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Gray comments on Just Try It: Quantity Trumps Quality - Less Wrong
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Job-hunting fits very well with the model in "Don't Fear Failure": the downside risk is zero. The worst case is accepting a bad job. Assuming you're a USian, jobs are at-will, so just leave then, and you're no worse off.
As a job-hunter, I've learned to model the probability of getting any one job as infinitesimal, so I don't get too hung up on any one application. Let them do the rejecting.
Is this true? I was always told that employers look down on a spotty employment history; they are less likely to hire someone whose job history is littered with jobs that have been held for less than a year.
Yes. (Their worst-case scenario: You're a "professional plaintiff" who hires on, sues for something or other, gets a (confidential) settlement, and moves on).
They also look down on being in the same job a long time (assumption: lack of motivation to advance, etc.). And they look down on gaps in employment (assumption: you were in prison).
To summarize the summary of the summary, HR reps hate people.