.png)
The 5-Year Pre-Retirement Checklist for Women
- Michelle Francis
- 3 days ago
- 7 min read
Most retirement planning articles treat the five years before retirement as a countdown. This one treats it as your most powerful planning window — because it is.
Five years feels like plenty of time. And then, for most women I talk with, it suddenly doesn't. The decisions you make in this window — about Social Security, healthcare, your investment mix, and where your income will actually come from — will shape your retirement more than almost anything you did in the decades before.
This checklist is designed specifically for women navigating this stretch. It accounts for the realities that often go unaddressed: longer life expectancies, income gaps from caregiving years, the possibility of managing finances independently, and the emotional weight of shifting from earning to drawing down.
Work through it at your own pace. Not everything will apply to your situation, but everything here is worth considering.
Year 5: Get a Clear Picture of What You Actually Have
You cannot plan for retirement without an honest inventory of where you stand. This year is about gathering, organizing, and assessing — before any major decisions are made.
Financial Inventory Checklist
List every retirement account — 401(k), 403(b), traditional IRA, Roth IRA, old employer plans you haven’t rolled over
Note the balance, investment mix, and tax treatment of each account — pre-tax, after-tax, or tax-free
Locate pension documentation — if applicable, request a current benefit estimate from your HR department
Pull your Social Security statement — create an account at ssa.gov and review your projected benefit at 62, 67, and 70
Identify any other income sources — rental income, part-time work, inheritance, a spouse or partner’s benefits
List all debts — mortgage balance and payoff date, car loans, credit cards, student loans
Review your current monthly expenses — get specific, not approximate
Once you have this picture, you’ll know what you’re working with. Many women are surprised to discover they’re in better shape than they assumed — or that there are specific gaps that need attention now, not later.
Year 4: Understand Your Income Plan
Retirement income doesn’t just happen. It has to be designed. This is the year to map out where your money will actually come from — and identify any gaps before they become urgent.
Income Planning Checklist
Estimate your annual retirement spending — include housing, healthcare, travel, food, insurance, and personal spending
Model your Social Security timing — compare taking benefits at 62, at full retirement age, and at 70 — the difference can be significant
Calculate your estimated income from all sources — Social Security + pension + investment withdrawals + any other income
Identify the gap — if projected income is less than projected spending, you need a plan to close it
Review your withdrawal sequence — which accounts will you draw from first, and in what order?
Understand your RMD timeline — Required Minimum Distributions begin at age 73 for most accounts — know what yours will look like
For a deeper look at building a tax-smart income plan, see Your Retirement Paycheck: Designing a Tax-Efficient Withdrawal Strategy on the Life Story Financial blog.
One thing many women overlook at this stage: if you’ve spent years as a lower earner, or had career gaps for caregiving, your Social Security benefit may be lower than expected. There are strategies — including spousal or survivor benefits — that can help. The time to understand them is now.
Year 3: Tackle the Tax Picture
Taxes in retirement are often more complex than people expect. The year you stop working, your income may drop significantly — and that creates a window of opportunity that many women never take advantage of.
Tax Planning Checklist
Review your current tax bracket and estimate your first-year retirement bracket
Identify your Roth conversion window — the gap between retirement and when RMDs or Social Security begins is often your lowest-income period
Evaluate whether partial Roth conversions make sense — converting pre-tax savings to Roth now can reduce your tax burden later
Understand how Social Security is taxed — up to 85% of your benefit may be taxable depending on your other income
Learn about IRMAA — Medicare Part B and D premiums rise with income — know the thresholds before they catch you off guard
Review capital gains strategy — low-income years in early retirement can be an opportunity to harvest gains at 0%
Understanding how tax brackets affect your decisions is foundational here. The Life Story Financial article How the 2025 Tax Brackets Could Influence Your Financial Plan walks through the key numbers and how to use them strategically.
And if you’ve been wondering whether a Roth IRA strategy makes sense for you, Backdoor Roth IRAs and Roth 401(k)s: A Smart Strategy for Tax-Efficient Retirement Income breaks down how these tools work and when they’re worth using.
Year 2: Sort Out Healthcare
Healthcare is consistently underestimated as a retirement expense — and for women, who on average live longer and often face higher lifetime healthcare costs, this is a particularly important area to get right.
Healthcare Checklist
Know your Medicare enrollment timeline — you become eligible at 65, and missing the enrollment window can result in permanent late penalties
Understand the gap between your retirement date and age 65 — if you retire before 65, you need a bridge plan — COBRA, a marketplace plan, or a spouse’s coverage
Learn about Medicare Part A, B, C, and D — understand what each covers and what it costs
Evaluate supplemental coverage — Medigap and Medicare Advantage plans vary significantly in cost and coverage
Estimate your lifetime long-term care risk — women have a higher probability of needing long-term care and spending more years in it
Explore long-term care options — traditional LTC insurance, hybrid life/LTC policies, and self-funding strategies each have tradeoffs
Review how your income level affects Medicare premiums — IRMAA surcharges kick in above certain income thresholds and can add thousands per year
Healthcare decisions interact with your income plan in ways that can be easy to miss. The sequencing of withdrawals, Roth conversions, and Social Security timing can all affect your Medicare premiums two years later. This is an area where coordination matters.
Year 1: Finalize the Plan and Prepare for the Transition
In the final year before retirement, the focus shifts from planning to preparing. This is about closing gaps, updating documents, and making sure everything is in place before your last paycheck arrives.
Final Year Checklist
Update your investment allocation — a portfolio designed for growth looks different from one designed to generate income and manage downside risk
Build a cash cushion — one to two years of living expenses in cash or stable assets reduces the risk of selling investments at a loss early in retirement
Update all beneficiary designations — retirement accounts, life insurance, and any other accounts with beneficiaries should reflect your current wishes
Review your estate documents — will, healthcare directive, durable power of attorney — are they current and do they reflect your wishes?
Finalize your Social Security timing decision — if you haven’t already, commit to a claiming strategy
Confirm your Medicare enrollment plan — if turning 65 near retirement, coordinate enrollment carefully
Have an honest conversation about your financial picture with anyone who will be affected — a spouse or partner, or adult children if appropriate
Schedule a comprehensive review with your financial advisor — walk through income, taxes, investments, and contingency plans together
Plan the emotional transition — retirement is not just a financial event; consider what structure, purpose, and social connection will look like
The financial and the personal are deeply connected in this transition. Women who feel most confident entering retirement are usually the ones who addressed both.
Questions We Answer Regarding Retirement
What if I’m already in year one and haven’t done any of this?
Start now. A compressed timeline is not a reason to skip this work — it’s a reason to prioritize it. Work backward from your retirement date and tackle the most time-sensitive items first: Social Security decisions, Medicare enrollment, beneficiary updates, and your investment allocation. A financial advisor who specializes in retirement transitions can help you move quickly and strategically.
How do I know if I have enough to retire?
The honest answer is that “enough” is personal. A commonly cited starting point is having 25 times your annual expenses saved — the basis of the 4% withdrawal guideline. But your situation depends on your specific expenses, income sources, tax picture, healthcare needs, and how long your money needs to last. Running actual projections for your own numbers, ideally with a financial advisor, gives you a much more reliable answer than any general rule.
Should I pay off my mortgage before I retire?
Not necessarily. Whether it makes sense depends on your interest rate, the tax implications, how much liquidity it would cost you, and what you’d be giving up in investment growth. Some women feel strongly about retiring debt-free for peace of mind reasons, which is completely valid. Others are better served by maintaining their mortgage and preserving flexibility. This is a decision worth modeling out rather than making based on a rule.
What if my spouse or partner handles most of our finances?
Now is the time to get involved, even if it feels unfamiliar. Understanding your own financial picture — the accounts, the income plan, the estate documents — is not optional. Women statistically outlive their partners and often find themselves managing finances independently at some point. Starting that learning process now, from a position of stability, is far easier than navigating it during grief or crisis.
I’m going through a divorce near retirement. Does this change the checklist?
Yes, significantly. Divorce near retirement affects your Social Security options, how retirement accounts are divided, your tax filing status, and your healthcare coverage. The five-year window actually becomes more important, not less, because the financial decisions made during divorce will shape everything that follows. Getting both a CDFA (Certified Divorce Financial Analyst) and a financial advisor involved early can make a real difference in outcomes.
Can I retire early if I haven’t hit all these milestones?
Retiring early is possible, but it raises the stakes on every item on this list. A longer retirement means more years of income to fund, more healthcare costs, greater longevity risk, and a longer Roth conversion window to manage. The checklist matters more, not less, if you’re considering an early exit from the workforce.
The Bottom Line
The five years before retirement are not a waiting room. They’re a planning window — and arguably the most financially consequential stretch of your life. The decisions made here about taxes, Social Security, healthcare, and income sequencing can mean the difference between a retirement that feels comfortable and one that feels precarious.
You don’t have to have everything figured out perfectly. But you do want to be working through it intentionally, with the right information and the right support.
At Life Story Financial, I help women navigate exactly this transition — building income plans, evaluating tax strategies, and designing portfolios that are built to last. If you’d like to work through your own five-year plan, I’d be glad to start that conversation.