Regrets and what we can Learn From them

If 2020 has taught me anything, it’s that life is uncertain. And because of this new perspective, I’ve started to questions some of my personal finance and life principles. Am I sacrificing too much today to stay the course for a brighter future? Should I be spending more today? Should I get a rental property? Am I working too much? And why has 2020 made me so tired and unmotivated all of a sudden? Ok- that last question is only somewhat related to personal finance but you get the idea.

Either way- to answer some of my questions I decided to learn from others and look into some common regrets people have. And the most honest regrets come from people on their death bed. I know, this post might be overly morbid- but I think it is a good exercise to reflect on the regrets of the dying in the hope that they can help me clarify my priorities.

So, several years ago, a palliative care nurse started to ask her patients about any regrets they had- or if they would have done things differently given a second chance. She then wrote a book called “The Top Five Regrets of the Dying“. And in that book she lists the main 5 regrets as below;

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 regrets it was a bit of an eye-opener. I can see myself having some of these if I was to die tomorrow. And it’s easy to see how modern society can foster these regrets in many people.

You might not think these regrets have anything to do with your personal finance but I think they are all inherently linked to a degree. And I think working towards financial independence is one way to minimise some of these regrets. You don’t even have to become fully financially independent- once you have cleared all your debt and built up an emergency fund- or as some like to call it- “FU money”- then you have more options open to you than most. And this can help you with these regrets. For instance, if your job making you miserable- well with your FU money and no debts you can afford to explore other options.

Be Your True Self

The most common regret of all was that people wished they had the courage to live a life true to themselves, and not the life others expected of them. Living on other peoples terms and doing what other people expect of you might get you so far in life- but it’s probably not what was best for you.

Keeping up with the Jones is one way that you might not be living a life true to yourself. Do you want to live a life that impresses you or one that impresses other people? Having the latest car or phone, or having the most flash home may improve your social standing to a degree, but if it’s financed with debt- you are not being true to yourself.

And when I get comments about how old my phone is, or that I should get a new car because I can afford it on finance I just shrug them off. I would rather own my old phone and car outright than tick-up new ones on finance. They both do what I need them to do, and I am not worried about what others think.

Work can be overrated

I wish I didn’t work so hard. That regret rings true to me on many levels. The last few months I have put all my energy towards my job- and I have been left exhausted- sure my bank accounts look good- but I haven’t had any time for myself. At least not quality time. I haven’t even had time to maintain this blog- sorry about that.

Modern society teaches you that you have to work and work hard. Sure you need money to fund your lifestyle- but there is a culture, at least in the professional world that I work in, that can pressure you to work more than you are paid for. I’ve experienced this. The feeling of unease, of being judged, as you leave work at your scheduled time while others stay late doing unpaid overtime.

It’s no wonder why one of the top regrets is that you worked too hard. The treadmill of a work existence can be toxic if it takes up most of your time. And when it does it feeds into all the other regrets as well. If you work too much you won’t be living a life true to yourself, you won’t have time to catch up with friends and it might not be making you happy. When you work towards financially independent you might not need to work as much as you otherwise have to.

Courage to express your feelings

This is a regret that I can understand. I have never been good at expressing my feeling- and judging some of my male friends- I think Kiwi blokes, in general, are not good at this either. The only time I think feelings are expressed with blokes is when their all a few beers deep- at least that is what I have experienced. And that’s not healthy at all.

And to be honest- I don’t know that I am the best person to even talk about how to avoid this regret. I guess you can try to share your feelings more openly and honestly. And in doing so- I think you will be living more true to yourself as well.

One great tip I have found is to just compliment people around you. Even if it’s for the small things like “thanks for making dinner”- things like that. Everyone likes compliments and letting someone else know that we appreciate them not only boost the mood of everyone around you, but it can also act as a gateway to expressing more of your own feelings more.

Expressing your feelings is not directly liked to personal finance, but when you start to engineer your financial life you might also find yourself working on your mental and fiscal health. After all- there is no point in being financially independent but miserable and unhealthy.

Let yourself be happy

When you first dive into the personal finance black hole and “go all-in” on the idea of financial independence, retire early, you can sometimes find yourself living in the future while sacrificing today in some way. This is perfectly fine- but if you find yourself unhappy in the moment you need to re-evaluate what you are doing.

I use to put so much pressure on my self to hit savings goals on par with the like of MMM. Having all my money allocated and automatically transferred to separate investments and accounts. And ultimately- it was making me unhappy in the moment. It’s the extreme opposite of having all your money paying off debts- I had all my money being transferred into investment. And sure if I kept on that extreme path I may have got to FIRE- but at what cost?

I now think that it’s more of a balancing act- and while you are on the journey you must let yourself be happy while also aiming for realistic goals. The one thing that has helped me with this is to open an account where I transfer a set amount of money into after I get paid. The money is then to be spent on whatever I want, whenever I want. Wanting to have every dollar you earn working for you is admirable, but no way to live- neither is the opposite- living beyond your means and having everything you earn assigned to paying off debt.

The Infinite Universe

This exercised has made me realised that my regret would probably be not having enough free time for myself. I don’t mean free time to do nothing, but free time to do what I want. Time with family and friend, time for my hobbies, time to exercise, and less trading of time for money. And that is why I am still motivated to invest in my future, to become financially independent.

We all live in an infinite universe- but we live with on a finite planet with finite resources. Of those finite resources- we often think of money as the most scarce resource. The one resource that we are always chasing- to earn more, to save more, and to invest more.

But, what 2020 has made abundantly clear is that time is the most scarce resource. You may have experienced time in a different way during the Covid lockdown. The time during the lockdown may have felt slow while you where cooped up at home- but now that you look back on it- time during lockdown may have felt very fast. I mean it’s already October!

We can’t just choose to stop spending time- wake up and decide- no today I don’t want to spend my time today. And you can’t just go and earn more time either. Time is the only resource that you start off being richer than most, you are probably richer in time than the Gates, Bezos and Buffetts of the world. Times is finite for all of us.

I think that when you are financially independent you own more of your time. You can afford the time to be yourself- rather than spend time to be what others expect you to be. You have the ability to stop the treadmill that is your work existence or to work part-time. So it makes sense to use your finite resource of time wisely.

So what’s your greatest regret so far, and will working towards finical independence help with your regret?


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  1. We are all so different. I’ve been retired for five years now, we are well past financial independence. I could have retired much earlier than I did but I loved my job. I have no regrets about working until I was 60, and no regrets about retiring then, the timing was perfect! My career was great fun, I honestly usually looked forward to going to work on Monday mornings just as much as I enjoyed going home on Friday evenings. I have no regrets about my relationships. My parents are gone now but we loved each other very much and were not afraid to say so. They were proud of me and told me that often and I was fortunate to have such great parents and told them often as well. My three grown millennial kids are doing well and self supporting and we all love each other very much, and say so. And best of all, my only spouse for these 42 years of marriage, and counting, is still my best friend. My advice to anyone is live a life that leaves you without regrets on your death bed. Also, don’t die in bed, die hitting a tennis ball or running a race or hiking to the top of the mountain!

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