Military Separation Transition Checklist: Complete 12-Month Timeline

Bottom Line Up Front: Successful military-to-civilian transition requires 12+ months planning. Key milestones: File VA claim (180 days out), start resume/LinkedIn (12 months out), attend TAP (90 days out), use terminal leave (30-60 days), maintain TRICARE (180 days free after separation). Most transition failures come from starting too late, not filing VA claim, or having no job lined up. This checklist ensures you don't miss critical steps.

12-Month Transition Timeline

12 Months Before Separation: Career Planning

Tasks:

1. ✅ Decide: Civilian career, federal employment, or entrepreneurship?
2. ✅ Research job market in desired location
3. ✅ Identify skill gaps (what certifications/training needed?)
4. ✅ Start networking (LinkedIn, veteran groups)

Career assessment:

• What did you do in military? (MOS translation)
• What do you WANT to do? (May be different)
• What pays well? (Research salaries)
• Where do you want to live? (Job market varies by location)

10-12 Months Out: Education & Certifications

Tasks:

1. ✅ Use remaining TA (Tuition Assistance) for courses
2. ✅ Take CLEP tests (free while active duty)
3. ✅ Get industry certifications:
   • PMP (Project Management Professional)
   • CompTIA Security+ (Cybersecurity)
   • A&P License (Aircraft Maintenance)
   • CDL (Commercial Driver's License)

Why now: TA ends at separation. Get training while it's free.

9 Months Out: Financial Preparation

Tasks:

1. ✅ Save 6-12 months expenses ($15,000-$40,000)
2. ✅ Pay off high-interest debt
3. ✅ Create civilian budget (no BAH, no BAS after TRICARE ends)
4. ✅ Research health insurance costs (if not converting to TRICARE Retired)

Financial reality check:

While active duty:

• E-6: $60,000/year total comp (base + BAH + BAS)

After separation (if unemployed for 3 months):

• Income: $0
• Expenses continue: $3,000-$5,000/month
• Need: $9,000-$15,000 savings buffer

6-8 Months Out: Resume & Job Search

Tasks:

1. ✅ Create civilian resume (1-2 pages, no jargon)
2. ✅ Create federal resume (if pursuing federal jobs)
3. ✅ Optimize LinkedIn profile
4. ✅ Start applying to jobs (yes, this early!)

Why start so early:

• Federal hiring: 6-12 months from application to start date
• Civilian hiring: 1-3 months average
• Multiple interviews, rounds, background checks

Apply to:

• 20-30 jobs (don't just apply to 2-3)

6 Months Out: File VA Disability Claim (BDD)

CRITICAL TASK:

1. ✅ Go to VA.gov, file BDD claim (Benefits Delivery at Discharge)
2. ✅ Claim ALL service-connected conditions (even "minor" ones)
3. ✅ Attend C&P exam (before separation)
4. ✅ Get VSO assistance (free - DAV, VFW, American Legion)

Timeline:

• File: 90-180 days before separation
• C&P exam: Within 45 days of filing
• Rating decision: Within 60 days of separation
• First VA payment: Immediately after separation (vs. 6-12 month wait if you file after)

4-6 Months Out: TAP (Transition Assistance Program)

Required attendance:

• 1-week course (Mon-Fri, full days)
• Covers: Resume writing, interview prep, financial planning, VA benefits

Tracks available:

• Employment track (most common)
• Education track (using GI Bill immediately)
• Entrepreneurship track (starting business)

Even if you have job lined up: Still attend (you'll learn something)

3 Months Out: Final Out-Processing Begins

Tasks:

1. ✅ Start clearing base (dental, medical, CIF, finance, etc.)
2. ✅ Get medical/dental records (full copies for yourself)
3. ✅ Schedule separation physical
4. ✅ Get copies of ALL military documents:
   • DD-214 (you'll get this at separation)
   • Performance evaluations
   • Awards/decorations
   • Training certificates
   • Security clearance documentation

2 Months Out: Benefits Decisions

Decisions to make:

1. ✅ Convert SGLI to VGLI? (or get civilian life insurance?)
2. ✅ Keep TSP or roll to IRA?
3. ✅ Healthcare: TRICARE (if eligible), VA, or civilian insurance?
4. ✅ Use terminal leave? (Sell leave days vs. take leave before separation)

1 Month Out: Final Steps

Tasks:

1. ✅ Out-process from base (final appointments)
2. ✅ Get DD-214 (Member 4 copy - guard this with your life)
3. ✅ Register with VA (if haven't already)
4. ✅ Cancel on-base housing (if applicable)
5. ✅ Forward mail (USPS mail forwarding)

Separation Day: Receive DD-214

Critical:

• Review DD-214 for errors BEFORE signing
• Common errors: Dates wrong, character of discharge wrong, awards missing
• Get 5-10 certified copies
• Store in safe place (you'll need this for life)

After Separation: First 90 Days

Tasks:

1. ✅ File for unemployment (if no job yet - you're eligible)
2. ✅ Apply for VA healthcare (if not done already)
3. ✅ Convert SGLI to VGLI (within 240 days)
4. ✅ Transition TRICARE (180 days free, then must enroll in VA or civilian insurance)
5. ✅ Continue job search (if not employed yet)

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Terminal Leave Strategy

What Is Terminal Leave?

Use accrued leave at end of service (instead of selling it)

Benefits:

• Still get paid (base pay + BAH + BAS)
• Still have TRICARE
• Still have base access
• But you're done working (job search, move, relax)

Example:

• 60 days terminal leave
• Effective separation date: July 31
• Last day of work: June 1
• June + July = full pay while off duty

vs. Selling Leave:

• Sell 60 days = 60 days × daily base pay rate
• Taxed at higher rate (lump sum = more taxes)
• Lose BAH, BAS for those 60 days

Recommendation: Take terminal leave (almost always better than selling)

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Common Separation Mistakes

❌ Mistake #1: Not Filing VA Claim Before Separation

Reality: You separate. File VA claim 6 months later. Wait another 6 months. 12 months with $0 VA income.

Fix: File BDD claim 90-180 days before separation. Get rating immediately.

❌ Mistake #2: No Job Lined Up

Reality: "I'll find job after I get out." 6 months later, still unemployed, savings depleted.

Fix: Start job search 6-9 months before separation. Have job lined up (or very close).

❌ Mistake #3: Not Getting Copies of Medical Records

Reality: You separate. Need medical records for VA claim. Records are lost/hard to obtain.

Fix: Get FULL copies of medical and dental records before separation.

❌ Mistake #4: DD-214 Errors

Reality: You sign DD-214 without reviewing. Later find your awards are missing, dates are wrong. Correcting takes months/years.

Fix: Review DD-214 line-by-line BEFORE signing. Demand corrections before separating.

❌ Mistake #5: Moving Without Job

Reality: You move to California (expensive). No job. Burn through savings in 3 months.

Fix: Have job first OR move to affordable location with good job market (Texas, North Carolina, etc.)

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Checklist (Print This)

12 Months Out:

• [ ] Decide civilian career path
• [ ] Start networking (LinkedIn, veteran groups)
• [ ] Research job market

9-10 Months Out:

• [ ] Use remaining TA for training
• [ ] Save 6-12 months expenses
• [ ] Build civilian resume

6 Months Out:

• [ ] File VA BDD claim
• [ ] Start applying to jobs (20-30 applications)
• [ ] Attend TAP

3 Months Out:

• [ ] Begin out-processing
• [ ] Get medical/dental records
• [ ] Apply for VA healthcare

1 Month Out:

• [ ] Get DD-214 (review for errors)
• [ ] Decide: Terminal leave or sell leave?
• [ ] Set up mail forwarding
• [ ] Plan healthcare transition

Separation Day:

• [ ] Receive DD-214
• [ ] Get certified copies (5-10)
• [ ] Verify out-processing complete

After Separation:

• [ ] File for unemployment (if no job)
• [ ] Convert SGLI to VGLI (if keeping)
• [ ] Transition TRICARE
• [ ] Continue job search

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Resources

Free Transition Assistance:

• Military OneSource: 800-342-9647 (career counseling)
• Hiring Our Heroes: Resume reviews, job fairs
• VA Veteran Readiness & Employment (VR&E): Education/career counseling
• American Corporate Partners (ACP): Free veteran mentorship

Job Search Sites:

• LinkedIn.com
• Indeed.com
• USAJobs.gov (federal jobs)
• RecruitMilitary.com
• HireHeroesUSA.org

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Verification & Sources

Official Sources:

• TAP (Transition Assistance Program): dodtap.mil
• VA Benefits Delivery at Discharge (BDD)
• DD-214 review guide

Last Updated: October 31, 2025

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Related Guides

• VA Disability Claims Step-by-Step
• Civilian Resume Writing for Veterans
• GI Bill Complete Guide

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Remember: Transition is a 12-month process, not a 1-week out-processing checklist. Those who plan ahead (VA claim, job search, financial prep) thrive. Those who wing it struggle. Use this checklist. Start early. Set yourself up for success.