What Should I Do Five Years Before Retirement?
The five years before retirement tend to have more dated, sequence-sensitive decisions than any other stretch of a career — Social Security timing, Medicare enrollment, pension elections, and tax coordination among them. A general timeline can help you see what to calendar and what to leave flexible.
Start with an income map, then calendar the dated decisions.
General planning structure only. No individualized Social Security, Medicare, tax, or investment recommendations are made here.
Five years out, the most useful first step is usually building an income map: listing every future income source and roughly when each could realistically begin. From there, a handful of decisions carry real deadlines — Social Security claiming age, Medicare enrollment windows, and pension elections among them — and are worth identifying early rather than discovering under time pressure. Debt, cash reserves, insurance coverage, tax coordination, and estate documents round out the review.
Official sources — the Social Security Administration, Medicare.gov, and a qualified tax professional or attorney — should confirm any figure, age, or rule that applies to your own situation.
Year by year, from five years out to your final year.
A general sequence. Your own timeline may compress, extend, or reorder depending on circumstances.
| When | General focus areas |
|---|---|
| Year 5 | Build a first-draft income map of every future income source. Request personal Social Security statements and estimates from ssa.gov. Note any pension plan documents and their election deadlines. |
| Year 4 | Begin tracking spending patterns to estimate early-retirement expenses. Review current life, disability, and long-term care coverage for whether it still fits. Start a conversation with an estate planning attorney if documents are outdated. |
| Year 3 | Revisit debt payoff timelines against your target retirement date. Confirm whether any old employer retirement accounts should be consolidated or reviewed. Ask a tax professional general questions about how withdrawals might be sequenced. |
| Year 2 | Study Medicare enrollment timing on medicare.gov, especially if you plan to retire before or around Medicare eligibility. Review survivor-option tradeoffs on any pension election with a spouse or partner. |
| Year 1 | Finalize the income map with realistic start dates. Confirm Social Security claiming plans against current SSA guidance. Complete Medicare enrollment steps within applicable windows. Review beneficiary designations, will, powers of attorney, and health care directives one more time. |
Decisions that are hard to reverse.
Pension payout and survivor elections
Many pensions require a one-time election of payout form and survivor option that cannot be changed later. If a pension applies to you, find that deadline early.
Social Security claiming choices
Once claimed, some Social Security elections are difficult to unwind. Review the tradeoffs on the SSA's official site before deciding.
Missed Medicare enrollment windows
Enrolling outside the applicable window can have consequences described on Medicare's official site. Confirm your specific timing well ahead of the date.
Large, irreversible account withdrawals
Some withdrawal or conversion decisions have lasting tax consequences. A tax professional should review any such decision before it is made, not after.
Questions worth asking directly.
- What does my income map look like once every source is listed with a realistic start date?
- Which decisions in my situation have real deadlines, and which are flexible?
- How might sequencing withdrawals across account types affect my taxes — and who should confirm that?
- What would happen to my household if I claimed Social Security earlier or later than planned?
- Do my current life, disability, and long-term care coverage still make sense as I approach retirement?
- Are my beneficiary designations, will, powers of attorney, and health care directives current?
Organize your own timeline before it opens right here.
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Related reading
A five-year plan is one piece of a broader retirement picture.
- Retirement planning overview
- Should I retire in 2026 or wait?
- The 2026 Roth 401(k) catch-up rule
- Social Security retirement age guide
- Retirement income planning guide
- Old 401(k) after changing jobs
- What to do after leaving a job
- Building a financial legacy for children and grandchildren
- Long-term care planning
- Financial planning
Five-years-out retirement planning questions.
Where to read the underlying material.
- Social Security Administration — Retirement benefits
- Medicare.gov — Get started with Medicare
- Investor.gov — Retirement toolkit: managing lifetime income
This article is educational and general in nature. It is not tax, legal, Social Security, Medicare, or individualized investment advice, and it is not a recommendation of any product or strategy. Laws, tax rules, plan terms, program rules, and product availability can change, and no outcome, benefit amount, tax result, or investment return is guaranteed. Confirm current rules with the Social Security Administration, Medicare, and your own tax professional or attorney. Full disclosures and contact Sarah.