The holidays are upon us, and with them come lively gatherings, hearty meals, and conversations that range from hilarious to downright awkward.
But here’s an idea to make this season extra meaningful: instead of tiptoeing around politics or enduring awkward silences, why not turn the conversation toward something insightful?
Ask your retired friends and relatives about their life in retirement. It’s a win-win—you’ll steer the chat toward valuable wisdom, and they’ll feel appreciated for sharing the lessons they’ve learned.
Retirement is one of life’s biggest transitions, and hearing firsthand accounts can give you a clearer perspective as you plan for your own future.
Many retirees emphasize that close relationships are key to a fulfilling and happy retirement. By opening up these conversations, you’ll strengthen your bond with loved ones, and one day, you might even pass on the wisdom you gather to help the next generation.
What do you enjoy most about retirement?
This thoughtful question is the perfect icebreaker, and the answers might surprise you. Some retirees will say they love the simple joys: sleeping in, no more daily commutes, or the freedom to ditch the suit and tie forever.
Others might share deeper insights, like the joy of pursuing hobbies they never had time for, reconnecting with family, or finally prioritising their health.
You might even discover unexpected passions—like a relative who’s volunteering for a cause they care about, learning an instrument, or diving into ballroom dancing. These stories can be inspiring and might spark ideas for what you’d love to do with your own post-work life.
What’s been the most challenging part of retirement?
This question can lead to some honest and thought-provoking answers. Common challenges include missing the camaraderie of coworkers, the mental stimulation of problem-solving, or the steady paycheck from work.
If these resonate with you, it’s worth considering a “semi-retirement” someday—working part-time or freelancing can give you a sense of purpose, social engagement, and extra income while still allowing for plenty of freedom.
If you could go back, what would you do differently?
Regret is a powerful teacher, and retirees often have plenty of insights to share. Some wish they had saved more aggressively or started planning for retirement earlier. Others might say they retired too soon or waited too long.
Hearing their reflections can help you think critically about your own retirement timeline and savings strategies. It’s like getting a cheat sheet for one of life’s biggest decisions.
What’s something you’re struggling with right now?
This question often uncovers the realities of retirement that people don’t talk about enough. Maybe they stayed in a big family home for too long, and now it’s expensive to maintain and isolating to live in. Or perhaps they’re facing health challenges that they wish they’d prepared for earlier.
For widowed retirees, loneliness can also be a major challenge. These honest insights can remind you to prioritize your health, think strategically about where you’ll live, and plan for life’s inevitable transitions.
What advice do you have for me, based on what you know about me?
Here’s where things get personal. Your retired friends and family know you well, and their advice can often hit home in ways that generic tips never could. They might share tailored guidance about saving, planning, or even navigating relationships as you approach your golden years.
You might be wondering: Why are these conversations worth it? Retirees are like walking encyclopedias of lived experience, and the holidays are the perfect time to tap into that wealth of knowledge.
Research shows that hearing stories from people similar to you can strongly influence your decisions—and when it comes to retirement, those decisions can have a lasting impact on your happiness and security.
Beyond practical tips, these conversations can deepen your connection with loved ones. By asking thoughtful questions, you’re showing them that their experiences matter and that they’re still valued and respected. Plus, they’ll probably love the chance to share their stories—it’s a win-win!
But fair warning: once the floodgates of wisdom open, you might find yourself needing a backup topic to gently transition the conversation. After all, retirees have decades of life lessons to share, and they might not stop until dessert is served!
This year, skip the small talk and use holiday gatherings as an opportunity to reflect, learn, and plan for the future. Whether it’s advice on managing finances, building fulfilling routines, or preparing for life’s unexpected challenges, your retired loved ones have wisdom that could make all the difference in your own journey.
So, pour another cup of cocoa, settle into the couch, and start the conversation. You’ll walk away with more than just holiday memories—you’ll gain insights to guide you toward a more fulfilling retirement.
The writer is the CEO, Enwealth Financial Services
