Here I sit, in rural Vermont, at age 58—enjoying the “messy middle” and plotting my next act.
At 58, my father retired. I’m lucky enough to still have him and my mother in my life (they were quite young when they had me), but I find myself reflecting on the vast differences between his retirement journey and my current one – even though they’re less than 20 years apart.
For my father, retirement was a well-earned shift into relaxation. He had a pension, a recliner, and plans for cruises and leisure. It was a simpler time when life after work was about stepping away from the hustle. That was 20 years ago.
Now I’m the same age he was, but my reality couldn’t feel more different. Retirement doesn’t seem to mean “rest” anymore—it means reinvention. Instead of a recliner or the deck of a cruise ship, today’s icons of retirement are a stand-up desk, a laptop, and maybe a side hustle. People are blending work and leisure, taking on second acts that are as much about purpose as they are about necessity. We’re navigating a gig economy, remote work, and a world where financial security feels like a constant juggling act, not a destination.
My dad’s favorite device was—and still is—a TV remote. Mine? My computer and AI. (I’ll admit AI was instrumental in brainstorming and crafting the very words you’re now reading.)
I started as a cynic about AI, assuming “that was for the next generation to figure out.” But, with a growth mindset (thank you, Modern Elder Academy), I’ve grabbed this new tech by the horns, started dabbling (hello, flow state), and stuck with it (grit matters!).
What began as a quirky experiment—writing jokes for an open mic—has become a tool for thinking, creating, and discovering. Somewhere along the way, I realized AI wasn’t just for brainstorming punchlines but also for exploring ideas about what it means to live fully engaged at this stage of life.
It’s fascinating to think about how retirement might evolve over the next 20 years. By then, the tools we use today will feel as quaint as my dad’s pension paperwork. The icons of retirement just might include virtual reality headsets, always-on companions, and smart home hubs. Instead of a cruise ship, we might see retirees traveling the world through immersive VR. Retirement might not even be a clear “end” anymore—more of a flexible cycle of learning, working, and exploring passions, supported by technologies we can’t yet fully imagine.
These generational shifts in retirement mirror the shifts in my own thinking. Tools I was once skeptical of now expand the possibilities for creativity and connection. They challenge me to think differently about what’s next. If 20 years ago was about leisure and today is about reinvention, then 20 years from now might just be about transcendence—a chance to redefine not just what we do in retirement, but who we are.
It’s humbling to think about how different our journeys are, and yet how similar the goal remains: to live a life that feels full and meaningful.
What tools or shifts are shaping your future? How do you see retirement evolving in your lifetime? Let’s share notes—after all, every generation reinvents what comes next.
-David
David Weaver is a relentless experimenter and habit-hacker. His blog, WhatIGotRidOfToday, a personal experiment in minimalism, became a popular TEDx Talk. David has created “Outsiderism” – a coaching practice designed to scale creative output, by training and mentoring more people to be more creative on a daily basis. David’s most recent experiment is KnockKnockUnited.com, a worldwide way to combat loneliness and create conversations amongst strangers.