Paycheck Chronicles

From The Mailbag: When To Plan For Leaving The Military


There is a single fact that is true for everyone in the military: they won't stay on active duty forever. One way or another, you or your family will separate from the service, retire, or (hopefully not) die while on active duty. Even when it is hard to imagine a time when you're not serving, thinking about it now can make it easier when it does happen.

Dear Kate,

I'm not re-enlisting at the end of this term. What do I need to do to plan for life after the military, and when should I start planning?


Oooh, what a question! I'm thrilled that Brian is thinking ahead, but also a little concerned if he's getting out in two weeks.

Dear Brian,

Thanks for asking! You didn't mention how much longer you have left on your enlistment, but the answer isn't much different if you have two years or two weeks.

The short answer is that you should start planning now. Today. Immediately.

Call your installation family readiness center (Airman and Family Readiness Center, Fleet and Family Services, Army Community Services, or Marine Corps Community Services) and ask them about every transition, financial readiness, and job hunting class they offer. Ask your command for permission to attend as many classes as possible. If you are married, take your spouse with you. You should, at the very least, be able to take the classes offered by your branch's Transition Assistance Program. They're required, but you might have to remind your command that they are required. The folks at the family readiness center can help you figure out how to do that.

Then start thinking about all the things you need to know:

What happens to your medical coverage?

Where will you live?

Can you take terminal leave, or will you sell back leave? Learn about the pros and cons of each option.

Understand your entitlement for your final move.

Will you be eligible for unemployment if you can't find a job?

How do you find a job in your field? How do you network? (Most jobs come from networking.) Do you need to set up a professional online presence?

What does your family's financial situation look like now? What do you want it to look like in the future? What can you do between now and then to get closer to your goal?

There is a ton to consider, and the earlier you start thinking about it, the more successful you will be. In my dream world, everyone would take a class in boot camp that helps them thinking about leaving the military. It seems crazy, but that's the ideal time to start.

Good luck on your transition!


Do you have transition questions? I'd love to answer them here! Email me at, and I'll answer those that are appropriate to a broader audience here on the blog. (I do manage to answer a remarkable number privately, but I can't answer every single email.)

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