A fruitful topic for holiday conversation: Retirement

As the holidays quickly approach, many people look forward to gatherings with family and friends. But if you dread going to your family’s annual Thanksgiving or holiday dinner because the main topic will be Aunt Mary’s countrywide tour to see the wackiest attractions in each state, or Uncle Joe’s political views, here’s a more interesting (and less divisive) approach: Ask those who’ve retired how they’re doing. They’ll probably be happy you asked, and you could learn some valuable lessons from their hard-won experience.

To help you break the ice, here are 10 questions you could ask:

1. What do you enjoy the most and least about retirement?
2. What’s the best thing you did to prepare for retirement?
3. What are your regrets about retirement? Specifically, what do you wish you’d done differently to prepare?
4. What’s on your “bucket list”? Have you done anything lately on your list or plan to soon?
5. When did you start Social Security? Why?
6. How are you drawing down your retirement savings to generate retirement income? Do you have an explicit strategy?
7. Did you buy a medical plan to supplement Medicare? If yes, did you buy a Medigap plan and Part D prescription drug plan, or Medicare Advantage Plan? How do you like it?
8. Do you work with a financial adviser? If yes, how did you select that person? Do you get help with your most important decisions?
9. Did you move or downsize your home? If yes, how’s that working for you?
10. What advice do you have to help me when I retire?

Think of these questions as conversation-starters. If you ask follow-ups, you might keep your relatives talking for hours. You’ll not only find out more about them but you might gain from their experience and discover ways you can improve your own retirement. 

And you’ll all feel better about the holiday time you spend together.

Steve Vernon

View all articles by Steve Vernon on CBS MoneyWatch»
Steve Vernon helped large employers design and manage their retirement programs for more than 35 years as a consulting actuary. Now he's a research scholar for the Stanford Center on Longevity, where he helps collect, direct and disseminate research that will improve the financial security of seniors. He's also president of Rest-of-Life Communications, delivers retirement planning workshops and authored Retirement Game-Changers: Strategies for a Healthy, Financially Secure and Fulfilling Long Life and Money for Life: Turn Your IRA and 401(k) Into a Lifetime Retirement Paycheck.

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