• Mar 6, 2025 • Read in ~16 mins
— By Dr. Sandip Roy.
“Life is made up of experiences, decisions, and paths, taken … and not taken.”
It’s a lie to say you “regret nothing” or “wouldn’t do anything differently” if you could live over again.
To live is to accumulate at least some regrets. It’s impossible to live a life without any mistakes and no regrets.
Here’s the thing: As we age, the regrets haunt us more than the pleasant memories. Until all memories start to fade…
So, before that time comes, find out the things you’d regret the most. And know how to fix them.
By the way, do you know why a life of “No Regrets” is such a bad idea?
10 Things You’ll Regret When You Are Too Old
Regret is more than a simple appraisal or judgment; it is typically loaded with feeling and therefore qualifies as a true emotion. But you don’t want too much of this emotion.
1. Playing It Too Safe When You Had the Chance
When you’re older, you might look back and regret not taking risks in life. What often keeps you tied to the safe and familiar is fear—of failure, rejection, or uncertainty.
Soon after a regrettable action, you feel strongly upset, thinking “what might have been.” But as time passes, these intense feelings fade. What troubles you most then are the chances you never took.
Missed opportunities—the career leap you didn’t take, a talent you never went after, or a relationship you shied away from—begin to haunt you in later years.
This is the curse of counterfactual thinking: you mentally simulate events that could have transpired but never did (Kahneman & Tversky, 1981; Xie & Beck, 2022).
These regrets of inaction, or “what I didn’t do,” sting more deeply and persist longer. In other words, the regret of your missed opportunities outlives the regret of your ill-chosen actions.
Why? Because failures at least offer closure and learning, while the undone leaves you wondering, “what if I had done it?”
Here are two ways to sidestep this regret before it’s too late:
i. Face Your Fear Head-On.
Don’t let fear write your story. Start by naming what scares you—then take one small, brave step toward it.
Each move forward chips away at the paralysis and builds a reservoir of courage. Celebrate those wins, however modest, to rewire your brain for action over avoidance.
ii. Risk Smart, Not Reckless.
Boldness doesn’t mean betting it all blindly. Take calculated risks that align with what matters to you—do your homework, weigh the odds, and act.
See missteps not as dead ends, but as data for your next move. A life with a few stumbles beats a life left unlived.
2. Leaving Your Passions on the Shelf
Did you know that women have more regrets than men?
- Women have to make trade-offs between career and family life more than men, that later on in life, evoke regret (Stewart & VandeWater, 1999).
- Two-thirds of their women had educational and/or career regrets (Landman and Manis, 1992).
When you’re too old to turn back, you might regret not chasing what lit you up inside.
Life’s daily grind—relationships, routines, expectations—can bury our dreams under “someday.” Too many of us wacth that “someday” gobble up our potentials and passions.
Fear—of the unknown, judgment, or failure—keeps us stuck, trading joy for safety.
This stings later in life. Unfulfilled potential haunts us more than external failures, because it’s a betrayal of our own calling (Gilovich & Medvec, 1995).
But here’s the rub: when you’re old, you won’t care about the excuses. You’ll feel the weight of a life half-lived, wondering why you didn’t at least try.
Here are two ways to keep this regret at bay:
i. Pinpoint What Sets You Ablaze.
You can’t chase what you don’t name. Dig deep: What makes your heart race? What could you lose yourself in for hours?
Reflect, journal, or even talk it out with someone wise—then list it. This isn’t about mastery yet; it’s about clarity. Knowing your passion is the spark; the skills can follow. Passions aren’t just hobbies—they let you find a meaning to your existence.
ii. Carve Out Time Like It’s Sacred.
Courage isn’t optional—act on what you’ve found. Block off time weekly, not just once, to dive into what you love.
Paint, write, tinker, explore—whatever it is, treat it like a non-negotiable meeting with yourself. Consistency turns a flicker of interest into a flame that fuels you for the long haul.
3. Letting Your Health Slip Through the Cracks
When you’re old, you greatest regret might be treating your health like an afterthought.
In chasing careers, wealth, or daily life demands, too many of us sideline our physical and mental well-being—only to pay the price later.
Regret over neglected health isn’t just about creaky joints or a diagnosis; it’s the gnawing realization that you could’ve lived more fully if you’d cared for yourself sooner.
Regret ranking studies show that the top six biggest regrets in life are (in descending order) around: education, career, romance, parenting, the self, and leisure (Roese & Summerville, 2005).
Of those, regrets tied to self-neglect hit the hardest because they’re deeply personal—we can’t blame anyone else.
As youth fades, those skipped workouts, junk food binges, or ignored stress signals add up to a life diminished.
Of course, aging amplifies the cost: chronic illness, fatigue, or a mind clouded by undefinable stress steal time you can’t reclaim.
Here are two ways to dodge this one before it’s too late:
i. Put Your Well-Being First.
Stop treating health like a luxury you’ll get to later. Fuel yourself with real food—think colorful plates, not processed shortcuts.
- See the healthiest foods you can eat for your brain firness.
Move your body daily, even if it’s just a walk. Sleep like it’s your job. And don’t skimp on your mind—carve out time for calm (meditation works wonders) or talk to a pro if the weight feels heavy.
These aren’t extras; they’re the non-negotiables for a life you won’t regret. Small, steady investments in your body and mind now can rewrite that future regret.
ii. Build Health Into Your Body.
Big changes start small. Swap one soda for water, take the stairs, or breathe deeply for five minutes a day—then stick with it.
Habits grow from consistency, not heroics. Over time, these quiet choices stack up, turning a body you once took for granted into one that carries you strong into old age.
4. Keeping Your Feelings Locked Inside
When you are too old to rewind, all the words you never said come back to haunt you.
Love left undeclared, gratitude unspoken, or frustrations swallowed—unexpressed emotions can fester into a quiet torment later in life.
We mourn the chances we didn’t take to connect with those we easily could have. This regret revolves around, “what is the most I could have lost if I asked him/her out?” In the end, it’s the unsaid that echoes loudest.
Aged, you’ll wish you’d risked the awkward moment. It could have given your clarity or closeness.
Here are two ways to avoid this regret before it settles in:
i. Master the Art of Openness.
Say what’s real—honestly, kindly, and without a script. Share your thoughts, listen intently to theirs, and let your face match your words.
It’s about creating a space of psychological safety and unrisked vulnerability. Misunderstandings shrink, bonds deepen, and you’ll sidestep the “if only I’d told them” sting.
Feelings aren’t meant to be caged—let them out and see if they can weave a richer life.
ii. Let Your Truth Out, Raw and Real.
Don’t hide behind a mask—speak your heart as it is. Whether it’s a quiet “I love you,” a firm “this isn’t working,” or a simple “thank you,” mean it.
You don’t need to shout or sugarcoat—just be you, unfiltered but respectful. Authenticity (with kindness) cuts through noise, builds trust, and leaves no room for what-ifs.
5. Letting Relationships Fade Away
When you’re too old to mend what’s broken, you might regret letting the people who mattered slip through your fingers.
Petty spats, missed calls, or just life’s relentless pace can erode ties with friends, family, or partners—leaving you with a hollow ache later on.
Regret over neglected relationships cuts deep because humans are wired for connection; studies show that loneliness in old age often stems from bonds we didn’t nurture (Cacioppo & Patrick, 2008).
Work and to-dos can crowd out what truly counts, but when the dust settles, it’s the faces—not the deadlines—you’ll miss.
In your final chapters, you’ll see it clear: joy lives in the laughter, the shared silences, the messy love of others. Don’t let it drift away.
Here are two ways to keep this regret at bay:
i. Show Up for Who Matters.
Time won’t wait—carve it out. Book that coffee date, call your sibling, plan a messy, loud family dinner.
It’s not about grand gestures; it’s about steady presence. Pour energy into the people who light up your world—they’re worth every minute.
ii. Talk Like It Counts.
Relationships thrive on real talk. Listen—really listen—to what they’re saying, not just what you want to hear.
Share your heart, too, with kindness and guts. Understanding their side doesn’t mean losing yours; it’s the glue that keeps you close.
6. Walking Someone Else’s Road
When you’re too old to start over, you might regret not forging your own path.
It’s tempting to bend to the script—parents’ hopes, society’s checklist, a friend’s nudge—and wake up decades later in a life that’s not yours.
Regret over conformity bites hard because it’s a quiet theft of self; research shows we grieve the roads we didn’t take when they aligned with our core (Gilovich & Medvec, 1995).
Expectations can feel like guardrails, but they’re often chains, pulling you from the dreams that hum in your gut.
Here are two ways to dodge this regret:
i. Name Your Own North Star.
Success isn’t borrowed—craft it yourself. What fires you up? What values anchor you? Sit with those questions, then write your own rules.
It’s your life—don’t let someone else hold the pen. Don’t wait to regret why you didn’t listen to that inner voice. Your path was always there, ake the first step.
ii. Stand Firm in Your Truth.
Live your answers, even when it’s messy or unpopular. Say no to what doesn’t fit, yes to what does—trust your compass.
The crowd might sway, but your path is yours alone, and it’s the one that’ll carry you home.
7. Living Your Life As Others Expect You To
When you’re too old to reshape the clay, you might regret shaping yopur life to fit someone else’s frame.
It’s not just about chasing dreams—sometimes it’s about who you even are. Too many of us mold ourselves to fit family traditions, cultural scripts, or a neighbor’s nod, only to realize too late we’ve lost our own outline.
Regret here isn’t loud; it’s a slow burn, a dawning sense that you’ve worn a mask so long it’s fused to your face. Conformity might feel safe, but it’s a thief of your truest self.
When we run into emotions or behaviors that don’t match how we see ourselves, it can feel threatening. This can lower our self-esteem or make us feel more negative. To protect ourselves, we often use various defense mechanisms (Kernis & Goldman, 2006).
People-pleasing is a defensive mechanism. It serves to avoid conflict, criticism, or rejection.
Here are two ways to sidestep this regret of living the life you didn’t dare to claim:
i. Anchor to What’s Yours.
Look inside—what values hum at your core? What desires keep knocking, even if they’re wild or quiet? Write them down, then chase one.
Set a date—a hike, a class, a bold no—and do it. Each step is a brick in a life that’s yours, not a borrowed shell. Let past compromises teach you, not trap you.
ii. Quit the Pleasing Game.
Stop bending till you break. Saying yes to everyone else often means no to yourself—and that’s a recipe for a hollow end.
Practice a polite, firm “not for me” when the ask doesn’t fit. Your life isn’t a favor to hand out; it’s yours to live, unapologetically.
ii. Stop People Pleasing
Stop people-pleasing — it’s defense mechanism to avoid rejection and seek approval from others.
When you are already trying to please others, making sure their needs and desires are met before your own, you live a life that you might regret.
8. Not Feeding Your Own Evolution
When you’re too old to stretch further, you might regret letting your growth potential go by.
It’s not just about skills missed—it’s the chance to be more. People lament the languages they didn’t learn, the crafts they didn’t try, the wisdom they didn’t seek.
Regret over this stings because growth isn’t optional—it’s oxygen for a vibrant life. Studies link continuous learning to a sense of purpose in later years (Schaefer & Lynch, 2018).
Opportunities to evolve knock often, but inertia or excuses slam the door. Don’t let that happen while you still have the time.
Here are two ways to dodge this regret:
i. Pledge to Keep Growing.
Make learning your heartbeat, no matter the calendar.
Commit to one new thing—a podcast series, a cooking technique, a random Wikipedia dive—and start today. Age doesn’t cap curiosity; it’s your fuel to stay alive, not just living.
ii. Fund Your Future Self.
Put money on it—earmark 3-5% of your income for growth. A class, a tool, a retreat—treat it like a non-negotiable investment. Spending on your mind now pays dividends in a richer, sharper you later.
9. Clinging to Old Wounds
When you’re too old to heal the rifts, you might regret not shedding the grudges that chained you.
The refusal to change yourself, to let go of past mistakes or bitterness, is what festers. Holding onto guilt or resentment—yours or theirs—builds a wall between the life you have and the peace you could’ve claimed.
Guilt can spark forgiveness. When people feel guilty, they are more likely to forgive others (Jordan & Flynn, 2015). This is especially true when people felt a connection with the person who did the wrong.
Interestingly, if someone felt guilty about hurting a friend, they also became more forgiving of other people who weren’t involved. So, our feelings of guilt can make us more forgiving in general.
Unprocessed hurt hardens, and so do you. Not adapting, not forgiving—it’s a regret that grows heavier with time.
In old age, you’ll wish you’d freed yourself sooner. The baggage isn’t worth it.
Here are two ways to avoid this regret:
i. Own Your Mess.
Stop dodging—face where you’ve stumbled.
Replay the moment: What could’ve shifted the outcome? Not to wallow, but to learn.
Admitting you were wrong isn’t weakness; it’s the first crack in the armor that’s holding you back.
ii. Reach Out and Release.
Forgiveness is easier if you redefine it as the act of ousting the offending person from your thoughts.
Plus, forgiving does not mean you are condoning them. Nor does it mean you have to declare it to them that you have forgiven them.
Simply, forgiveness is pushing out that toxic person who lives rent-free in your head.
10. Missing the Life Right in Front of You
Reclaim the moment before you’re old and staring back at it with regret in your soul.
Dwelling on yesterday’s shadows or losing your head over tomorrow’s what-ifs robs you of now—the only place life actually happens.
People look back and ache for the sunsets they didn’t see, the laughs they didn’t savor, because their minds were elsewhere.
Research ties mindfulness to lower regret and higher well-being; living present keeps you from stacking up “I wish I’d noticed” moments (Brown & Ryan, 2003). The past can’t be rewritten, the future’s a guess—but today’s yours, and losing it stings.
In old age, you’ll long for the now that you let blur. Don’t.
Here are two ways to hold onto this regret-free:
i. Root Yourself in Now.
Mindfulness isn’t fluff—it’s power. Pause: feel your breath, notice the air, hear the hum around you.
Start small—five minutes a day—and watch it pull you back to the present. It’s not about erasing thoughts; it’s about meeting this moment as it is, raw and real.
ii. Count the Good, Out Loud.
Gratitude anchors you here. Thank the barista, hug a friend and say why they matter, whisper a quiet “I’m lucky” to the sky.
Science backs it—gratitude boosts happiness by spotlighting what’s already yours (Emmons & McCullough, 2003). It’s not just feel-good; it’s a lens to see today clearly.
Being thankful makes a person happier, as science shows.
Final Words
We can’t live a life without regrets or mistakes. But we could reduce the chances of it.
One sentence advice: You should more frequently throw caution to the wind and act boldly more often.
√ Also Read: Why Is A Life of “No Regrets” Such A Bad Idea?
√ Please spread the word if you found this helpful.
