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How to Successfully Transition Out of the Military


Transitioning from military to civilian life or retirement is not something to take lightly. Nearly 50% of military Veterans indicate their transition to civilian life was more difficult than expected. While there are many steps you can take and procedures you can put in place to help ease your transition, waiting until the last minute to start the process can lead to delays and setbacks along the way.

One of the most important things you can do to make your military transition successful not only for you, the servicemember, but for your family as a whole is to make sure you are talking with and keeping your spouse in the know.

It’s also vital to plan ahead for medical and financial changes when you’re transitioning out of the military. Since financial planning after a military career can be overwhelming, we’ve compiled a guide to help you transition out of military life with ease.

Download our FREE! Transition Timeline

When and Where to Begin Your Transition from the Military

Retiring from the military is not as simple as retiring from the traditional, civilian workforce. With numerous financial and medical issues to solve before retirement, utilizing our “Retiring from the Military” checklist will help ensure your retirement process runs smoothly:

  • More than 12 months from retiring: Start determining your qualifications for retirement and eligibility benefits — and assess your finances so you can start paying down any debt.

  • 4 to 6 months from retiring: You’ll want to develop a transition plan and begin scheduling physical and dental appointments. Consulting with a Veterans Affairs counselor will help you identify whether a disability claim needs to be filed.

  • 2 to 4 months from retiring: Now is the time to submit your leave request and start obtaining retirement or separation orders. This time should also be used to make copies of all your personnel and medical records.

Separation from the Military Checklist

Use our “Separation from the Military Checklist” to help ensure you’ve done all the necessary preparation to avoid any unforeseen circumstances. For traditional military transitions, you should start your financial and medical transitions about six months before your official leave date.

  • Gather Medical Records and Paperwork: Start gathering your medical records and investigate any medical issues while you’re still enlisted. Having all the proper paperwork ready and on hand will also help when you’re applying for disability claims.

  • Budget Properly: Your next move after the military will also dictate how much income you need. Where you live will play a large role in this. You need to understand what benefits you will be losing, how to replace them, and at what cost. Also understanding civilian vs. military pay will help better understand what your new income needs to be.

  • Investments: Understand what to do with your TSP. If your new position offers a 401(k), you’ll want to know what the matching contribution is to maximize your retirement savings.

  • Life Insurance: Make sure you have a plan in place to continue protecting your family should something happen to you. Shop around, ask questions and learn the difference between term and whole life insurance.

  • Enroll in Transition Classes: Taking military transition classes is a mandatory requirement. The earlier you enroll, the more time you will have to take advantage of the knowledge and resources you learn from the class.

  • Continuing Education: If you have a GI Bill and want to enroll in college, speak with a career counselor or education service officer. If you want to transfer your GI bill, now is the time to do that. Organizations such as Vets2Industry and VetJobs can assist in continuing education and job placements.

  • Certify Your Training: If your future career requires educational certifications, you can start earning them while you’re still on active duty. Take certification courses early in the transition process. Organizations such as PM ProLearn can help in this process.

  • Update Your Resume and Start Networking: When you transition to civilian life, you don’t want to send an outdated resume to potential employers. Resume styles may have changed since you first joined the service, and a modern resume with your military accomplishments can set you apart from other candidates. Updating or creating a LinkedIn profile can also help you connect with other military Veterans and professionals in the field you’re interested in joining.

  • Update Family Dynamics: Your life is about to change, and it’s vital that your family is also prepared for it. Taking time to learn the needs of your family and the benefits available to them for their transition will enable a smoother transition process for everyone. SpouseLink is a wonderful way for military spouses to connect even after transitioning from the service.

AAFMAA Resources on Transitioning Out of the Military

Regardless of your situation, transitioning from the military requires a lot of work and preparation, so the sooner you start, the better off you’ll be in the long run. Make sure to use the AAFMAA Military Retirement/Transition Timeline to get squared away.

Our videos on transitioning out of the military will also be very informative throughout the process..

What to do with your TSP While Leaving the Military

Budgeting Vets 2 Industry

This article was originally published May 26, 2022.