We asked people aged 80 and older to share their biggest regrets. Their raw honesty reveals lessons about relationships, health, career, and more.
Read on to gain insights from their experiences, and I’ll share a few of my own regrets along the way.
Relationships and Connections
1. Words Left Unspoken
“I regret being too prideful to tell my aunt I loved her. She wasn’t easy to get along with, but her bright blue eyes still haunt me because I never said what I should have.” – Anonymous
2. Lost Connections
“I let some of the most incredible people drift out of my life. I didn’t appreciate their value until it was too late.” – Patricia Campbell
3. One-Sided Friendships
“We spent too long maintaining friendships where the effort wasn’t mutual. Once we let go of those relationships, we opened the door to meaningful connections with people who truly cared.” – Sarah Johnson
Personal Anecdote: I had a friend like this when I was younger. We would only see each other if I put in the effort to organize something, he would never ask me to hang out or check in.
One day, I decided to stop reaching out until he did first. He never did, and the friendship just died out.
Letting go of one-sided friendships like that was one of the best decisions I ever made.
4. Sibling Protector Regret
“I wish I had protected my younger sibling better from our dad’s abusive behavior. I was just a kid too, but I regret not doing more to shield them from harm.” – Thomas Green
Personal Anecdote: I grew up as the eldest sibling, and I know how heavy that responsibility can feel.
There were times I wish I’d spoken up for my younger brother in school when he was bullied. To this day, I regret not doing more to make sure he felt protected.
5. Standing Up for Myself
“I regret staying silent when I should’ve stood up to people who deserved to be put in their place. My parents said it wasn’t worth it, but they were wrong.” – Christopher Ramirez
6. Toxic Relationships
“I regret staying with people who used and mistreated me. I didn’t value myself enough to walk away sooner.” – Lauren Ward
7. Regretful Pressure
“I regret marrying my ex-wife and adopting two kids because she pressured me into it. I should’ve ended the relationship much earlier.” – Steven Harris
8. Lost Friendships
“I regret cutting ties with my best friend in school. He was kind and supportive, but I ignored him to fit in with the popular group. I regret it every day.” – Anonymous
Lesson:
Relationships are the heart of life, and regrets about connections often linger the longest.
Be intentional about who you let in, who you hold on to, and what you leave unsaid.
Missed Opportunities
9. Missed Rockstar Moment
“In 1981, I had the chance to hook up with Keith Richards during The Rolling Stones’ Tattoo You tour.
He was kind and charismatic, but I chickened out. I still think about it sometimes.” – Anonymous
10. Exchange Program Regret
“I regret not taking part in a foreign exchange program. It would’ve been an amazing experience.” – Charles Evans
Personal Anecdote: When I was in high school, there was an exchange program to Japan, and I hesitated because I thought I’d miss my family and friends too much.
I’ve always loved Japanese culture and still wonder what life would’ve been like if I’d taken the chance.
11. Missed Navy Opportunity
“I regret not joining the Navy. My sister joined the Air Force, retired with a great pension, and here I am still working away.” – Robert Wilson
12. Unasked Family Stories
“I regret not asking my parents more about their lives before they passed away. It’s something I’ll never have the chance to do again.” – Elizabeth Bell
13. Selling the Camper
“I wish I hadn’t sold the camper. I could’ve taken my family on more trips to experience the beauty of nature.” – Anonymous
14. Selling the Condo
“I should’ve kept that condo. It would be worth a lot now, or I could’ve given it to one of my kids.” – Donald Taylor
15. Missed Travel
“I wish I had traveled more when I was younger and been more selective about where I chose to live. Settling for less has been a mistake.” – Samantha Young
16. Photo Mishap
“One of my regrets is not properly loading my camera film during a snowy camping trip with my wife. We took beautiful photos, but the film came back blank.” – Michael Turner
Personal Anecdote: I had a similar experience during a road trip through the mountains. I didn’t check my camera settings, and every photo came out blurry.
I still remember the views, but I wish I’d been more careful.
Lesson:
Missed opportunities often result from hesitation or lack of foresight. Seize the moment when it comes to pursuing dreams, building memories, or preserving stories.
Career and Financial Planning
18. Career Indecision
“I regret not committing to one career path or trade. I kept hopping around and never became a master at anything.” – Andrew Nelson
Personal Anecdote: Early in my career, I switched jobs frequently because I couldn’t decide what I wanted.
Looking back, I wish I’d picked one direction and focused on becoming an expert. It’s something I’ve tried to correct in later years.
19. Settling for Safe Jobs
“I stayed in positions I was overqualified for instead of taking risks on better opportunities. I wish I’d been braver.” – Amanda Cooper
20. Delayed Retirement Savings
“I didn’t start saving for retirement early enough. Every year, I told myself I’d make up for it the next year, but I did that for 30 years.
Now, I’ll never recover the lost time and money.” – Daniel Thomas
Personal Anecdote: I remember the first time someone told me about compound interest in my 20s, but I brushed it off.
It wasn’t until much later that I realized how much money I’d left on the table by not starting earlier.
Health and Wellness
24. Smoking’s Price
“I started smoking because I thought it made me look cool and tough. After being diagnosed with stage 1 kidney cancer at 56, I finally quit. I wish I’d never started.” – Paul Davis
25. Health and Hearing Neglect
“I wish I’d worn hearing protection to avoid the tinnitus I have now. If I’d known how to protect my knees, I’d have avoided the damage I deal with today.” – William Walker
Personal Anecdote: When I was younger, I used to go to loud concerts without ear protection, thinking it was no big deal.
Now, I have mild tinnitus, and I constantly wish I’d been smarter about protecting my hearing.
26. Late Healthy Living
“I wish I’d started eating healthier and exercising much earlier in life. It would’ve made a big difference.” – Jessica Mitchell
27. Drug Abuse Consequences
“I regret abusing Adderall to handle work stress. It cost me seven years of my life, and now I’m struggling to rebuild. I’ll never own a home and will probably work until I can’t anymore.” – Matthew Morris
Personal Anecdote: I didn’t abuse drugs, but I relied heavily on caffeine and junk food to get through long workdays in my 20s.
It eventually caught up to me, and making lifestyle changes later was much harder than if I’d started earlier.
Lesson:
Your health is an investment. The earlier you prioritize it, the less you’ll regret later.
Family and Parenting
28. Only Child Regrets
“I wish I’d given my only child a sibling. My own siblings have been a source of comfort, and it pains me to think she’ll be without close family when I’m gone.” – Karen Mitchell
29. Fewer Children
“My husband and I wish we’d had more children. Parenting has been such a joy, and we regret not having at least one or two more.” – Kimberly Rodriguez
Personal Anecdote: I don’t have children, but I’ve often thought about what my family dynamics might look like later in life.
Seeing older friends who have big families has made me think about how those choices shape our later years.
30. Painful Selfishness
“The regrets that haunt me the most are from times I was selfish and hurt people I loved. I wish I could undo the pain I caused them.” – David King
31. Florida Mistake
“Moving to Florida has become a big regret for me. There’s plenty more I could list, but at the end of the day, I lived my life.” – Matthew Hall
Personal Anecdote: I once made a hasty decision to move to a new city for a job, only to realize it wasn’t the right fit for me.
I stuck it out for two years, but I often wonder how things would’ve turned out if I’d been more thoughtful about the move.
Lesson:
Parenting and family life bring profound joys and challenges. These regrets show the importance of living with empathy and foresight.
Missed Experiences and Risks
32. Fear of Risks
“I regret not being bold enough to move or take career risks. I always found reasons to hold myself back.” – Nathan Kelly
Personal Anecdote: I once had an opportunity to join a start-up early in its journey but declined because I was afraid of leaving the stability of my corporate job.
That company ended up becoming very successful, and I sometimes think about what might have been.
33. Missed Travel
“I wish I had traveled more when I was younger and been more selective about where I chose to live. Settling for less has been a mistake.” – Samantha Young
34. Exchange Program Regret
“I regret not taking part in a foreign exchange program. It would’ve been an amazing experience.” – Charles Evans
35. Delayed Happiness
“I wish I’d moved to the city I love much sooner instead of waiting. It’s one of the best decisions I ever made, but I wish I’d done it earlier.” – Michael Brown
Personal Anecdote: I used to dream of moving abroad in my 20s, but I let fear and excuses hold me back.
Now, while I love my life, I always wonder how that experience could have shaped me.
Lesson:
Missed experiences often stem from fear or hesitation. Take the leap when you can—you may not get a second chance.
Conclusion
Regrets are a natural part of life, but they don’t have to define us.
Each of the 35 stories shared here, along with my own experiences, underscores the importance of being brave, thoughtful, and intentional in how we live.
Whether it’s nurturing relationships, taking risks, prioritizing health, or planning for the future, the message is clear: live with as few “what-ifs” as possible.