Retirement Readiness Checklist

Retirement isn't a single decision — it's the result of many decisions made over years. A readiness checklist helps verify the pieces are in place before pulling the trigger.

This page is the checklist.

5+ years before retirement

Financial

- [ ] FI number calculated (current spending → adjusted for retirement spending → 25-30× target)

- [ ] Portfolio at 70%+ of FI number

- [ ] Retirement accounts maximized (401(k), IRA, HSA)

- [ ] Asset allocation appropriate for horizon

- [ ] Tax diversification: traditional + Roth + taxable

Healthcare

- [ ] Current health needs and trajectory understood

- [ ] Long-term care planning underway (insurance or self-fund decision made)

- [ ] HSA maxed if eligible

Lifestyle

- [ ] What does retirement look like for you?

- [ ] What about for your spouse?

- [ ] Where will you live?

- [ ] What will you do?

Documents

- [ ] Will exists and current

- [ ] Power of attorney in place

- [ ] Healthcare directives in place

- [ ] All beneficiaries reviewed and current

1-2 years before retirement

Financial

- [ ] FI number reached or very close

- [ ] Bucket strategy planned (cash, bonds, stocks)

- [ ] Withdrawal strategy planned

- [ ] Tax projection for first retirement year

- [ ] Emergency fund: 1+ year of expenses

Social Security

- [ ] Claiming strategy decided (delay vs. claim early)

- [ ] Spousal coordination if married

- [ ] Apply 3-4 months before intended start

Pension

- [ ] Election decided (J&S vs. single life vs. lump sum)

- [ ] Pension max insurance considered if applicable

- [ ] SBP if military

Healthcare

- [ ] Pre-Medicare bridge plan (ACA, COBRA, spousal coverage)

- [ ] Medicare enrollment timing understood

- [ ] Long-term care plan finalized

Lifestyle

- [ ] Retirement test run? (week-long "retirement" practice)

- [ ] Activities and structure planned

- [ ] Social connections maintained

6 months before retirement

Financial

- [ ] Final tax-year considerations (Roth conversions, charitable giving)

- [ ] Withdrawal plan implemented (cash bucket built)

- [ ] Cash flow plan: when does money come from where

Healthcare

- [ ] Healthcare insurance for first day of retirement confirmed

- [ ] All medications, providers, treatments under continuous care

- [ ] HSA strategy for non-contributing years

Employer

- [ ] Notice given (per company policy)

- [ ] 401(k) plan for retirement (leave in plan, roll to IRA)

- [ ] Stock option/RSU vesting addressed

- [ ] Final paycheck and benefit close-out planned

- [ ] Severance / retirement benefits negotiated if applicable

1 month before retirement

Financial

- [ ] First withdrawal scheduled

- [ ] Tax withholding adjusted for retirement income

- [ ] Direct deposit changes pending

Operational

- [ ] Email forwarding set up

- [ ] Personal contacts saved

- [ ] Work files appropriately archived/transferred

Lifestyle

- [ ] Friends and family informed

- [ ] First-week plans made

- [ ] Year-one plans roughed in

Day 1 of retirement

What should already be done

- All checklist items above

- First withdrawal made or scheduled

- Healthcare active

- Mental preparation done

What might still need attention

- Emotional adjustment

- Time-structure adjustment

- Identity adjustment

First year of retirement

Financial

- [ ] Withdrawals on plan

- [ ] Spending tracked vs. budget

- [ ] Tax situation managed (estimated taxes if needed)

- [ ] Portfolio rebalancing scheduled

Healthcare

- [ ] Coverage confirmed and providers in network

- [ ] Annual checkup

- [ ] All medications continued

Lifestyle

- [ ] Routines established

- [ ] Social activities engaged

- [ ] First-year reflection

Adjustments

Anything not working? First year is the time to adjust:

- Spending estimates may need revision

- Time use may need restructuring

- Plans for year 2+ may need refinement

Years 2-5 of retirement

Financial

- [ ] Annual review of plan

- [ ] Tax planning ahead of RMDs

- [ ] Roth conversion ladder if appropriate

- [ ] Estate documents review every 3-5 years

Healthcare

- [ ] Medicare transition planning (if in pre-Medicare bridge)

- [ ] LTC insurance / planning still adequate

- [ ] Health changes incorporated into plan

Lifestyle

- [ ] Ongoing engagement

- [ ] Travel, hobbies, projects on track

- [ ] Relationships maintained

Major life changes

Spouse death

- [ ] Survivor benefits applied for

- [ ] Estate executed

- [ ] Plan revised for single situation

- [ ] Social and family support engaged

Health crisis

- [ ] Insurance limits checked

- [ ] LTC plan activated if needed

- [ ] Plan revised for changed needs

Move

- [ ] State residency change implications

- [ ] Estate documents updated

- [ ] Healthcare network change

Family changes

- [ ] Beneficiaries updated

- [ ] Will revised if needed

- [ ] Estate strategy revised

Common failure patterns

Retiring without having done the math

Vague sense it's enough; specific calculation never done. May or may not actually be enough.

No bridge plan for healthcare

Retire at 60; figure out healthcare later. Expensive surprise.

No tax planning

Withdraw from accounts haphazardly; pay more tax than necessary.

Estate documents from 20 years ago

Outdated; reflects family from then; may not be valid in current state.

Lifestyle plan: "I'll figure it out"

Retire; don't know what to do; depression. The non-financial side is real.

Year 1 spending exceeds plan

Travel, projects, freedom-spending in year 1. Plan was for steady-state but year 1 isn't.

No survivor planning

Plan works for couple. When one dies, plan breaks.

A realistic timeline

The full readiness work takes 3-5 years of focused planning, plus periodic checkpoints over decades.

Don't try to do all of this in the last 6 months before retirement. Build it up incrementally.