I work part time for an IT guy for my company, and have learned a lot about a few things and a little about some other stuff. I am working on my Master's Degree in Information System Security, but the school I am taking it from didn't require a related undergraduate degree, so I have holes in my knowledge. I've been looking at jobs on Craigslist/Dice.com/random websites, and I have a lot of the troubleshooting skills and other related skills they have, plus I have practical experience which people are always demanding, so I'm in good standing there.
However, the glaring area of deficit for me is Windows Server and Active Directory. while I have access to a domain, and can add computers to a domain, my interaction with Windows Server, including adding groups, modifying groups, adding users, and adding computer to a group, I have little to no practice with, and after asking my boss, it is unlikely he will show me any of it (yes, dick move by him).