Except for a some blue-chips and what seem like some damn good longer-term bets (often backed with some prudent underlying derivatives), I'd have to essentially agree with the gist of your current investing philosophy, Higgie: mostly be a damn good day-trader!
Getting back to Strauss and Howe, they mention in their Fourth Turning writings that in a First Turning, that even bad people get harnessed to socially useful tasks — and I can see why. In a First Turning, you have essentially a non-distorted, healthy economy with a good balance of private- and public-sector involvement. Towards the end of a Third Turning or early in a Fourth Turning, you can easily have (as we have now) major economic malaise (presently helped along via the gargantuan efforts to keep the whole economic system from collapsing).
I know that there may be plenty of the "less-government crowd" which doesn't agree with me here, but I think it would be a positive social development for Americans to have much better partnerships among businesses, state labor departments, nonprofits, other governmental entities, and universities — paired together in order to do what they reasonably can to find meaningful, challenging, self-actualizing work for the kinds of "bright square-pegs-in-round-holes" you have just written about. This does generally not mean "make-work": it means doing an effective job at finding meaningful, creative, needed work for creative, hard-to-employ persons in a way that serves both the employed as well as the social good. There could be an "employment specialist panel" consisting of, say, department of labor folks, university folks, and industry folks (and maybe some others) who do a sincere job of trying to employ these people; the employment solution, in many cases, may be "portfolio jobs" which entail working for more than one organization at one time in various labor/entrepreneurial/research capacities. It could also be combined with innovative, specialized academic programs which aim to make practitioner-scholars who have the best chance to succeed while engaging in novel, rewarding work and serving the social good. (Part of this would also ideally entail mentoring/coaching to assist such employed creative persons in handling portfolio careers, in handling risk and even business/research failure when/if it arises, etc.)
(Well, maybe when the next First Turning rolls around, we'll finally get it...but maybe Obama can get a toehold on it at least
Thanks again, Higgie and all, for the great thoughts. —Best regards, Marc