Let’s face it: retirement can be a roller coaster—exciting one minute, daunting the next.
I’m the first to admit I don’t have all the answers, but over the years—both as an educator and now as a retiree—I’ve noticed how mindset can shape everything from our finances to our sense of purpose.
As baby boomers, we’re often told that “success” in retirement means a cushy bank account and plenty of time to travel.
But if I’ve learned anything, it’s that real fulfillment goes deeper than a budget or a bucket list. It’s about what we choose to do with the freedom that retirement grants us, and it’s about the everyday decisions that can either lead us to thrive or leave us struggling for direction.
In my own transition from a bustling career in education to a quieter (but still surprisingly busy) retired life, I’ve come to see that our generation—often labeled as traditionalists in many ways—is also at the forefront of shifting the narrative on what “successful aging” looks like.
We’re living longer, staying active, and redefining what it means to be “done” with our professional lives. In the spirit of that ongoing shift, here are seven key decisions I believe determine whether we flourish or flounder after we retire.
I’ve also tied in a few lessons I picked up from both my teaching days and my conversations with fellow retirees.
My hope is that one or two of these points resonates with you as you navigate your own retirement journey.
1. Prioritizing meaning over money
When you’ve spent decades working, it’s natural to measure success by a paycheck.
However, retirement can highlight just how limiting that view is. Finances do matter—you need to feel secure—but if you’re only focused on your bank balance, you might overlook the deeper sense of purpose that makes each day worth waking up for.
From what I’ve observed (and personally experienced), folks who find ways to serve others or immerse themselves in fulfilling hobbies tend to stay more enthusiastic about life after retiring.
Whether it’s volunteering at a local literacy program or babysitting the grandkids, focusing on activities that give you a sense of meaning can create a richer, more satisfying chapter in your life.
Winston Churchill once famously said, “We make a living by what we get, but we make a life by what we give.” I can’t help but think that this sentiment rings especially true once we leave the workforce.
2. Staying socially active and connected
It’s incredibly easy to drift into solitude when you don’t have a workplace that keeps you engaged with peers every day.
For me, I sometimes had to force myself out of the house during those first few months of retirement, because I didn’t have that built-in community of fellow teachers or students.
But I quickly realized that isolation can chip away at your sense of purpose and happiness.
Psychologists have long confirmed that maintaining social bonds is crucial for emotional and cognitive health.
Even the simplest connections—like meeting a friend for coffee or attending a local book club—can uplift your mood and broaden your perspectives.
I’ve started going to a weekly potluck gathering with some neighbors who also happen to be retirees, and it’s brought a lively new energy into my routine.
I’ve met so many wonderful people who remind me daily that success isn’t about withdrawing from the world; it’s about staying open to new friendships and experiences.
3. Being open to continuous learning
When I left teaching high school English, I vowed never to let my curiosity fade.
After all, it was that curiosity that first drew me into education in my early twenties. One of the biggest transitions I see among my fellow retirees is deciding whether to keep learning or let that part of life drift away.
We baby boomers might not be in a formal classroom anymore, but we’re taking up new languages, enrolling in painting courses, or dabbling in online tutorials about everything from yoga to photography.
Studies suggest that lifelong learning helps keep our brains sharp and may even ward off memory-related issues.
Bill Gates once said, “I believe that if you show people the problems and you show them the solutions, they will be moved to act.”
In retirement, I find that being aware of where I still have room to grow—whether in technology or cooking—sparks my desire to act, learn, and engage. That mentality is a game-changer for anyone wondering how to keep life feeling fresh after sixty.
4. Embracing a flexible mindset
Have you ever noticed that the older we get, the easier it is to think, “I’ve seen it all,” or “I know what works for me”?
But the truth is, a rigid mindset can limit our potential during retirement.
If we cling to the idea that we should rest on our laurels and do things “the way they’ve always been done,” we risk closing ourselves off to the joys and opportunities that come with change.
Being flexible might mean learning to navigate new technology (which can feel daunting) or adjusting your daily routines in ways that keep you both physically and mentally engaged.
I’ve had to adapt my schedule quite a bit now that I volunteer at a community literacy program. At first, the thought of committing an extra five to six hours a week felt overwhelming.
But once I opened my mind to the value of that experience—helping adults improve their reading skills and feeling useful in a new capacity—I realized how rewarding change can be.
There’s a reason Brene Brown points out in her works that vulnerability and openness often lead us toward new growth opportunities.
5. Taking charge of your health
In our working years, we often put health on the back burner.
There are meetings to attend, deadlines to meet, kids to raise—so cooking a balanced meal or making time to exercise can feel like a luxury. Now, in retirement, the health equation changes.
We’re more aware that our bodies need attention, and we typically have more control over our schedules.
Deciding how much effort to put into your well-being is a major fork in the road, potentially the difference between thriving and declining.
For me, this means morning walks with my rescue dog, Tilly, and experimenting with healthy recipes on the weekends when my grandchildren come over.
I’ve found that these small choices add up to a stronger sense of vitality—both physically and mentally.
Albert Einstein famously said, “Life is like riding a bicycle. To keep your balance, you must keep moving.”
And that “moving” can be literal—by keeping active and maintaining our health—or figurative, by continually progressing toward better self-care.
6. Nurturing intergenerational relationships
One major shift I’ve seen among my peer group is the increasing value we place on relationships with younger generations.
Many of us are grandparents or mentors to younger people, and this gives us a wonderful chance to stay connected to what’s going on in the world right now.
Whether it’s texting with grandkids or asking them about their TikTok dances (they may roll their eyes, but they secretly love that we’re interested!), staying in tune with younger folks can help us better understand today’s cultural and technological shifts.
When I was still teaching, I learned more than I ever could have imagined from my high school students.
They taught me about new music, social issues, and technology trends. Now, as a retiree, nurturing those cross-generational bonds can be just as rewarding—but it’s not something that happens automatically.
You have to make the decision to invest time and emotional energy into younger people. Not only does it bridge the so-called generation gap, but it also helps keep us young at heart.
I mentioned in a previous post on DMNews how volunteering at a local high school’s drama club reignited my own creative spark. That spark, in turn, has brought more joy to my day-to-day life.
7. Finding a deeper sense of purpose
Finally but perhaps most importantly, retirement can feel aimless unless we find a guiding sense of purpose.
When the nine-to-five job is gone, it’s easy to wake up feeling unsure of what the day is meant for.
That’s where this decision comes in: Will you actively seek out a new purpose—be it family, community, personal passions, or even faith—or will you drift from one day to the next?
I’ve known people who pour themselves into charity work because they believe making a difference in their communities matters more than ever at this stage of life.
Others I know have taken up artistic pursuits—like learning to paint or returning to a childhood love of writing music—that add a creative spark to their existence.
In my case, blogging about personal development and relationships helps me stay intellectually engaged, and I still relish the thrill of helping others discover new insights, much like I did when I was a teacher.
Psychological studies suggest that when we attach ourselves to a cause or a passion, we boost our emotional well-being, our sense of belonging, and even our physical health.
It’s about feeling part of something bigger than ourselves, a point Viktor Frankl emphasized in his seminal work on finding meaning in adversity. Of course, retirement isn’t necessarily an “adversity,” but the idea of seeking meaning during a time of transition holds true.
So, how do you see success evolving in your own life journey?
I’d love to hear what new purpose you’ve discovered—or how you’re planning to find one.
After all, as we baby boomers continue to rewrite the playbook on retirement, it’s never too late to start shaping your life on your own terms.
Let me know what you think, and remember: You have the freedom now to craft the most meaningful chapter of your life—make it count.
