Regrets

January 9, 2023

“Regrets, I’ve had a few. But then again, too few to mention…” might be the lyrics of a good Frank Sinatra song but it is bad “psychology, neuroscience, and when you get down to it, history,” writes David McRaney in his review of The Power of Regrets.” The author, Daniel H. Pink, says a “no regrets” mindset is “…not a blueprint for a life well lived. [It is] …forgive the terminology – bullshit.”

Regret is a negative emotion, but it is not unhealthy or abnormal. Pink explains “It is …universal, an integral part of being human. …It clarifies. It instructs. Done right, it needn’t drag us down; it can lift us up.” It balances positive emotions and helps stimulate learning and growth. It helps us survive. Like everything in life, in excess it is a problem. But too little is also an issue.


Pink sorts regrets into four categories and “Connection Regrets” are by far the most common. We “…have a massive amount of regret about fractured or unrealized relationships,” explains Paula Davis in Psychology Today. And those regrets are either “open door” or “closed door,” depending on the possibility to change them.


In my case, it was my wife dying of cancer that simultaneously opened my eyes to my negligence as a husband and slowly closed the door to my chances to do any more about it. Most of our marriage, I treated her how I would want to be treated instead of how she needed to be treated. On our premarital counseling personality test, she scored 100% on “feelings” and I got 0%. I was a bull, and she was a China shop. It was a match made in heaven, but the journey took some detours down roads paved with my good intentions. I tried to be sensitive, and she tried to be understanding, but we still ended up with a lot of broken glass. The good thing was that we always cleaned up the mess together.


Barbara and I finished well because she was good, and I got better at learning from my regrets. As Pink explains, “All regrets aggravate,” but they can be productive instead of destructive if they motivate you to positive actions. So, instead of ignoring or despairing you can use the negative feelings as instructions
for “…making better decisions, …improving your performance, …deepening your sense of meaning.”

The regret-fueled changes that I made helped Barbara and I cram a lifetime into 7 months. That’s because when facing death, you live in the moment and time stands still. However, when facing retirement, time marches on closing the door for compounding to grow wealth. This fact is often lost on the young because the perception of time is not constant. It speeds up with age, which is why a survey from Magnify Money “…found that the biggest [financial] regret among Americans is not investing sooner.”

If you have similar regrets, you are not alone. The survey finds that “Investing regrets are the norm… [and most people] …believe investing regrets are inevitable.” However, repeating the mistakes that led to regrets is not inevitable. You may be behind, but Pink reminds us that saving for retirement “…is like the
old proverb. The best time to plant a tree was 20 years ago, and the second-best time is today.”


Frank Sinatra’s daughter revealed that he grew to hate My Way. Contrary to what he sang, he had more than a few regrets. The ones he mentioned most were about ignoring his family. I regret that I wasn’t a better husband. But Pink tells us the purpose of regrets is to make us feel worse today “…to help us do better tomorrow.” I became a better husband and am now a better father and grandfather. Regrets have also made me a better advisor and can make you better at managing your finances. We can’t change the past. But we don’t have to repeat it. There might have been a better time to do something, but until the door closes, we always have the second-best time – today.

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