Use this financial checklist to systematically prepare for retirement. Cover every category — income, healthcare, taxes, estate planning, insurance, and debt — so nothing falls through the cracks.
Income Readiness Checklist
| ✅ | Task | Status |
|---|---|---|
| ☐ | Check Social Security estimate at ssa.gov | |
| ☐ | Decide Social Security claiming age (62, 67, or 70) | |
| ☐ | Total all retirement account balances (401k, IRA, Roth, brokerage) | |
| ☐ | Confirm pension amount and payout options (if applicable) | |
| ☐ | Calculate 4% withdrawal rate from savings | |
| ☐ | Add all income sources: SS + pension + withdrawals + other | |
| ☐ | Compare total income to estimated expenses | |
| ☐ | Build 1-2 year cash buffer in savings account |
Healthcare Checklist
| ✅ | Task | Status |
|---|---|---|
| ☐ | Plan for healthcare before Medicare (if retiring before 65) | |
| ☐ | Research ACA marketplace or COBRA options | |
| ☐ | Understand Medicare enrollment timeline (sign up 3 months before 65) | |
| ☐ | Choose: Original Medicare + Supplement vs. Medicare Advantage | |
| ☐ | Review Medicare Part D (prescription drug coverage) | |
| ☐ | Budget for out-of-pocket healthcare costs (~$371K for a couple, per Fidelity’s 2026 estimate) | |
| ☐ | Consider long-term care insurance or self-insurance strategy | |
| ☐ | Max out HSA before retiring (if eligible) |
Tax Planning Checklist
| ✅ | Task | Status |
|---|---|---|
| ☐ | Plan tax-efficient withdrawal order (taxable → tax-deferred → tax-free) | |
| ☐ | Consider Roth conversions in low-income years before Social Security | |
| ☐ | Understand Required Minimum Distributions (RMDs start at 73 if born 1951-1959, or 75 if born 1960+) | |
| ☐ | Plan for state income tax (some states don’t tax retirement income) | |
| ☐ | Estimate tax bracket in retirement | |
| ☐ | Consult a tax professional about retirement-specific strategies |
Estate Planning Checklist
| ✅ | Task | Status |
|---|---|---|
| ☐ | Create or update will | |
| ☐ | Establish or review trust (if applicable) | |
| ☐ | Assign durable power of attorney (financial) | |
| ☐ | Assign healthcare power of attorney / advance directive | |
| ☐ | Update ALL beneficiary designations (retirement accounts, life insurance, bank accounts) | |
| ☐ | Organize important documents in one secure location | |
| ☐ | Share account information / executor instructions with trusted person | |
| ☐ | Review and update annually |
Insurance Checklist
| ✅ | Task | Status |
|---|---|---|
| ☐ | Review life insurance needs (may no longer need large policy) | |
| ☐ | Evaluate long-term care insurance | |
| ☐ | Update homeowners/auto insurance | |
| ☐ | Consider umbrella liability insurance | |
| ☐ | Review disability insurance (not needed after retirement) |
Debt Checklist
| ✅ | Task | Status |
|---|---|---|
| ☐ | Pay off credit card debt completely | |
| ☐ | Pay off car loans | |
| ☐ | Decide: pay off mortgage or keep investing? | |
| ☐ | Eliminate all consumer debt before retiring | |
| ☐ | Calculate debt-free monthly expenses |
Lifestyle & Budget Checklist
| ✅ | Task | Status |
|---|---|---|
| ☐ | Create detailed retirement budget | |
| ☐ | Test-drive the budget for 6+ months while working | |
| ☐ | Plan for travel and hobbies budget | |
| ☐ | Consider downsizing / relocating to lower cost area | |
| ☐ | Plan for social connection and purpose | |
| ☐ | Consider part-time work or consulting for transition |
Key Numbers to Know
| Number | What It Means |
|---|---|
| 25x rule | Retirement savings needed = annual expenses × 25 |
| 4% rule | Withdraw 4% of savings in year 1, adjust for inflation |
| Age 59½ | Penalty-free 401(k)/IRA withdrawals |
| Age 62 | Earliest Social Security (permanently reduced) |
| Age 65 | Medicare eligibility |
| Age 67 | Full Social Security retirement age (born 1960+) |
| Age 70 | Maximum Social Security benefit |
| Age 73 or 75 | Required Minimum Distributions begin (73 if born 1951-1959; 75 if born 1960 or later, under SECURE 2.0) |
The Bottom Line
Go through this entire checklist before setting a retirement date. The most common regrets are not planning for healthcare costs before 65, not understanding the tax impact of withdrawals, and underestimating how long retirement lasts. One thorough planning session now prevents decades of financial stress.
For more on retirement planning at every age, see the Retirement Planning hub.
For more on retirement planning at every age, see the Retirement Planning hub.
The content on Wealthvieu is for informational purposes only and should not be considered financial, tax, or investment advice. Consult a qualified professional before making financial decisions. Full disclaimer · Editorial policy