Academic trajectory and maximizing diversity

I am concerned over the issue of academic trajectory. I find myself in a smaller and smaller career box as I complete my degrees. I wonder if the abrupt nature of my field jumps might look poorly to an employer/graduate school. As of now my background includes the following:

AA (Social Work), AGS, CERT (Behavioral Science), BA (Anthropology), MED (Educational Technology)

The precipice I find myself at now is to either get a second masters to qualify for a higher license in Librarianship or simply take a graduate certificate in a topic I would like to teach postsecondary. What in your opinion would best complete my educational background; certificate, 2nd Masters or doctorate? I am looking for something a employer would find most appealing.

If you have any program reccomendations related to cultural studies, history, behavioral science, or education I would love to hear them.

 

As someone who has both hired and been hired my own view is that educational credentials serve two basic purposes. The first is a general purpose which is to indicate that you are the type of person who can handle college level or graduate level study. The second is a specific purpose to evaluate whether or not the person has the requisite education in a specific subject area. 30 years ago I would have said that the general purpose aspect of an academic credential was more important (at the Master's level) and that the second part would be taken care of by OTJ training. These days, with everyone and their brother having a college degree, I think having the specialized credential is more important.

So the answer comes down to what do you want to do? You obviously have demonstrated through your advanced degree that you have satisfied the general purpose prong of education. Any further education should be directed at the specialization you wish to target. Another way to think about it is that having one advanced degree you have demonstrated you have the ability to do the work, with a second advanced degree it's now time to demonstrate you can deliver value--and that means something targeted towards the specific career or job position you want to hold. That's how I would look at it as an employer.