Pocket watch

There is a difference between pocket watching and recognising a stupid purchase. Most people collapse the two together and they shouldn't.

Pocket watching is about interest in someone's financial position. How much they earn, where it comes from, what they're worth. That curiosity usually comes from a place of comparison or envy and it really is none of your business.

But clocking a stupid purchase is different. That is not about their money. That is about their judgment. And judgment is observable. You are not monitoring anyone's bank account. You are watching someone make a decision and recognising it for what it is.

Let's say I go to the club and buy a £599 bottle of 1942. I know it's a stupid purchase, other people know it is a stupid purchase. Five or six shots for £30 would have the same effect. The bottle gets bought because you can and you want to, fair enough, but the reality does not change. That same Don Julio is no more than £150 in a store. You just paid to hold a fancy bottle. That is a stupid purchase and knowing that while you do it does not make it any less stupid.

The "people can spend their money how they want" point is true. Nobody is arguing against that. But that line gets weaponised to shut down any and all criticism and that is where it stops being valid. Yes, autonomy is real. Nobody is stopping you. But freedom to act does not mean freedom from assessment. You can do something and someone else can simultaneously think it was a terrible call. Both things coexist just fine.

Spending on image over substance. Buying things to signal to people who genuinely do not care. Prioritising a moment over a position. So when someone looks at a purchase and thinks that was dumb, they are usually reading something true about the priorities behind it, not just the transaction itself.