
We’ve all seen them – the “top button brigade”.
It’s that way of doing things where compliance quietly becomes the main thing. The only thing, sometimes.
In classrooms, it shows up in small but oddly loaded ways. A dress code where “smart” stops being about how someone looks overall and becomes about a single detail – a top button done up, even when the shirt doesn’t quite fit right, even when everything else looks fine.
And I find myself wondering what that actually teaches.
Because the message isn’t really about presentation. It’s about the rule itself. The “what” (looking smart) gets replaced by the “how” – follow the instruction exactly as written. No judgement. No interpretation. Just compliance.
And I don’t think that stays in the classroom.
As a youth rugby coach, I see echoes of it all the time.
Players who are technically good, sometimes really good, but something shifts when things become uncertain. The moment a law is breached they freeze. They look for the referee. They stop playing.
It’s like they’ve learned, in one part of life, that mistakes are something to be avoided at all costs… and then they carry that into a sport where mistakes are actually part of how the game works.
Where the game doesn’t really exist without them.
There’s a phrase I’ve come across before: the tension between the letter of the law and the spirit of the law. And that feels quite close to what I’m noticing here, even if I don’t fully have the language for it.
It feels less like theory and more like something you can see playing out in real time.
Barry Schwartz talks about something similar when he writes about practical wisdom and the way systems can slowly replace judgement with rules when trust starts to fade.
I keep coming back to that idea. Because rules themselves aren’t the issue. It’s what happens when they become the only thing we’re allowed to rely on.
When judgement gets removed from the equation.
Schwartz calls it something like the “booby prize” of rules – this idea that when we stop trusting people to think, we replace thinking with checklists. Boxes to tick. Instructions to follow.
And it works on paper. You get consistency. You get control. You get predictability.
But something else gets lost in the process.
What you end up with, sometimes, is what I think of as a “jobsworth” mindset – people who can follow instructions exactly but struggle when the instructions don’t quite fit what’s in front of them.
And I see hints of that on the pitch too.
Not as a criticism of the players, more as something they’ve absorbed from elsewhere.
Playing the advantage
Rugby and sport in general offers a different model.
The advantage rule is one of the clearest examples of judgement in action. A law is broken, but the game doesn’t stop. The referee reads the situation and asks a different question: who benefits most if we let this continue?
It requires feel. Timing. Context. A kind of trust in what’s unfolding.
And the players who grow most in that environment are usually the ones who learn to stay in motion when things are unclear. They don’t collapse the moment something doesn’t go to plan.
They adapt.
They keep playing.
There’s something quite human in that. Something we sometimes lose when we move between systems that prefer certainty over judgement.
Reconciling two worlds
I don’t think this is about rejecting rules.
I believe in discipline. In structure. In small habits that create order. There’s something grounding about doing simple things consistently – like making your bed in the morning. Not because it’s morally significant, but because it sets a tone.
But there’s a difference between useful structure and rigid control.
Between something that supports judgement… and something that replaces it.
One feels like a foundation you can stand on.
The other starts to feel like a script you’re not allowed to step outside of.
And over time that shapes behaviour more than we probably realise.
People stop asking “what makes sense here?” and start asking “what am I allowed to do here?”
Those aren’t quite the same thing.
The “canny outlaw”
There’s another phrase I’ve come across: the “canny outlaw”.
It sits in an interesting space.
Not someone who breaks rules for the sake of it, but someone who can sense when a rule no longer serves the purpose it was designed for. Someone willing to bend, or step sideways, in service of a better outcome.
In sport, that might be a player who keeps the game alive when others have already stopped.
In life, it might be something quieter than that.
But I think there’s something in it we often miss when we focus too heavily on compliance.
Because if everything becomes about following the map exactly as it’s drawn, we lose the ability to respond when the map doesn’t match the terrain.
And it rarely does.
I keep coming back to that.
That maybe the real skill we’re trying to build isn’t perfect obedience or perfect rebellion – but something more nuanced.
Something closer to judgement.
Something closer to trust in your ability to see what’s needed in the moment, rather than what the rulebook says in theory.
And I’m not sure I’ve fully landed that thought yet.
It’s still moving around a bit.
Which is probably why it stays interesting.
Where have you noticed, in sport or in life, that someone following the “rule” actually made it harder to do what was clearly the right thing in that moment?