I think I disagree with this. School is a very specific, highly-structured environment. Few people actually have the choice between "staying in school or working at Org X". I think the usual choice is between "staying in school" and "figure out what to do with your life in a self-directed way", which I think is a really meaningful choice. It probably involves trialing at some organizations. It probably also involves spending a bunch of time reading.
It indeed is kind of unclear what it means because the person asking the question probably doesn't have much experience being self-directed. I expect if people's diagram looks like the last one you draw, I expect them to make worse decisions than if it looks like the second-to-last one you draw, because the most likely outcome is that they don't work at either ORG1, ORG2, or ORG3, but instead do something quite different.
I think it's important for people to consider plans that look like "change the basic circumstances of my life, then reorient". This post feels like it pushes people to only consider options they already have planned out, which (in my opinion) gets rid of most of the benefit of dropping out of school (which is usually the first time someone in their life is actually capable of fully directing their attention to what they want to do with their life).
I tend to agree. A lot of people seem to talk about dropping out, but without great ideas about what they would do next.
People quitting to work for an alignment org that deems them useful - I'm in favour of it.
Programmers quitting their jobs to learn about AI safety - hard to have a better safety net than that, so go for it!
But students who are not yet useful enough to be hired, without enough indicators of excellence to suggest they could quickly become a top apprentice, without any particular distaste for the school system, and without any affinity for entrepreneurship? Many such people should stay in the school. If they are interested in academics, or theory, or they need a US visa, then especially so.