Top 8 Financial Questions That Baby Boomers Want to Ask Financial Experts

For many baby boomers, retirement and growing old is a frightening prospect. Gone are the days of the employer paying a guaranteed lifetime pension income. Now, the onus is on them to build one and try to figure out how much they’ll need to live on while accounting for various unknown variables such as market volatility, lifetime expectancy, unpredictable healthcare costs, and inflation.

Here are the biggest questions keeping people ages 60 to 79 up at night—with answers from financial experts.

Top 8 Financial Questions Baby Boomers Want Answered

1. How Much Money Will I Need to Retire Comfortably?

Derrick Kinney, founder of Success for Advisors and Good Money Framework: “I’ve discovered one simple, proven strategy: live on a practice-retirement budget. Here’s how it works: 12–18 months before retiring, practice living on the amount you think you’ll need—while you’re still earning your full income. It’s a no-risk test drive. Most people are surprised by what they learn. Some discover they can live on less and retire earlier than expected. Others realize they may want to work a bit longer.”

2. Will I Outlive My Retirement Savings?

Stoy Hall, CEO and founder of Black Mammoth: “It happens when spending outruns growth or income dries up. We keep expenses from outpacing the growth of your assets. We hold a dedicated cash fund for ugly markets, so we are not forced to sell at a loss. That avoids sequence risk, the silent killer.

We don’t marry a 3% or 4% rule [for the percentage of your retirement funds to withdraw each year]. We set a smart starting paycheck, watch the portfolio, then adjust. If markets drop, we pause raises or trim wants. If markets run, we give you a raise. Flexibility is key; you must retain cash-flow flexibility. This planning must be done prior to retiring.”

3. What if Inflation Rises While I’m Retired?

Hall said, “Social Security has a cost-of-living adjustment [that] keeps up with inflation. Our investments will also adjust over time if we keep some growth in the mix. The real lever is spending. When prices bite, pull back on nonessentials. Maybe fewer big trips for a season. Maybe different choices than what you have always done. Keep core bills matched to steady income and let the portfolio work.”

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4. How Will Taxes Impact Me in Retirement?

Carolyn McClanahan, founder and president of Life Planning Partners: “People often wait to take money out of retirement plans until they have required distributions and will live on other savings or take social security early to meet cash flow needs. In doing that, they may have very low taxes early in retirement and be in the 0%, 10%, or 12% tax bracket. However, once they reach the required distribution age of 73, they may have to pull a lot [of money] out of retirement plans, putting them in the 24% or 32% tax bracket.

The smartest way to manage taxes in retirement is to always make sure to take enough from retirement plans or capital gains to fully utilize the 10% and 12% tax brackets throughout the early years of retirement. This reduces future required distributions and may allow the retiree to delay Social Security.”

5. Should I Keep Investing in Stocks at My Age?

Stephanie McCullough, founder of Sofia Financial: “For most of our working lives, retirement accounts are long-term money. But as we get closer to retirement… some of our dollars aren’t really long-term anymore. If you’re planning to withdraw some money in the next five years or so, that’s short-term money. I’m a big believer in having five to eight years of anticipated withdrawals not in stocks, but instead in vehicles with little downside risk… [and ] the rest of it… invested for the long term [in stocks].

Longevity and inflation are risks as much as stock market downturns, and we have to plan for them as well. Having a decent portion of your long-term dollars in stocks is still the best way to address those risks.”

6. Is Downsizing or Relocating a Smart Financial Choice?

McClanahan: “If you want to age in place, make sure your home is aging-friendly. If it is large or requires significant upkeep, it may be worthwhile to downsize and move to a home that takes less work. This may result in savings by reducing the cost of your home and its upkeep.

More importantly, if it allows you to age in place successfully, you can potentially save tens of thousands in long-term care costs. Aging in place, if done correctly, can be much less expensive than moving to an aging community or assisted living.”

7. How Do I Budget for Rising Healthcare and Long-term Care Costs?

Hall: “Pre-fund an HSA before retirement. Let it grow and spend it tax-free on premiums, deductibles, drugs, dental, and vision. Then plan for long-term care [LTC], decide now if you will self-fund with a side bucket or cap the risk with insurance. Traditional LTC or a life policy with an LTC rider can keep one spouse from being wiped out caring for the other. We all will end up needing health care as we age, and this will ensure you have enough to withstand that cost.”

8. What’s The Best Way to Leave Money to My Children or Grandchildren?

McCullough: “Bill Perkins, author of ‘Die With Zero,’ would suggest that instead of prioritizing a legacy at our death, which we have no idea when [it] will occur, we should look to make that transfer at a time most beneficial to the recipients. I like this thinking, and often work with clients to see how they can make more substantial gifts during their lifetime.

I recognize that’s not always feasible given all the uncertainty in our own lives. …If you have an old life insurance policy with a manageable premium, keep it going. Knowing your family will receive that money can give you permission to spend your other assets. Also, be aware of the inherited IRA rules that came into effect in 2020.“