer force, but by enduring purpose, trust, and the courage to change.
The battlefield - whether geopolitical or corporate - is still human terrain. If you’re stuck in scoreboard culture, you’ve already been out-thought.
Three ways to use this in your world:
→ Zoom out on purpose. Schedule a short “step-back” review weekly: does your current plan still serve the mission? If not, change the method—not the mission.
→ Read the ground as it is. Separate wishful thinking from reality. Kill tactics that no longer work, even if you built them.
→ Practise existential flexibility. When conditions shift, make the bold move that advances your long-term purpose - even if it breaks your old playbook.
Sandhurst didn’t just teach me to make plans. It taught me to unmake them.
To step back, read the battlefield, and adapt. Not for ego, but for the greater mission.
That mindset - resist rigidity, embrace the infinite, out-think the chaos - has never been more necessary than now.
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