We often think of retirement as the end of one chapter in life, but from where I stand, it’s really the start of another.
After talking with plenty of people in their golden years, one recurring theme always comes up: regrets.
So many folks wish they’d done certain things sooner, but now that they’ve stepped off the 9-to-5 treadmill, they finally have the chance to make them happen.
If you’re not yet at retirement age—or even if you are—there’s so much wisdom we can take from these common regrets.
Why wait until later to do the things that make life richer and more meaningful? Let’s look at seven of the most frequent “I wish I’d done that earlier” reflections and how retirement can be the perfect time to cross them off the bucket list.
1. Traveling more (or differently)
I still remember a conversation I had with a former colleague who had just retired.
She was glowing with excitement about an upcoming trip to Peru, something she’d dreamed of doing for ages but never “had the time” (or so she believed).
It made me realize how many of us plan to see the world later—once the kids are grown, the mortgage is paid off, or our careers aren’t so demanding.
Here’s the kicker: life rarely slows down all on its own.
Sometimes, we just have to step off the hamster wheel and book that flight. Retirement offers a built-in pause button, giving people the freedom to chase after the travel goals they’ve postponed for decades.
But you don’t have to wait until retirement to pack a bag. Even if you have limited vacation days, try sneaking in short weekend trips or exploring your own city like a tourist.
Sometimes the best adventures are found just a few train stops away. And if you’re heading into retirement soon, take it as your chance to finally see those dream destinations—Peru, Bali, New Zealand—whatever’s on your list.
2. Prioritizing health and wellness
“As Stephen Covey once said, ‘Begin with the end in mind.’”
It’s a quote that often gets thrown around in productivity circles, but it’s also incredibly relevant for health. Many older adults admit they wish they had started caring for their bodies decades earlier.
From daily stretching to balanced diets to regular checkups—health and wellness are the foundations that support a more active, joyful retirement.
I’ve certainly seen family members put off exercising because they were “too busy.” By the time they did start, they had a laundry list of aches, pains, and doctor’s orders.
Of course, it’s never too late to turn things around, and many retirees do just that.
They join walking clubs, practice yoga, or start cooking nutrient-rich meals—finally having the space and time for daily healthy rituals.
If you’re pre-retirement (or even years away), consider that building small, sustainable habits now is so much easier than overhauling your routine later.
And if you’re in retirement, the same principle applies: focus on small wins. As a single mom, I squeeze in evening stretches after my son goes to bed, and it’s a ritual that keeps me grounded.
Trust me, your future self will thank you for the healthy steps you take today.
3. Pursuing a passion or creative hobby
I’ve lost count of the number of retirees who say something along the lines of, “I always wanted to write a novel, but never had the time.”
Whether it’s playing a musical instrument, painting watercolors, or learning to speak Italian, these creative sparks often get pushed to the back burner during our busiest decades.
I get it. Life can be hectic. When I was working in digital communications full-time, it felt like there was never a second to even think about personal hobbies.
But if there’s one thing I’ve learned, it’s that ignoring your passions is a direct route to frustration. Retirement finally gives many people the hours they need to pick up that guitar or start that novel.
If you happen to still be juggling a job and other commitments, you might think you don’t have time. But even setting aside 15 minutes a day can keep your creative flame alive.
You might have read my post on making time for personal projects (even when life is chaotic), and I stand by that approach—small, consistent efforts add up over time.
4. Building deeper relationships
As Sheryl Sandberg has said, ‘If you’re offered a seat on a rocket ship, don’t ask what seat! Just get on.’
That quote might seem more about career than relationships, but I think it also applies to those chances we get to connect with people throughout our lives.
Too many times, we miss out on forging lasting bonds because we’re busy chasing the next promotion or ticking off another work milestone.
I have a close friend who retired last year, and he confessed to having neglected many of his friendships during his peak career years. He assumed those connections would always be there.
Now, with more free time, he’s making amends—inviting old friends for coffee, calling distant relatives he barely spoke to, even planning weekend get-togethers.
It’s not just about avoiding loneliness; it’s about rediscovering the true joys of shared experiences.
Whether you’re on the brink of retirement or still climbing the career ladder, don’t wait until life slows down to cultivate meaningful relationships.
Send that text, plan that dinner, and be present with the people who matter. Work will come and go, but strong, nurturing bonds can sustain you through all of life’s seasons.
5. Learning new skills or going back to school
I’ve always believed that learning doesn’t have an expiration date. In fact, according to a study from the Journal of Adult Development, continuous learning in older adults can significantly improve cognitive function and overall life satisfaction.
Yet, one of the biggest regrets people express is not returning to school or taking courses that truly interested them—either for career advancement or just out of sheer curiosity.
Retirement offers a prime opportunity to explore those postponed educational dreams. I know someone who, at age 65, enrolled in a photography course.
It wasn’t about getting a degree; it was about finally honing a skill that sparked joy. It’s amazing how learning something new can fuel your sense of purpose, no matter the stage of life.
If you’re not retired, online courses and weekend workshops can be a flexible solution. You might be surprised how a single class can ignite a passion you never knew you had.
And if you are retired, think of lifelong learning as both a mental workout and an opportunity to connect with like-minded people.
It’s never too late to pick up a new language, learn to code, or deep dive into ancient history.
6. Spending quality time with family
We hear this regret so often: “I wish I’d spent more time with my kids when they were younger” or “I regret missing out on my grandkids’ special moments.”
As a single mom, I’m hyper-aware of the balance between work and family, and I still catch myself falling into the trap of “I’ll do it tomorrow” when it comes to planning a fun day out or having heart-to-heart chats.
Retirement can be a blessing in this regard. Grandparents often step into the role of mentor or caretaker, forging bonds they didn’t have time for when they were busy raising their own children.
But why wait for retirement to start making those connections? A 2019 study showed that shared family time—like having meals together—can boost emotional well-being and reduce stress for everyone involved.
Even small, consistent efforts make a huge difference. Take the time to have a weekly video call with a distant sibling or dedicate one evening a week for family dinner without phones.
These seemingly small acts build memories, and memories are what make our lives truly rich.
7. Volunteering or giving back
Perhaps most crucially, a lot of people regret not giving more to causes that resonate with them.
Whether it’s mentoring at a local community center, helping out at a food bank, or just checking in on neighbors, there’s something deeply fulfilling about being of service.
Robert Greene once noted, “The future belongs to those who learn more skills and combine them in creative ways.”
While he was referencing personal development, I interpret it as: if you have knowledge, time, or resources, using them to uplift your community can be a powerful experience.
During our working years, it’s easy to be consumed by the daily grind. Retirement, however, can free up the mental and physical space to dive into volunteer work wholeheartedly.
And if retirement is still a distant dot on your horizon, you can still give back in smaller ways—regular donations, occasional weekend volunteering, or sharing expertise with someone just starting out.
Not only does this make a difference to others, but it also adds depth and meaning to your own life.
Wrapping up
Time has a knack for flying by, doesn’t it? One day we’re starting our first job, the next we’re looking at retirement brochures and pondering how to spend our golden years.
Hearing the regrets of older folks has reminded me that we don’t have to wait until retirement to do the things that make life richer. In fact, many regrets can be minimized or avoided if we take action earlier.
Here at DM News, we believe that every stage of life brings its own opportunities.
Whether it’s traveling, nurturing relationships, or going after personal goals, it’s never too late—or too early—to start. Think about what you’d love to look back on and feel proud of.
Because the good news is that retirement may offer a second chance to chase those dreams, but you can also lay the groundwork for them right now.
If any of these seven points spoke to you, why not pick one and commit to making it happen?
Book that trip. Sign up for that class. Carve out an evening for family. Volunteer at a local shelter. These steps don’t need to be gigantic leaps; they can be small, manageable changes that build momentum over time.
After all, life is not just about earning a paycheck or checking off milestones. It’s also about the stories we create, the relationships we nurture, and the passions we let shape our days.
Retirement might give you a fresh opportunity to dive into those missed moments—but there’s nothing stopping you from starting today.
