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Just about every job I want to apply for requires a transcript which I won't be getting until january 14. Do I just spend my vacation preparing cover letters, resume, writing sample etc. and then apply when grades come out or is there something else I can do?

It depends on the job. If it's a job with no formal hiring dates (such as a judicial internship), you should apply now and state in your cover letter that grades haven't been released yet, and that you'll forward a transcript as soon as it's available. If it's a job where decisions are made at a specified date after January 14 (for example, the organization says it will accept applications until January 30 and make decisions afterward), then just send everything at once when you get a transcript.

and what if there is a formal hiring period that ends before january 14?

Explain your situation in your cover letter and hope for the best.