The approaching holidays present a golden opportunity to help you gain valuable insights that will help you better plan your retirement. And it’s a win-win—you can also engage with relatives and friends whom you might not know very well and avoid those awkward silences.

The ice breaker: Ask them thought-provoking questions about their views on retirement.

Recent research from the Stanford Center on Longevity shows that wrestling with provocative questions can help engage you with your own retirement planning. The research showed that you’ll have better outcomes if you spend time thinking about how retirement might improve your life and the goals that are important for you instead of relying on untested assumptions about retirement.

The questions you ask will depend on the life stage of the people you’re chatting with.

Questions for people who haven’t yet retired

Retirement is usually on the radar for most people in their 50s and early 60s who are still working. Chances are good they’ve been thinking a lot about their own retirement.

You can start with this question: At what age do you want to retire?

If you pose this question to a group, you’ll most likely see a wide range of answers.

Then follow up with this question: Why do you want to retire at that age?

As with the first question, chances are good you’ll hear a wide range of answers. By hearing how others think about retirement, you’ll gain insights into your own retirement planning, especially if they have insights and reasons that you hadn’t yet thought about. Also, it can help you focus on the important questions, rather than just drifting along making assumptions that might not be realistic.

Finally, be sure to ask these questions: How do you define retirement? Do you want to stop working altogether, or do you want to work part time for a while?

With retirements lasting 20 to 30 years or more, the concept of retirement is evolving, and it can include working in some fashion during the early part of your retirement years. The challenge can be finding work that brings in needed money but still allows you to enjoy life. But you might gain ideas about the type of work you could do by hearing others’ answers to these last questions.

Questions for retirees

If you ask the right questions, you can gain hard-won wisdom from relatives and friends who’ve already retired. I’ve found that most retirees are glad to talk to people about their retirement if sharing their experience will help others, especially their loved ones.

Lead off with this question: What do you like about your retirement?

Often, you’ll hear they like the freedom of time to pursue activities, travel, reconnect with family and friends, and take care of themselves. But you might also hear answers that surprise you and could trigger your own reflections. For example, some retirees like “feeling time rich” and now enjoy spending time taking courses at a local community college, playing a musical instrument or joining a band, or learning to dance.

Next, ask this: What don’t you like about your retirement?

Common answers often include missing their work friends and the money they made during their working years. Some people also felt stimulated by the challenges they faced on the job. Hearing this can help you think about how you might address these issues during your retirement.

Follow up with this question: What do you regret and wish you’d done differently in regards to your retirement?

Most retirees learned the hard way from mistakes they made with their retirement planning. They might have retired too early, too late, or made poor choices with their finances. If you’re like many people, the anticipation of future regret can motivate you to develop plans that will help you avoid making future mistakes.

Finally, be sure to ask this: What advice do you have for people who haven’t yet retired?

Many retirees are glad to pass along their advice from their lived experience. The challenge might be that they talk so long that you want to move on to other topics!

Most likely you’ll hear that your relatives and friends are also still wrestling with these important life questions, and talking about them can bring you closer and help you make the most of your holidays!

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