Continuing to work off the backlog of posts racked for future reference.  Here, from the spring of 2008, is Econ Log's Arnold Kling, with some career advice for academicians.  The entire post is worth reading (in Internet years, finding it and the follow-on posts still in the same place is marvellous).  Start here.
My tip on becoming a successful academic is to be careful how you define success. Any tenured professor has a great life by most standards. However, the default sentiment in academia is bitter jealousy. The folks at lower-tier schools think they belong at top-20 schools, the folks at other top-20 schools think they belong at Harvard, and the folks at Harvard think that they deserve more recognition than the other folks at Harvard.
That bitterness is corrosive in other ways. Instead of recognizing that your institution is in the same business as Harvard, and ought to offer similar intellectual challenges to students, and seek comparable research visibility, you can get stuck in whingeing about your students, or dismissing your colleagues as time-serving mediocrities.  (Administrators, on the other hand, are lousy everywhere.  I have sources in high places.)
Once you get on the ego treadmill, not only do you become bitter, but you have to start viewing others not for their intrinsic qualities but for their usefulness as stepping stones. If you can stay off of the ego treadmill, then success becomes more a matter of being near friends and living in an area with the type of amenities you prefer.
Perhaps I hit the jackpot, managing to hold jobs close by to challenging small boat racing, plus serious railroading, both prototype and model, nearby.  Plus some pretty good music departments.  Somehow the status hierarchy doesn't stop good music programs from emerging all over higher education.

And in athletics, the status hierarchy is what you make of it, thus a volunteer assistant coach at a high school might finish his career taking a Big Ten team to a bowl game.  Perhaps the education side of higher education might emulate that.  Yes, it takes some receptiveness on the part of the prestige programs to considering promising people without the proper credentials, but how many people might take their midtier graduate school or first tenure-track job as consignment to obscurity.

There's a Megan McArdle reaction in Atlantic, offering some qualifications to Mr Kling's advice.  And yet there is material for further consideration.
Getting tenure is an all consuming process that leaves very little time for developing other hobbies. And the job virtually definitionally does not attract the kind of people who will be happy putting their career on a back burner to family or lifestyle.
It's also not the kind of job that's conducive to having much of a personal life, particularly in advance of that seven-year-up-or-out review.  Perhaps that rigid status hierarchy, which Ms McArdle has previously noted, only makes for unhappier academics (and strained relationships?)

But the inward focus of a lot of academicians may have less to do with location than with internal motivation.
They usually seem to go where the best job is, regardless of whether or not the local area suits them. In many cases, this further focuses them inward on academia, because there aren't all that many other people around who share their interests.
That's a case for developing new interests, or perhaps for buying a train set.  Easier to sneer at everybody else and hang out in your little bubble.  Never mind the irony of hanging out with the same people whose perceived mediocrity fills your life with disengaged students.  Better to be comfortably miserable than to discover that drilling and tapping 2-56 calls for a different kind of patience.

I'm glad I copied the following comment from the bull session, as it appears to have vanished from the current comment thread.
Grad schools have always been filled with people who have never fit in anywhere until they got there; it's a minority devotion. Now, I don't expect you all to value you it like we do. You don't have to. But a bunch of people sitting around sneering at people who have chosen a different lifestyle then them seems pretty lame to me. If you don't like the academy, don't enter it; but don't tell me that there's no one who does.
It cuts both ways.

Fortunately, I got to get out without risking getting bored.

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