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How has nobody suggested the obvious yet? Keep your current job while you interview, test the waters and see what's out there. You might find something you enjoy more with a big enough raise to cover the college credits. You don't have to quit to start looking elsewhere. I know you're talking about career, not just job, but I'd argue the same still applies.
Thanks for this. Justifies some of what I've recently been doing. I've been at this job for almost 20 years. I've been awarded the top employee honor at work, essentially the "outstanding achievement" award for employees. Not sure why. This was just a few years ago, when I essentially quietly quit.
Recently received notification I had been moved to the final search committee for a major leadership role at a neighboring college. Regardless of the outcome, this was primarily an attempt to see what interest there still is out there. This would be a CIO role, one I'm more than capable of running with considering the size and scope of the school. I just don't know if that is even how I want to end my working life.
Nobody prepared me for any of this. I guess none of are technically.