The Transition Roadmap

Every deadline that matters, in the order they hit — from a year out through your first six months as a civilian.

Free, no account, nothing to sign up for. Check items off as you go and this page will remember where you left off.

Know someone with a separation date?

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Veterans Crisis Line — dial 988, then press 1. Or text 838255. Free, confidential, 24/7. You don't have to be in crisis to call.

Prefer it on paper?

The whole checklist as a PDF — all 62 items, laid out to print. No email address, no account, nothing to sign up for.

Download the checklist

How to use this

Find where you are. Start there. Don't read the whole thing tonight.

Each phase lists only what matters in that window. Some things can only be done before you take off the uniform, and those are called out.

Every phase ends with one line: if you do nothing else, do this. On the days when you can't face the list, do that one thing.

This covers what to do and when. It doesn't quote dollar amounts, pay rates, or eligibility formulas, because those change and stale numbers are worse than none. For current specifics and for organizations near you, use VeteransDirectory.org.

Already out? Even years out — start at "First 30 days after separation." Some of it will already be done. Some of it won't be, and it's not too late.

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Part one

Before you separate

12 months or more out

You have the most valuable thing in this whole process, which is time. Almost every mistake people make in transition is a timing mistake.

Employment & career

Finances

Administrative

If you do nothing elseGet on the TAP calendar.

180 days out

Your benefit windows are opening — and two of the most important ones close before you separate. This is the highest-stakes phase in the roadmap.

Benefits & entitlements

Benefits Delivery at Discharge (BDD) lets you file for VA disability compensation between 180 and 90 days before separation, using VA Form 21-526EZ with the BDD box marked. The VA reviews records and schedules exams while you're still in. The goal is a decision within about 30 days of separation, though actual timing can vary. Even when it takes longer, BDD still gives you a significant head start over filing after you separate. This window does not reopen.

Employment & career

Finances

Administrative

If you do nothing elseFile the BDD claim.

90 days out

The BDD window closes. Your job search becomes real — most employers hire on a 60-to-90-day horizon, so this is when applying starts to convert.

Benefits & entitlements

Employment & career

Housing

Mental health & wellness

Family & relationships

If you do nothing elseIf you missed the BDD window, put "file Intent to File" on your calendar for separation day.

Final 30 days

Almost entirely paperwork — and this is the paperwork you'll be living with for the rest of your life.

Administrative

Health coverage — read this one twice

TAMP — the Transitional Assistance Management Program — provides 180 days of premium-free TRICARE coverage after separation, but it is not automatic. It mainly applies to involuntary separations, certain Reserve activations, sole survivorship discharges, and a few other specific situations. A routine end-of-contract separation usually does not qualify.

Finances

Networking & community

If you do nothing elseRead the DD-214 before you sign it.

Part two

After you separate

First 30 days

No formation, no orders, no structure. For a lot of people this is the hardest month, and it's also the month with the most deadlines. That combination is why this phase is short and blunt.

Benefits & entitlements

Mental health & wellness

Administrative

Employment & career

If you do nothing elseGet the Intent to File or the claim submitted.

Days 30–60

The novelty is gone and the search is real work. Treat it like work.

Employment & career

Benefits & entitlements

Finances

Family & relationships

If you do nothing elseSit down with a County Veteran Service Officer.

Days 60–90

Either momentum or a plateau. Both are normal. What matters is diagnosing which one you're in.

Mental health & wellness

Employment & career

Networking & community

If you do nothing elseName what isn't working and change that one thing.

Days 90–180

Long enough out to see the shape of your civilian life. This phase is about catching the deadlines that are still open and taking stock honestly.

Finances

Benefits & entitlements

Employment & career

Mental health & family

If you do nothing elseSet a calendar alert for day 240.

Staying on track

Pick the one thing

Every phase has a single line at the bottom for a reason. Do that, and you're not behind.

Put deadlines in a calendar

Not in your head. Day 60, day 120, day 240 — these are the ones that quietly expire.

Get an accredited person on your side

A County Veteran Service Officer costs nothing and knows things you'd take years to learn.

Expect the dip

Most people hit a low somewhere between month two and month four. Knowing it's coming makes it survivable.

Ask early

The pattern that hurts people is waiting until it's urgent. Any organization in the directory would rather hear from you at month two than month twelve.

You've done harder things

It doesn't feel that way, because this is unfamiliar rather than difficult. Unfamiliar passes.