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.

Further Reading

• CalculatingYourFiNumber — Financial readiness
• BucketStrategyForRetirement — Withdrawal structure
• PreMedicareBridgeStrategies — Healthcare bridge
• EstatePlanningForRetirees — Document preparation
• RetirementSpendingPatterns — Spending evolution
• RetirementPlanningGuide — Cluster index