That saying is also oddly appropriate here because the joke for anyone who lived in boston is that the city is built on paved-over cow paths.

(yes yes fun-police, it's actually a myth https://www.bostonmagazine.com/news/2018/03/06/boston-street... but the truth of it being a bunch of ad-hoc cities that coalesced into one entity isn't too far off from the truth. My favorite bit of Boston artwork is road silhouettes of all the Boston-area squares: http://andywoodruff.com/blog/boston-squared/ )

It is a strange saying. My guess is this is something that's lost in translation—a leaky metaphore—and the people using it don't think about real cow paths.

Real world space is (generally) 2 dimensional, and these cow paths are often very predictable and sensible. They're usually the result of architects thinking that sometimes people actually walk or bike, instead of always driving cars.

In the world of bureaucracy & information tech, the space can be very convoluted, and shortcuts aren't really the same kind of thing (queue XKCD comic on spacebar heating).

Cows tend to pass where other cows passed. Herd behaviour. Something like a real world effort optimisation.

No use trying to optimise in a week using one brain something that found a local minima (or maxima) over years and multiple people.

Normally the change (and effort) to achieve a better minima (or maxima) has to made on a variable you just can't see or imagine.

Something on the line of Chesterton’s Fence.

Those aren't cow paths, those are people paths. Cows are not known for their tendency to walk in straight lines. Edit: notice they still had to put up fencing to keep people from cutting off even that minimal switchback.

This might be a dialect issue. Where I'm from, "cow path" is the normal way of saying what also called a "desire path" by others. According to the wikipedia, I'm not completely out to lunch: https://en.wikipedia.org/wiki/Desire_path

I hadn't heard "cow path" before, but a quick google suggested it was a synonym for "desire path" so I went with that.