I am coming to the end of a military career. I have a Master's in IT and have MCSE and CISSP certifications. I have moved to upper management but still like to work hands on from time to time. I would like to teach, research, or work at the corporate mid-level in security. Should I train for more certifications or should I pursue more college-based work to remain viable for this career change?
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If you want to teach at the community college level you're probably good to go, as you also are for the corporate mid-level in information security. If you want to teach at a four-year institution or something at the graduate level, you'll need to gear up and go for your PhD; the same thing goes for research work as well. For these latter kinds of positions, you really need a doctorate and should probably also pick something interesting and valuable for your dissertation topic as well.
Best of luck in your work or studies.