Sometimes, I can’t help but notice how some folks in their 60s just seem to radiate contentment. It’s like they’ve discovered a secret formula for living a meaningful life—complete with fewer burdens of regret weighing them down.
But here’s the good news: we can all learn from their experiences. Sure, none of us can predict the future, and it’s inevitable that we’ll make a few mistakes along the way. However, there are certain pitfalls we can dodge to help secure more happiness in our later decades.
Let’s dive into the seven common regrets people often have—regrets that truly joyful 60-somethings manage to steer clear of.
1. They avoid regrets about neglecting health and wellness
I remember a time in my 20s when I absolutely neglected my fitness. Late-night pizzas, skipping workouts, and piling on stress from my corporate job seemed like the standard recipe for success. Then one day, I realized: success means nothing without a sound mind and body to enjoy it.
It’s the same realization the happiest folks in their 60s come to—preferably sooner than later. They don’t beat themselves up, and they don’t turn fitness into a source of obsession. But they do listen to their bodies, stay active, and practice a healthier lifestyle.
According to the American Heart Association, consistent exercise can decrease the risk of chronic diseases such as heart conditions and diabetes. If you’re juggling a busy work life (like me), think about scheduling walking meetings, cycling on weekends, or even a yoga class in the evening. Consider it an investment in your future self.
2. They don’t regret missing out on deep connections
I’ve lived in multiple countries and have met all sorts of people, from tech entrepreneurs to spiritual teachers. Through these experiences, I’ve seen firsthand how crucial genuine relationships are for a meaningful life.
One big regret I’ve noticed among those less satisfied in their 60s is letting important connections slip through the cracks. They might get stuck on the hamster wheel—focusing solely on ambition, finances, or personal goals—and forget to nurture meaningful friendships or family ties.
But the happiest older folks don’t let that happen. They schedule Zoom calls with old friends, travel for reunions, and make weekly dinners with family a priority.
As research by Harvard’s Study of Adult Development famously indicates, strong relationships correlate with better health and longer life.
It’s not just the time spent with loved ones; it’s the sense of belonging, emotional support, and shared memories. So consider blocking out some recurring “relationship time” on your calendar, just like you would an important work meeting. Because that’s exactly what it is.
3. They steer clear of regrets about playing it too safe
Do you ever wonder if you’re taking enough risks in life? This question always makes me think of a Tim Ferriss quote: “People will choose unhappiness over uncertainty.” It’s a powerful reminder that we often stay in comfortable, familiar zones, even when we suspect we could aim higher or take a more fulfilling path.
The 60-somethings who are truly content often talk about the leaps of faith they took earlier in life. It might have been starting a side hustle, relocating to a new city, launching a small business, or tackling a dream project they’d put on the back burner.
Sure, it can be intimidating. But the fear of the unknown is often overshadowed by regret if you never try.
At Small Biz Technology, we’ve heard from countless entrepreneurs who left behind safe corporate jobs to build their own enterprises. Even if they faced setbacks, they rarely regretted the pursuit of their ambition. After all, you learn tons from every misstep, whether you succeed or fail.
4. They don’t end up regretting unspoken truths
“Speak your mind, even if your voice shakes.” It’s a piece of advice I wish I could credit to one specific person, but it seems to be a wise sentiment shared by many. That said, it can be tough to follow through. Fear of conflict, fear of judgment—these can hold us back from asserting ourselves.
But bottling things up is a surefire way to accumulate regrets. I once had a falling out with a close friend and chose to stay silent for years. By the time I finally worked up the courage to address the issue, we’d both missed out on the chance to repair our bond sooner. We wasted that period of potential growth.
The happiest people I’ve observed in their 60s are those who don’t dwell on what could have been said. They approach tough conversations when necessary. They share their truths with compassion (not aggression).
As a result, they maintain healthier, more honest relationships—and skip that gnawing regret of never having said what really mattered.
5. They avoid regrets about not forgiving themselves and others
I’ve mentioned this in one of my previous posts, but it bears repeating: resentment is like carrying a suitcase full of bricks everywhere you go. And let’s face it, life is hectic enough without extra weight on our shoulders.
According to Brené Brown, “Holding onto resentment is like drinking poison and expecting the other person to die.” The truly joyful 60-somethings I’ve spoken with embrace forgiveness, both for themselves and for others.
When we talk about regrets, the theme of harboring grudges or holding onto guilt typically ranks near the top. Letting go may not be the easiest thing in the world, but it’s a game-changer.
That’s backed up by research. Psychologists have found that forgiveness is closely tied to lower stress levels and higher overall satisfaction.
It doesn’t mean forgetting a wrongdoing or making excuses for harmful behavior, but rather freeing yourself from the vicious cycle of anger and blame.
6. They dodge regrets about working too hard at the expense of everything else
Don’t get me wrong—I’m a big fan of hustle culture. I love new ventures, brainstorming ideas, launching them, and seeing how they grow. But there’s a fine line between being dedicated and turning into a workaholic who never takes time off.
I once fell deep into the “always be grinding” trap. I believed it was the only path to success, but guess what? It led to burnout and left me too frazzled to actually appreciate my achievements.
Over the years, I’ve realized that if you make work your entire identity, you risk losing out on the simple joys in life—time with friends, personal hobbies, or just the sweet pleasure of doing absolutely nothing.
Warren Buffett famously said, “Chains of habit are too light to be felt until they are too heavy to be broken.” In other words, the habit of overworking can sneak up on you until it’s incredibly hard to stop.
Happier seniors often talk about balancing meaningful work with personal time, and they say that’s key to their long-term well-being. There’s no one-size-fits-all formula, but building boundaries—like setting definitive “off” hours or taking real vacations—can help you avoid the regret of feeling like life passed you by.
7. They don’t regret overlooking lifelong learning
Ever meet someone in their 60s who’s still curious about everything? They’re reading new books, attending workshops, trying out the latest apps, or learning new languages. If so, you’ve probably noticed how lively and spirited they are.
On the flip side, a massive regret for many is not continuing to grow intellectually and creatively. Cal Newport, in his book Deep Work, talks about the profound benefits of challenging your mind.
He argues that deep, focused learning can enhance creativity and problem-solving skills—traits that keep us feeling young and engaged, no matter our age.
In my experience, there’s a huge psychological boost from being in “student mode.” Whenever I dive into a new book or skill—whether it’s something business-related, spiritual, or purely out of curiosity—I feel energized.
It’s almost like the “beginner’s mind” breathes new life into the daily grind, preventing that dreaded sense of stagnation. As we age, that thirst for knowledge can be a huge factor in maintaining a fulfilling life.
Final words
There’s no guaranteed way to enter your 60s totally free of regrets. Life is messy. Mistakes happen. But focusing on these seven areas—health, relationships, risk-taking, honest communication, forgiveness, balanced work habits, and continuous learning—can greatly minimize the “I wish I had” moments.
If you’re reading this as someone in your 20s, 30s, 40s, or 50s, consider it a friendly challenge to take a proactive approach. After all, it’s often the simple, everyday choices that add up to a life well-lived.
Whether it’s calling that friend you haven’t heard from in ages or carving out an hour each morning to read and exercise, take steps now that future you will be grateful for.
Because, let’s face it: The real joy in life is looking back and knowing you made the most of your time, without wondering how things might have turned out if only you’d taken that leap, said those words, or forgiven that grudge sooner.
Here’s to moving forward with fewer regrets—and a happier future in the making.
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