After over 35 years advising successful pre-retirees and retirees, I can tell you this: financial peace of mind doesn’t just come from hitting a magic number. It comes from having a clear plan—one that gives you confidence in how much you can spend, how much income you’ll have, and how you’ll weather the curveballs life may throw you.

If you’re 50–65 and within 10 years of retirement, this article is your guide to getting your financial house in order.

Let’s review the checklist I use to help my clients create a financially secure life they love.

Start with the Vision of Your Retirement

Too many people begin with the numbers. That’s where I started years ago, until I saw the results of people who had done this.

They lacked the sense of fulfillment they thought the money would bring, such as peace of mind, security, and joy.

When I began with clarity, everything changed, literally everything.

To get started, answer these questions:

• What does your ideal day in retirement look like?
• How do you want to spend your time?
• Where do you want to travel and live?
• How much will it cost to fund your dream?

While some focus on downsizing their homes and traveling, others prioritize their health, family, or community. There is no correct answer.

Once you define what your future life looks like, including how you feel about it, you can begin shaping the financial plan that supports it.

Inventory What You Have and What You’ll Need

Before you can design an income and investment plan, you need to get organized.
Some of the questions to consider:

• Where is your money invested and what is the value (checking, savings, IRAs, 401(k)s, Roths, brokerage)? This is your balance sheet.
• What are your income sources (employment, pension, Social Security, rental income)?
• Do you have any debt, such as a mortgage, car, or credit cards?
• What are your monthly “need-based” and “want-based” expenses, now and in retirement?

If the thought of creating a plan is overwhelming, please know that it is normal when you don’t have a plan. Once you make a plan and begin executing the necessary steps to achieve it, everything changes.
I’ve worked with millionaires who didn’t know where their money was going or how much they needed. Once we identified the amount and required action, the stress began to melt away. They could finally make informed decisions.

Replace Your Paycheck with Predictable Income

For decades, you’ve had income coming in from your job. That changes for many in retirement, causing unwanted feelings of overwhelm, stress, and worry.
Creating a predictable income is one of the most critical elements of most people’s financial plan. The goal isn’t to guess what you might need, but to build a guaranteed or sustainable income stream that you can count on month after month, year after year, regardless of what happens in the market.
Examples of income sources often include:

• Social Security
• Pension income (if available)
• Guaranteed annuity income
• Income from investments (interest, dividends)
• Part-time work or side business (optional but impactful)
• Income from rental property

The magic happens when you align your “need-based” expenses with your guaranteed income.
For most people, that means less time lying awake at night wondering if they will outlive their money or if the stock market will wipe out their lifestyle.
When your basics are covered, you will feel more peaceful, secure, and joyful.

Shift From Growth to Preservation

Most people focus on accumulating assets. That works well until you approach retirement. While you likely want some growth, you don’t want it to come at the expense of a financially secure tomorrow.
That’s why you need to build a coordinated investment plan designed around your risk tolerance, income needs, and time horizon. It’s not about “beating the market.” The goal is to fund your future life while minimizing the risk of significant losses you may not have time to recover from.
This may include adjusting your asset allocation, diversifying your investments, or setting aside specific accounts for short-, medium-, and long-term withdrawals.

Plan for Taxes, Now and Later

Taxes don’t go away when you retire. In fact, for many, they increase, especially once their Required Minimum Distributions (RMDs) begins.
This is where many pre-retirees miss out on opportunities.
With strategic planning, we often help clients:

• Convert traditional IRAs to Roth IRAs in lower-income years
• Maximize deductions before retirement
• Create tax-efficient withdrawal strategies
• Reduce the tax impact of Social Security benefits
• Shift assets into tax-advantaged vehicles

Smart tax planning doesn’t just help you now. A good tax plan is coordinated with your investment and retirement plans and continues to evolve over the life of your portfolio, spanning years or even decades.

Secure Your Healthcare and Long-Term Care Plan

One of the biggest mistakes I see is underestimating healthcare costs.
Whether it’s Medicare premiums, supplemental coverage, or unexpected out-of-pocket expenses, the truth is that health care can be one of your most significant expenses in retirement.
Long-term care costs are one of the biggest costs in retirement.
Whether you use a hybrid policy that combines life insurance with long-term care or self-fund through designated assets, you must have a strategy. Otherwise, you could risk depleting your savings, or worse, becoming a burden on your loved ones or having to remarry.

Align Your Estate Plan with Your Goals

Your estate plan is much more than a trust or will. It’s your plan for how your assets are managed and transferred during your life (if you’re incapacitated) and after your death.
Here’s what you need to review:

• Is your trust updated and funded?
• Do your beneficiary designations match your intentions?
• Are assets titled to coordinate with your estate plan?
• Do you have medical directives and powers of attorney in place?
• Have you accounted for changes in tax law?
• Do you need an Irrevocable Life Insurance Trust?

Even wealthy families can unintentionally cause legal chaos by skipping this step. A proper estate plan ensures that your values and your wishes are honored.

Build In Flexibility

Retirement is not a static target. You may want to move, start a business, help a child, or support a cause. Inflation may rise. The market may dip. Life will happen.

That’s why the best financial plans are resilient.

They include:

• Emergency funds for unexpected costs
• Liquidity if needed
• Flexible withdrawal options
• “What if” contingency scenarios
• An inflation hedge

In short, a sound financial plan doesn’t just prepare you for what you expect; it also protects you from what you don’t.

Conclusion: The Financial Planning Checklist for Pre-Retirees

A financial plan is your roadmap to a financially secure tomorrow, and this checklist will help you get started.

Most people want to ensure their financial house is in order. This checklist will help you determine your next best step.

If you have questions or need support, start here:

This article is for educational purposes only and is not intended to replace financial, tax, or investment advice. Please consult your team of professionals before making any financial decisions.

Disclosure

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This information is for educational purposes only. It is not intended to replace the advice of any advisor or specialist, nor to provide investment, financial, tax, retirement, planning, or healthcare advice.

Always consult with a qualified professional before making any financial decisions or changes.