Five years out is not too early — it's exactly the right time. This is the window where you still have enough time to course-correct if something is off, maximize final contributions, make strategic tax moves, and put all the pieces of your retirement plan together before you actually need them.

Most people coast through this period without a structured plan. They know retirement is coming, they're saving, and they assume things will work out. That assumption costs them. The five-year window is where intentional planning pays off more than at any other point in your financial life.

This is also the window for Roth conversions — converting traditional IRA or 401(k) funds to a Roth while you're still in a manageable tax bracket, before Social Security, RMDs, and other income sources stack up and push you into higher brackets permanently.

Your portfolio needs to transition from pure accumulation to income generation. That doesn't mean moving everything to bonds — it means building a structure that can support consistent withdrawals without being devastated by a market downturn in your first few years of retirement, when sequence-of-returns risk is highest.

Estate planning cannot wait. A will or trust, updated beneficiary designations, a durable power of attorney, and a healthcare directive should all be in place before you retire. These aren't morbid documents — they're acts of love and responsibility for the people who depend on you.

• ✓The five years before retirement are your most powerful planning window — use them intentionally.
• ✓Roth conversions during this window can save tens of thousands in lifetime taxes.
• ✓You still have time to close savings gaps — maximize catch-up contributions and reduce discretionary spending.
• ✓Healthcare, Social Security strategy, and estate planning all need to be mapped out before retirement day — not after.
• ✓A comprehensive retirement readiness review now reveals gaps while you still have time to fix them.

Year 5 — Know Your Number: Calculate your exact retirement income target. Map out every income source — Social Security, pension, portfolio withdrawals, part-time work. Identify your monthly income gap and determine what your portfolio needs to generate to close it. If there's a shortfall, you have five years to address it.

Year 4 — Maximize Contributions: Contribute the maximum to your 401(k) — $23,000 in 2024, plus $7,500 in catch-up contributions if you're 50+. Max your IRA. If you have an HSA, fund it to the limit — it's the only triple-tax-advantaged account available and can be used for healthcare costs in retirement.

Year 3 — Start Roth Conversions: If you're in a lower tax bracket now than you expect to be in retirement, begin converting traditional IRA funds to Roth. This reduces future RMDs, tax-free income in retirement, and can lower Medicare IRMAA costs. Work with an advisor to find the right conversion amount each year.

Year 2 — Build Your Income Plan: Design your retirement income structure — guaranteed income floor, portfolio withdrawal strategy, Social Security claiming timeline, and cash reserve buffer. Evaluate whether an annuity belongs in your plan. Map out your first three years of withdrawals in detail.

Year 1 — Lock In Your Foundation: Finalize estate documents — will or trust, beneficiary designations, power of attorney, healthcare directive. Confirm your Medicare enrollment timeline. Review all insurance coverage — life, long-term care, supplemental health. Brief your family on your plan. Walk into retirement day fully prepared.

• ✗Coasting through the final five years without a written plan — this is the window where intentional decisions matter most.
• ✗Missing the Roth conversion window — once RMDs begin and Social Security kicks in, your tax bracket may be locked in at a higher rate for life.
• ✗Not updating your estate plan — outdated beneficiaries, no trust, and missing directives can leave your family in chaos at the worst possible time.
• ✗Moving entirely out of growth assets too early — you still need your portfolio to grow for 20–30 years after retirement.
• ✗Failing to plan for the healthcare gap if retiring before 65 — going uninsured or underinsured before Medicare can be financially devastating.

→What Is Retirement Readiness? →What Are the Biggest Retirement Mistakes? →What Is Retirement Income Planning?