What We May Regret

Calculate the risks you are willing to take based on the regrets you might have 5, 10, or 50 years down the road.

If you type in Regret to Google, you get 765,000,000 results.

There is a reason why it populates millions upon millions of results. Regret makes your skin crawl a little. For humans, it is a big piece of who we are, and it lives at a very high cost in our heads. Everyone wants to avoid paying these high costs. People may ask individuals whose time is coming to an end, what they regret so maybe they can avoid that same fate. Or if you ask anyone what their biggest regrets in life may be, it is met with a long, deep breath out and a pause as the brain unearths one of the scariest things, regret. Thanks to this, much of our culture tries to optimize for the avoidance of regrets at all costs.

If you type in No Regrets to Google, you get 161,000,000 results.

No Regrets is a bloodline to our culture. Popular songs, tattoo shops, movies, conferences, and books are all titled No Regrets. It convinces anyone to stop and look twice because everyone is led to believe we should have no regrets. We are taught to avoid it at all costs and that regret is poison. Regret can linger in our heads and eat away at us for years. 

Image courtesy of Reddit.

Except I believe that is dead wrong.

About a month ago, I was in Seattle with some friends to visit a friend. My friends and I love to take a saying and beat it to the absolute death when we are together. It just so happened that on this trip, everything was about “take risks.” The day before we arrived in Seattle, I had just posted “You are Already Naked, Jump”. It was a piece I had written about taking risks at a young age because early in your career, you really can’t get much closer to rock bottom. It was fitting. My friends ensured I practiced what I preached during that trip. Any decision we made or agreement we had to reach on where to eat, what to do, or people to see, all was met with someone saying, “take risks.”

Never eat Asian food but we want to go out to an Asian restaurant? Take risks.

Why should you jump in the sub-32-degree bay water? To take risks.

Should I do a five-mile run in the rain? Take risks.

It was all in good faith, but it led me to think what exactly is taking a risk? Sure, it is a strong belief to embody but what does that actually look like?

I think the best way to view risk is through the lens of regret.

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We shouldn’t avoid regret at all costs. It is a powerful tool. It informs. It is healthy. It is valuable. Regret makes you who you are today. All the regret culminates into the person you become and for the most part, you are probably better because of it. You learn and grow from it. Don’t optimize to avoid regret, instead leverage it.

I think the best way to know if you should take a risk is to have a sense of your future regret. I believe this is especially helpful with big, important financial decisions. It helps to inform you on how things may turn out if they don’t go as planned or don’t happen at all. Risk is the regret that may come from this. It is not about deleting all regrets; it is about understanding what your future regrets may be and using that to guide your current decision-making process.

I am still young but if you asked me what I regret, I think my list would be few. Sure, I regret some things in high school and maybe a thing or two in college, but I am still quite young to have a long list of regrets. Also in college, I was always saying yes, sometimes too much, and I worked tirelessly to be able to afford all the activities we did. There is not a ton that I wish I did or financial investments I wish I had made. My college experience wasn’t made that way. I am sure some regrets will come down the line when the responsibilities become greater, and the time becomes less. However, part of the value in always saying yes is I didn’t miss out on a lot. Of course, on the other side of that, I wasn’t exactly flush with cash either, even on a relative basis. 

Much of regret is borne out of what you didn’t do, so by saying yes I  wasn’t allowing regret to happen. It wasn’t me trying to avoid it either. It was me knowing I would regret not participating in these things down the line, even though it may have meant risking much of the money in my bank account to make it happen.

In college, I never had crazy investment opportunities to triple my net worth or invest in anything with an outsized return that would have had ripple effects down the line. Instead, I had opportunities to create memories and experiences to last a lifetime. After college, the flip switches. Now, we have opportunities to invest and now we have real opportunities to take risks with our money because we finally have some. Whether or not you should assume that risk I think can be evaluated on if you may regret the final costs or decisions that come years or decades later.

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Jeff Bezos put it well when discussing why he felt the need to start an online bookstore, Amazon.

“The framework I found which made the decision incredibly easy was what I called the regret minimization framework. I wanted to project myself forward to age 80 and look back on my life and I want to have minimized the number of regrets I have. And I knew that when I was 80, I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the internet that I thought was going to be a really big deal. But I knew the one thing I might regret is not ever having tried. And I knew that that would haunt me every day. So when I thought about it that way it was an incredibly easy decision.”

It is less about minimizing the number of regrets we may have. It is more about calculating the risks we are willing to take based on the regrets we might have 5, 10, or 50 years down the road. Jeff Bezos knew not participating in the internet may haunt him. The risk of taking part in the internet and failing was much less than the risk of not trying at all. The evaluation of risk was all rooted in what he may regret.

In the Power of Regret, Dan Pink calls this boldness regrets. It is built on “if only I had taken that risk.” People regret inactions more than actions. It is rooted in coulda, shoulda, woulda. It leaves the question of “What if?” We know what happens next when we act but inaction leaves a lingering “What If?” We hope to use our limited time to grow but a boldness regret stunts this growth.

If a friend came to you with an investment opportunity and you deem it worthy of a possible investment, it may be best to view it through the lens of “Will I regret not participating in this opportunity in the future?” We never know how much we can risk but we all have a strong gauge on what we may regret. So if you are wondering if you should risk investing $25,000 in your friend's fitness venture? It may be best to look at it through the lens of “Will I regret my inaction?” Will I always be left with “What If?”

There’s also an important caveat here. Every piece of your life should not be about minimizing regret. Jeff Bezos used that framework because it was a huge decision on where his life may go and what he wanted to see happen. It wasn’t trivial and affected him on a fundamental level. It was not a simple decision on what shirt he might buy or what lawnmower he might need. I can’t ever remember a time when I deeply regretted buying something so small. Always trying to anticipate regret in everything you do, no matter how little, is surely to lead to discomfort and displeasure.

Rather, if the decision involves a fundamental change, piece, or investment in your life, I think the decision may be made easier if you forecast the future through the lens of regret. Deciding what to pour your money into at a young age is a foundational part of your future. We all have our safe investments like our 401k but naturally, we also want to assume risk. Make a few “riskier” investments with regret in mind but also within reason. This can give you a good gauge on how much risk you can stomach but you can never get there if you avoid regret at all costs. Investments are sure not to work out and some financial decisions will not lead to the most optimal results but that is all part of life.

Regret is a necessary part of life and it is much more painful than failure. Ask yourself which decision, path, or action may help you lay a strong foundation, take a reasonable risk, strengthen a meaningful relationship, or do what is best for you. It is not what microwave you might regret not buying. Anticipate regret on large, meaningful decisions. It will help you to decide how much risk you can take and help you to limit your future regret. If we know what we may regret, we can know what we are truly willing to risk. That is how to live a life well lived and that is how my friends like to say to “take risks.”

Appreciate you reading.

-Scantron