When I retired from the military eight years ago, I had no idea of what to expect in the civilian job market. My first job, fortunately, was with a military contractor - and was semi-IT related. What helped was that as a defense contractor workingaround the military, I was working with many other former military folks, and there was this informal support network to get me through the do's and don't of the civilian workplace, like - NEVER, NEVER reveal your salary to anyone except your wife, don't worry about being fired for an honest mistake, etc., NEVER tell your perspective employer what you make at your last job, DO negotiate perks, etc. It really helped, and after four years I went into a pure private sector job - and survived thattransition as well.
Unfortunately, thi is the only thing I know that helps - the militay tries to prepare people for the transition through the various transition offices - but as those are typically run by career goverment civil servants who haven't had to survive in the private sector with its economic business cycles, they usually are not too much help.
Hope this helps.
