I can attest that I had those exact reactions on reading those sections of the article. And in general I am more impressed by someone who graduated quickly than one who took longer than average, and by someone who wrote a book rather than one who hasn't. "But what if that's not the case?" is hardly a knock-down rebuttal.
I think it's more likely you're confusing the status you attribute to Kaj for candidness and usefulness of the post, with the status you would objectively add or subtract from a person if you heard that they floundered or flourished in college.
What I has in mind was his devotion to the cause, even as it ultimately harmed it, we think more than compensates for his lack of strategic foresight and late graduation.
With that book, we think of him less for not contributing in a more direct way to the book, even as we abstractly understand what a vital job it was.
Though of course that may just be me.
I have become convinced that problems of this kind are the number one problem humanity has. I'm also pretty sure that most people here, no matter how much they've been reading about signaling, still fail to appreciate the magnitude of the problem.
Here are two major screw-ups and one narrowly averted screw-up that I've been guilty of. See if you can find the pattern.
It may not be immediately obvious, but all three examples have something in common. In each case, I thought I was working for a particular goal (become capable of doing useful Singularity work, advance the cause of a political party, do useful Singularity work). But as soon as I set that goal, my brain automatically and invisibly re-interpreted it as the goal of doing something that gave the impression of doing prestigious work for a cause (spending all my waking time working, being the spokesman of a political party, writing papers or doing something else few others could do). "Prestigious work" could also be translated as "work that really convinces others that you are doing something valuable for a cause".
We run on corrupted hardware: our minds are composed of many modules, and the modules that evolved to make us seem impressive and gather allies are also evolved to subvert the ones holding our conscious beliefs. Even when we believe that we are working on something that may ultimately determine the fate of humanity, our signaling modules may hijack our goals so as to optimize for persuading outsiders that we are working on the goal, instead of optimizing for achieving the goal!
You can see this all the time, everywhere:
There's an additional caveat to be aware of: it is actually possible to fall prey to this problem while purposefully attempting to avoid it. You might realize that you have a tendency to only want to do particularly prestigeful work for a cause... so you decide to only do the least prestigeful work available, in order to prove that you are the kind of person who doesn't care about the prestige of the task! You are still optimizing your actions on the basis of expected prestige and being able to tell yourself and outsiders an impressive story, not on the basis of your marginal impact.