Top 5 Regrets of the Dying and Adjusting Life Accordingly

Two or three years ago I stumbled across an article that changed my life. Maybe you’ve seen it or read the book; it’s called The Top Five Regrets of The Dying, by Bonnie Ware.

Bonnie was a caregiver for many years, who looked after terminally ill patients. She spent a lot of one-on-one time with dying people and helped them deal with emotions, reflections, and making peace before passing away.

Specifically, these dying people were asked about regrets and things they would do differently if they were given a second chance at life. Bonnie recorded the five most common answers she heard from everyone. They were…

  1. “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”
  2. “I wish I hadn’t worked so hard.”
  3. “I wish I’d had the courage to express my feelings.”
  4. “I wish I had stayed in touch with my friends.”
  5. “I wish that I had let myself be happier.”

When I first read these top five regrets I thought, “I wonder if I’ll be saying the same things when I’m on my deathbed? … Maybe if I take this life advice and start to implement changes in the way I live NOW, I could avoid some of these regrets later?” 🤔

Ever since then, I started thinking and doing things differently with the hopes of living the *least* regrettable life possible. Here’s some specific stuff I’m doing and actions I’m taking…

My First and Biggest Takeaway: No One Had Money Regrets

Did you notice that none of the top regrets have anything to do with “more money” or “more stuff”?

That was my first big takeaway: Stop prioritizing money and consumer crap. It’s not what truly matters or what you’ll cherish in the end.

Regret #1: “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

I would have never guessed this to be the No. 1 life regret. But the more I think about it, the more I can relate. I’ve spent A LOT of my life trying to impress other people and suppressing my dreams in order to fit in and feel “accepted.” My old career path, the way I used to dress, talk, and act… Most of this I was doing because that’s the way others were doing it.

Want to hear something really embarrassing? When I quit my job in 2018, I typed into Google, “what should I do on a sabbatical?” It’s not that I didn’t have my own list of things to pursue, it’s that my natural instinct was to check what everyone else was doing before making my own life decisions. Kind of sad.

It’s not all bad though, because the decisions I’ve made in my life have led me to become who I am today. And since discovering the FIRE community and reading more empowering books like The Art of Non-Conformity, I am starting to dance to the beat of my own drum more.

Here are some other things I’m doing to live a truer and more authentic life:

  • My wife and I talk about our life goals, regularly. We have clear priorities and due dates, making sure we actually do the things we’re dreaming about.
  • We are working toward financial independence! In the meantime, we’re taking advantage of any freedoms we’ve already earned or have been blessed with.
  • I started a massive “someday maybe” list. Anytime I get bored I check out the list for ideas. These are my ideas, not other people’s.
  • I’m cautious of how much social media I intake. Checking out other people’s lives is fun, but it can be dangerous and addictive.
  • When I ask for someone’s advice or opinion, I take it as optional, not mandatory.

Regret #2: “I wish I hadn’t worked so hard.”

Bonnie says people “Deeply regretted spending so much of their lives on the treadmill of a work existence.”

Ready for another embarrassing personal story? In 2016 my parents came out to visit me from Australia. I welcomed them by working 60 hours that week and making other people show them around LA. I even got a little snappy at them for “visiting me when it was my busy season at work.” I was an asshole, and it brings me to tears just thinking about it. Sorry, Mum and Dad.

Working too hard was 100% my fault. Even my boss told me to take time off to hang with my family. But I didn’t because a) fear of being called a slacker by coworkers and b) I wanted to make more sales so I could earn more money. Two really dumb reasons.

Thankfully, my workaholic days are behind me now. Let’s hear it for Financial Independence! That’s why we’re all here – to build a solid money foundation so that work becomes optional, not mandatory.

But even well before hitting your FI number, there are a bunch of ways to have a better work/life balance. Better yet, a lot of companies these days are embracing and promoting a healthier work lifestyle and environment. 

Going forward, here are some things I’m trying to balance my work/life better:

  • Pursue work that’s in line with my values.
  • Take advantage of remote working! (no commute, different workplaces, travel while working)
  • Take a lot of time off, especially for big family occasions and life events.
  • Work smarter, not harder — maximizing my most efficient times of the day.
  • Turn off phone/computer more regularly, being more present during off time.

Regret #3: “I wish I’d had the courage to express my feelings.”

Have I told you readers lately that I love you? 😍 And how beautiful and handsome you all are?

Kidding aside, I really am trying to express my feelings a lot more. Here’s a few examples of stuff I’m trying to do more:

  • Express appreciation when people help me. I’ve begun emailing authors after reading their books, writing thank you letters, and telling people the impact they’ve had on me.
  • Calling people instead of texting/emailing. Voice gets my *feelings* across, text does not.
  • Sticking up for myself when I’m being crapped on. (Previously I’d just let my wife fight my battles for me 🤣 but now I’m learning to be a big boy)
  • Journaling and blogging has really helped me share more feelings. Stuff that would otherwise never have been released.
  • Asking better and *deeper* questions when having conversations with friends. This brings a deeper connection vs. just surface level topics.

Regret #4: “I wish I had stayed in touch with my friends.”

I guess it’s a lot easier these days with Facebook and other online platforms. (Bonnie’s article came out in 2009, Facebook was invented in 2004, and most of her patients were of the older generation and probably didn’t use social media).

Regardless, I think “staying in touch” is a lot more than just having a ton of FB friends or wishing an old pal happy birthday once a year. It’s making the effort to reach out, re-connect, reminisce about past shared events, and support each other.

I think the pandemic brought many old friends back together (virtually). I certainly reconnected with more old friends this past year than in prior years. Checking in and visiting old friends regularly is high on my priority list going forward.

Regret #5: “I wish that I had let myself be happier.”

The earlier in life you realize that happiness is a choice, the sooner you can take ownership and start building systems to improve your experience and memories.

I’ve spent the last 3 years studying happiness. It’s an ongoing process, not an overnight switch.  Here are the quickest and simplest routes I use to boost my happiness. I do these consistently, building a habit of happiness.

  • Doing good deeds for others. I believe the quickest route to happiness is making others happy.
  • Daily appreciation. Simply focusing on all the things you do have, vs. all the things you don’t have.
  • Constant celebration. It doesn’t matter how big or small the occasion, I’m going to celebrate it. Every day is a celebration. 🥳
  • Beware of negative people. I’ve become hyper sensitive about who I surround myself with. I’ve got no problem sharing my happiness with others (it’s unlimited!), but I do have a problem with people trying to share their negativity with me.
  • Get outside more. The sun shines on those who are outside.
  • Sleep well, eat healthy, exercise and have plenty of sex. Hahaha! Oops, that was an overshare. But seriously, taking care of your basic human needs is key to happiness.

Cheers to Fewer Regrets in Life!

Well, there you have it!  Live true to yourself, don’t overwork, express your feelings, call your old friends, and work on your happiness. Easy peasy.

You and I will probably have some regrets on our deathbed, but they aren’t going to be the common ones!

Any of you readers spent time with people at the end of their life? Anything to add?

Love you all,

– Joel

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  1. Steven June 14, 2021 at 9:28 AM

    Thanks for sharing this – things that everyone should reflect on no matter what age you are! I read ‘Die With Nothing’ a few months ago and this fits in nicely with the themes I’ve been thinking about lately since reading that book!

    1. Joel June 15, 2021 at 12:00 PM

      Just added that to my reading list! :). Thank you!

  2. steveark June 14, 2021 at 12:15 PM

    I don’t have one foot in the grave yet but I am past sixty and I’m happy to say I can’t think of anything significant I’d change in my life if I had it to do over again. I definitely didn’t work too hard and enjoyed my family and my career. Raised three independent and financially stable kids to adulthood, had a great relationship with my parents, we’ve stayed happily married going on 44 years and ended up debt free millionaires by the time I was 50. I have always been a happy person and that’s just increased since I retired five years ago. There have been and always will be problems to address but those have been few and far between.

    1. Joel June 15, 2021 at 12:06 PM

      I agree with you. If given a chance to reverse big mistakes or money losses in life, I can’t say that I’d want anything changed. I believe this feeling will continue as I get older, as long as I’m constantly learning and trying my hardest to be better.

      Congrats on 44 years married!!! My wife’s parents just past their 40th, and my parents are 38 years I think!

    2. Leslie December 31, 2021 at 9:55 AM

      May i ask what your career is, and how you are a retired millionaire? Dud you get a family inheritance of some sort?
      Or did you get a kick start at life and have a parent that was wealthy to loan you money to maybe start your own business?
      Sorry if im being blunt. I just hate my job, and i dont know which direction to take in life. I would love to start my own business, but i have no money to start one, and im starting to take classes for school, but i dont know which career path i want to take, that will actually need the degree that i go for. And i have a hard time retaining information. So learning things is hard for me unless im shown how to do it step by step with soneone showing me how its done.

      Thank you for reading and im happy for your success! I look foward to receiving any feedback please. Take care.

      -the struggle is real-

  3. David @ Filled With Money June 14, 2021 at 7:08 PM

    The #1 regret kinda is unavoidable. We are biologically social creatures and we can’t really help but let other people’s decisions influence our line of thinking.

    The only way I think we would ever live a life true to ourselves is if we truly live alone shut out from the outside world and what they are up to so that we can make decisions with zero influence. Currently, I know of zero person in the world who does this.

    No one’s blaming you for googling that, Joel! I’m sure you’re not the first person to Google that nor would you be the last.

    1. Joel June 15, 2021 at 12:13 PM

      Hey David! I don’t think these are necessarily black and white regrets, more like a scale… Everyone has different levels of authenticity and outside influences, and it’s on each person to find what feels best for them.

  4. Drago Grejck June 15, 2021 at 8:34 AM

    I have absolutely loved this piece! Definitively one of such articles you should read once every year to keep on track and not let life go unlived…


    1. Joel June 15, 2021 at 12:16 PM

      Gracias Drago! That’s why I started blogging in the first place. I wanted to scribble down notes and ideas I can read back to myself in future years :). Have a great week my friend!

  5. Jason Brown June 15, 2021 at 8:52 AM

    #2 – I wish I hadn’t worked so hard — is the one that I always think about. My dad was a workaholic (he just retired at age 70, which shocked me because I didn’t think he’s ever stop working) – and due to his work habits he was nonexistent in my life until I was 18. He has since expressed remorse over this and we have a great relationship now.

    The other story that I always think about is regarding a previous boss at a former job. She was forced into retirement before she was financially ready due to rapidly declining health. She was nearly 80 years old! As I sat and watched her address her staff with tears streaming down her face, I thought, “I never want to be in this situation.” Sadly, according to published reports, about 25% of Americans will be forced to work until death because they have $0 saved for retirement.

    Thanks for the deep thinking post Joel!

    1. Joel June 15, 2021 at 12:19 PM

      I think the FIRE movement is helping many people avoid regrets around finance and working too hard. So glad to hear your Dad has health left and time to reflect and pass on his wisdom from regrets. Others are not so lucky.

  6. Jeff June 15, 2021 at 11:14 AM

    I’m glad I gave up on the “Keep up with the Joneses” mindset early in life. Life isn’t all about money and who has the most stuff, but it’s hard being around so many people that think so! Good to know there are so many others out there like me.

    I can’t imagine the feeling some of the people with these regrets had knowing they spent their lives going after the wrong things. Hopefully, more people can start to change their mindsets soon after reading articles like this.

    1. Joel June 15, 2021 at 12:25 PM

      I agree that as more people drop the keep up with the Joneses mindset, they start living happier lives. :)

  7. Celia July 2, 2021 at 10:10 AM

    Great article! I really relate to regret #1. I was asking the same thing when I left my job in December and went on sabbatical. I am changing my career and launching my business as a life coach. I left a job with stable income to venture on my own. It is exciting and scary at the same time.

    1. Joel July 2, 2021 at 11:58 AM

      Congrats and good luck with it Celia! Ultimately, even if you fail (you won’t btw) you will still feel better living a life true to yourself vs. something thats not really you. Congrats on taking the leap – I’m excited for you!!!