7 Questions To Ask Retirees


7 Questions To Ask Retirees



I recently came across an article by Mark Patterson in U.S. News & World Report that caught my eye. The author of The Failsafe Retirement System had just returned from an AARP convention and was bursting with valuable intel about the methods and practices of the happy retirees he met.

He crafted his findings into what he found to be the seven most consequential questions for folks to ask themselves when planning for retirement. My team and I decided to share five with the Retire Sooner Facebook Group for their thoughts and comments. Some of the answers might surprise you.

1. Which expenses increased and decreased when you retired?

Mary K. said her health insurance — Medicare Part B, supplemental, and prescription drug coverage — went up. Furthermore, her motorhome insurance increases annually. The higher outflow isn’t ideal, but the silver lining is that being a full-time RVer means she doesn’t carry the burden of homeowner’s insurance.

Gilen C. decided to spend more money and time on hobby supplies and activities he’d never been able to enjoy.

What decreased? Indira V. said her average mileage went down despite her vacation expenses rising. FD stopped eating out and spent more time on the golf course. Jennifer S. enjoyed spending less money on a work wardrobe.

2. What was the smartest thing you did to prepare to retire?

Brian G. took full advantage of the excellent newsletters, podcasts, and personal finance gurus that helped him become debt-free. He said paying off his house gave him a feeling of accomplishment and security for the future. He is ahead of the game with eight to ten years left before retirement.

Kevin R. became debt-free several years before retirement, including paying off his mortgage. This accomplishment significantly reduced expenditures and allowed him to save more.

Mary K. also found her way clear of debt. She created a retirement income and expense spreadsheet three to four years before leaving her job. Because life can be messy, she gave herself the freedom to adjust it as expenses changed. She advises folks to keep track of the money they have in all their various accounts, which takes some effort. Valerie P. bought her retirement house in advance and rented it out to earn income until she was ready to use it.

Mark H. says take responsibility for your future. He started early, setting up an IRA while serving in the US Navy in the 1980s. He committed to living frugally and eventually married a woman who practiced financially responsible habits. Together, they built a nest egg by diversifying assets and adopting a value/dividend investing strategy. They’ll be retiring soon and plan to be mortgage free.

Amy V. further stressed the importance of marrying someone responsible. She says her spouse has patiently and consistently encouraged them to save, live within their means, and prioritize important decisions.

Bipin P. emphasized having a backup plan so that there’s something to lean on in difficult moments. He also believes it’s never too late to start a “side hustle” to create another income stream. His new gig provided supplemental income to use today and leave his children tomorrow.

Because he retired in his late forties, Brandon J. kept his money in three tax buckets (pre, post, no-tax) to create flexibility for all that life he had yet to enjoy. People laughed at Michael B. when he started saving at just twenty-three years of age. They no longer laugh. Dave B. moved to a big retirement community with all sorts of fulfilling activities.

Finally, and I promise I’m not making this up, Michelle D. recommended reading my latest book, What the Happiest Retirees Know: 10 Habits for a Healthy, Secure, and Joyful Life. What can I say? She has good taste!

3. What non-financial aspect of retirement living surprised you the most?

Leslie B. thought it would be easier to learn how to structure her day. After four weeks, she hasn’t mastered it yet but is optimistic that she’ll get there.

Finding contentment and patience with a slower-paced life has helped Deb S. learn to enjoy each day, not just weekends. Tom L. echoed Deb’s sentiment. He almost likes the weekdays more than weekends!

4. If you could change one thing about your retired life, what would that be?

Mark H. wishes he had had enough forethought to pre-plan which part-time job would make him happy during retirement. Likewise, Julie C. wishes she had more confidence that her retirement savings would last.

John F., Connie J., and Deb S. all want cheaper health insurance. Gregory T. didn’t save soon enough and wished he could afford more toys. Sid C. doesn’t like having to deal with Medicare.  I’m sensing a recurring theme here!

5. Do you believe you retired too early or late, and if so, why?

Mitch G. is still trying to answer this question. He retired a year ago at fifty-nine. Feeling restless, he’s looking to work part-time to stay busier. But, even with a workout routine, traveling, catching up with friends, and volunteer work, he still has more time on his hands than he prefers. John F. retired at sixty-one and felt the same way.

Mark H. wants to retire within the next year but still has a monthly mortgage of roughly $1,300. He’s considering selling the house, moving to a smaller city, and using cash to buy property. His biggest concern is the cost of health insurance. He was quoted $2,500 per month for himself and his wife.

John F. could retire at sixty-one, about three years sooner than he’d expected, thanks to a buyout. Tom K. regrets quitting at forty-six without enough of a plan for a purpose-driven second act. Now, he’s planning to go back to work. Julie C. is retiring later than she’d initially hoped.

Carol H., Mary K., and Chuck C. are all thrilled with their retirement decisions. They felt they timed it perfectly.

The two questions we haven’t yet tested with our audience are: What was the dumbest thing you did (or did not do) in your retirement planning? And, what advice would you give a pre-retiree about preparing for retirement?

If you or someone you know has valuable insights, head to the Retire Sooner Facebook Group to share that wisdom. One of the reasons I was so eager to hear what Mark Patterson had to say about the retirees he met at the AARP convention was that in all my years of financial advising, few things have proved more beneficial than the acumen of happy retirees. They’ve walked the walk, and we are lucky each and every time they’re willing to talk the talk.


This information is provided to you as a resource for informational purposes only and is not to be viewed as investment advice or recommendations.  Investing involves risk, including the possible loss of principal. There is no guarantee offered that investment return, yield, or performance will be achieved.  There will be periods of performance fluctuations, including periods of negative returns and periods where dividends will not be paid.  Past performance is not indicative of future results when considering any investment vehicle. This information is being presented without consideration of the investment objectives, risk tolerance, or financial circumstances of any specific investor and might not be suitable for all investors. This information is not intended to, and should not, form a primary basis for any investment decision that you may make. Always consult your own legal, tax, or investment advisor before making any investment/tax/estate/financial planning considerations or decisions.  Investment decisions should not be made solely based on information contained in this article. The information contained in the article is strictly an opinion and it is not known whether the strategies will be successful. There are many aspects and criteria that must be examined and considered before investing.


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