Your 50s.
Prepare the landing.

Catch-up contributions

Starting the year you turn 50, the IRS allows additional contributions to retirement accounts:

• 401k catch-up: $7,500 additional in 2026, on top of the $23,500 base. Total possible: $31,000.
• IRAIndividual Retirement Account (IRA)A personal retirement savings account with tax advantages. Two main types: Traditional (tax now, pay later) and Roth (pay now, tax-free forever).Full definition catch-up: $1,000 additional, on top of $7,000 base. Total: $8,000.
• HSAHealth Savings Account (HSA)A tax-advantaged account for healthcare costs, available with a high-deductible plan; contributions, growth, and qualified withdrawals are all tax-free.Full definition catch-up (age 55+): $1,000 additional.

A married couple both 50+ on HDHPsHigh-Deductible Health Plan (HDHP)A health insurance plan with cheaper monthly cost but a bigger amount you pay yourself before insurance starts covering bills. Required if you want a tax-free Health Savings Account.Full definition can shelter $80,000+ per year across these accounts. The catch-up window is the last chance to materially alter the retirement portfolio. Detail at Accounts.

The Roth conversion window

Between retirement and age 73 (when Required Minimum Distributions start), you may have low-income years where Roth conversions are unusually cheap. Converting Traditional IRA dollars to Roth at a 12% or 22% bracket beats taking RMDs later that push you into a 32% or 35% bracket plus IRMAA Medicare premium surcharges.

The math is specific to your situation: current balances, expected retirement income, Social Security timing, state tax. Run scenarios at Roth Conversion Sweet Spot and Roth Conversion Calculator. The strategic frame is at Roth Conversion Timing.

Social Security claiming

Claiming at 62 (early) reduces your benefit by approximately 30% from full retirement age. Delaying to 70 (the maximum) increases it by 24% above FRAFull Retirement Age (FRA)The age at which you qualify for your full Social Security benefit, currently 67 for anyone born after 1960.. The break-even age between claiming at FRA vs delaying to 70 is approximately 82 to 83. If you expect to live past 83, delaying wins on lifetime benefits. If you expect to live shorter, early claiming wins.

The "bridge strategybridge strategyA retirement-income approach where you delay Social Security to age 70 and fund living expenses in the bridge years from Traditional IRA or 401k withdrawals. Trades portfolio principal for a larger guaranteed inflation-adjusted income stream for life." funds living expenses from retirement accounts during the delay years to enable claiming at 70. Detail at Social Security Strategy and the math at SS Bridge Calculator.

IRMAA: the surcharge most people don't see coming

Medicare Part B and Part D premiums are means-tested. Income above approximately $106,000 (single) / $212,000 (MFJMarried Filing Jointly (MFJ)A tax filing status where a married couple combines their income and deductions on one tax return.) MAGIModified Adjusted Gross Income (MAGI)Your taxable income with certain deductions added back in. The IRS uses this slightly different number to decide if you qualify for some tax breaks.Full definition triggers Income-Related Monthly Adjustment Amounts that can add hundreds of dollars per month per person to Medicare premiums. The brackets are cliffs, not phase-ins; one dollar over the threshold can cost thousands per year in additional premiums.

Roth conversions, IRA distributions, and capital-gain realizations all count toward MAGI for IRMAA purposes. Plan around the brackets in years approaching age 65. Detail at IRMAA and the calculator at IRMAA Estimator.

The healthcare bridge to Medicare

If you retire before 65, you need to bridge healthcare to Medicare eligibility. Options: COBRAConsolidated Omnibus Budget Reconciliation Act (COBRA)A federal law that lets you keep employer health insurance for up to 18 months after leaving a job, at full cost.Full definition from your employer (expensive but identical coverage for up to 18 months), an ACA marketplace plan (subsidized if your taxable income is in the right range), spouse's plan if they're still working, or self-funded if you can absorb the cost.

The ACA subsidies are large in the income range that early retirees often inhabit, since taxable income from a Roth-heavy portfolio can be intentionally kept low. Detail at Healthcare in Early Retirement.

Eliminate debt before retiring

Entering retirement with a mortgage payment, car loans, or credit card debt forces a higher withdrawal rate from the portfolio. Higher withdrawal rate equals lower safe-withdrawal-rate margin equals higher chance of running out of money. The 50s are the last comfortable decade to pay these down before they become a permanent fixed cost on a smaller income.

Mortgage payoff specifically is contested: low fixed-rate mortgages may be worth keeping if expected investment returns exceed the rate. The NPV decision tool handles the comparison.

What to do this month if you're in your 50s

• Take catch-up contributions if not already (50+).
• Run a Roth conversion model for the 5 years after expected retirement.
• Build the IRMAA bracket lookup into your tax planning.
• Decide on the Social Security claiming strategy. Run break-even.
• Plan the healthcare bridge from retirement to Medicare.
• Eliminate any consumer debt; decide on mortgage payoff with NPVNet Present Value (NPV)The sum of all future cash flows from a decision, each discounted back to today's value, minus any upfront cost. Positive NPV means the decision creates wealth. Negative NPV means it destroys wealth at your discount rate.Full definition math.

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