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7 questions to ask as you’re nearing retirement

June 05, 2024 | 6 min read

For people preparing to exit the workforce, the future holds both promise and uncertainty. Modern retirements often span multiple decades and require resources to last far longer than past generations. While living longer can give us more quality time with loved ones, finances are arguably the greatest wildcard. Here are seven question you should ask today as you're nearing retirement to help plan for golden year that are truly golden.

Do I have a vision in place for my retirement?

Having a vision of what you want to achieve in retirement can help you plan more effectively. Where would you like to live when you retire? Do you see yourself moving to a smaller house? A new city?

How do you want to spend your time? Solo hobbies, volunteer activities or a favorite pastime might bring you enjoyment. Getting specific about your ideal schedule can help solidify your vision. Imagine your daily routine, weekly activities and monthly travels or events.

Creating a blueprint of your future retirement lifestyle in this way can help you construct a financial plan that can support that vision.

You could also include loved ones in discussions about your retirement plans. Maybe their input and expectations for how they want to share this next chapter of life with you are important to you. Taking the time now to imagine and define your retirement will help with mapping out the steps to make that vision a reality.

Do I have a clear picture of all my expenses?

Retirees often worry they won’t have enough money to last 20+ years. You can overcome that fear with a practical budget that distinguishes between necessities and other purchases. A budget that separates essential costs from discretionary spending can help ensure your lifestyle remains sustainable on your projected retirement income. 

Evaluate your spending habits now and decide if you can make any changes before retiring. Pinpoint where your money is going each month. The results can guide your preparation for what may need to be a more frugal lifestyle after you leave the workforce. Identify ways to reduce costs or boost savings.

Have I planned for Social Security?

When deciding on the timing of collecting your Social Security benefits, it's essential to consider how the start date will affect the monthly amount. The longer you wait, up to age 70, the larger your monthly benefit will be. Starting earlier means getting more months of lower payments. Waiting until later raises your monthly benefit, but it also means relying on other sources of income in the meantime.

Your ideal start date could vary based on your other retirement income, health, family situations and your preference between getting less money now or more money later. Take time to carefully weigh the advantages and disadvantages of different start dates, given your specific retirement situation and priorities. 

Do I know what my other retirement income sources will be?

As you plan for retirement, estimate the money you'll have coming in from sources other than Social Security and pension plans. Creating a retirement income strategy with the help of a qualified financial advisor can be invaluable. They can help you project income from personal investments, part-time work or side businesses. Your advisor can also craft a personalized investment plan for you and help monitor its progress.

If you realize you need to boost your savings further, take advantage of employer-matched retirement plans like 401(k)s if they’re available to you. Beyond that, contributing to a Traditional or Roth IRA each year is a smart way to save more on a tax-advantaged basis. If you’re trying to catch up, doubling down on contributions or limiting expenses can help maximize the time you have left to save.

As you’re nearing retirement, it’s crucial that you identify guaranteed income sources and balance them with your anticipated expenses. An experienced advisor can provide a professional opinion on how realistic your estimations are and the best savings options for your situation.

How will I navigate rising health care costs?

Rising health care costs in retirement are a concern for many people. While completely predicting medical expenses is impossible, having realistic expectations and financial goals helps ease worries about outliving your savings.

If you have one available, a health savings account (HSA) can be a smart way to save for future medical expenses. You can withdraw funds from your HSA tax-free to pay for qualified medical expenses like deductibles, copays, dental/vision care and more. Contributions you make over the years can grow to offset retirement health care spending.

Signing up for Medicare coverage is another way to prepare for your health care needs in retirement. Educating yourself on what is and isn't covered and anticipated out-of-pocket costs allows for better planning and budgeting. 

Speak with a Medicare advisor who can get to know you and provide guidance on estimating expected costs based on your health and retirement details. They may also tell you about additional coverage options worth exploring. Register for A Deep Dive into Medicare Benefits, a free educational workshop where you can learn:

  • Coverage types.
  • Coverage timelines.
  • How to shop for plans tailored to you.
  • How to switch coverage, if needed.

Getting a more accurate sense of your medical costs will help you feel more confident about your ability to navigate potential health care obstacles.

Have I considered long-term care?

Did you know long-term care typically isn’t covered by Medicare? Long-term care insurance helps you with Activities of Daily Living in the event of chronic illness or disability – and it’s usually more affordable when you get it early in life. Knowing what it costs is a crucial aspect of retirement planning.

Long-term care coverage can be complex. It might include private insurance and personal spending or Medicaid. But rest assured – an insurance advisor can help you understand what goes into it and what might be good options for you. 

Have I thought about my legacy?

While retirement income is probably top-of-mind for you, it’s also important to think about the legacy you’ll eventually leave to your loved ones. Consider creating an estate plan so your assets are distributed as you wish after your passing. Plus, your estate plan could also have an impact on you while you’re still here – like the person you allow to make medical decisions on your behalf. An estate planning specialist can help you get started and answer your questions along the way.

Proactive planning is crucial as you prepare for the next phase of life. Use these questions if you’re nearing retirement age to get organized and track your progress over time. Remember that each person’s journey to a comfortable retirement is unique. There is no one-size-fits-all solution – the right approach depends on your goals.

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