First, make a list of the pros and cons regarding your military life.  This exercise isn't meant to persuade you to remain in the service.  More than likely you'll see that your list of 'cons' to leave will be longer than your list of 'pros'.  The important thing here isn't the 'pros' or the 'cons'.  The important thing is that you are starting to track your thinking and beliefs about leaving the military.  There are many emotions that come with major life changes.  If you don't start to organize your thoughts either with 'pros/cons' lists or 'to-do' lists, etc, you'll have trouble keeping your emotions out of your decisions.  We can all agree that emotions do not help make the best informed decisions.

Next, put together a rough timeline of your remaining years of service.  If you don't have years then do the best you can to put together a timeline with your remaining months of military service.  It's self evident that the longer you have to create this timeline, the more information you can begin to plan for.  I call this timeline your 'bridge to civilian life'.  This is an exercise that will give you confidence as you transition out of the military.  It will involve concerted effort to compile the different activities.  You'll benefit from mentors online or from your personal network that can help you populate this timeline of activities.  This activity should be shared with your family so they are aware of the number of deadlines and activities that must be met or completed before your military transition is complete.

Your timeline can be broken into atleast two parts.  Part I should have the deadlines and activities in your last 6 months (180 days) of military service.  You can find 6 month timelines easily by Googling them or by attending Transition Assistance classes on base.  Most of these 6 month timelines focus on Veteran's Administration (VA) engagement and TAP class attendence.  Part II should include all deadlines and activities before the last 6 months of military service.  Part I and Part II activity timelines will reflect your last year before you leave the military. Your first attempt to create this timeline should be quick.  Get a list of deadlines and activities on a piece of paper or excel document and then put them on your Part I and Part II timeline.  Don't look for perfection.  If excel is too complicated, then use a pencil and paper or an old-school calendar.  The important thing is that you take the time to create this list of the programs you'll be applying to and appointments you'll need to attend.  Without this timeline, it will be difficult to communicate to your family how much work needs to be done before you leave the military.

Lastly, continue to build your network of people who recently transitioned from the service or retired, and those people who can mentor you through the last part of your service obligation.  Overseasveteran.com is one example, but there are many VSOs (Veteran Service Organizations / Veteran Service Officers) who have experiences to share that demystify miliary transition / retirement.  Remember the question - 'How do you eat an elephant?', answer - 'One bite at a time."  Create your two part timeline and gradually chip away at your timeline and 'to-do' list.  You can do it in a timely manner and be done with your deadlines and activities the day you leave the military.  

*Disclaimer.  For entertainment purposes only.  I am not a financial professional.  Modify your decision making as necessary.