A person’s choice can make sense within a life you have only heard summarized.

You are almost always judging a decision from outside, with the middle removed. What reaches you is a short account that leaves out the money, the history, the obligations, and the earlier attempts that made this particular option the reasonable one. From inside their life the same choice may have been the least bad of a narrow set.

Before concluding that someone has erred, ask what would have to be true for it to make sense. Then ask them, if the relationship allows. Curiosity costs you nothing here and often changes the picture completely.