For readers near or in retirement
The Five Years Before and After You Retire
The decade around retirement holds most of the decisions that cannot be undone: pension elections, Social Security, Medicare, Roth conversions, the house and the estate. Here is each one, in order, with the free tools and guides we have for it.
Who is this page for?
People roughly 55 to 75 who want to understand each decision before they make it, whether they work with a CPA or adviser or handle it themselves.
Most of our readers have spent decades saving and investing, often with a seven-figure portfolio, a paid-off or nearly paid-off house, adult children and grandchildren. Some are five years from retiring; some stopped work last year; some have been drawing income for a decade and are now thinking about required distributions and what to leave behind. Most work with a CPA, planner or attorney. What they share is that they want to understand the rules well enough to check the numbers, ask good questions and decide with full information.
Everything below is free: the calculators run in your browser and the guides cite their sources. The examples are hypothetical and the figures are for 2026. Where a rule has exceptions or depends on your state, we say so and point to the source.
Which ages matter?
Ten birthdays change the rules between 50 and 75. Most retirement plans are built around them.
| Age | What changes |
|---|---|
| 50 | 401(k) and IRA catch-up contributions begin ($8,000 and $1,100 in 2026). |
| 55 | HSA catch-up of $1,000 while you are covered by a high-deductible plan. |
| 59½ | Withdrawals from IRAs and 401(k)s no longer carry the 10% early-withdrawal penalty. |
| 60 to 63 | Larger 401(k) catch-up of $11,250 in the years you turn 60, 61, 62 and 63. |
| 62 | Earliest Social Security claim, at 70% of the full benefit if your full retirement age is 67. |
| 65 | Medicare eligibility; the seven-month Initial Enrollment Period surrounds your birthday month. |
| 67 | Full retirement age for anyone born in 1960 or later. |
| 70 | Social Security reaches its maximum (124% of the full benefit at a full retirement age of 67). |
| 70½ | Qualified charitable distributions from an IRA allowed, up to $111,000 in 2026. |
| 73 or 75 | Required minimum distributions begin: 73, or 75 if you were born in 1960 or later. |
Sources: IRS contribution limits for 2026; IRS Topic 558 (early distributions); SSA; Medicare.gov; SECURE 2.0 for the RMD ages.
What do you need to decide in the five years before?
Six things: whether the money is enough, how much more to save, the pension, health cover to 65, the house, and how much risk to carry into the switch.
Is the portfolio enough to stop working?
Test it against your real spending, not a rule of thumb, and include a bad first decade.
Start with what you spend today, add what changes in retirement (travel up, commuting and payroll tax down, health insurance up before 65), and subtract guaranteed income: Social Security, pensions, annuities. What is left is the yearly draw on the portfolio. A draw near 4% of the balance has historically lasted 30 years in most markets; a draw well above 5% needs a plan to cut back if markets fall early. Our guide to how much you need to retire works through the method.
How much can you still put away?
In 2026, up to $32,500 in a 401(k) at 50 and over, or $35,750 in the years you turn 60 to 63.
The regular 401(k) limit is $24,500; the catch-up at 50 adds $8,000, and SECURE 2.0's larger catch-up for ages 60 to 63 adds $11,250 instead. IRAs allow $8,600 at 50 and over. One change catches high earners: if your prior-year wages from the employer were above $150,000, catch-up contributions must go in as Roth, so they no longer lower this year's taxable income. Our guide to maxing out a 401(k) covers the rules.
Lump sum or pension for life?
Compare the lump sum with what it would cost to buy the same lifetime income, and decide who carries the longevity risk.
A pension election is usually irrevocable, and so is the survivor option that goes with it. A lump sum gives control and something to leave heirs; the annuity gives income you cannot outlive and, often, a survivor benefit for a spouse. The deciding questions are health, the plan's funding, how much other guaranteed income you have, and whether you would invest the lump sum well. Our guide on pension lump sum vs. annuity walks through the comparison.
How will you cover health care before 65?
Budget for it as a line item: employer retiree coverage, COBRA, a spouse's plan or an individual marketplace plan.
Retiring before 65 means paying for coverage until Medicare starts, and it is often the largest new expense in the first years. If you are still covered by a high-deductible plan, the last years of work are the last chance to add to a health savings account: the 2026 family limit is $8,750, plus $1,000 at 55 and over, and contributions stop once you enroll in Medicare. See our HSA guide.
Pay off the mortgage, downsize, or stay?
Decide on the numbers and on where you want to live at 80, not only at 65.
Paying off a low-rate mortgage from savings trades an investment return for a guaranteed one and can leave you short of cash; paying it off from an IRA adds income tax. Downsizing can free equity and cut costs, and gain on a main home is excluded up to $250,000, or $500,000 for a married couple filing jointly, if you meet the ownership and use tests (IRS Topic 701). Our guide to downsizing, renting or aging in place sets out the trade-offs.
How much risk should the portfolio carry at the switch?
Enough growth for a 30-year retirement, with several years of withdrawals held where a bear market cannot reach them.
The years just before and after retirement are when a market fall does the most lasting damage, because withdrawals lock in the losses. Many retirees hold two to five years of planned withdrawals in cash and high-quality bonds and keep the rest invested for growth. See asset allocation by age.
What do you need to decide in the five years after?
Six more: Social Security, Medicare, the order of withdrawals, Roth conversions before RMDs, giving, and the estate.
What do you need to do about Medicare?
Enroll during the seven-month window around your 65th birthday unless you have qualifying employer coverage, and watch your income two years earlier.
The Initial Enrollment Period runs from three months before the month you turn 65 to three months after. Missing it without other qualifying coverage can mean a Part B penalty of 10% for each full year you could have enrolled, usually for life (Medicare.gov). The standard Part B premium is $202.90 a month in 2026; higher-income beneficiaries pay more under IRMAA, which for 2026 starts above $109,000 of modified adjusted gross income for single filers and $218,000 for joint filers, based on the 2024 tax return (CMS; SSA, 2026). See our guide to Medicare enrollment and IRMAA.
Which accounts should you draw from first?
Usually taxable accounts first, then tax-deferred, then Roth, with deliberate exceptions to fill low tax brackets.
The conventional order lets tax-advantaged money grow longest. The exception is the gap between retirement and required distributions, when income may be unusually low: drawing some IRA money or converting it to Roth then can cost less tax than taking larger forced withdrawals later. Our guide on withdrawal order explains when to break the rule.
Should you convert to Roth before RMDs start?
Often, in part: the years between retirement and RMDs are the cheapest time many retirees will ever have to pay the tax.
Required minimum distributions start at 73, or 75 if you were born in 1960 or later. Before then, a couple can convert enough each year to fill a chosen bracket. In 2026, the 22% bracket for married couples filing jointly ends at $211,400 of taxable income, about $243,600 of income with the standard deduction alone. That is above the first IRMAA threshold of $218,000, so from 63 onward a conversion that fills the bracket can raise Medicare premiums two years later. Our guide to Roth conversions before RMDs shows how to size them, and the Roth conversion calculator plans them year by year.
How should you give to family and charity?
Use the annual exclusion ($19,000 per recipient in 2026) for family, and qualified charitable distributions from 70½ for charity.
A qualified charitable distribution sends IRA money directly to charity, up to $111,000 in 2026; it counts toward your RMD and stays out of taxable income. A 529 plan for a grandchild can be front-loaded with five years of annual exclusions at once, $95,000 per giver, using an election on Form 709 (IRS). See qualified charitable distributions and gifting to children and grandchildren.
What should the estate plan cover now?
Current beneficiaries on every account, a will or trust, powers of attorney, health care directives and a plan for long-term care.
Beneficiary designations override a will, so they are the first thing to check. Most non-spouse heirs of an IRA must empty it within ten years, which can push them into high brackets in their peak earning years; Roth money avoids that income tax. The federal estate tax exclusion is $15 million per person for 2026 (IRS), and some states tax estates at much lower levels. Read estate planning basics, the inherited IRA 10-year rule and long-term care planning.
How do the decisions fit together?
They interact, which is why the order matters. A decision in one year sets the tax, premiums or income of the next.
Take a hypothetical couple who retire at 64 and 62 with $2.4 million: $1.6 million in IRAs, $500,000 in a taxable account and $300,000 in Roth IRAs. They plan to delay the higher earner's Social Security to 70. That choice means drawing more from savings for six years, and it opens a window: with little taxable income, they can convert IRA money to Roth each year at 12% or 22%, shrinking the IRA before RMDs begin and leaving Roth money that heirs can inherit without income tax.
But from 63 onward, each year's income sets Medicare premiums two years later, so the conversion size has to respect the IRMAA thresholds as well as the tax brackets. And if they sell the house and buy smaller, any gain above the home-sale exclusion lands in the same tax year. None of these decisions is hard alone. Together they are a sequence, and getting the sequence right is worth more than any single choice.
Our retire-at-60 case study runs a similar household through five calculators in order, and the what-if demo lets you test six of these decisions against a simple plan.
What should you ask your CPA or adviser?
Ask how the decisions fit together. The calculators answer one question at a time; a good plan answers them together, with your own accounts and taxes.
If you work with a CPA, a planner or both, these are the questions worth bringing to the next meeting. If you manage the money yourself, they are the questions to answer on paper.
After-tax spending, year by year
Ask to see your spending after federal tax, RMDs and IRMAA for each of the first ten years, with every account, pension and benefit included.
Roth conversions and RMDs
Ask how much to convert in each gap year, and what the tax now saves against the required distributions and surcharges later.
Social Security and Medicare dates
Ask whether both spouses' claiming ages were tested together, including the survivor benefit, and how they fit Medicare enrollment.
Which account to draw from
Ask which account each year's spending comes from, how much, and what that order does to lifetime tax.
Cash and bond ladders, and property
Ask how many years of spending are held in cash and bonds, and how any property beyond your home fits the plan.
Every assumption, in writing
Ask for the return, inflation and life-expectancy assumptions behind the plan, so you can rerun the numbers yourself.
If you are already retired
Most of the second list still applies. Check your beneficiary designations, confirm your RMD age (73, or 75 if you were born in 1960 or later), look at whether a Roth conversion or a QCD would lower next year's tax, and compare your income two years ago with the IRMAA thresholds.
Frequently asked questions
What should I do in the five years before retirement?
Test your spending against your portfolio and guaranteed income, make the last catch-up contributions (up to $35,750 in a 401(k) in the years you turn 60 to 63, in 2026), decide on any pension election, arrange health coverage until Medicare at 65, settle the mortgage and housing question, and move several years of withdrawals into cash and high-quality bonds.
When do required minimum distributions start?
At 73, or 75 if you were born in 1960 or later, under SECURE 2.0. The years between retirement and that age are often the lowest-income years of your life, which is why many retirees use them for Roth conversions or for drawing IRA money at low tax rates.
How much more is Social Security if I wait until 70?
With a full retirement age of 67, waiting until 70 pays 124% of the full benefit, against 70% at 62. Benefits rise 8% for each year of delay past full retirement age. For a married couple, the higher earner delaying also raises the survivor benefit.
Can Roth conversions raise my Medicare premiums?
Yes. Medicare Part B and Part D premiums rise with income under IRMAA, based on your tax return from two years earlier. For 2026 the surcharges start above $109,000 of modified adjusted gross income for single filers and $218,000 for joint filers. A conversion at 63 or later can therefore raise premiums two years later, so size conversions with the thresholds in view.
Do I need an adviser to make these decisions?
Not necessarily, but most households near retirement work with a CPA, a planner or an attorney for at least some of them. Either way, running your own numbers first with the free calculators on this site lets you ask better questions and check the answers you get.
Start with the free tools
Every calculator and guide above is free. Our free newsletter sends new guides and calculators, and the year's numbers when they change.
When should you claim Social Security?
Later often pays, especially for the higher earner in a couple: with a full retirement age of 67, claiming at 62 pays 70% of the full benefit and waiting to 70 pays 124%.
Benefits rise 8% for each year you wait past full retirement age, up to 70 (SSA, 2026). For a couple, the larger of the two benefits becomes the survivor's benefit, so the higher earner's claiming age protects whoever lives longer. Claiming early can still make sense with poor health or no other assets to bridge the gap. Our guide to when to claim Social Security covers break-even ages and spousal rules.