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Free retirement transition guide

The Final 10 Years Before Retirement May Require a Different Strategy.

Get the 10-decision guide for coordinating investments, employer retirement plans, taxes, Social Security, healthcare, Medicare and retirement income.

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The 55–65 Retirement Opportunity Guide

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Know the timeline

Organize the milestones from age 55 through Social Security, Medicare and later RMD years.

Connect the decisions

See how investments, taxes, healthcare and income can affect one another.

Find the gaps

Use ten decisions to identify what still needs an answer before the final paycheck.

Who it's for

For households roughly 55 to 65, or within about ten years of retirement.

  • You have built savings and now want to know how they become retirement income.
  • You are not sure which decisions come first: retirement date, Social Security, rollover or healthcare.
  • You want a one-page view of the ages and dates that matter to you and your spouse.
  • You would like a structured agenda before talking with any professional.

What's inside

Ten decisions, a milestone worksheet and an age-by-age checklist.

  1. Why the final decade is different: moving from saving to converting savings into income.
  2. The 10 decisions as checklists: retirement date, spending number, income floor, 401(k)/403(b), investment-risk transition, Social Security, healthcare bridge, Medicare timeline, tax window and retirement paycheck.
  3. Personal milestone worksheet: fill in your dates for the Rule of 55, 59½, catch-up years 60–63, Social Security at 62, Medicare enrollment, full retirement age, age 70 and your first RMD year.
  4. Age-by-age checklist: 55–57, 58–60, 61–62, 63–64, and 65 and after.
  5. 2026 reference figures, common mistakes and official help.

Sample checklist items

  • I have a target retirement date and an earlier-than-planned contingency.
  • I know how much of essential spending Social Security and any pension would cover.
  • I have compared at least three Social Security claiming ages.
  • I have a plan for withdrawals if markets fall early in retirement.
  • I have projected taxable income from retirement through my RMD age.

Milestones the worksheet covers

General rules (your exact dates go in the worksheet)
AgeMilestone
55Rule of 55 for the plan of an employer you leave in or after that year
59½The 10% additional tax on early distributions generally ends
60–63Higher 401(k) catch-up limit ($11,250 in 2026)
62Earliest Social Security retirement benefit
65Medicare eligibility for most people
67Full retirement age if born in 1960 or later
70Delayed retirement credits stop
73 / 75RMDs begin (born 1951–1959 / born 1960 or later)

Prefer to read first? See planning from 55 to 65, retirement income and Social Security planning.

Education first

Use the resource to identify the questions that need a deeper answer.

No account transfer or product decision is required to use the guide. Individual recommendations require individual facts and an appropriate advisory process.