NancyLebovitz 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.
I've heard people claim that leaving a job in less than a year looks very bad on the resume. True?
I have heard that many times over the course of my adult working life. I tend to agree with it mostly, although I doubt that it applies equally to all types of work, and it may have been more true in the past than it is in today's economy and with today's technology. I would think that it could vary wildly between say a position such as "Office Manager" and that of "Newspaper Reporter". The reason(s) for leaving would matter a great deal as well. Leaving a job for a much better job (better pay, more prestige, etc.) is quite different than leaving a job due to personality clash or poor work performance. There also could be a big difference depending upon the values of the employer in charge of doing the hiring. The person(s) with decision-making responsibility might place more emphasis on other traits and accomplishments, and not care terribly much that the employee left a job or jobs after a short time of being employed.