There are a few articles that I will never forget…

The first one that comes to mind is most definitely, The Top 5 Regrets of the Dying.

I don’t remember how I found this random article, but I remember that it stopped me in my tracks. I immediately reflected on where I was headed life… and realized that I had failed miserably on 4 of the top 5 regrets. So, I printed off the list and posted it on my refrigerator where it stayed for two years… until I could confidently say that those regrets were regrets no more.

I’ve written about regrets before because I talk a lot about money and wealth, but if there is one thing in the world that costs more than anything else, it is regret.

A good measure of your life is to “live with no regrets,” so a trick to doing that is figuring out what regrets other older and wiser people have, and make sure that you don’t make the same mistakes. 

Well, that’s what I immediately tried to do after reading Bronnie Ware’s article years ago. She is a palliative nurse who counseled the dying in their last days for over a decade. She recorded their dying epiphanies on her blog, which eventually blew up and is now a book.

Here are those top 5 regrets of the dying that she found:

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

This was the most common regret of all. When people realize that their life is almost over and look back clearly on it, it is easy to see how many dreams have gone unfulfilled. Most people had not honored even a half of their dreams and had to die knowing that it was due to choices they had made, or not made. Health brings a freedom very few realize, until they no longer have it.”

When I see this one, I immediately think of Dr. Suess’ quote:

“Today you are You, that is truer than true. There is no one alive who is Youer than You.”

We all grow up and go through this funnel “system” called school. 99% of us don’t know what to do, so what do we do? We go down the route that many around us expect of us. We take the path of least resistance and go with what we know.

Going into college the only things I knew were jobs that were in the corporate world (seriously I knew 0 entrepreneurs or financial professionals), so that was the route I knew best. In addition, I was good at math and science, so I became an engineer – knowing that I never wanted to do the technical work. My dad was an engineer, so I just figured it was best. It wasn’t until I learned there was another way that at the age of 25 I started pursuing a life that was true to me.

Subsequently, that is when things started to change internally (and externally!).

But as soon as you make a change, it is not all sunshine from there. It takes committed action and work to make things a new habit. When I started YoPro Wealth coming out of the corporate world, I still had that corporate voice. So, one of the many reasons why I wanted to start is so that I could be me and my voice all-out. I may curse or tell people that they’re idiots with their money, or only appeal to a very motivated crowd, but that is me… and that is who I want to appeal to, and that is where my ultimate level of greatness lies, and that is where yours is at, as well!

This is the most common regret of the dying for a reason. We are most successful and happy when we are more our true selves, and many people eventually realize that… but they always think it is too late to do so. The sooner you start living a life that is true to you, the easier.

Plus, think about it: our best friends in the world are that way because they are the people that we are most comfortable being 100% ourselves around. Right? Life is too short to be around anybody where you can’t (or won’t) be your full self around.

Be you through-and-through… and the happiness and long-term success can only show up and stay in your life.

Level of Success

Be yourself; everyone else is already taken.” – Oscar Wilde

2. I wish I hadn’t worked so hard.

This came from every male patient that I nursed. They missed their children’s youth and their partner’s companionship. Women also spoke of this regret, but as most were from an older generation, many of the female patients had not been breadwinners. All of the men I nursed deeply regretted spending so much of their lives on the treadmill of a work existence.”

Everything in life is a balance. Working hard is absolutely necessary, but it is also absolutely necessary to NOT work so hard.

Everyone says the quote, “Work hard, play hard!”… but I’ve found that this is only part of the equation. In one of my favorite YouTube Videos of all-time, Eric Thomas shares a great quote from 50 Cent:

Sleep?! Sleep is for those who are broke.” – 50 Cent

I love 50 and especially love that quote, but let’s be honest – that is bullshit.

Trust me. I’ve tried it.

When I first created my investing algorithm, I was working over 50 hours per week in addition to my full time engineering job. On top of that, I was trying to be a rockstar by partying hard with my friends 2 or 3 times per week, and still made time to be on the beach or TPC. Basically, I did everything but take care of my health.

I had trouble sleeping due to everything going on for months, and would average 5 hours per night at most. Guess what happened within 3 months? My body shut down on me. I had a massive anxiety attack where I couldn’t breathe well. Any time I fell asleep, I would instantly shoot up gasping for air as I would stop breathing. It was hell. I thought for sure that I was going to die, and I never want to go to that place again.

So, as great as the 50 Cent quote is, realize that there is a balance. Work hard, play hard AND rest hard. That is the most powerful combination for your success, and also prevents it from being one of your “regrets of the dying.”

Work Hard Play Hard

3. I wish I’d had the courage to express my feelings.

Many people suppressed their feelings in order to keep peace with others. As a result, they settled for a mediocre existence and never became who they were truly capable of becoming. Many developed illnesses relating to the bitterness and resentment they carried as a result.”

Some people are good at this, some people are not.

Researchers have found that every person falls into one of four major behavioral functions:

Controller, Analyzer, Supporter or Promoter

controller analyzer supporter promoter 4 behavioral functions

The lion or owl type of people are much closer to the thinking side than the feeling side, and that is definitely where I reside.

In general, you really want to focus on and leverage your strengths. That is where you’ll have the most financial success… but when it comes to communication, since everyone is different, it is important to find a balance in all of these behavioral types. You really want to develop the weaker areas so that you can connect with and understand as many people as possible.

Plus, think about this: do you more often wish you hadn’t expressed your feelings, or wished you had? When you think of the big picture, I’d imagine most people would say they regret NOT expressing their feelings more with the truly important people in their lives, so error on the side of caution and express your true feelings while you still can. Again, it goes back to being comfortable with the people in your life so that you feel free to do this openly.

By not expressing our feelings or what needs to be said (in order to keep peace with others), what do we do? We cause regret and lost the internal peace with ourselves. We worry about it and think about it too much. In order to keep internal peace, you have to let the feelings, emotions, regrets, or any other negative feeling in the past go.

4. I wish I had stayed in touch with my friends.

Often they would not truly realize the full benefits of old friends until their dying weeks and it was not always possible to track them down. Many had become so caught up in their own lives that they had let golden friendships slip by over the years. There were many deep regrets about not giving friendships the time and effort that they deserved. Everyone misses their friends when they are dying.”

I’ve found that this one is much easier if you do the same thing you should do in any other area of life: simplify.

Find those core people who will be your best friends until the day you die, and treat them just like family. In my opinion, it is better to have 5 GREAT friends than 50 good ones (just like it is more valuable to have 1 GREAT skill than it is to have 100 decent skills). Find those people that give as well as take, and allow you to be your best you. Those are the ones that you need to stay in touch with… forever.

Happiness in general is a complex beast, but the one common element among happiness whichever way you slice it is the importance of relationships. This is one area that you need to put well above money, right up there with health.

5. I wish that I had let myself be happier.

This is a surprisingly common one. Many did not realize until the end that happiness is a choice. They had stayed stuck in old patterns and habits. The so-called ‘comfort’ of familiarity overflowed into their emotions, as well as their physical lives. Fear of change had them pretending to others, and to their selves, that they were content, when deep within, they longed to laugh properly and have silliness in their life again.”

How powerful is that comment: “Happiness is a choice.”

Wow. In addition, one of my top 5 favorite quotes that I mention in the book comes from David Wood. He said, “Wealth is a choice.”

Just know this: anything that you want, you can have. Whether it is money, happiness, or anything else, it is up to you. You have to make the decision and go after it. You are the driver of your life. If you want something, you have to go get it because nobody is going to bring it to you.

Choose to be happy. Choose to be great. Choose to be yourself.

You can delegate authority of who manages your money or some things, but you cannot delegate responsibility of any of the important areas of your life. That is solely on you.

Make the decision, and let yourself be your best self.

Summary & Action Items:

  • The secret to success and happiness is to be 100% you. The more you are yourself, the more you reach your true potential.
  • Your best friends in the world are those that you are most comfortable being yourself around.
  • Hard work matters, but what matters even more is being sure to also NOT work so hard. Smell the roses, take a deep breath, relax, and find balance in the work your ass off/live your ass off ratio.
  • Many (me included) try to keep peace with others by not expressing are feelings, but all that we do instead is not keep peace with ourselves. We regret not saying the things we need to say.
  • Strong vibrant health and relationships should be at the top of anybody’s priority list. Find those that bring you to life the most, and stick with them and keep in touch with them until the day you die.
  • Happiness is a choice. Wealth is a choice. You are in control of your own life, and need to act accordingly. The choice is yours to make.


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