Conduct A Regret Minimization Exercise To Help You Move Forward

One of the main reasons why I wrote my WSJ bestseller, 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 with 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.

Related post: The Negatives Of Early Retirement Nobody Likes Talking About

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. The experience was so life changing that I chose to publish an ebook about everything I learned in the process and then some. I'm happy to say the ebook has helped thousands of people. And it continues to be a valuable and unique resource.

Get The eBook Now button

11+ 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 adventure 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.

In addition to becoming a solopreneur, I decided to invest in private growth businesses as well through various venture capital funds. I got rejected from a lot of startups like Airbnb and Uber. If I had joined them when I applied, I would have made millions. To minimize regret, I'm now regularly investing in private growth businesses through funds.

Check out the Innovation Fund, which invests in the following five sectors:

  • Artificial Intelligence & Machine Learning
  • Modern Data Infrastructure
  • Development Operations (DevOps)
  • Financial Technology (FinTech)
  • Real Estate & Property Technology (PropTech)

Roughly 35% of the Innovation Fund is invested in artificial intelligence, which I'm extremely bullish about. In 20 years, I don't want my kids wondering why I didn't invest in AI or work in AI!

The investment minimum is also only $10 while most venture capital funds have a $250,000+ minimum. You can see what the Innovation Fund is holding before deciding to invest and how much. 

Published my book during the pandemic

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 Buy This Not That, 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

Related: Why I'll Always Regret Selling My Business For Millions Of Dollars

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. I think most people will regret sacrificing love for money if they are rich and single at a later age. Most people would rather have someone and be middle class or even poor if they could find the love of their life.

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).

Reduce The Worse Types Of Regret

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. The pandemic, for example, was an experience in hedging your life.

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. Harness fear, the main ingredient necessary to achieve financial independence. If you do, you will do everything it takes to get there.

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.

Reader Questions And Recommendations

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?

For more nuanced personal finance content, join 60,000+ others and sign up for the free Financial Samurai newsletter. Financial Samurai is one of the largest independently-owned personal finance sites that started in 2009.

32 thoughts on “Conduct A Regret Minimization Exercise To Help You Move Forward”

  1. Hi Sam,

    Just read your latest newsletter. Great reading and on the mark, as always.

    I totally agree on the regret minimization. And on the health benefits of early retirement. In my case, of course, it was retirement from a corporate career. Corporate politics and all the time wasted in endless meetings were not for me. Of course, at age 72 I am still not retired. The huge difference is that I love what I am doing and I am my own boss, and have been for decades now.

    I am decades ahead of you in age, so I speak from your future. Health is huge. Nothing is guaranteed in life, but being reasonable goes a long way towards staying healthy. At 72 I have zero aches and pains, and I am on zero meds. That’s a good thing to aim for. And as for fear of getting older, I can honestly say that every decade of my life so far has been the best one yet. May the same be true for you.

    That said, don’t live life in a bubble. Pink Floyd once sang that “all you touch and all you see is all your life is ever going to be.” Very true. I cherish all of the adventures I’ve had in life. They make up the fabric of your memories.

    When I look back, I think the other big stressor is debt. Owing too much and thus having large monthly payments can be the source of ongoing misery. You struggle to stay ahead. You need to make a lot of money just to pay the bills. Having as little debt as possible minimizes that stress. Having zero debt, as we have now, feels wonderful.

    Living where living expenses are excessive can be very stressful. In our case, moving from California to Tennessee was a win-win in every way.

    You said that one of your biggest regrets is having children late. That shouldn’t be a regret. Having kids early means having to sacrifice a lot. Which means you don’t get to do a lot of the crazy, wonderful stuff that you’ll remember the rest of your life. I had my son when I was 45. That worked great. And should my son look forward to inherit some money at an age where it can make a difference in his life, it’ll happen sooner with older parents. :-)

    I always did tell my son, though, to start saving early. Crucial, that one.

    I saw that you worked at Credit Suisse a good many years, which coincided with your Credit Suisse’s Chairman of the Board at the time. I know Walter Kielholz well. He and I played ball together and were in the military together as cannoneers in the Swiss Artillery. He was “Killy” amongst us guys. :-)

    Happy Holidays!


  2. Great post Samurai, I too was late the the call of ‘fatherhood’, but I think it made me a better father. I wasn’t ready to commit in my 20’s, as I was still out for ‘ME”. That feeling of when your children played hide and seek for your book made my heart melt. Your kids will always remember that, because everything prior to your book becoming a reality, they were there to witness it. Amazing!

    1. Thanks Jim. Having kids is such a big responsibility, it’s probably best for more people to wait until they feel ready. But now, to be able to spend so much time with them every day is a blessing. Definitely some pros of having kids late as well.

      Today, after six sessions, my boy finally knows how to ride a bike! Other parents paid a bike teacher, but I wanted to have the satisfaction of being the one who taught him. It is a special moment and we caught it on camera.

  3. A lingering observation I have is in regards to the children of FIRE parents. I have many FIRE friends and come from a family with an early retirement tradition. In my experience small children who grow up with parents that do not work do not have an example of how to become FI. Often they are born after the sacrifices and 60 hour work weeks. In their experience a Tuesday morning is for sleeping-in and taking a walk in the park. When they reach adulthood the tendancy is to keep on skiing and leisurely reading books.

    1. I think it depends on the parents. Most people who retire early continue to do something productive. My kids know I work by writing 2 to 3 hours a day. I also bring them to water the trees and plants and pull the weeds with me at the rental properties.

      Being able to see what your parents do and see them work I think is more meaningful then your parents being away all day and then coming back for dinner. But of course, I’m biased.

  4. I regret neglecting my health and letting athletic abilities fade…

    You’ve said in previous posts that a dying/sick man will trade anything to be healthy again (or something to that effect) and it has stuck with me. I find that when I’m down (sick, injured, etc.) I say, as soon as this passes I’m going to turn it all around and get back into shape. This is never going to happen to me again, and so on. However, each time after I bounce back (and lucky to do so) I find that fighting spirit fades. Sure, I’ll make an attempt and maybe go for 1-2 months or so eating right, working out 5-6 days a week, but eventually work, kids, and other things slowly take priority again and health takes a back seat. Then I settle into working out maybe 3-4 times a week and the “cheat” meals increase. Then I start rationalizing that even if I don’t do xyz, I’m still better than average. Then there is the notorious, I’ll start again tomorrow. After a few weeks or months of this I find myself back out of shape again and the cycle repeats.

    I used to be an avid triathlete, and a triathlon coach. I’ve trained countless athletes from the couch to completing Ironmans. However, due to work, kids, life, I let it all slip away. I stopped coaching, stopped racing, stopped riding, and really stopped working out even close to my previous levels. I suppose the shift was due to having kids and the fact that it felt selfish to train so much with kids around. I thought going for long runs, and rides would make me miss time with them. So, they were my excuse. They were the reason I didn’t workout as I should/could.

    I decided this summer after watching my wife race an Olympic triathlon after 12 years of not racing that I would do the same. She however, upon returning to the sport won her age group and got third overall in the race. I had a bit of a different story…

    I signed up in May for a race which was to take place in September so there was plenty of time to train. However, between the kids sports, family trips, a vacation to Italy and then getting COVID (again) I ended up letting the whole summer slip by without training.

    A week ago, I decided to do the sprint triathlon anyway. I hadn’t trained in years, but figured why not just wing it. Surely, my muscle memory would prevail and the kids would get to see me race which would be a plus. I got my race bike out of storage and gave it a once over. I had flat tires in my tubes and worn brakes. I changed the wheels out and swapped for my race wheels, and figured the race was short enough that the brakes should be fine. I wasn’t going to be racing hard, so handling wouldn’t be a problem. I decided to leave them as they were.

    The race started out okay. I took off too quick in the swim (nervous energy perhaps) and realized since I hadn’t swam in about 8 years, I should back off the pace. I finished the swim okay, about 4 minutes slower than normal, and headed out on the bike course. Unfortunately, I took a spill during the bike leg. I was going down a hill at around 35-40mph, and around a blind turn there was another racer who had crashed laying across the path on the line I was taking. I didn’t have time to stop or adjust my line due to the curve I was on and because I had worn brakes, so I tried my best to slow without locking up the brakes. However, due to my speed, I was forced to lock them up, and I started to skid. I slide across the road perpendicular to my path and knew it wasn’t going to be good. I eventually, hit a trench endoed and was slammed to the pavement on my chest. Bam, welcome back to Triathlon. I had fallen before in a race (only once during the USA National Championship 11 years prior) but this time it was different. This time I didn’t just pop up and get back on the bike and go racing, likely due to age. This time, I felt shaken up. I got myself off the road to help avoid others crashing because of me, like I had because of the other dude. Then I took assessment of my body. I didn’t feel anything broken, but I did feel terrible. My chest ached and my arm was covered in blood from the fall. The funny thing was my immediate thought was about my kids. I thought what if I don’t finish this race and they don’t get a medal to play with? So, I forced myself to get back on my bike (which was broken) and found a way to pedal through the rest of the course using one gear all the way back to transition. I then decided that It was only a 5k to the finish so may as well go for it. I ran the balance of the race at an easy 8min mile pace and finished. I gave my kids the medal when I finished and they didn’t want it because it was too sweaty, ha!

    Anyway, hours later after the adrenaline wore off, I started to feel the real pain. My chest did in fact hurt. Slowly, more pain crept in. I found breathing hard, and then lifting things was hard. Then even moving around was tricky. I brushed it off thinking it was just sore but couldn’t be anything that bad. Days went by, and the pain got worse. I couldn’t hold up my kids or jump around with them. I couldn’t play catch or get them prepared for their football games. I just felt weak and a stabbing pain when breathing and moving around. That’s when the fear set in. What if this doesn’t go away. What if I don’t bounce back. What if I really hurt myself and I can’t do all these things again… (the story goes on, but I’ll spare you the details) I’m heading to the doctors shortly to find out why my chest and lungs still hurt. I assume broken or fractured rib.

    So here I am, once again, saying… I will not let myself get out of shape. I will not do a race without training for it. And I will not neglect to perform maintenance when my bike (or anything else) requires it.

    I’m hoping that the doctor can give me the magic solution and fix me up again. However, that doubt is in my mind. What if they can’t. What If I can’t do all the things I used to do again. What happens if…

    Regret to me only happens when you realize you can’t do the things you’ve always could but chose not to. So, going forward I’m going to start doing things and not putting them off until tomorrow. Including going to the doctor to checkout odd pains, rather than waiting to see what happens next.

    1. Holy moly! What a story. I hope your kids read this so they can appreciate how hard you try to get that metal and how you got back up even with all the pain in the broken bike and finished. Because imagine if you did not finish? You would’ve been filled with regret that you went so far only to give up.

      It sounds like your level of health and fitness is far beyond the average person. Because what percentage of the average person does triathlons or even mini triathlons? A quarter of one percent maybe?

      Your two-pack abs still are better than 99% of folks one one-packs. So I’d let go of the desire for four-packs. We’re old! Although, I don’t know exactly how old you are :-)

  5. Hi Sam,
    Long time follower with a question about my 401k. In bad times I never know what to do with my 401K. I always seem to follow the rule of leave it alone and invariably lose a lot and years of plodding back only to lose in the next down cycle. I’m in a projected year of retirement fund 2025. I alway feel foolish and regret not knowing how to navigate my 401k..Do you have an article that deals with this topic? Thanks for the always positive and human approach to your newsletter.

  6. My regret continues to be that I did not save and invest enough even going back to my 20s when I had few if any financial obligations. This is really hard for me to shake especially in light of the 20 year bull market I fear we will not be seeing again for a very long time. I can only now work as hard as I can, capitalize on as much opportunity as I have in front of me, and do what I can to ensure 20 years from now, I don’t have the same regrets.

  7. Thanks Sam. I regret not reading more of your articles.

    I think I will regret quitting my job if I could have negotiated a severance or gotten laid off. I know some people who quit their jobs before only to realize they could’ve gotten laid off if they just hung on for another month.

  8. I think one tricky thing is that what you value changes as you age. Prestige and money (assuming you have enough – whatever that means for you) become less important and family, health and relationships become more important. It kind of reminds me of Settlers of Catan where at the beginning you’d kill for bricks and wood to get you going but by the middle of the game, their value is pretty low.

    I try to ask myself “in 15 years, what will I wish I’d done today?” which helps me frame decisions in an attempt to minimize regret. I’m not quite mentally ready to give up chasing money and prestige just yet, which is a struggle, but I do think I’ll get there over time. :)

    Your kids’ excitement just radiates through that photo! What a wonderful moment – thanks for sharing!

  9. Hi Sam,

    In Jan 2022, we had a net worth of about 8.5M, 40% real estate, 60% equity exposure. Despite reading your passive income articles over and over again, I regret not being able to generate more passive income with less principal risk. We do well in RE, but not enough to live on.

    I left my good paying tech career in 2019 to pursue a second career in landscape design. No regrets making the change and giving it a try, however at the end of the day its still a job, the fulfillment and satisfaction level is not what I thought it would be.
    Prior to a month or two ago, I felt like my wife (51) and I (52) could walk away from full time jobs whenever we wanted to, now I am not as confident and wondering about going back to tech to chase money.

    Curious on your thoughts to re-create the confidence or in setting a new course without regrets?
    Finally, thanks for what you do! My biggest takeaway from your book was to establish Roth IRAs for my college age sons who work summer jobs and a little bit during school.


    1. my first time reading this site and trolling some comments. The perspective is great to read. So I am throwing some out.

      I’m 38, net worth of $2M and have two kids. So different life stage but I would kill to be in your position at 50. It is enviable. My work is a means to an end which is providing and spending time with my family. I hope to be able to retire or partially retire early but it does seem like a mirage that is always just out of reach. Just another $500K, just another $1M and we’ll be good is what I say.

      if i was you at 50 and still chasing money (totally possible), I would want my younger self to transport to the future and slap the shit of me. $8.5M is no joke. You could sell everything and make a risk free $350k/year in treasuries at this point.

      I try to put myself in someone’s position with $1M net worth. Surely they would say if I only had $2M I could live the life I wanted. Hoping this perspective sinks in to me at some point in the near future.

  10. Frugal Bazooka

    Regrets are built into the study of Economics, which after all is just the study of human behavior vis a vis obtaining or creating goods and services. Opportunity cost is present in every single decision we make, therefore I submit regret amounts to nothing worthwhile….if we’re being logical and not emotional.
    Of course humans are emotional, sentimental and in these modern times seemingly (and ironically) overly gloomy. I can think of 3 things in my life that I have regrets about, but each one was a decision that had a benefit and opportunity cost. I made the choices that were right for me at the time and my instincts tell me not to dwell too much, no matter how dumb they were in retrospect.

    1. Healthy outlook. Sometimes our regrets are us second guessing what was indeed our best judgement at the time. Go easy on yourself. Do due diligence and give it your best. There are lots of good future yous and good ways to be and live

  11. Sam, the picture of your kids celebrating in the bookstore has value that cannot be calculated — priceless. Thank you for being willing to share.

    The only parts of us that will truly be left after we are gone are our children, and any memories we have created in the people we have touched, both positive and negative.

    It will take some additional time to reflect on this post…. it is an important one in your substantial body of work.

    1. Thank you. It really was a special moment capturing them on video. It’s such a balance between work and being present and available for our children. We really don’t have that much time with them.

      Enjoy your time personally reflecting!

  12. HI Sam—

    Long time reader….I regret not investing in real estate like Fundrise as you recommended due to not understanding how it should be utilized in a retirement portfolio. Using Vanguard Advisors presently and they don’t recommend these. Now retired @70 and just watched my portfolio decrease by 20%.

    Not sure if it is too late or how to incorporate real estate into my asset mix for passive income?

    1. Hi Chuck,

      It depends on what your current passive income amount is and net worth allocation percentage into real estate.

      I wish I had a much larger percentage in private real estate as well this year. But at least we had a good run right? Now it’s time to spend more time enjoying life more.

      Heartland real estate rents continue to rise, but the pace of increases will slow. Currently, I’m happily stacking cashing with the 1-year T-bill at 4%+.

      1. Hello, can you please write an article on how to buy this 1 year T-Bill at Schwab/Merril/Vanguard brokers? It seems confusing to me to buy and figure out the auction dates etc. I want to put about ~1M into 1 year tbill and get 4% on that cash.

  13. Great choice of four pillars and lots of food for thought. I used to carry a lot of guilt, stress, and wishes/wants and it made me really unhappy and unsettled all the time. Especially carrying guilt, which is different from regret but similar in some ways.

    Once I started letting go and being happy and appreciative of where I was in the present, I just felt so much more at peace.

    Right now I don’t have any major regrets. That’s not to say I won’t later on. But I really don’t like the feeling of regret, dissatisfaction, and guilt. Maybe that makes me less successful or less liked though. But in any case I feel at peace with a lot of things.

    1. Congrats for being able to eliminate regret and find peace! That is unusual some thing I hope you share how are you did it.

      Let it go is easier said than done. But we must try since desire is the cause of all suffering.

  14. I don’t see how hindsight regrets could be something to dwell on. If you didn’t have complete information at the time, there’s no way you can be accountable for the outcome.

    For example: If you have a child with a terrible congenital condition and only find out later that you and your spouse always had a high chance of that outcome for any children, does that invalidate the existence of that child? Would any parent in that situation regret having children?

    If we do the best we can and then muddle through, that’s all that life asks of us. It’s a decent working definition of excellence.

      1. Hi,
        Why did you set up a revocable trust instead of an irrevocable trust? Creditors can still attach to a revocable trust. After 5 years an irrevocable trust is safe from all.

          1. Because after 5 yrs the asset is safe from potential estate creditors..Nursing homes, etc. They will take all the assets including life insurance if it’s not in an irrevocable trust for tye previous 5 yrs.

            1. Got it. Do you work in a high liability profession or have past history of being sued? Just curious to know what was the catalyst to go the irrevocable, never to be changed route. How old are you? Maybe I need to do some adjusting. Thx!

  15. Hey Sam, do you take post requests? Sorry if this is not the right place to ask. I want to know your thoughts about brokered CDs. I understand them I think in a basic sense but I am not sure exactly for which situations they are appropriate. Or is it everyone should take the higher rate they offer over regular CDs?

    And when you think CD rates (both regular\brokered) might peak. I think that CD rates are driven by the Fed funds rate but with a large lag time. If the Fed Funds rate gets to 4.0-4.5% what does that mean for 1y, 2y, 5y CDs and when? My other question is what to do with the cash in the mean time? Seems the dollar has continued to be strong (against other currencies anyway) so maybe cash is fine? Seems counter-intuitive given inflation being so high.

    1. Hi Travis, thanks for your questions. You have any regrets? And if so, how did you deal with your regrets?

      I’ve got some comprehensive posts on CDs if you check out my search box. Thanks

  16. Hi Sam – I’m a long time-reader of your blog. On wealth regret, do you recommend making extra mortgage principal payment during a recession (assuming there’s already a rainy day fund), or saving more cash? thanks!

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