Honestly I have never set a long term goal. For the most part I just keep searching out work and hoping to get shows!
I do a mailing annually to theatres I'm interested in working with, and I keep up with what's going on in the industry thru a variety of trade websites/publications. I read and see a lot of plays so that I'm familiar with shows I may be asked to do. This business is very fluid, and it's often hard to plan ahead. I did go to grad school and have worked in New York-both things on my "list". At the moment I've decided stability is needed, so I'm gunning for resident PSM position somewhere.