
A meaningful retirement isn’t one built on stockpiles of cash or multiples of millions.
We can find meaning and clear our path from the distractions that lead to regrets. Is there a formula for fulfilling a happy life?
How to Live Life With No Regrets
For those seeking an early exit from the office, there are some triggering events. An event that compels us to Google search terms like, “Help! I’m in Cubicle Hell!” or “Can I still retire early in my parent’s basement?”
My own personal “cubicle from hell” anecdote goes like this: I had just completed a two-year project that at times kept me from my family on weekends, evenings, and some holidays as well. It was around then that I realized, that even with a great manager and a job role that suited me well, this whole corporate scene was simply not sustainable for me.
Eventually, I stumbled across an insightful little study that pulled it all together for me, “The Top 5 Regrets of the Dying.” Sounds pretty grim, right? I figured, at 42 years old, I had a decent amount of runway to make some serious course adjustments. Boiled down, the list is as follows:
The Top Five Regrets of the Dying:
Regret #1: I wish I’d dared to live a life true to myself, not the life others expected of me
This one is elusive for me. I’m just not sure what anyone expected of me, honestly. So I struggle with this regret. I never had pressure growing up to take on a profession or a family business. I was sort of left to figure it out on my own, so long as I stayed out of trouble.
Did I want to become a lawyer or a doctor? Nah. But I was sure I’d land on something, hopefully by the time I finished college.
With over two decades of career experience in a career, I didn’t pine for, I have no regrets. And bonus, I’ve found that the early retirement mindset adds a clarity of purpose.
The first regret on the list may resonate most with women who are expected to be housewives, raise children, and run a household. We’ve come a long way as a society, and nowadays, this is a choice, rather than an expectation.
It’s a little mind-blowing, and ultimately sad, to consider how many more women from generations past might’ve contributed in all the fields historically dominated by men.
Regret #2: I wish I hadn’t worked so hard
Here’s a regret that brings me back to the fall of 2014. All of the hard work that went into that project-from-hell did yield some worthy rewards via bonuses, recognition, and a for-reals sense of accomplishment. And yet, with two newborns arriving at the outset of the project, I felt I’d missed out on too much time with them, and my wife.
With the list of regrets now etched in my brain, I’ve gone on to turn down multiple promotions at work. Sounds crazy, when you consider how raises and bonuses can help you achieve early retirement sooner.
But, I couldn’t risk taking on more when my family needed more of my presence. Thankfully, and somewhat unexpectedly, management respected my decisions.
Regret #3: I wish I’d dared to express my feelings
It can happen at home and at work. We hold back on showing gratitude. We hold back on letting people know how we feel about important things. Maybe a loved one isn’t treating us with respect? Maybe we have a crush on someone and we’re too afraid to approach him or her?
Taking risks is the lesson here. We need to be willing to breach any discomfort by saying “I love you”, or “I think you’re wonderful”. We need to be ready to say to our bosses and colleagues, “I value my time with my family, and working on weekends is not sustainable for me.”
Regret #4: I wish I had stayed in touch with my friends
This regret, in my opinion, is one we can all remedy with relative ease. Maybe it’s harder here in the states to maintain bonds of friendship because of our vast geography. Just about every close friend during childhood moved out of state after college. Thank goodness for Facebook?!?
Contrast our situation in the States with Blue Zones – communities where people live to 100+ with good health (and, I imagine, fewer regrets). Blue Zone societies are woven together by multi-generational families that stay intact.
Very few children move away from home. The village pub is where you’ll find 90-somethings mingling and joking with their contemporaries (i.e., the kids they grew up with)
We may not live in Blue Zones but we don’t have to live on the island of Sardinia to maintain strong bonds with friends. Give an old friend a call this Sunday night. Heck, write a letter, or even an email.
Texting and social media help us keep more connected, but it has to be done with intent. Simply sharing a funny video or photos is good, but you can’t beat picking up the phone and having a conversation.
Regret #5: I wish that I had let myself be happier
Straight from the article: “…they longed to laugh properly and have silliness in their life again.” Cling to this observation and let it sink in for a bit. Time has a wicked way of steering you into comfort zones and familiar patterns. Those patterns could be the culprit that’s keeping you from being happier.
As we age, we get set in our ways. And maybe that’s a coping mechanism? So it can become harder to embrace change, be a kid again, and embrace the absurd. Remember to flex those laughing muscles whenever you can. It’s healthy, and it seems, it helps you live a life of no regrets.

It means freeing your mind of worry so you can have a full life TODAY. We often forget to focus on the here and now while forging full steam towards that early retirement milestone…
Remember to slow down and make today count!
Call a friend (or two) whom you haven’t talked to in over a year. Have fun and be silly once in a while. Remember to laugh and to express how you feel to those you care about. And most important of all, be true to yourself!
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I resonate most with the regret about allowing yourself to be happy. I have this a lot just because of anxiety/depression, but even when everything in life is going great, I can still be miserable. If we think about how temporal our time is on Earth, I do think it would change the way we live our lives.
Thanks for opening up about that. I couldn’t agree more with your point on our finite time here. It really should make us pause and rethink things more than we tend to do.
Sadly the friends moving away is not unique to the US, I live in South Africa and so many old
friends have emigrated looking for greener pastures. If only they would all have gone to the SAME place, but no, now they are all over the world and impossible to visit in one trip!
I also think the comment around housewives is a double edged sword, because many women who would prefer to be housewives now no longer have that option due to financial pressures, and it’s no longer seen as the default.
That’s certainly true for some of my friends who hail from the Netherlands and India. Lucky for me, they wound up here in Minnesota. For those friends they grew up with, prepare to log some miles!
It’s a great point with respect to stay at home moms and dads. I suppose a middle ground is when one spouse can at least reduce to part time work. That’s what we’ve done and it seems to be alright.
I read the story you linked about the parents who lost their 8 year old son, it hits home with a 9 year old at our house. We had a time a few years back where my wife had a massive blood clot in her leg, and during her almost month long stay in the hospital it was a very real possibility that she could lose her leg, or even her life if one of the clots went to her lung or somewhere else. It really woke us up to the idea that while it’s important to plan ahead for the future, it’s also important to live for today as well – loving those around you, enjoying special times with family, and doing your best to live and love your best life now – not only in the future.
It’s funny though. If you’re not careful it’s easy to slip back into a routine again, and start taking things for granted again if you’re not careful. To brush things off that you should be doing today, because you’re “busy” or because you have a to do list that “has to get done”. The post is a helpful reminder to not take for granted all of the blessings that we have, and to make sure you let your loved ones know how much you care. Thanks for the reminder!
Thanks, Peter. Yes, that story really hit home for me too. I took stock since reading it, and had a much more engaged weekend with my family. Now to have the carry into each day forward… So important. Yet as you point out, all too easy to let slide.
Love that you walked through the five too regrets with your own thoughts. Makes me want to do the same…
Thanks, Angela. This was actually a re-write of a hastily put together post from my very sloppy beginnings on this blog. I feel a lot better about it now, especially with Amanda’s superior story in the feature.
So you are saying we should all own. Oscar Myer wiener-mobiles?
I can get on that trend. Would this be an odd form of FIRE, like Fat-FIRE?
Maybe Wiener-FIRE?
That story is heartbreaking. Life really is short.
I’m very fortunate to live the way I want. These days I have no regrets and I don’t have to meet other people’s expectations.
It sure is, Joe. Appreciate your thoughts on this – it is possible to avoid regrets, but not so easy to avoid tragedies. Owning your relationships is the best way, it seems, to mitigate the worst situations when and if they occur.
Thanks for sharing Amanda. That car crash sounds very scary. We definitely can’t forget the here and now.
I have a very similar answer to the first one, Cubert. I have no idea what others would have expected out of me and don’t really consider any regrets there. Certainly a shade in some of the other categories.
Max
Thanks Max! Hard to avoid shade in most of these — it’s a good list to continually keep mindful of as we drone through our routines!
So true. Often times we miss the journey in search of the destination.
A great article Cubert and thought-provoking. On the whole my only regret of the 5 you mentioned would be No. 4 and friends, though in fairness this is a two-way thing so they must also shoulder some responsibility, usually I’m the easiest of people with whom to keep in touch. As for regrets in general, no, I shall turn it around and replace ‘dying regrets’ with a number of ‘thank goodness I had the balls to do that’ moments in my life – and then to follow will be what I hope is a list worthy of the number of years spent sticking around this earth.
Thank you, Ben (and thank you, Amanda!)
I’m with you on #4. I know I’ve not been the best at keeping in touch, reciprocating birthday cards and Christmas cards and such. But I’ve experienced the reverse too. Even in a social media wired world, not everyone is “plugged in” to Facebook, Twitter and so on. So picking up a traditional phone call is the best approach.
LOVE the “thank goodness” view you offer. We should all take stock in how awesome our world is and its opportunities – even as we struggle to fight the climate and social problems here now.
I so agree with Amanda’s “say ‘Yes'”. I have been intentionally doing that with friends. Let’s get together sometimes. YES! Friday is open, let’s meet at… Sure, it’s driving my planning and I-need-more-notice wife nuts, but it’s really better to keep in contact with our friends than to just let time pass.
Thanks for sharing!
Hey Kevin … I can relate to this. There was a time before kids and before good friends moved away where we’d get to bond just about every weekend. Nowadays, we find ourselves immersed in chores, work, and scraping to put together a date night here and there. Time is such a precious commodity.
Thank you writing this. I identify with many of the points on here. When I was planning like crazy for FIRE, I thought that somehow by hitting that 25X number would make me happy. We hit it. But I still have anxieties and still get sad. Not to take anything away from FIRE, but there is a huge emotional aspect of hitting FIRE that’s not often discussed.
Wow, that is really cool of you to share that, Angel. I felt the same way when we paid off our mortgage. Surprisingly, it didn’t really affect me at all. Even after several years and constantly updating our progress whiteboard. I fear that leaving work will feel the same way – and I’ll have missed the importance of making each day count.
Power message here buddy. We tend to get a life-threatening wake up call once or more in life. Better heed it, follow your dreams, be generous and live in the moment, to get the most out of life.
Thanks, Ryan! I think I need to rewrite this post once a year so I avoid forgetting the message. So easy to get trapped in a narrow focus and miss the meat of life…