A Regret Minimization Exercise To Help You Move Forward


One of the main reasons why I wrote Buy This, Not That was to help readers feel less regret by making wiser choices. Regret is one of the worst feelings, especially if it is a type of regret that could have been prevented through knowledge.

The easiest way to stop saying, “If I knew then what I know now, life would be better,” is to simply learn from someone who has experienced what you might experience. But it can’t be learning from just any experienced person. It has to be from someone who is willing to share both the good and the bad.

It feels like most of us tend to conduct revisionist history, where we make bad things seem less bad to make ourselves feel better. However, if we mask the pain, we rob those we want to help of the truth. And if you don’t know the truth, you may end up making suboptimal decisions, which can lead to more regret!

Hence, as soon as you find me writing how everything is awesome, please slap my head to stay balanced. As a perennial optimist, I have a tendency to always look at the positives.

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A Regret Minimization Exercise To Feel More Fulfilled

Every year, I recommend you go through a regret minimization exercise. It can be at the beginning of the year, mid-year, or at the end of the year.

Pretend you are thirty years older and ask yourself what you’d regret NOT doing. The goal is to crystallize the things you want to do or know you should try but are too afraid to act on for whatever reason.

Your regret minimization framework exercise should encompass at least four main categories:

1) Health

2) Wealth

3) Career

4) Family And Friends

There is no absolute correct answer given we all have different goals. Further, the future is never guaranteed. However, going through a regret minimization exercise helps you discover what’s important so you don’t wake up years from now and wish you had acted.

The longer we live, the more regrets will will have. But thankfully, we end up learning from our regrets and making better choices in the future. Therefore, old regrets tend not to get repeated.

Let’s discuss each of the four main categories. Review what you’re doing and ask yourself what you will regret not doing in the future.

Health Regret Minimization

It takes years of unhealthy eating, a lack of exercise, and mental abuse before the body breaks down. If your body breaks down too much, you might short-circuit your life. At the very least, poor health habits may lower the quality of your life in the future.

Your goal is to listen to people who practiced unhealthy habits and are now paying the price. If you do, you may take action now to improve your chances of not ending up like them in the future.

Listen to your body to protect it from further harm. Unhealthy habits tend to sneak up on you.

What happened to me:

I experienced chronic back pain, sciatica, heart palpitations, and TMJ for years while working in banking. Mentally, I was always stressed to deliver solid quarterly results.

At age 34, I reached a point where I no longer wanted to sacrifice my health for money. Every year I worked after age 34 felt like I was taking a year off my life. So I negotiated a severance.

10+ years later, I do not regret putting my health first. Yes, it would be nice to have a lot more money. But the health benefits of early retirement are priceless. Thankfully, I no longer experience any of those physical ailments that afflicted me during work.

I know if I don’t continue to eat in moderation and exercise three times a week, the back half of my life will suffer. I also know if I try too hard in softball or tennis, I might badly injure myself. Hence, I will continue to eat well, exercise, and play in moderation.

Wealth Regret Minimization

Unlike health, we quickly discover how not having enough income can crimp our lifestyles. However, what’s not as obvious is how a lack of income, savings, and investing can result in a restricted retirement in the future.

When we are young, we have more energy and think we are invincible. Tomorrow never comes until it does. You must save and invest today because you will eventually no longer want to or be able to work.

After writing on Financial Samurai since 2009, I’ve come across too many people who woke up with very little or nothing in their 40s. They YOLOed a little too hard, took too much risk, or just winged it for decades when it came to their finances.

One of the biggest pushbacks in my 401(k) savings by age guide, my net worth for the above-average person guide, or my book, is that my financial targets are too aggressive. My goal is to highlight what you COULD have if you saved and invested aggressively. They are not the end all be all targets.

The vast majority of readers will use my guides as motivation to save and invest more and take more calculated risks. Even if you do not achieve my targets, you’ll get farther than if you had easy targets or no targets. My goal is to help you see and realize your potential.

What happened to me:

Luckily, I went through the 2000 dot bomb without a lot of money. Unfortunately, by the time the 2008 – 2009 financial crisis came, my net worth was significant and it took a 35% beating in six months that took 10 years to build.

Fortunately, I learned from the event and created a net worth allocation framework to better withstand any type of economic upheaval. The great thing about experiencing financial loss is it brings you closer to congruency – where you invest according to your true risk tolerance.

Also, because I landed a job that required 60+ hours a week, it encouraged me to save and invest as much as possible so I could one day escape. If I had a more leisurely 9-to-5 job, I would not have thought so much about building more wealth.

Encounters with racism, nepotism, and bullying also encouraged me to start Financial Samurai as an outlet. I found ways to make money online and build a rental property portfolio to further protect our economic future. As a result, both my wife and I are beholden to nobody.

Today, I know I will regret dying with too much. Hence, I’ve entered the decumulation phase to spend more than average and give more intentionally. Ironically, this year’s bear market has helped us naturally get rid of wealth! Thanks Jerome!

Career Regret Minimization Guide

Will you regret spending your life in your current career? Jeff Bezos asked himself this question before he quit his hedge fund job. He recognized the internet was growing and had to start an online bookstore called Amazon.

Whatever you want to do for a living, make sure your job brings meaning to you. Because I guarantee if you spend your entire life working mainly for the money, you will regret it.

Palliative care nurse Bonny Ware, said the number one feedback she received was, “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

As a result, consider retiring by a certain age to do something else not retiring after achieving a certain financial figure. That something else can be taking a break, traveling, raising children, starting a business, and more!

What happened to me:

Right before graduating college in 1999, I had an opportunity to move to Shenzhen, China to be a manager at an eyeglass parts manufacturing company. It wasn’t a sexy job, but if I went, I could have improved my Mandarin, participated in China’s economic boom, and helped build a business with equity.

However, I passed on this incredible opportunity because I landed a job at Goldman Sachs in NYC after going through 55 interviews over seven months. I felt there was no way I could pass on a frontline job at a top investment bank coming from a non-target college.

After 9/11/2001 happened, I started feeling regret for not going to China. After all, I had minored in Mandarin and studied abroad in 1997. Hence, I tried to rectify my regret by going to business school part-time from 2003 – 2006 to learn more about entrepreneurship.

After trying to make Managing Director one year and failing, I decided to leave. Even though it usually takes several years of trying before making Managing Director, trying once was enough to minimize regret. I was excited to work on Financial Samurai instead.

Entrepreneurial regret minimization

When the financial crisis hit, I finally started Financial Samurai. My desire to make up for lost entrepreneurial opportunity is one of the reasons why I’ve been able to publish three times a week without fail since July 2009. The more I worked on Financial Samurai, the less regret I felt by not starting sooner.

To further scratch my entrepreneurial itch, I also consulted at several startups from Series Seed to Series E. I knew I’d regret never doing anything startup-related living in San Francisco during the tech boom.

Finally, even though I didn’t want to write a book once the pandemic began, I knew I would regret it once the pandemic was over. So I gutted it out with two young children at home for two-and-a-half years.

Writing an instant Wall Street Journal bestseller felt nice, for a week. But I was able to experience and capture a moment that felt 10 times better.

When my book came out, I took my family to an independent bookstore in San Francisco. There my five and two year old played treasure hunt where they’d go look for my book.

Being able to see the joy on their faces when they finally found the book and shout, “Hooray for daddy!” was the best feeling ever!

Hooray for daddy! Kids shouting once they found Buy This, Not That in the bookstore

Family Regret Minimization

Family should always come first. If you neglect your family relationships, you will likely regret it later on. Keep in touch with family members, support their endeavors, and make amends before it’s too late. Deep down, you know if you’ve been an absentee son, daughter, uncle, aunty, mother, or father.

You will also need to decide whether you want a family of your own or not. It is an individual choice whether or not to have kids. Ask yourself, in thirty years will you have enough friends and relatives to depend on? Will you regret not having anybody to carry on your legacy? Only you can decide.

Without family, hopefully you have friends. Your true friends will celebrate the good times with you and support you through the bad times.

Make amends with your enemies. At least forgive them so you can feel lighter and move on.

What happened to me:

One of my biggest regrets is having children late. I was too busy trying to make money and climb the corporate ladder in my 20s and half of my 30s. With the number of hours I worked, I simply didn’t have the bandwidth to care for children.

In addition, I had an aggressive net worth target before having kids. Even after I reached this target, I felt like I needed more to raise kids in expensive San Francisco or Honolulu. Oh how delusional I was when families with multiple kids and lower levels of wealth make it work in expensive cities.

I wish someone sat me down in my 20s and told me kids will be the greatest joy (and heartbreak) in your life. Therefore, if you’re even thinking about having kids, it’s better you have them sooner, rather than later. Your biology might not cooperate if you wait too long.

Today, I asked myself whether we would regret having a third. With a boy and a girl, the answer is no. We are too old and there may potentially be too many complications. Further, we simply do not have enough energy or life remaining to care for a third without feeling guilt about not spending enough time caring for the others.

Spending more time with family is crucial

Since I waited too long, I’m trying to spend as much time with my kids as an older parent. After crunching some numbers, I realized older parents without day jobs can actually spend a total amount more time with their children than younger parents! Older parents just need to make a bigger effort during the first 20 years of life.

Proactively, we’ve set up revocable living trusts and put together comprehensive death files to act as instruction manuals. Further, both my wife and I have secured new 20-year term life insurance policies to cover our children until they are adults.

If something were to happen to us and we did none of these three things, we would feel a tremendous amount of regret. Now we can leave this earth more peacefully.

In terms of my parents, I will regret not spending more time with them before they go. Due to COVID, they are unwilling to visit us in San Francisco. Therefore, I will visit them once or twice a year. I will also call them and FaceTime them at least three times a week forever.

The Different Types Of Regrets

Please conduct your own regret minimization exercise in the above four categories. After you’re done, you will re-focus your efforts on what truly matters to you.

You may think there’s only one type of regret. But as I learned from the book, Big Feelings, there may actually be six types of regret!

  1. Hindsight regrets: you made the best decision that you could then, but you know more now.
  2. Alternative-self regrets: you have a vague sense of regret that comes from wanting to live different lives.
  3. Rushing-in regrets: you made a decision that you weren’t sure about or weren’t ready to make at the time.
  4. Dragging-out regrets: you waffled about a decision for a long time, even though you sort of knew what you need to do.
  5. Ignoring-your-instincts regrets: you had a gut feeling that you weren’t making the right decision but acquiesced to others’ needs or opinions
  6. Self-sabotage regrets: you made a decision that you knew wasn’t good for you, but you did it to protect yourself from feeling another emotion (rejection loneliness, vulnerability).

As a Financial Samurai, you are analytical, logical, methodical, confident, and courageous. That’s what happens when you empower yourself with knowledge and hearing different perspectives. So hopefully you will only experience regrets one and two above.

But if you experience regrets three through six, then work more work needs to be done to help change your future behavior. Big Feelings encourages you to first grieve what wasn’t. Then remind yourself what you gained. Finally, remember that regret will pass, or at least soften.

I’ve come to realize most of us will rationally take action to minimize future regret. We can’t help experiencing initial regret since it’s hard to know what we don’t know. But through experience, we will naturally alter our behavior because we grow wiser.

How Regret feels, illustration in the book Big Feelings by Liz Fosslien
Illustration by Liz Fosslien, Big Feelings

Impossible To Live Life With No Regrets

Let us accept that living a life of no regrets is impossible. We can’t possibly foresee every outcome.

However, what we can do is deeply research a topic before making any big decision. Part of this research includes listening to perspectives from people who’ve been where you plan to go.

Further, if you simply try your best before making a decision, it will help minimize the negative feeling when things don’t turn out well. When there’s nothing more you could have done, it’s hard to feel as bad.

Finally, I firmly believe you will regret more of the things you don’t do than the things you try. The fear in your head is almost always worse than reality.

Once you’ve decided you’re making the right choice using my 70-30 decision-making framework, go for it with 100% certainty! At the same time, be humble and aware enough to know that 30% of the time, you’re going to get it wrong.

Unless your decision is catastrophic, you will learn from your errors and make better choices going forward.

Readers, what are some of your regrets? What will be some of your regrets if you don’t act? What are some strategies you’ve found to help you minimize regret or reduce the number of times you feel regret?

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