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.
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