MachinegunJoe: Great question!
Deciding to get in was tough enough. Deciding when to get out even tougher. You've invested lots of time, effort, and dedication serving our Nation thus far and making the transition is something to be weighed carefully.
I guess one of the first questions to consider is: Have you accomplished all you wished to accomplish while in the Military?
Also, you might take some time to explore what you plan to do after you transition. Do you wake up each day motivated to stay or go? Could a new job or location or potential promotion make it worth staying?
Lots to think about for sure!
Check out some of the articles on GOING CIVILIAN when you get a chance.
Hopefully, others will comment with some insight.
I dont know what the current conditions are in the military. I was in in the 90's. I had to decide to stay or go at least 13 months before DOS. Long story short, I blew out my knee and the decision was made for me. OUT! No home, no job, baby on the way....It was rough for several years.
My advice is if the conditions are okay in the military stay in. Its hard out here in the civilian world....especially now with the economy sucking and the insurances increasing. If you just had enough then try to line up a job or a plan before getting out. If you had any type of injury during your service, file a claim with your local VA office. Keep a copy of your medical records. Even if it is approved at zero%, you still have it covered if you get reoccurring problems. Use your GI bill! or better yet take as many college courses while still in and then use your GI bill when you get out. Pay off any debt you have before seperation is also a good idea. Also look at the government jobs available before seperating.