Only make choices that you would not make in reverse, if things were the other way around. Drop out of school if and only if you wouldn’t enroll in school from out of the workforce. Continue school if and only if you’d switch over from work to that level of schooling.
Flitting back and forth between both possible worlds can make you less cagey about doing what’s overdetermined by your world model + utility function already. It’s also part of the exciting rationalist journey of acausally cooperating with your selves in other possible worlds.
It’s probably a useful mental technique to consider from both directions, but also consider that choices that appear symmetric at first glance may not actually be symmetric. There are often significant transition costs that may differ in each direction, as well as path dependencies that are not immediately obvious.
As such, I completely disagree with the first paragraph of the post, but agree with the general principle of considering such decisions from both directions and thank you for posting it.