The Pre-Retirement Financial Checklist: What to Do in the Five Years Before You Retire 

Retirement is one of life’s most significant transitions. After decades of saving and investing, the focus begins to shift from building wealth to turning that wealth into reliable income that can support the life you envision.

In the five years before retirement, most people find themselves asking the same question: Am I truly ready? Retirement readiness isn’t just about reaching a certain age or savings amount. It’s about entering this new phase of life with clarity, confidence, and a strategy that works for the long-term.

At Granite Bay Wealth Management, we work with clients during this critical period to help them move confidently from accumulation to lifelong financial independence.

Here are 7 key steps to take:

1. Define Your Retirement Goals & Lifestyle

Before running the numbers, take time to define what this next chapter really looks like for you. Do you plan to relocate, travel extensively, or spend more time with family? How you plan to live will determine how much income you need and where best to draw it from.

Start by asking:

  • How much will I need each month to maintain my desired lifestyle?
  • Where do I plan to live, and how much will that cost?
  • Are there new activities or pursuits I want to fund?

A clear vision makes every financial decision more purposeful and helps your advisor design a retirement plan tailored to how you truly want to live.

2. Analyze Your Retirement Cash Flow & Expenses

As you approach retirement, tracking your spending becomes more important than ever. Understanding where your money is going now helps identify what will change—and what won’t—once your regular paychecks end.

With your advisor, review:

  • Fixed and discretionary expenses
  • Health care and insurance costs
  • Potential income sources such as Social Security, pensions, or rental income

A detailed cash flow analysis will help determine whether your current savings strategy will sustain your lifestyle or if adjustments are needed before you transition to retirement.

3. Adjust Your Investment Strategy for Retirement

The years just before retirement are critical for protecting the wealth you’ve built. That doesn’t necessarily mean avoiding risk altogether, but making sure your portfolio’s mix of growth and preservation aligns with your timeline and goals.

Your financial advisor can help you:

  • Rebalance investments for risk tolerance and market conditions
  • Evaluate potential income-producing assets
  • Incorporate tax-efficient withdrawal strategies

Now is an ideal time to stress-test your plan under different market scenarios to ensure you can withstand volatility without jeopardizing your long-term stability. At Granite Bay Wealth Management, we utilize the Monte Carlo Simulation, a practice used to gauge the impact of risk and uncertainty in financial forecasting . This allows us to test how realistic your retirement age and future spending are.

4. Implement Tax-Efficient Retirement Planning Strategies

Proactive tax planning in the five years before retirement can make a meaningful difference in your lifetime wealth. This is when you have the flexibility to position assets, convert traditional IRAs into Roth IRAs, and plan distributions strategically.

A fiduciary advisor will help coordinate your investment and tax decisions, minimizing what you owe while maximizing what you keep. Small adjustments now can create substantial tax advantages once you begin drawing from your retirement accounts.

5. Plan for Healthcare and Medicare Costs

Healthcare is one of the most commonly underestimated retirement expenses. Even with Medicare coverage, retirees often face additional costs for supplemental insurance, prescriptions, and long-term care. Along with life expectancy, the price of healthcare continues to rise, making it even more crucial to plan ahead.

Planning includes:

  • Understanding Medicare enrollment timelines
  • Evaluating supplemental coverage options
  • Considering how healthcare costs fit into your long-term financial plan

Addressing these factors early will help prevent unexpected expenses from disrupting your retirement income strategy.

6. Update Your Estate and Legacy Planning

The years leading up to your retirement are also a good time to review and update important legal and estate planning documents.

Your plan should reflect your current wishes and circumstances, including:

  • Updating wills, titles, and beneficiary designations
  • Reviewing powers of attorney and healthcare directives
  • Planning charitable gifts or family transfers

Estate management often takes a backseat to investments, but in retirement planning they’re equally important. Thoughtful planning in these areas helps protect both your legacy and the people you care about most.

7. Evaluate Your Purpose in Retirement

Retirement planning often centers on finances, but how you plan to spend your time is just as important to consider. Many people prepare for the monetary side of retirement without thinking about their new “why.” What will replace the structure, identity, and sense of purpose that work once provided?

As you think ahead to life after work, ask yourself:

  • What do I want my days to look like?
  • What activities bring me a sense of fulfillment?
  • How do I plan to stay engaged, connected, and challenged?

As you approach this transition, reflect on what will give your days meaning, whether that means travel, volunteering, pursuing new interests and hobbies, or spending more time with family and friends.

Transitioning from Saving to Living on Your Wealth

The final stretch before retirement is your opportunity to fine-tune details, anticipate challenges, and address potential gaps before they can become problems. Working with a fiduciary advisor ensures that nothing is overlooked—from investment allocation and tax strategy to income distribution and estate planning. Knowing that your financial and lifestyle goals are aligned will allow you to focus on enjoying your retirement.

At Granite Bay Wealth Management, we specialize in helping clients move from accumulation to preservation with confidence. We build personalized strategies designed to protect what you’ve earned and support the life you envision, with clarity at every step.

You’ve spent decades building your financial foundation. Now it’s time to make sure it works just as hard for you.

Contact us today to start preparing for your next chapter.