Millgram's "Practical Reasoning for Serial Hyperspecializers" is an odd little paper—I have taken to thinking about it as a defense of the aesthetic mode of life (though it never identifies itself in such terms) built on top of a quasi-Schopenhauerian view of interest and boredom (the one sketched in "On Being Bored out of Your Mind", itself an interesting paper—which if this post were to be thorough I'd have reread —containing the remarkable claim that there hasn't been much philosophical work on boredom). One of the odd things about it, and I suspect this is just a matter of presentation, is that the "ecological niches" Millgram talks about when the talk turns to agents all seem to come down to occupational niches: so the contrast between the non-serial specializer ("Piltdown Man", an entity which is "imprinted" for a niche once and lives out its life within it) and the serial specializer is that the former will be once and for all a factory worker (and will be screwed if the manufacturing jobs go away), whereas the latter will be a "VLSI engineer, comics inker, Cobra gunner, French professor specializing in eighteenth-century poetry, adventure travel agent", etc. (this particular list is rather too heterogeneous to be credible if one isn't also independently wealthy or a rare genius with an enviable background, but one gets, I suppose, the point) who is, potentially, doing a bunch of other things in parallel with these varied careers. What's odd about this way of putting it is that the disadvantages that accrue to Piltdown Man are largely economic: you might be out of a job. And the advantages that accrue to the hyperspecializer are similar. This makes some of the later argument about hyperspecialization leading to deliberation of ends less compelling, immediately, than it perhaps could be. "Since the niches are paradigmatically novel", says Millgram, "the problem cannot be solved by using prestored guides to behavior … Rather, the behavior-guiding goals have to be computed on the fly." But these are different claims: how here to behave may not be clear because "here" is new, but one's goals could be carried over quite easily: one wishes to live relatively comfortably, say. (Millgram's points about interest and boredom survive this: I wish to live relatively comfortably, and either fishing or criticizing can serve this end (if only!); should I be a fisherman or a critic? It wouldn't hurt to try one and see if I like it.)
(I'm really not sure how far to take the talk of niches, in terms of occupations. It does seem more than merely expository. At one point Millgram writes: "The point of having serial hyperspecializers is that they can exploit narrow niches—niches that don't have room for many occupants. That means that, for serial hyperspecializers, the Kantian question, what would happen if everybody did that … is simply be side the point." I am sure that Kantian moral theorists are already capable of explaining why it isn't immoral to become a dealer in antique typewriters, and my admittedly nonexpert understanding has it that the universalizability test has application to questions beyond that concerning whether to deal in antique typewriters or to be a subsistence farmer.)
The really odd point, to me, comes at the close of the section devoted to the question: "should we be serial hyperspecializers?" The conclusion:
Those caveats notwithstanding, as far as the big picture goes, my guess is that the first-glance practical-inductive take on whether to invest one's resources in serial hyperspecialization, and whether to endorse the canons of practical-inductive reasoning, has it right. Piltdown Man is boring, and serial hyperspecializers are interesting. Social institutions and lives tailored to Piltdown Man are frustrating; creativity, novelty and originality, intellectual and otherwise, feel much better. And to be a Piltdown Man is for changes in one's environment to be nonrecoverable catastrophes. It's a no-brainer.
The last sentence but one again seems a little occupation-centric; one could, it seems to me, be Piltdownish enough without being utterly destroyed when the factory closes. (Surely the important point is about the priority of deliberation of ends over means, and someone could keep pretty much all the higher-level ends constant who, after being laid off from the factory, learned to pull shots at a café. Piltdown Man needn't be specialized in all the ways Millgram presents it.) But look at the contrast between Piltdown Man and serial hyperspecializers again. Based on "On Being Bored out of Your Mind", one would have thought the sentence would read: "Piltdown Man is bored, and serial hyperspecializers are interested." (In many things, in series and in parallel!) But it can't quite say that, because while I've no doubt that Millgram, from the perspective he currently occupies, regards the relatively static life of the average Piltdown Man type as something it would be pretty boring to live, that is no guarantee that Millgram, were he actually to be such a person, would himself be bored. Things could be just fine for him: he's got his little routine, etc. (A machinist by day, a model train enthusiast by night—both things that involve creativity, novelty and originality, for that matter.) In fact, one might even suspect that the serial hyperspecializer is bored and interested in close to equal measure—interested in the early phases, neither very much as mastery has been gained, and bored thereafter, unable to settle into mature enjoyment. (One might have thought that serial hyperspecialization was a good design solution because it would let one find something one enjoyed and then, having found it, stick with it, but this does not seem to be part of Millgram's picture—and one's sticking with it, in any case, would not, it seems, be done qua serial hyperspecializer.)
It may well be true, on the other hand, that Piltdown Man is unexciting and boring (when Walter Lowrie calls the Judge a "prosy person", that means in part, I take it, that he is a bore), and serial hyperspecializers interesting, especially from the sort of perspective that Millgram apparently occupies, but the latter are not necessarily admirable on that account (when Odysseus "cast aside the heavy bonds / of known, of household things", because "Nostalgia for the voyage hurt him everywhere, and for morning / arrivals in harbors that you enter, / with such joy, for the first time", it's not just that he's bored with Ithaca—he's bored with Penelope), and, in any case, the desire not to be boring but interesting (rather than not to be bored but interested) is one that is neither universally had nor universally to be heeded even where it is had.
(That said, I think a lot of what Millgram says about deliberation of ends is spot on, if a little too confidently and unequivocally put—he just seems to push it into a function argument with odd consequences.)
 But then, if this post were thorough, would it thereby be made better, or worse, qua blog post?