Poking Fun of Deathbed Regrets While Having No Plan to Repeat Any

The world is yours now, do with it as you will. Until that night when all again is still.
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We’re all going to die someday babes. #morbid

Deathbed regrets should have more research funding. It seems like invaluable information if you take it as advice. See, I don’t see people as lacking in good advice and good direction. There are some really general golden nuggets of advice floating around that people still ignore.

Just off the top of my Lily-head:

*Spend time with your children instead of money.

*Strive to be the man you want your daughter to marry.

*Don’t take things too personally. No one thinks about you as much as you do.

*If you don’t understand basic personal finance then you’re forked.

I went to my deathbed on my 27th birthday. I asked myself who I wish I could be and what exact legacy I wanted to leave behind. I couldn’t ask my 27th-year-old self about these things because everything started with a “but.” I’m damn annoying that way.




Oh my Buddha I’m so surprised unfulfillment was #1………..not.

“I never pursued my dreams and aspirations.”

When you spend 40+ years at a 9-to-5 grind and take that as your destined reality, when exactly will you find the time and energy to pursue anything by retirement age?

Related: What Fatty Fatty Fat FatFIRE Looks Like To Me


“I wish I’d have traveled more.”

Yup, expected. Even if your mind is young, your body – the vessel – is tired. Plus the majority of people hate their job so if 40+ years haven’t cultivated enough apathy for work, then a tired body will.

Related: 16 Part-Time Jobs with Good Health Insurance and Benefits


“I wish I had children.”

I believe a person can live a full life without children – absolutely – and not everyone was meant to be a parent. A lot of people shouldn’t even be parents honestly.

From what I heard, children are intensifiers, like kitchen spices. So if you wanted a good life like you spice up a good dish…eat children…? Lol just kidding. See there’s that morbid thing again. *Thumbs up*

But seriously though, this regret is totally scary because I’ve been on and off the fence about having biological children. Maybe we should play it safe and since we’re on the fence so there wouldn’t be any regret later?

Related: What Is The Real Cost of Raising a Kid If Done Frugally?




“I wish I’d tuned the world out more.”

I can’t relate to this problem 😉


“I wish I was content with what I have.”

Oh yay I literally just mentioned that my last post. Contentment is key because “having enough” is really a mental challenge.


“I wish I didn’t wait to start it tomorrow.” “I wish I would have kept going.”

It’s good to have dreams and aspirations even if ours might not come true. We all need something to make us look towards the sky. Otherwise, it’s going to be a boring life.

Related: What The Hell Are Deep Life Goals?


“Happiness is a choice, I wish I knew that earlier.”

Me too brother.





“I wish I said ‘I love you’ more.”

Aw. That’s pretty easy to fix. I don’t think this will be a regret of mine, at least I hope not. I grew up in a household that never, ever say that to each other – I think it’s a Chinese thing. But now, Mr. Hippo and I said ‘I love yous’ to each other maybe 3 times a weekday and 20 times over the weekends. It wasn’t until I married Mr. Hippo that I started saying it and got into the habit of saying it. When the conversation gets quiet and there’s nothing else to say, we say it just to appreciate each other.


“I should have been the bigger person and resolved my problems.”

It seems to be popular opinion that besides saying ‘I love yous,’ you should also say sorry more often. Considering over 50% of marriages end in divorce perhaps being the bigger person and working through problems is why this is so common of a regret.


“I worked too much and never made time for my family.”

I love it when another blogger features interviews of highly salaried, highly ambitious people. A common struggle in those interviews is how they balance their career and family. I think I almost went down that path. In the end, there is rarely a good family/work split among super highly salaried employees.

That was one reason why Mr. Executive and I broke up. It’s really hard to build a relationship with a person who is dedicated to working every hour of every day. It was hard for me to imagine being married to someone like that…probably because he would be at the office 24/7.

Mr. Hippo balances out his work and home life. He is not obsessed with getting ahead, which was the middle ground I was looking for. Money isn’t much past the FI point simply because there isn’t that much one really needs.

But it’s easy to get caught up and trap yourself in financially with a big salary.

Related: The Marriage Fight That Made Me a Better Wife


“I worked too much and never made time for my friends.”

When I was a teenager, my friends had LOADS of time but NO money. Now that a lot of us are grown and working…we have money but no time. When there is time, that is reserved for dating around so you won’t have to die alone. Boo, what farce.


“I wish I stayed in touch with friends.”

This is the regret when your spouse has already passed away and then you suddenly start wanting old friends back, old memories, your youth back. Did I get that right? 🙂


“I wish I ran with a better crowd.”

Haha, this is the deathbed version of saying “all my friends were fake and I wish I had the courage to see that I hated them.” (??)

You can’t choose your family but you can choose your friends. More importantly, you are the AVERAGE of the closest 5 people you know. <- A genius quote from my friend Valerie.



Overall Health


“I wish I’d left work at work.”

I hear this one from people when they’re still alive. When I was young, if my dad had a bad day at work, he takes it out on me because I was the one he could pick on. My husband is better. When I ask him about work, he doesn’t remember. He has already blocked it out after a hard day. It’s hard when you’ve braised in an 8+ hour bad day to not take it home with you. It is misery to-go and worst that it affects everyone around you.


“I should have saved more money for my retirement.”

I can’t believe this wasn’t #1. This was about #7 or #8 on a list of 10.


“I wish I wouldn’t have compared myself to others.”

That’s the end result when it comes to comparing yourself to the Jonesessesses too much. I think the best financial advice I’ve heard this week is when someone said they played the lotto scratchers instead of saving because he doesn’t know how his friends afford their lifestyle and he feels like he needs to keep up. And he will keep up by buying lottery tickets and eventually winning the lottery one day to balance out the money he has lost.

Of course, the correct reply to that was…”Do you want to win the lottery? Start investing.”


“I wish I took better care of my body.”

Alright well, this is pretty self-explanatory and not surprising at all. Health brings us a freedom that we don’t realize we have until we’ve lost it.

Related: Being Frugal is Easier When You’re Young & Healthy



Hey Wallflowers!


 “I should have spoken my mind instead of holding back and resenting things.”

I am honest to all heavens deliriously lucky…no, wait, WE are ALL deliriously lucky to live in at least a Western country. Free speech, religion and not fearing to have your head chopped off by an imperial whackjob.


“I wish I had more confidence in myself.”

Yup, this is a one. I’m glad I learned how to be confident slowly with each year I’ve grown. I think I came a long way from being a shy devious 8th-grader.


“Not having the courage to live truthfully.”

I knew everyone had skeletons in their closet. This sentence is bloated with that.

It’s hard being honest with yourself. I think many of these deathbed people were born around the 1940s or 1950s? Times were different back then. They had a problem with women voting back then. Going online and finding your community was not possible back then. It was much harder so there is no reason for others now to repeat it now.



I love these deathbed regrets because they’re SUCH obvious issues we have dealt with in our current lives. The struggle of meeting our potential, balancing work with play, and dealing with interpersonal relationships. I do not want to carry any more of these to the grave.

Yes, I know this is morbid (people keep telling me that for some reason) but don’t be afraid of death! Listen to more black metal music! Let’s start a conversation! What is a potential regret that you can catch yourself from?



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20 thoughts on “Poking Fun of Deathbed Regrets While Having No Plan to Repeat Any”

  • Well… I just hope I go out with a bang. Breaking my neck in the powder after pulling a 1080 switch seems pretty good, or maybe my chute goes out diving. At least it’ll be cool! 😎

    Workaholic… I’m not really sure. I actually like it, the challenge is too addicting. Might have to check that later down the line.

    If I had to say… Being buried in an avalanche of burritos or something maybe an interesting way to go? At least you could try and eat your way out.

    • LOL I vote chute diving!! DO it in a women’s dress. There was this guy from Seattle who worked at the airport and decided one day to steal a plane. He had the time of his life driving it (no one could figure out how he got the plane started as someone without any training) — and then he crashed it on a mountain, not sure if on purpose or…yeah. Yeah. We got audio of him right before he crashed too. Very different way to go.

      Are you a workaholic Will? I think you’ll pull out 🙂

      Being buried in an avalanche of burritos or something maybe an interesting way to go? At least you could try and eat your way out.

      • That’s a one hell of a crazy story. Went out with a bang at least. 😅

        As for being a workaholic… For now I would say so, I don’t seem to mind getting off work at 1am… (Even though I have enough to retire.) For now… Maybe just for now.

  • leave work at work. my father had a hard job as a prison guard in a max. security prison. it was stressful as all hell and to this day i’m still impressed he never had to rant about the crap in his work day when he got home.

    we’re spending as much time with friends as possible. one of them died last year at age 48 and most of my friends knew him and it gave us all a little more incentive to make the extra effort when time and obligations are tight.
    freddy smidlap recently posted…The World Says I Should Want That? I Don’t

  • In general, I don’t like to think about death. But this post is much more than that. It is about what we can do with our life NOW.

    I really like these kind of posts. I don’t find them morbid or depressing at all. I find it inspiring. It inspires me to live up to my potential and do better for others.

    I’m not sure if I can name a potential deathbed regret that I can catch myself from. I’m still working on being a better person so that I won’t live with any regrets.

    I like your “Strive to be the man you want your daughter to marry”. I think that’s a really good one and it is what I am trying to do.

    I like your bit on “saying I love you more”. We say it often, but I think it’s cute that you break the silence with “I love you”. I’m going to try that one day!

    I don’t think I’ll have any of the above mentioned regrets. But the ones I would always like to improve on is “following your dreams and aspirations”, “living truthfully”, and “having more confidence in myself”.

    Thanks for a great post and wonderful read 🙂
    Dr. McFrugal recently posted…Weekend Reflections: 8/19/2018

    • Dude we’re seriously the same on this. It’s what we can NOW from the collected information of those before us with more experience. Lova ya Doc!

      I said “strive to be the man you want your daughter to marry” to my husband and he didn’t get it. He said “ewww” LOL! I think he missed the point. It’s amazing advice.

  • Cool post Lily!

    Hopefully that doesn’t make me seem weird by saying talking about death is cool?

    Oh well.

    We ALL can learn a lot from the death bed regrets of those before us. There is a reason that the majority of the regrets are the same, so we should take them seriously! They are regrets that the majority of us have, and they are giving the living one last piece of advice before they pass.

    I am going to take it, especially “I should have spoken my mind instead of holding back and resenting things.”

    I was not that confident in myself while I was a teenager, and there are still a few things that eat at me, where I could have easily avoided by simply speaking my mind!

  • Is there something we should know about? Lot of posts regarding death lately. lol 🙂

    Well I do think it is a great mental exercise to fast forward and imagine what regrets you would have on your deathbed and then work backwards so that they are addressed before it is too late.

  • Great list. Now that I’m older and have noticed how the self made entrepreneurs live, or maybe it’s a cultural thing running on Asian blood, I think the over working attitude is particularly prevelant for parents who are self employed or work in environments with no pension so there’s the constant worry of what about the “old me” if I don’t hustle now?

    No surprise all that hard work goes into real estate. For all the workers without a company pension, 401k, or live in countries with no social security, buying houses in stable westernized cities is their only self funded pension plan.

    Tell someone in Asia to slow down, go home for dinner with the family on the weekdays, work life balance instead of striving for monopoly and they ask me which palace I escaped from.

    • Lol I know right. I heard in Japan the working environment and culture are crazy tough. Does China have anything like a pension or 401k plan in their system at all???

  • I love how you pick apart each one! I feel like some regrets are inevitable, though, unless we all become psychic. I can think of lots of regrets that I already have — not asking my grandma more about her younger days when she was still “with it” enough to remember, showing up late to my final ballet recital in high school (oops), not opening a Roth IRA when I was in my first teenage job. Of course, not focusing on regrets can help us all lead happier lives.

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