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This transition checklist is a killer resource for separation/retirement

No matter your timeline.
Shannon Corbeil Avatar
Photo by Senior Airman Jesse Hanson

Transitioning out of the military might seem straightforward — after all, servicemembers are given an out-processing checklist — but there is a lot to consider when setting yourself up for success after the structure of the military. From squaring away finances, medical records, insurance, and more, it can be overwhelming. Luckily, AAFMAA (American Armed Forces Mutual Aid Association) has prepared one of the most in-depth checklists out there. Not only is it thorough, but it starts you off as early as three years out. 

Whether you’re planning to separate from the military sometime in the future or you just want to gather some information, we highly recommend looking it over. Here are some of the highlights of how it can prepare you for success no matter what your timeline is. 


The AAFMAA Transition Timeline covers how to handle your finances from three years out until your final day in the service. While on Active Duty, it’s easy to grow accustomed to steady paychecks and housing or BAH, but that’s not guaranteed to civilians. To be financially ready for unforeseen challenges, AAFMAA recommends saving at least three to six months’ worth of living expenses — which is a great emergency fund to have as a civilian too. Active Duty is also a great time to initiate investments such as a Roth IRA and the TSP in the blended retirement system. At one to three years out, AAFMAA’s checklist urges you to understand the funds in your accounts and offers help as you determine your investment strategy. 

Health and insurance

While in the military, you might not realize how extensive TRICARE coverage is. If you need to go to urgent care, it’s covered. You know who your primary care physician is. Medications are included. And dental is included. As a civilian, you’ll have to do your own research about what kind of coverage you and your family need and what you can afford. 

The Transition Timeline also includes a checklist of tasks to get your medical history and benefits in order. From your out-processing appointments (be sure to list every single condition you might have currently in case they worsen or qualify you for disability down the road) to ordering copies of your medical history and vaccinations, you want to stay organized and ahead of the game. 

Additionally, your SGLI (Servicemembers’ Group Life Insurance) terminates when you separate. To keep your family protected you’ll need to replace it before you lose it. Fortunately, AAFMAA has experts in military life insurance who can offer great advice and some of the most competitive policies available to Veterans — even before you transition.

Future employment opportunities

You can begin thinking about your civilian career while still on Active Duty. From networking on LinkedIn to translating your military achievements and experience for a civilian resume to exploring the GI Bill and education benefits, there are many pathways you can pursue. Start early to prevent feeling overwhelmed, and more importantly, so you don’t find yourself without a job (or paycheck).

The DOL’s Transition Assistance Program (TAP) will also help guide you starting 12 months out, while AAFMAA’s checklist guides you through the different workshops and services offered. 

The final (miscellaneous) push

One to three months out from separation gets busy. You’ll have leave that you can use or “buyback,” a potential move to plan (packing, shipping, utility and internet bills to pay and close out, housecleaning), and new benefits to understand (Space-A!). The checklist will keep you from trying to do it all in the final week. Remember, you and your family will have friends to say goodbye to if your separation or retirement comes with a relocation. You should be prepared for it all.

During this time, you may also be interviewing for a new job, which takes time to research medical and dental benefits, stock or cash bonuses, 401(k) options, and whether the job is a good fit and will satisfy you. 

If it seems overwhelming, that’s normal. There is a lot to consider when you transition from the autopilot lifestyle of the military (move here, live here, do this job, everyone makes the same amount and goes to the same doctor). That’s why having a clear, thorough checklist to help you keep track of all your to-do’s is an amazing resource. Making plans with AAFMAA’s timeline will give you time to educate yourself, accomplish the tasks, and set yourself up for success as a civilian.

Shannon Corbeil is an actor, writer, and host with a masters degree in Strategic Intelligence. A prior U.S. Air Force Intelligence Officer, she now specializes in writing about military history and trivia, veterans issues, and the entertainment industry. She currently resides in Los Angeles, CA.