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Free 10-page Retirement Readiness Workbook

Retirement Readiness
Workbook

Seven decisions to make before you leave the uniform—and a 30-day plan to begin with clarity.

Free PDF · 10 pages · No email signup required. Save a copy to print or use alongside your own records.

Start with the whole decision

Retirement is not a date. It is a system.

Military retirement planning is strongest when pension income, TSP assets, VA benefits, healthcare, housing, family responsibilities, taxes, work, and purpose are considered together.

Clarity comes before optimization.
01

Define what retirement must accomplish

Describe the ordinary life, family commitments, work, travel, service, and legacy the plan must support.

02

Build the guaranteed-income floor

Separate dependable monthly income from market-dependent assets and understand the deductions that affect spendable income.

03

Give every investment account a job

Coordinate TSP, IRA, and taxable assets around time horizon, risk, taxes, and expected withdrawals.

04

Place veterans benefits inside the larger strategy

Document established benefits, verify eligibility, and understand how each benefit strengthens the household plan.

05

Plan healthcare before the transition

Map coverage, enrollment actions, prescriptions, dental, vision, family needs, geography, and long-term care considerations.

06

Reduce fixed obligations and preserve margin

Review debt, housing, reserves, and recurring commitments so retirement retains flexibility.

07

Retire toward purpose

Build the next chapter around identity, contribution, relationships, structure, and legacy—not only the absence of work.

Your 30-day starting plan

Turn the briefing into movement.

Week 1

Build the command picture

Gather retirement estimates, TSP statements, Social Security estimates, VA decisions, insurance records, debt balances, and twelve months of core spending.

Week 2

Map income and obligations

Create a one-page view of expected income, taxes, healthcare, housing, family commitments, debt, savings, and discretionary spending.

Week 3

Stress-test the plan

Examine the expected plan, a market decline, and a major family or healthcare expense. Identify where flexibility would come from.

Week 4

Make the next three decisions

Choose the three decisions with the greatest effect on the next twelve months and assign a date, document, conversation, or qualified professional to each.

Keep your complete retirement workbook.

Download the 10-page workbook with a monthly cash-flow worksheet, preparation timeline, document checklist, readiness tracker, stress-test exercise, and 30-day action plan.

Download the free workbook

Educational information only; not individualized legal, tax, investment, financial-planning, medical, or veterans-claims advice.

A practical preparation check

Know what is verified. Know what comes next.

Use V for verified, R for researching, and N/A where an item does not apply. Record the next action and a follow-up date for each unresolved item.

Income and obligations

Confirm pension estimates and deductions, established benefits, housing costs, debt payments, and family commitments. Separate projected income from confirmed income.

Coverage and timing

Verify healthcare enrollment, survivor and beneficiary decisions, application windows, and expected first payments with the responsible office.

Cash flow and reserves

Dependable net monthly income minus planned monthly uses equals your margin or gap. Include annual bills divided by 12; do not deduct amounts already withheld from income twice.

Documents and next actions

Gather official estimates, service records, account statements, insurance records, and applicable family documents. Obtain the exact application checklist from the receiving agency.

Prepare in stages

Begin with estimates and eligibility checks, then confirm agency filing windows, submit within those windows, and reconcile actual payments after retirement. Suggested planning windows are not official filing deadlines.

Official starting points

DFAS: military retired pay · OPM: civilian federal retirement · Social Security · TSP · VA benefits · TRICARE · IRS: retirement plans

October 2026 edition. Verify requirements with the responsible agency. Keep private records in secure storage; do not submit them in public comments or website signup forms.