Ok, two things that we have learned after we transitioned out of the military. One, definitely save up as much money as you can while you are still in the military, especially if you are a two income home and you have future plans of becoming a one income household. Rainy day fund comes in mightily handy when you are in the midst of a transition. Two, and this was the one that hurt us pretty bad, purchase some form of health insurance apart from Tricare - something you can upgrade at a later time...especially if you have a preexisting condition. We ended up pregnant right as my husband was getting out. My due date was right after his separation date and Tricare unfortunately does not continue coverage once you're out. We had to purchase a premium called Continued HealthCare Benefit and believe me, it was not cheap! We applied for Medicare but we didn't qualify. Either way, most insurance companies won't touch you if you have a preexisting condition. I know this scenario may not apply to retirees so I am mainly speaking to young service members who are getting ready to separate. These are the two main things I wish we had better preparation for right before we had decided to get out of the military. I hope that it helps someone in some way, shape, or form. Thanks!