Riffs:

<<Why don't more painters have hacking jobs?>>

I think pg is right in highlighting age here. Generally speaking you need to get started young. Beyond this, there is a natural synchronicity in all "arts" when engaged at a high level, which is why the renaissance produced true "renaissance men." The trick is to start early but resist the all too common impulse to mediocrity in the context of specialization -- pg's association with elite institutions certainly helps here.

<<What should I read to learn more about history?>>

I find pg slightly misguided here. One of the world's best historians was my former advisor (Martin van Creveld), and his technique was to find a subject that he could fall in love with and immerse himself in it passionately for a year or two (ultimately however long it took him to write a book about that subject). I think a strong passion for a particular subject can make up for the otherwise dense and uninteresting material. Looking for books that make things "exciting" is a recipe for an understanding of history that is as piecemeal as one's own reading habits.

<<Couldn't you add something equivalent to Lisp macros to languages like Perl or Python?>>

Yes, of course. One could also quote the apocryphal McCarthy / Norwig story here.

<<How can I avoid turning into a pointy-haired boss?>>

Starts off generally correct and "startups" are certainly one solution to this problem, but I'm not sure they are the only solution. For instance, this basically assumes that your startup can exist as a flat organizational structure with only hyper-intelligent and interesting people. But what if, heaven forbid, you need to add a customer service division?

The truth is that really smart people generally don't want to be middle managers in large firms. The work isn't that interesting, and the compensation is to a certain degree adjusted more highly to compensate people for walking around in suits and clucking their tongues all day. Rather than pointing finger with the negative stereotype ("pointy-haired boss"), I think it is more appropriate to think of these people as corporate trash men, compensated more highly because of a generally undesirable job (after all, managing Dilbert and Dogbert probably isn't a recipe for life long engagement).

<<I'm about to become a teacher. How can I be a good one?>>

Agree. Probably a lot that could be added here about how to engage personally with students, although this goes beyond mere "teaching" to "mentorship"

<<Two startups want to hire me. Which should I choose?>>

Perhaps strangely, I generally disagree with the principle that you should go with the startup that is more likely to succeed. I think you should find the subject that you are personally most passionate about and pursue it with all the passion you have. Since you give a sh*t (a rather rare things these days), you will naturally become very good at that particularly area. Only then find startups in your particular area of interest. They should all want to hire you. Then, of course, you will pick the one that matches your passion, which should be the one that is executing most successfully towards their stated goal.

<<How can I become really good at Lisp programming?>>

I'm not very good at Lisp...

<<What philosophy books would you recommend?>>

Very tricky topic and a bit "recursive," in that pg references "what philosophy is supposed to be teaching" without defining it -- this in itself obviously a "philosophical" question.

Also, it's not at all clear from the response what pg has actually read. There are quite obviously a lot of genres of philosophy. Some of them, even if you consider them complete nonsense (like books of canon law derived from dogmatic theological principles), are extraordinarily useful to read if you care about understanding the progress of history, inclusive of why dogmatic patterns of thinking about particular subjects dominate at many period in time.

That said, I think everyone should at the very least have a basic knowledge of the Socratic dialogues, which are an excellent process in stimulating the mind and evaluating one's own presuppositions -- the approach of the majority of people is anything but the "examined life," and the only process of moving beyond the basic assumptions of a particular age is to examine them in the light of reason.

<<I want to start a startup, but I don't know how to program. How long will it take to learn?>>

Generally agree with pg, but I think the plethora of online learning aids means that it is better to learn the fundamentals on your own or in a week long course (i.e. how to build your first rails app), then "apprentice" yourself at a very low wage until you grasp the fundamentals. Also, I don't think this is a question merely of "smarts" but of an engineering/builder disposition, which some people simply don't have. I don't think "answering phones" is going to help you get that disposition.

This actually leads to a general critique of pg's "philosophy." Startups may be a very good solution to some problems, but are are certainly not a panacea for all problems. Ipso facto, it is important to more carefully define the problem scope and characteristics before defining the solution.