Pre-Retirement Checklist: 6 Moves to Make Before You Stop Working

1. Calculate Your Retirement Income Gap and Withdrawal Plan

The most critical step in preparing for retirement is ensuring you have a clear plan for generating income once the paychecks stop. This means understanding how much monthly cash flow you’ll need to support your desired lifestyle and where it will come from.

Take inventory of the assets, expenses, and income sources you have entering retirement, including:

• Social Security benefits
• Workplace retirement plans (e.g., 401(k), 403(b), 457(b), or pension)
• Traditional or Roth IRA
• Health Savings Account (HSA)
• Taxable brokerage accounts
• Real estate income
• Alternative assets (e.g., private equity, cryptocurrency, collectibles, etc.)

Once you understand your income gap, you can start making decisions about when to retire, how to spend your savings, and where to optimize for taxes. A fiduciary financial advisor can help you run projections, identify shortfalls, and create a withdrawal strategy that supports your lifestyle throughout retirement.

2. Decide When to Take Social Security

Social Security plays a vital role in many people’s retirement income plans. While you can begin collecting benefits as early as age 62, your monthly payout won’t reach its maximum until age 70, with your full retirement age falling somewhere in between, depending on your birth year.

Taking benefits early results in a reduced monthly payout, while delaying past your full retirement age increases it by up to 8% per year. So, what’s the right choice? This depends on your health, life expectancy, marital status, and other income sources.

A fiduciary financial planner can help you evaluate different claiming strategies in the context of your overall plan, so you can make a confident decision that aligns with your long-term goals

3. Explore Roth Conversions While You’re in a Lower Tax Bracket

During the years before retirement, you might find yourself in a lower tax bracket than you will be after you begin tapping savings, especially if you’ve stopped working but haven’t yet started taking Social Security or withdrawals.

One way to take advantage of this is by converting your traditional retirement accounts to a Roth IRA. After paying income taxes on the transition, Roth conversions allow you to grow and, eventually, withdraw your funds tax-free in retirement. 

Strategic conversions can help reduce future required minimum distributions (RMDs), avoid higher Medicare premiums, and give you more flexibility in managing taxes later. With the help of a financial advisor, you can plan your conversion scenarios and understand how it can benefit your retirement plan.

4. Reassess Your Investment Allocation

Nearing retirement presents an opportunity to reassess your investment allocation. While you may have been more aggressive during your working years to maximize growth, it’s smart to evaluate your portfolio and take action to ensure protection against risks, like market volatility, sequence-of-returns, and inflation.

Financial advisors often recommend shifting from an accumulation strategy—usually including a portfolio of growth equities—to a more conservative one focused on preserving capital and generating income, commonly including bonds or fixed-income assets. 

But what works for you can vary and won’t be the same as someone else’s plan. For instance, being too conservative can also be risky. Consider consulting an investment advisor to develop and refine a plan for your needs.

5. Plan for Healthcare and Medicare

Healthcare is one of the largest and most unpredictable expenses in retirement, especially as you get older. As you approach age 65, it’s essential to understand your Medicare options, including what’s covered, what isn’t, and how it works alongside any employer or retiree health plans you may have.

You’ll also want to weigh the costs of premiums, out-of-pocket expenses, supplemental coverage (like Medigap), and potential long-term care needs.

6. Finalize Estate and Legacy Plans

It’s crucial to ensure your estate plan reflects your current wishes as you enter the next chapter of your life. This includes updating beneficiaries on your estate planning documents and retirement accounts, confirming powers of attorney (POA), reviewing your will or trust, and documenting how you’d like your assets handled.

Without clear, up-to-date instructions, your loved ones could face probate delays, unnecessary taxes, or legal complications down the road.

A fiduciary advisor can help you align your financial plan with your legacy goals and coordinate with estate planning professionals as needed.

Don’t Go Into Retirement Without a Plan

Staring retirement in the face can be downright overwhelming. Getting everything right can feel complex, and it can be challenging to know when it’s truly best to stop working and begin the transition.

Having a clear, personalized plan can make all the difference. A financial advisor can help coordinate all the points we discussed above and deliver a structured roadmap that works for you, including income, taxes, investments, healthcare, and estate planning.

It’s important to prioritize working with a fiduciary professional. These individuals work in your best interest and often hold reputable credentials such as Certified Financial Planner (CFP), Chartered Financial Consultant (ChFC), and Chartered Retirement Planning Counselor (CRPC).

How to Find the Right Financial Advisor

If you’re right near retirement, now is the time to meet with a financial advisor. The right professional can help you check every box and retire with confidence. Our matching tool connects you with vetted fiduciaries who specialize in retirement planning. Just select your state below and complete the form to get matched with a professional in minutes: