I’ll be the first to admit, turning sixty was a real eye-opener for me.
Back in my younger days, I thought “success” meant climbing the corporate ladder, buying a nice house in the suburbs, and one day retiring with a decent pension.
But let’s face it: times have changed. Many folks in my generation—especially those in the middle class—aren’t content to just rest on their laurels or spend the rest of their days on the golf course.
Dare I say, we’ve grown wiser, and our perspective on what it means to “make it” has evolved right along with us. Sure, we want a comfortable lifestyle, but it’s no longer all about the savings account or the property portfolio. Instead, a deeper, more holistic view of success is taking center stage.
Today, I talk about four distinct ways that some “middle class boomers” like me are reshaping the idea of success in their later years.
1. Realizing that enough is worth more than excess
When I was a kid, I remember older folks often saying, “You can never be too rich or too thin.” Sure, it was a joke but that really was an era of bigger is better—bigger houses, bigger cars, bigger bank balances.
But in recent years, there’s been a shift happening. Many of my contemporaries are waking up to the fact that continually chasing after more can be exhausting and, frankly, unfulfilling.
I’ve chatted with friends who’ve downsized from large suburban homes to cozier apartments simply because they realized they didn’t need all that extra space. Instead of storing a lifetime’s worth of knickknacks, they’re clearing the clutter and focusing on what truly adds value to their day-to-day lives.
It seems that paring down possessions is a step toward opening up new avenues for enjoyment—be that traveling, cooking, or even spending quality time with grandkids. In short, “enough” really can feel like more.
2. Viewing health and wellness as the ultimate wealth
For much of my working life, my health often took a back seat.
Long days at the office, too many late nights, and not enough exercise—sound familiar? It caught up with me eventually: I had lower back issues and a mild cholesterol scare that forced me to reevaluate my routine.
Now, I see a lot of folks like me making a similar pivot. We’re no longer ignoring those yearly check-ups, and many of us have become downright evangelists about daily walks or yoga classes. I’m the first to say I’m no fitness guru, but a brisk morning stroll has done wonders for my physical and mental well-being.
The truth is you can’t enjoy retirement—or any stage of life—if you’re constantly battling health problems. This renewed emphasis on wellness also extends to mental health. Meditation apps, journaling, and therapy are no longer taboo topics; rather, they’re just part of the toolkit for staying strong and vibrant.
Seeing friends pick up new activities—like tai chi in the park or water aerobics—reminds me that the quest for health doesn’t have to be a grind. It can be enjoyable, even liberating. When you feel good in your body, other aspects of success (like relationships and personal growth) become far more achievable.
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3. Finding joy in giving back
One of the most surprising (and rewarding) lessons I’ve learned over the past few years is that giving back isn’t just good for the world—it’s good for us, too.
For many boomers I know, the drive to leave a legacy or make a positive impact is becoming a core part of how we define success in our later years.
I know friends who’ve found deep fulfillment in becoming active in community organizations or tutoring kids after school. Others are channeling their professional expertise into consulting gigs for nonprofits or offering free services to those in need.
It’s not about making headlines or writing big checks—it’s about showing up, lending a hand, and realizing that our time and experience are incredibly valuable resources. As an added benefit, research has also shown that giving boosts our own happiness.
I think giving also helps combat the sense of invisibility or loss of relevance that can sometimes sneak up as we get older. When we contribute to something greater than ourselves, it reaffirms our place in the world. It reminds us that we still matter. In that way, giving becomes more than charity—it becomes purpose.
4. Embracing a “second act” mindset
In my parents’ generation, retirement usually meant the end of the road, at least when it came to work or ambition. Once you got that gold watch and said your goodbyes, the expectation was to slow down—maybe travel a little, play some golf, and then fade quietly into the background.
But I really think things are changing.
Many of us are starting to see retirement not as an end, but as a new beginning—a chance to finally pursue the things we didn’t have time for during the 9-to-5 grind.
I’ve got friends who’ve gone back to school, launched small businesses, or turned hobbies into part-time gigs. One friend of mine started a dog-walking service in her neighborhood, and now she’s got a waitlist and a full calendar. Another started making handmade pottery and sells her pieces online and at local markets.
And me? I went back to college. It wasn’t about chasing a diploma so much as chasing curiosity. I also started writing on this website, sharing reflections and connecting with others who are navigating this same chapter of life.
The idea that we can reinvent ourselves—even after sixty—is not just empowering; it’s downright exciting. We’re not limited by the career choices we made decades ago. In fact, with a lifetime of experience under our belts, we’re probably more equipped now than ever to try something new, meaningful, or creative.
Parting thoughts
I often say that this chapter of our lives feels like a chance to rewrite the script—and for many in my generation, that’s exactly what’s happening. We’re redefining success as something more balanced, purposeful, and deeply personal.
Maybe the biggest lesson I’ve learned is that there’s no one-size-fits-all path. One friend might find joy in volunteering at the local senior center, another might run a small crafts business, and another might be building the best possible bond with their grandchildren. All are valid, and all can embody success in its truest form.
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The question is, what does your next chapter look like? If you’ve been feeling the itch to try something new or to shift your priorities, I hope you’ll take that first step. In the end, success in later life isn’t about how much you’ve acquired—it’s about how much you’ve grown, how deeply you connect with others, and how meaningful your contributions feel to you.
So here’s to turning the page and redefining what matters most. Are you ready to see where your own story goes from here?
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