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Family Conversation-Starters About Retirement: Five Questions That Can Get People Talking (and Not Just About Money)

Last week here on the AgingOptions blog, we offered some helpful ideas from NerdWallet about how to have “the money talk” with aging parents during holiday get-togethers. As the article warned, conversations about money can often turn into arguments, and nobody likes that during festive family times! This week we offer a different approach, one that can turn the conversation about retirement away from a narrow focus on money and toward a more qualitative view.

We found this insightful article on the Forbes website. In it, retirement writer Steve Vernon shares some helpful questions you can toss out when you’re together with family. These are the types of questions that can get people talking and hopefully avoid defensiveness – and the answers can help you as you chart your own course toward retirement.

Ask the Right Questions and You Can Make the Right Choices

Instead of confronting family members about their financial health and future goals, Vernon encourages us to use our holiday gatherings as a time to open up the table to more wide-ranging discussions, the kind we may never have had before with loved ones. This can be especially helpful if you are making your own plans about retirement and seeking wisdom from others.

Vernon explains that “by asking questions—of yourself and others with hard-won life experience—you have a better chance of making the right choices.” 

Try These Five Questions to Get Ideas Flowing

To get the conversation flowing, and involve as many loved ones as possible, Vernon provides us with five thought-provoking questions about retirement. We have quoted these questions verbatim from his article:

  1. What would you consider to be a successful retirement?
  2. What would a good “average day” in retirement look like (not doing things on your bucket list)?
  3. What’s on your “bucket list” to do after you retire?
  4. How did you (or will you) decide when to retire?
  5. For relatives who are already retired: What advice do you have for those of us who are still working, based on your experience? For example, are there things you wish you’d done differently? What steps are you glad that you took? 

Looking Beyond Money Toward a Fulfilling Retirement Experience

These questions may seem open-ended, but they’re anything but arbitrary. Research shows that wrestling over tough decisions begins by engaging with those decisions emotionally. Talking these issues through with loved ones and envisioning life as you age opens the door to making smarter choices down the road, whether retirement is looming or still years away.

It’s a known fact that stating your goals and visualizing them has a strong effect on your motivation. Envisioning your retirement lifestyle is one way to keep it as a sort of north star, something to move towards as you go about your working life. 

The Forbes article does advise caution. Before throwing these questions out there, be aware of timing. “Look for the best time to ask these questions,” Vernon warns. “It might—or might not—be best to bring up these questions during the big holiday dinner. Instead, you might bring them up when you’re relaxing before or after dinner, or maybe while taking a walk outside to burn off that holiday meal.”

Protect Loved Ones from Becoming Financial Victims

The sad fact is that many aging adults experience a diminished ability to make rational decisions, which makes them an easy target for financial fraud, exploitation, and other manipulations. If you have a loved one that you worry about along these lines, Vernon provides three further questions that you could gently pose to them next time you see them. Again, these are quoted verbatim from the article:

  1. Do you get stressed or easily flustered when dealing with your bank, insurance company, or investment firm?
  2. If you learned something important about finances (either yours/ours, or just in general), would you feel comfortable bringing it to my attention? 
  3. Have you received any odd emails lately, Grandma?

If the area of your parent’s cognitive ability as it affects their finances is a concern for you and you would like further resources to help you speak with an aging loved one about their finances, insurance company and retirement provider TIAA has a guide for just such situations. It could provide you with helpful tips as you broach potentially sensitive topics.

Your holiday gatherings shouldn’t be a chore, but they shouldn’t be overlooked as an opportunity, either. Speaking to your family about retirement and other provocative issues doesn’t have to be tedious or contentious. With the right questions, you may even spark some great discussions and gather a treasure-trove of unexpected wisdom.

My Life, My Plan, My Way: Get Started on the Path to Retirement Success

At AgingOptions we believe the key to a secure retirement is the right retirement plan – yet statistics show that 70 percent of retirement plans fail. That’s why for nearly two decades we’ve been dedicated to the proposition that a carefully-crafted, fully comprehensive retirement plan is the best answer to virtually any contingency life may throw your way as you age.  Our slogan says it all: My Life, My Plan, My Way.

When it comes to retirement planning, most people focus on one fairly narrow issue: money. Financial planning is an important component of retirement planning. However, people heading towards retirement often make the mistake of thinking that a little financial planning is all that’s required, when in fact most financial plans are woefully inadequate. What about your medical coverage? What if you have to make a change in your housing status – will that knock your financial plan off course? Are you adequately prepared legally for the realities of retirement and estate planning? And is your family equipped to support your plans for the future as you age?

The best way we know of to successfully blend all these elements together – finance, medical, housing, legal and family – is with a LifePlan from AgingOptions. Thousands of people have discovered the power of LifePlanning and we encourage you to the same. Simply visit our website and discover a world of retirement planning resources.  Make certain your retirement planning is truly comprehensive and complete with an AgingOptions LifePlan.  Age on!

(originally reported at


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