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10 retirement questions for the holidays

It’s holiday time again, and many readers will be gathering with their extended families to celebrate. If you dread going to your family's annual holiday dinner and hearing -- once again -- about Aunt Betty’s experiences with her singing group or Uncle Bob’s views on the economy, here’s a more constructive approach: Ask them how they’re doing in their retirement. Most likely they’ll be glad to talk about themselves, and you could learn some valuable lessons from their hard-won experience.

If you’re worried that they might think you’re being nosy, tell them you’re asking these questions so you can learn from their life’s lessons. My guess is they’ll be glad to help, and it will make them feel useful.

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

  • What’s on your “bucket list”? Have you done anything lately on your list, or are planning to in the near future?
  • What is the best thing you did to prepare for retirement?
  • What are your regrets – what do you wish you had done differently to prepare for retirement
  • What do you enjoy the most about retirement?
  • What do you like the least about retirement?
  • When did you start Social Security? Why?
  • If you don’t mind telling me, how do you invest your retirement savings? Why?
  • How are you using your retirement savings to generate income? Do you have a systematic method?
  • Do you work with a financial advisor? If yes, how did you select that person? Did they help with your most important decisions?
  • What advice do you have for me to help me in retirement?

Don’t feel stymied if your relatives haven’t yet retired. If they’re approaching their retirement years, you can still ask most of these questions. In a few cases, you might ask what they are planning to do instead of what they actually did to prepare for retirement, or how they anticipate their retirement will be.

With these 10 questions, you’ve got plenty of conversation-starters. If you show interest and ask follow-up questions, you might keep your relatives talking for hours as well as discover ways you can improve your own retirement. And you might even find a way to talk with older relatives about the more sensitive retirement planning issues. Happy holidays!

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