In short: This checklist breaks retirement preparation into a year-by-year sequence, from 10-plus years out through your first month retired. Each stage focuses on a few priorities — saving and investing, Social Security and income timing, healthcare and long-term care, and estate and legal documents — so nothing important gets left to the last minute. Start wherever you are; the order of the steps matters more than the exact age.
As the saying goes, “The best time to plant a tree was 20 years ago. The second-best time is now.” Just like that tree, your retirement benefits from careful planning and preparation to grow into something rewarding.
This article draws on years of experience in retirement planning, and it walks you through a comprehensive 10-year checklist to help you stay on track for the years ahead. Whether you’re years away or just around the corner, it’s never too early, or too late, to start preparing for the retirement you’re working toward.
A note on the ages below: They illustrate a sample timeline for someone targeting retirement around age 55. Map the “years before retirement” heading to your own target date, the sequence is what matters, not the specific age.
Pre-Retirement Checklist at a Glance
| Years before retirement | Illustrative age | Focus areas |
|---|---|---|
| 10+ years | 45 | Maximize savings, diversify, set a target number, estate basics, insurance review, healthcare and HSA |
| 9 years | 46 | Refine investments, weigh Roth conversions, cut high-interest debt, check your Social Security record |
| 8 years | 47 | Track down old accounts, broaden investments, full health checkups, research long-term care |
| 7 years | 48 | Draft a retirement budget, strengthen emergency fund, review trusts, assess home equity |
| 6 years | 49 | Test income vs. budget (4% guideline), consolidate accounts, secure documents |
| 5 years | 50 | Set a target date, plan Social Security timing, build a withdrawal strategy, review Medicare, reduce risk |
| 4 years | 51 | Finalize Social Security strategy, map all income sources, estimate medical costs, legal review |
| 3 years | 52 | Test the lifestyle, update your estate plan, audit accounts, shift more conservative |
| 2 years | 53 | Lock in the budget, get health-coverage quotes, plan activities, appraise your home |
| 1 year | 54 | Clear debts, set up withdrawals and a tax plan, final catch-up contributions, health screenings |
| 1 month after | — | Roll over old employer plans, put the income plan into action |
10+ Years Before Retirement (Age 45)
Saving and Planning
With more than ten years until retirement, prioritize maximizing your savings. In 2026, you can contribute up to $24,500 to a 401(k), plus an $8,000 catch-up contribution if you’re 50 or older — or $11,250 if you’re between 60 and 63 and your plan allows. The IRA limit is $7,500, plus a $1,100 catch-up at 50 or older. Take full advantage of any employer 401(k) match. (One 2026 change to note: if your prior-year wages topped $150,000, workplace-plan catch-up contributions are made on a Roth, after-tax basis. Limits are set by the IRS and adjust most years, so confirm the current figures.)
Consulting a financial professional can help you set a retirement savings goal that accounts for life expectancy, expenses, inflation, and taxes. If there’s a shortfall, look for ways to increase your savings.
Life can be unpredictable, so help protect your savings by diversifying your portfolio according to your risk tolerance. A common guideline is limiting employer stock in your retirement plan to 10–20% of your total savings. If you roll over employer stock into an IRA, ask about potential tax-saving strategies.
Picturing your daily life in retirement can make it feel more tangible and help motivate you to save. Plan for social activities and other parts of your future lifestyle.
Tax-Efficient Income Strategies
Taxes can meaningfully affect your retirement income. Meet with a financial professional to discuss the tax implications of your income sources. A mix of tax-efficient income sources can help extend your retirement funds and reduce the chance of unexpected tax bills.
Estate Planning
Create or update your estate documents and any trust agreements. Consider how permanent life insurance might support your legacy and estate planning goals, and make sure beneficiary designations on financial accounts are current.
Confirm your will is up to date and that you’ve assigned durable powers of attorney for both medical and financial decisions. Create or review your advance healthcare directive. These documents form the foundation of your estate plan and provide important protection for you and your loved ones.
Insurance Coverage to Review
Review your coverage as retirement approaches:
- Life Insurance: Consider whether it fits your goals for protecting loved ones and transferring assets.
- Disability Insurance: Keeping it until retirement helps safeguard your income.
- Long-Term Care Insurance: Plan for potential long-term care costs. Some hybrid life insurance and long-term care policies may offer tax-advantaged benefits, and premiums are often lower when a policy is purchased earlier.
Manage Healthcare Costs
Healthcare is one of the largest expenses in retirement. Medicare covers retirees 65 and older, but it involves premiums and out-of-pocket costs for most services, and retirees are often responsible for a meaningful share of those costs. If you retire before 65, you’ll want other healthcare coverage in place until Medicare begins.
A Health Savings Account (HSA) can cover many retiree out-of-pocket healthcare costs. If your health plan doesn’t include an HSA, you can open and fund one separately. It’s a useful way to set aside money for medical and long-term care expenses, and it can add to your retirement flexibility: after age 65, you can use HSA funds for any purpose, though you’ll owe income tax on distributions not used for qualified medical expenses.
9 Years Before Retirement (Age 46)
Refine Investments
Adjust your allocation as retirement nears, generally shifting some exposure from stocks toward bonds to help protect savings. Target-date funds are one option if you’re unsure how to balance your portfolio. Plan for possibilities like an earlier-than-expected retirement due to illness or a layoff.
Before retiring, weigh converting pre-tax accounts (a traditional IRA or 401(k)) into a Roth. You’d owe taxes upfront on the converted amount, but qualified withdrawals in retirement are generally tax-free. This can make sense if you scale back work and land in a lower tax bracket. Consult a tax professional about a bracket-maximization strategy for Roth conversions.
Financial Progress
Increase your retirement contributions if you can. This is a good time to review your asset allocation with your advisor and rebalance if needed. Check your Social Security statement online to confirm your earnings are recorded correctly.
Focus on reducing high-interest debt. A debt-free retirement offers considerably more financial flexibility and peace of mind.
Health Focus
Build on the health habits you started last year. Establish regular mental-health routines like meditation or journaling. Look into whether a high-deductible health plan makes sense for HSA eligibility.
Legal Updates
Review beneficiaries on all accounts and insurance policies. Life changes — marriages, divorces, births, and deaths — can affect who should be listed.
Skill Development
Start identifying skills that could translate into consulting or freelance work later. Many retirees find part-time work both fulfilling and financially helpful.
Home Improvements
Consider minor renovations that could add resale value if you plan to downsize eventually.
8 Years Before Retirement (Age 47)
Track Down Forgotten Funds
List your past jobs and check for forgotten retirement savings, pensions, or stock options. Consolidating old accounts into your current plan makes them easier to manage. Move idle cash into high-interest savings or certificates of deposit.
Investment Expansion
Look beyond traditional retirement accounts. Consider whether a taxable brokerage account or real estate might diversify your retirement income. Use a retirement planning tool to project your current savings trajectory, or ask your advisor about investment management support.
Comprehensive Health Check
Schedule dental, vision, and hearing checkups. These often get overlooked but can become significant expenses in retirement. Set specific health milestones, such as target blood pressure or cholesterol levels.
Long-Term Care Research
Start researching long-term care insurance. The earlier you buy a policy, the lower the premiums typically are.
Retirement Priorities
Create a “must-have” versus “nice-to-have” list of retirement experiences. This clarifies your financial priorities and helps you save for what matters most to you.
Location Research
If you’re considering a move, research the cost of living in your target locations — housing costs, taxes, healthcare access, and lifestyle amenities.
7 Years Before Retirement (Age 48)
Setting a Retirement Budget
Estimate your retirement expenses: housing, food, taxes, travel, hobbies, and insurance. Plan for Medicare Part B premiums and any additional coverage. Revisit your plan as your health, family, or other circumstances change.
Financial Security
Reevaluate your emergency fund. As retirement approaches, having 6–12 months of expenses saved becomes even more valuable. Look for discretionary spending you can redirect into savings.
Family Health History
Review your family medical history to identify health risks worth planning for. This can make your healthcare cost projections more accurate.
Trust Documents
If you have trust documents, review and update them so they still reflect your wishes and current family situation.
Retirement Lifestyle Test
If you can, test a part-time schedule or take a sabbatical to get a feel for retirement. It can offer valuable insight into how you’ll want to structure your time.
Home Equity Assessment
Compare your home’s current value to your remaining mortgage balance. Understanding your home equity gives you a clearer picture of your overall net worth.
6 Years Before Retirement (Age 49)
Income Evaluation
Estimate whether your savings and expected income can cover your budget. The 4% rule is one way to gauge a sustainable withdrawal rate — it isn’t perfect, but it’s a reasonable starting point. Stress-test your plan with a financial adviser and adjust as needed. This is where dedicated income planning can help.
Account Consolidation
Simplify your finances by consolidating old retirement accounts. Check for unclaimed retirement benefits from previous employers — this happens more often than people expect. If you’re eligible for a pension, evaluate your options for taking it as a lump sum or annuity payments.
Fitness Routine
Establish a consistent fitness routine you can carry into retirement. Even something as simple as tracking daily steps can make a real difference in long-term health.
Document Security
Store all legal documents securely, and let trusted family members or your executor know where to find them.
Vision Refinement
Revisit and refine your retirement vision based on what you’ve learned. Your priorities and goals may have shifted.
Home Inspection
Get a professional home inspection to catch potentially costly repairs before they arrive. Addressing them before retirement can prevent financial surprises later.
5 Years or Less Before Retirement (Age 50)
Finalize Your Plans
Set a specific target retirement date and confirm your income sources look sustainable. You may have started this earlier, but as the date nears you’ll want to get more specific about when you plan to stop working. Aim to enter retirement with a high degree of confidence that your income can last the full course of your life.
Decide When to Take Social Security
You can start collecting anytime between ages 62 and 70. A useful starting point is your “full retirement age” (FRA) as defined by the Social Security Administration, which falls between 66 and 67 depending on your birth year. That’s the age at which you receive your “primary insurance amount,” the base level of your monthly benefit.
Claiming before FRA generally reduces your benefit. Delaying past FRA increases it — benefits rise by about 8% for each year you wait, up to age 70. A dedicated Social Security analysis can help you compare the trade-offs.
Build a Withdrawal Strategy
Part of your retirement income will come from your savings and investment accounts. Identify a withdrawal strategy that can cover your income in retirement while aiming to reduce the risk of exhausting your savings too soon.
List every account that can generate income to get a clear sense of your “retirement paycheck.” Social Security and pension payments can usually be estimated with reasonable accuracy. The amount you draw from savings may vary, but you can project the potential income it can produce. You might also explore income-generating options such as annuities.
Review Medicare and Reduce Investment Risk
Medicare will be the cornerstone of your retirement healthcare coverage. Study your options well before turning 65 so you can make timely decisions — and consider long-term care insurance, hybrid life policies, or self-funding if affordable. Medicare can be complex, so it’s worth reviewing with a professional.
As retirement closes in, review the level of risk in your portfolio and consider reducing exposure to investments subject to significant market swings. A market downturn just before or after you retire can meaningfully affect the size of your nest egg, and in turn the income you can draw from it.
Think About Long-Term Care
Genworth’s Cost of Care Survey has estimated the average cost of a private nursing-home room at more than $9,000 a month — over $108,000 a year. One way to prepare is a long-term care insurance policy. Another is a hybrid life insurance policy: if you need care while living, you draw from the policy; if you never need it, the policy pays your heirs a death benefit. If you can afford it, self-funding out of pocket is also an option.
Get Major Expenses “Off the Books”
Address big-ticket items — home repairs, appliance upgrades, a car purchase — in the last 1–3 years before retiring. Clearing them now helps you avoid large expenses later, when your cash flow is less flexible.
Location Considerations
Decide where you’ll live: stay put, downsize, or explore senior housing. If you move to a lower-tax state, check whether certain retirement income is exempt from state income tax.
Revisit Your Plan Regularly
Adjust your plan as the economy and your circumstances change. Meeting with a financial professional yearly helps you address changes and stay on track toward your goals.
4 Years Before Retirement (Age 51)
Financial and Medical Coverage
Consider whether an annuity’s lifetime income option fits your plan; any guarantees are subject to the claims-paying ability of the issuing insurer. If you’re retiring before 65, plan your health coverage — COBRA, a spouse’s plan, or an Affordable Care Act plan.
Income Strategy
Finalize your Social Security claiming strategy. The age at which you claim can meaningfully affect your lifetime income. Build a complete list of potential income sources: Social Security, pensions, annuities, rental income, investment withdrawals, and any part-time work.
Medical Cost Estimation
Estimate your annual medical costs in retirement — premiums, deductibles, copays, and medications — and reevaluate all insurance coverage, including life insurance.
Legal Review
Have an attorney review your legal documents to confirm they’re current and compliant with today’s laws.
Budget Practice
Start “practicing” living on your retirement budget. This gives you time to adjust and surface any unrealistic expectations.
Property Tax Research
Research property-tax considerations for seniors in California, including any exemptions or reductions you might qualify for.
3 Years Before Retirement (Age 52)
Retirement Lifestyle Testing
Try out your retirement plans to see whether they match your expectations. Review your estate plan while you’re at it: confirm your will is current (and write one if you don’t have it), and check beneficiary designations on your accounts, retirement plans, and life insurance policies. These designations override your will — if an outdated name, such as an ex-spouse, is listed, that person could inherit the account instead of your intended heirs. Consider having an estate attorney create a financial power of attorney and a living will/advance healthcare directive, naming someone you trust to make financial and medical decisions if you can’t.
Financial Audit
Conduct a thorough audit of all financial accounts. Work with your advisor to rebalance toward a more conservative allocation that helps buffer against market volatility.
Healthcare Review
Review your out-of-pocket medical expenses from recent years to sharpen your healthcare cost projections.
Digital Documentation
Create digital copies of all legal and financial documents, stored securely with appropriate password protection.
Community Connections
Identify local organizations where you might volunteer. Building these connections before you retire can ease the transition.
Downsizing Preparation
Begin decluttering and preparing for a potential downsize. This takes longer than most people expect.
2 Years Before Retirement (Age 53)
Budget Finalization
Lock in your retirement budget based on everything you’ve gathered. Run final projections with your financial advisor to confirm you’re on track.
Healthcare Transition Planning
Get specific quotes for COBRA and ACA health plans if you’ll need coverage before Medicare eligibility.
Activity Planning
Create a specific list of post-retirement activities — clubs to join, classes to take, and travel you hope to enjoy.
Home Valuation
Get a professional appraisal so you understand your home’s current market value, especially if selling or downsizing is part of your plan.
1 Year Before Retirement (Age 54)
Retirement Preparation
Wrap up your career on a positive note. Use your remaining work income to clear debts and set financial boundaries with dependents. Relocating to a lower-cost area is one way to stretch your retirement budget.
Withdrawal Strategy
Set up your specific withdrawal strategy and tax plan with your financial advisor, and confirm all income streams and their start dates. Make your final catch-up contributions to retirement accounts.
Health Screenings
Schedule major health screenings before any change to your health insurance coverage.
Family Communication
Share your retirement plans and the location of important legal documents with trusted family members.
Transition Celebration
Plan a meaningful way to mark your transition to retirement. This milestone is worth marking.
Housing Finalization
Complete any planned moves or renovations before your retirement date.
Your First Month in Retirement
Roll over any inactive employer plans into IRAs for easier management — a retirement plan rollover can simplify this. Put the income plan you built with your financial advisor into action, and enjoy your retirement. Working through this checklist can help you approach retirement with confidence and readiness for what’s ahead.
Conclusion
A well-built retirement checklist works like a roadmap for the transition from your working years into retirement. Following this 10-year plan helps you address the pieces that matter — financial stability, healthcare, and lifestyle — and supports a smoother, more confident move into the years ahead.
If you’d like help tailoring any of these steps to your situation, Randall Wealth Management Group can work through them with you. Book a complimentary consultation to get started.
