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Generally speaking, are there good "milestones" to suggest that a graduate student should initiate their job search? Roughly a year from completion? More? Less? Is there a particular time of year a job search should be kicked off?

Basically: The job search, how do I time it?

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The following is condensed from advice for academic job hunts that I've read here and here - I imagine it should be somewhat applicable for jobs in industry as well:

  • If you would be applying for a position at Fall, begin applying from summer the previous year - applications tend to be sorted during committee meets, and the earlier you apply, the fewer applications are there, so there are higher chances of getting your application noticed. Hence, you'll want to draft your research statement, teaching statement and curriculum vitæ (CV) the summer before your search. If you are applying for industrial as well as academic positions, you probably want more than one resume, since achievement, skills, and goal-oriented resumes can be more effective in the industrial setting.

  • The middle of January is when most schools stop accepting applications. Even then, keep submitting to any position you find through February, particularly if someone there recommends you apply. You will probably hear back with invitations for interviews in January and February, but sometimes even March and April.

  • Get your letter writers primed as early as possible. You'll need at most six letter writers, but no less than three, and you'll want to ask them at least a month in advance with all your documents.

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  • Is the timetable (second point) specific to a country or a discipline? The third point about recommendation letters definetely is, since not all postdoc positions ask for them. – Tommi Aug 22 '19 at 11:26
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If you're talking about job searches in general, it's never too early to start making contacts with potential future employers. Getting on their "radar screen" early can only help you when it comes time to apply formally for jobs; in addition, if you are their "preferred" candidate, you may find a job posting "stressing" your particular research direction.

When it comes time for the actual submission of applications, academic positions typically operate on an annual cycle that depends on the field, and you should plan accordingly, as given in the response by shan23. The timing for other jobs varies, in particular depending upon the state of the economy. However, at the absolute minimum, you should start applying six months before your anticipated graduation; in the current circumstances, I think twelve months ' advance lead is also acceptable. Further out, the crystal ball is probably too cloudy for both employer and applicant.

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