How to Ensure a Smooth Transition to Military Retirement
Military retirement transition has gotten complicated with all the programs, benefits changes, and civilian job market challenges flying around. As someone who went through this process myself and counseled hundreds of transitioning service members, I learned everything there is to know about making the jump from active duty to retirement life. Today, I will share it all with you.
Understand Your Benefits
Probably should have led with this section, honestly. Before you can plan anything else, you need to know exactly what you’re entitled to. Pull your latest benefits statement from DFAS and verify your projected retirement pay. Check your TRICARE eligibility, understand your Survivor Benefit Plan options, and confirm your TSP balance. The VA also has benefits separate from DoD retirement—disability compensation, healthcare, home loans, education benefits. Don’t assume you know what you’re getting; verify everything in writing.
Financial Planning
Your paycheck is about to change dramatically. If you’re retiring at 20 years, your pension is roughly 40-50% of your base pay depending on your system, and you’re losing BAH, BAS, and all those tax-free allowances. Create a realistic post-retirement budget that accounts for your actual take-home pension after taxes, SBP premiums, and TRICARE costs. Most retirees need second careers or side income to maintain their active-duty lifestyle. Work with a financial counselor through your installation’s Personal Financial Management program—they understand military retirement better than civilian financial advisors.
Healthcare Options
TRICARE and VA healthcare are separate systems, and you can use both. TRICARE Prime costs less but requires referrals and network providers. TRICARE Select costs more but gives you freedom to see any TRICARE-authorized provider. If you have a VA disability rating, you can also use VA healthcare—often with no copays for service-connected conditions. That’s what makes dual coverage endearing to us retirees—you can use whichever system gives you better access to the care you need.
Job Transition
Unless you’re retiring at 65+, you’re probably going to work another career. Your military skills absolutely translate to civilian jobs—leadership, project management, logistics, technical expertise, security clearances. Defense contractors actively recruit military retirees. The Transition Assistance Program (TAP) is mandatory, and while it sometimes feels like death by PowerPoint, the resume workshops and employer connections are valuable. Start networking 12-18 months before retirement. Update your LinkedIn profile. Attend job fairs. Talk to people who’ve already made the transition in your field.
Mental Health and Support
The transition is harder than most people expect. You’re leaving a structured environment with clear missions and hierarchies for civilian life where none of that exists. Your identity has been “military” for 20+ years—now you need to rebuild who you are as a civilian. This is normal, and it’s okay to struggle with it. Use counseling resources through Military OneSource, the VA, or private therapists. Stay connected with other veterans who understand what you’re going through. Mental health support isn’t weakness—it’s smart planning for a successful transition.
Family Considerations
Your retirement affects your whole family. Your spouse has been living military life too—frequent moves, deployments, the commissary, military healthcare. Now all of that changes. Include your family in transition planning. Discuss where you’ll live, whether you’ll work another career, how your income will change. Kids might be leaving schools and friends. Spouses might need to find new jobs or adjust to you being home more. Open communication prevents resentment and helps everyone adapt together.
Stay Connected
Don’t cut ties with the military community. Join veteran organizations like MOAA, your branch’s association, the American Legion, or VFW. These groups provide networking, advocacy for benefits, and social connections with people who speak your language. That camaraderie is what makes veteran organizations endearing to us retirees—we still need that sense of belonging to something bigger than ourselves.
Documentation
Keep copies of everything: your DD-214, retirement orders, medical records, VA disability rating letters, SBP elections, and any other service-related documents. Scan them and store digital copies in the cloud with backup on a external drive. You’ll need these documents for VA claims, employment verification, benefits applications, and legal matters. DFAS and the VA lose paperwork all the time—having your own copies saves you massive headaches down the road.
