Let me ask you something: what comes to mind when you think about turning sixty? For many people, it’s retirement parties, and, while we don’t like to admit it, the slow fade into irrelevance.
But here’s the thing—that couldn’t be further from the truth.
I’ve been in my sixties for a while now, and I can tell you from experience that this decade can be one of the most rewarding of your life. The trick is making the right choices. Not the choices society expects you to make, but the ones that actually matter for your happiness and wellbeing.
After watching friends navigate this phase of life—some thriving, others struggling—I’ve noticed patterns. The people who seem genuinely content and energized in their sixties aren’t necessarily the ones with the biggest retirement accounts or the fanciest vacation homes. They’re the ones who’ve made five specific choices that set them up for success.
Today we dive into these.
1. Choosing to embrace what’s ahead instead of mourning what’s behind
Here’s something most people don’t expect: your sixties can actually make you happier than you were in your forties or fifties. Sounds crazy, right?
Well it’s backed by experts. As Dr. Laura Carstensen, director of the Stanford Center on Longevity, points out:
“Aging brings some rather remarkable improvements—increased knowledge, expertise—and emotional aspects of life improve. That’s right, older people are happy. They’re happier than middle-aged people, and younger people, certainly.”
But this requires you to live in the present. The people I know who are thriving in their sixties have stopped looking backward with regret and started looking forward with curiosity. They’re not mourning their lost youth; they’re celebrating their gained wisdom.
Sure, your body might not move the way it used to, and you probably can’t pull all-nighters like you could in your twenties. But you know what you’ve gained? Perspective. Patience. The ability to cut through nonsense and focus on what really matters.
I remember chatting with a neighbor recently who kept lamenting how she “used to be able to” do this or that. Meanwhile, another friend my age was excitedly telling me about the pottery class she’d just signed up for. Guess which one seemed more content?
The choice is yours: you can spend your sixties grieving your thirties, or you can spend them discovering what this new phase has to offer.
2. Choosing to stay connected rather than withdrawing
One of the biggest mistakes I see people make as they enter their sixties is pulling back from social connections.
Maybe they’re embarrassed about retirement, or they feel like they don’t have anything in common with younger people anymore. Whatever the reason, it’s a choice that can seriously impact their quality of life.
The World Health Organization puts it plainly:
“For older adults, social connection is particularly important to reduce risk factors such as social isolation and loneliness. At this stage of life, meaningful social activities can significantly improve positive mental health, life satisfaction and quality of life; they can also reduce depressive symptoms.”
Notice they said “meaningful” social activities—not just any social interaction will do. It’s about finding connections that matter to you.
Some of my most fulfilling relationships have developed in the past few years. There’s something liberating about friendships in your sixties. The pretense is gone. You’re not trying to impress anyone or climb any ladders. You can just be yourself.
Whether it’s joining a book club, volunteering at the local food bank, or simply making an effort to stay in touch with old friends, the key is to resist the urge to withdraw.
Your social circle might look different than it did in your thirties, but it can be just as rich—maybe even richer.
3. Choosing purpose over leisure
I can’t tell you I have all the answers, but one thing I’ve learned is that pure leisure gets old fast. The fantasy of endless golf games and afternoon naps might sound appealing when you’re stressed out at work, but the reality is often different.
The people who seem most alive in their sixties are the ones who’ve found something meaningful to do with their time.
This doesn’t mean you need to start a new career or solve world hunger. Your purpose might be mentoring young people in your former field, tending to a garden that feeds your neighbors, or writing letters to your grandchildren. The specific activity matters less than the sense that what you’re doing has meaning.
I’ve found my own sense of purpose through writing these pieces. It’s not about the money or recognition—it’s about feeling like I’m contributing something useful to the world. On my daily walks, I often think about the topics I want to explore next, and that sense of having something to look forward to, something to contribute, makes all the difference.
What gives your life meaning? If you can’t answer that question easily, it might be time to do some exploring.
4. Choosing growth over stagnation
Here’s a question: when was the last time you learned something completely new? Not just a new fact or piece of trivia, but a genuine new skill that challenged you?
Too many people treat their sixties like a time to coast on what they already know. But the most vibrant older adults I know are still growing, still learning, still pushing themselves in new directions.
Maybe it’s learning a new language, picking up an instrument, or diving deep into a subject that’s always fascinated you.
I think about Warren Buffett, who in his nineties is still reading voraciously and making investment decisions. Or consider the countless people who go back to school in their sixties(like I did!), start new hobbies, or tackle projects they never had time for when they were busy climbing the career ladder.
The choice to keep growing isn’t always comfortable. Learning new things means accepting that you’re a beginner again, which can feel awkward when you’re used to being competent. But that discomfort is worth it for the sense of vitality it brings.
5. Choosing optimism over resignation
This might be the most important choice of all. Your attitude toward aging itself can literally add years to your life.
Yale psychologist Becca Levy led a fascinating study that surveyed 660 older Ohioans about their attitudes toward aging. The results? Those with a more positive outlook went on to live, on average, 7.5 years longer.
Think about that for a moment. Your mindset about aging could be worth nearly a decade of additional life. That’s more than most medical interventions can promise.
But here’s the thing about choosing optimism—it’s not about denying reality or pretending everything is perfect. It’s about focusing on what’s possible rather than what’s lost, what you can control rather than what you can’t.
Not every day in your sixties will be sunshine and rainbows. You’ll face health challenges, you’ll lose people you care about, and yes, there will be limitations you didn’t have before. But you get to choose how you respond to those challenges.
Will you let them define your experience, or will you treat them as just one part of a much larger, more complex picture?
The bottom line
Your sixties don’t have to be about decline and retreat. They can be about discovery and growth. But that outcome isn’t automatic—it requires making conscious choices about how you want to live.
Will you embrace this new phase or resist it? Will you stay connected or withdraw? Will you find new purpose or just drift? Will you keep growing or coast on what you already know? And perhaps most importantly, will you approach these years with optimism or resignation?
The choice, as they say, is yours. What are you going to choose?
