re: 5 months away from graduating w/ an MA - When should I start applying for jobs?

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She spent a considerable amount of time on the school's career website which can be very helpful to most students.

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This. Your uni has a career services dept or center, it almost certainly has resume & interviewing classes, and it has a job bank & career fair during spring. Even your undergraduate institution probably has those things, which may still be accessible to you as an alumnus. If so, use both school's resources. I also like idealist.org for nonprofit jobs (many health systems/hospitals are nonprofit). Training is a natural fit for your skill set, but it's still a form of teaching...so if you're burned out on teaching, look elsewhere.