Considering grad school/career change. (applying, interview, degree, jobs)

[scarletneon]

I am slowly considering possibly going back to school for a graduate degree in something that is totally unrelated to what my background is right now. Basically, I'm in journalism, and I'm thinking about getting involved in transportation planning. For some reason I've always been sort of a road geek (now that i live somewhere where there's actually transit, I am now a transit geek/ranter ), and in fact I used to write articles about it in my college classes.

Right now I'm trying to figure out how to get in with the CTA (for those of you not from Chicago, the Chicago Transit Authority). I've been applying for jobs there that I'm qualified for (i.e. customer service, administrative, and pr-ish positions) but no dice. Close one time, but no interview call. I try to attend rallies, hearings, etc. when I can and write about them for Associated Content. I have wanted to go to board meetings but I always seem to be working on those mornings.

My actual, direct question (I swear I'm not just rambling in my own thread ), has to do with my boss. The publication I work for actually has to do with the transportation industry (it's not a hard hitting news pub., more like we like to profile our advertisers and say nice things about them), and she knows someone that works at the CTA. I have met him as well. I have also vaguely met someone that retired from there. These aren't guys that are/were in any sort of planning position... more like garage management. What I'm wondering is, if I should discuss this with her... how I feel like I have an interest, and if she would be willing to allow me the time to go to the meetings and/or if she would mind if I tried to talk to these guys she knows. I wouldn't want it to come off as me trying to use her to further my agenda, I guess. I wouldn't want it to come off bad, I'll put it that way.

Also, I have someone on my facebook friends list that has the degree I'm looking into and I believe does work for the CTA as well, but we haven't met in person, so I wouldn't know how to approach that without seeming weird and stalkerish.

(I've come to the conclusion that I need to get more training in something, because my journalism writing concentration isn't what I really enjoyed about that field - I prefer the design end but most of my training is self taught and that isn't getting me the cash either. I just don't know if I should move on to something else or not.)

I'd appreciate any insights.
Also, I use too many smilies.