A transition is coming—whether you’re ETS’ing after one enlistment or retiring after 20+ years. One thing’s for sure: the military will cut your orders, but they won’t hand you a comprehensive roadmap for the next chapter. And here’s the truth—what you do (or don’t do) in the last 6–12 months before separation can either make your transition seamless… or painfully expensive.
This isn’t just about turning in gear and signing paperwork. It’s about setting your family up for stability, locking down your benefits, and avoiding the “I wish I had known” regrets so many Veterans face.
Here’s the must-read checklist you need before you hit that 30-day countdown.
12 Months Out: Plant the Flag Early
Start TAP (Transition Assistance Program) Now. Don’t wait for the last-minute class. You can attend TAP up to 18 months before ETS and 24 months before retirement. Take it early so you actually have time to act on the information.
Get a Mentor. Choose someone who has either retired from the military, or had their own military transition, but who also has enough civilian experience to balance their military and civilian lens that will ultimately paint the picture taking shape for you. There are non-profits and private entities offering mentorship services to both active duty and military spouses.
Pro Tip: You can’t start planning your next step too early.
Medical Records Audit. Request your full health record from Military Treatment Facility (MTF). Comb through it. If your sprains, injuries, or deployments aren’t documented—get them added now. Future VA claims depend on it.
Financial Readiness Check. Meet with a Personal Financial Manager (PFM) on base. Budget for civilian life: no BAH, no BAS, no COLA. Do the math on what your family’s real cost of living will be.
Pro Tip: This number is important to understand when you’re negotiating job offers and considering what lifestyle you can/will afford.
Career Strategy. Whether it’s federal service, corporate America, entrepreneurship, or education—map it now. Don’t wait until your last day in uniform to decide.
6 Months Out: Lock in the Essentials
Start Your VA Claim with BDD (Benefits Delivery at Discharge). If you’re within 180–90 days of ETS/retirement, file now. This ensures benefits can kick in soon after separation.
Update DEERS & ID Cards. Make sure your spouse and kids’ records are accurate and their ID cards won’t expire right after your last day in service.
Life Insurance Decision. Decide if you’ll keep SGLI through conversion to VGLI, or shop civilian life insurance while you’re still in excellent health coverage. Waiting can mean higher premiums—or denial.
GI Bill Transfer (If Eligible). If you plan to transfer your Post-9/11 GI Bill benefits, ensure you’ve met service requirements before you hit retirement/ETS. Once you’re out, you can’t transfer.
90 Days Out? It’s Crunch Time
Medical Separation Physical. Schedule your separation health exam early. This is crucial for your VA claim and for catching anything you need documented before discharge.
TSP Strategy. Decide whether to roll over your Thrift Savings Plan or keep it. Don’t cash it out—you’ll lose years of tax-free growth and get hammered with penalties.
Housing & Relocation Plans. If moving, book transportation (DPS) and housing plans now. The closer you get to your date, the harder it is to secure movers and good housing.
Final Career Moves. Line up interviews, polish your resume, and secure a LinkedIn presence that reflects your civilian career goals.
30 Days Out: Last-Minute, High-Stakes Details
DD-214 Accuracy Check. Triple-check your DD-214 before you sign. Dates, awards, deployments, MOS—all of it. Fixing it after separation is a nightmare.
Pay & Benefits Verification. Review your final LES carefully. Confirm leave balance payout, separation pay (if any), and deductions.
Healthcare Bridge. Ensure TRICARE retirement enrollment (if retiring) or civilian healthcare (if ETS). Don’t leave your family uninsured.
Contact VA & DFAS. Give them your permanent address, not your unit or barracks. Lost mail = lost benefits.
The Overlooked (But Critical) To-Do’s
Disability Claims Evidence. Don’t just list conditions—collect supporting evidence: X-rays, physical therapy notes, deployment exposure documentation.
Reserve & National Guard Affiliations. If ETS’ing but considering the Guard/Reserves, line it up before separation. Breaks in service can impact benefits.
Tax Implications. Consult a tax professional about severance pay, relocation, and retirement pay. Many Veterans leave money on the table with poor tax planning.
Networking. Start plugging into Veteran networks, LinkedIn groups, and local VSOs before you hang up the uniform.
For Military Families: Your Parallel Checklist
Spousal Employment/Education Benefits. Spouses may be eligible for MyCAA (education funding) or hiring preference programs. Don’t miss out.
Healthcare Enrollment. Double-check TRICARE transition coverage or employer coverage timelines. Gaps in coverage can be costly.
Children’s School Records. If relocating, request transcripts early and research school districts in advance.
Budget Shift Awareness. Military families often underestimate the financial shift after losing tax-free allowances. Re-do the family budget together.
Mental Health Transition. The family dynamic changes when service ends. Know where to access support networks (Military OneSource, Vet Centers, community groups).
Your Future Hinges on Preparation
The day you take off the uniform for the last time will come fast—and the paperwork shuffle won’t stop just because you’ve moved on. Those who thrive in transition are the ones who prepared early, checked every box, and treated this chapter with the same discipline they brought to their military careers.
Don’t leave your benefits, finances, or family’s security to chance. Start now. Your service earned these opportunities—your preparation will ensure you don’t lose them.
When the uniform comes off, the mission isn’t over—it just changes.
And this checklist? It’s your new operations order.
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