And organizations have super high pain tolerance.

The organization slowly evolves along with the complexity in a demented kind of synergy and learns how to deal with it.

That rings so true.

But the thing is, pain is a warning signal. If you go jogging completely drunk and hit a tree with 6 mph, it will be painful, yes, but the pain will warn you not to do it again.

But what if you move 12 times faster?

If you drive a light motorcycle completely drunk and with no helmet, and hit a tree, pain will not be able to save you.

For company legacy codebases, yes they are dysfunctional but they have found a kind of precarious equilibrium in so far as they exist because they are making money and thus are useful by some metric. The slow movement and requirement to work somehow balances the unstoppable (with in company practices) growth of entropy and messiness.

And in a way, the money is an analgetic for the pain. Or more sharply, big companies act like junkies on a money drug because money is the only thing that ever counts.

Figure what happens if entropy is grown 100 times faster...