Printable checklist for your desk
Print this timeline, check things off as you go, and bring it to our meeting.
Download the PDF (large print)The short version. The big decisions arrive on a timeline, and several have deadlines that cannot be fixed afterward. This page lays them out by how far you are from retirement.
Five to ten years out
- Use catch-up room. For 2026, workplace plans allow an extra $8,000 at age 50 and over ($11,250 at ages 60 to 63), and IRAs allow an extra $1,100. If your pay from your employer was over $150,000 last year, catch-up contributions generally must be Roth. [1]
- Look at the low-income years. The years between stopping work and starting Social Security and required withdrawals can be good ones to study for Roth conversions. See our conversion guide.
- Check your Social Security record at ssa.gov and fix any missing years. [2]
- Review beneficiaries on every account. See our beneficiary guide.
One to two years out
- Choose your Social Security plan. Compare your benefit at 62, full retirement age, and 70, and coordinate with a spouse. See our Social Security guide. [3]
- Map your healthcare. If you retire before 65, plan how to cover the gap. If you work past 65 with employer coverage, learn how special enrollment works. See our Medicare guide. [4]
- Ask about your workplace plan options: staying in the plan, rolling to an IRA, or other choices, and any rules your plan has.
- Project your taxes for the first few years of retirement, including how each source of income is taxed.
The year you stop working
- Medicare: your initial enrollment window is the seven months around your 65th birthday month, and employer coverage can change the timing. [4]
- HSA: stop contributions about six months before applying for Medicare. [4]
- Age 59½: most withdrawals from retirement accounts after this age avoid the 10% additional tax, though regular income tax still applies.
- Income-related Medicare amounts: if your income dropped because you stopped working, you can ask Social Security to use a more recent year. [5]
After retirement begins
- Age 70½: qualified charitable distributions from an IRA become available. The 2026 limit is $111,000 per person. [6]
- Age 73 or 75: required withdrawals begin, depending on your birth year. See our required withdrawals guide. [7]
- Every year: revisit your tax projection, beneficiaries, and withdrawal plan.
Key dates and numbers at a glance
| Item | Number or date |
|---|---|
| 401(k), 403(b), 457(b) limit for 2026 | $24,500, plus $8,000 catch-up at 50+ ($11,250 at 60 to 63) |
| IRA limit for 2026 | $7,500, plus $1,100 at 50+ |
| Medicare initial enrollment | Seven months around your 65th birthday month |
| Medicare open enrollment | October 15 to December 7 |
| Full retirement age (born 1960 or later) | 67 |
| Qualified charitable distributions | Age 70½ |
| Required withdrawals begin | 73 (born 1951 to 1959*) or 75 (born 1960 or later) |
*See our required withdrawals guide for the 1959 note.
Questions worth asking
- What are the three biggest decisions I need to make in the next 24 months, and what are their deadlines?
- Which of my accounts and benefits have a window that cannot be reopened?
- What does my plan look like if I retire two years earlier or later than I expect?
Frequently asked questions
What should I do five to ten years before retirement?
Use catch-up room, look at low-income years for Roth conversions, check your Social Security record, and review beneficiaries on every account.
When does Medicare enrollment start?
Initial enrollment is seven months: the three months before your 65th birthday month, the birthday month, and the three months after.
When can I make qualified charitable distributions from an IRA?
From age 70½. The 2026 limit is $111,000 per person.
Sources and review notes
General education, not individualized investment, tax, or legal advice. Discuss tax decisions with your tax professional, and recheck annual limits before using this page for another tax year.