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Guides · Retirement planning

Retirement planning guides: dates, numbers and decisions

The calendar and the numbers behind a retirement plan: which dates matter for your birth year, what changes every January, and how Social Security, Medicare and withdrawals fit together. Practical guides for people in their late 50s through their 70s, built on official figures.

Calculators ready · guides in progress Verified October 23, 2026

What should you know about retirement planning first?

Most retirement decisions come with a date attached: the first month you can claim Social Security, your Medicare enrollment window and the year your required minimum distributions (RMDs) begin. Getting one wrong can mean a permanently smaller check, a late-enrollment penalty that lasts as long as you have coverage, or an IRS penalty on a withdrawal you forgot to take.

Our view: write your own dates down once, then revisit them every fall when Social Security, Medicare and the IRS publish next year’s numbers. The guides here show how one decision changes the next, so you can plan them together rather than one at a time.

Which retirement planning questions can you answer right now?

Each of these questions opens a free calculator or reference page that works out the official answer for your own situation in a minute or two. There is no sign-up and nothing to download, and every result shows the official figures and sources behind it, so you can check the math yourself.

Latest retirement planning guides

No retirement planning guides are published yet. The calculators below already answer the questions people ask most, using the official figures — start there, and new guides will appear on this page.

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Calculators for retirement planning

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