Despite the differences that divide us as humans, we all share common, universal emotions such as fear, love, sadness, anxiety, envy, gratitude, and regret.

Two roads diverged in a yellow wood,
And sorry I could not travel both.

So, what can regret teach us about life? Let’s find out together.

Regret is a cognitive emotional state that involves blaming ourselves for a bad outcome. Like putting hot cheese and chili on your roller-grill hot dog at QT and realizing ten miles later that you’ve made a terrible mistake. (C’mon, don’t act like you’ve never been there.)

Chili AND hot cheese from a gas station has regret written all over it.

Regret is a thief. It can literally rob your life of joy and happiness. It is the enemy of imagination, creativity, and, most importantly, contentment. You simply cannot be content and regretful at the same time.

Regret is the most private feeling or emotion we own. Nobody really wants to air all of their dirty laundry, right? Deep down, we all have a lockbox full of those cringeworthy decisions. Decisions that, when replayed in our minds, can stop us in our tracks.

Then took the other, as just as fair,
And having perhaps the better claim,
Because it was grassy and wanted wear;
Though as for that the passing there
Had worn them really about the same,

Daniel H. Pink is an expert on regret. He’s also the author of five New York Times bestsellers, including his latest, The Power of Regret: How Looking Backward Moves Us Forward. The book is based on two large and unprecedented research projects in which Pink collected over 16,000 regrets from regular people like you and me. According to Pink, “Regret is not dangerous or abnormal, a deviation from the steady path to happiness. It is healthy and universal, an integral part of being human.”

Pink synthesizes all that feedback into four buckets of regret. See if any of them resonate with you.

First, there are foundational regrets. These are things like not going to college or not saving more money in your 401(k)—the kinds of decisions that would have brought you more stability later in life. These are the regrets that start with “if only.” As in, if only I had purchased $10,000 of Apple stock in 2007 when I bought my first iPhone. By the way, that investment you didn’t make is now worth $502,966.

Second, there are boldness regrets. That is, “I wish I had taken more aggressive action.” These regrets usually harken back to chances not taken, to a fear of boldness, or to a fear of rejection or embarrassment. For example, what if you had pursued that graduate degree or followed your dream of opening that fondue restaurant? What could have happened? Where might you be today? The regret is tied completely to your lack of boldness at that moment. Imagining a life unlived can be torturous.

And both that morning equally lay
In leaves no step had trodden black
Oh, I kept the first for another day
Yet knowing how way leads to way,
I doubted if I should ever come back.

The third type of regret is moral regret. These are the regrets pertaining to our actions, meaning that we didn’t align our behavior with our own values or what we believed our values should be. Maybe you stopped paying taxes for a few years. Or, maybe your resume isn’t exactly 100% accurate but you got the job anyway. These are regrets that may not be known to anyone else but you-and they can be haunting.

The fourth type of regret is connection regret. These typically stem from relationships that we didn’t maximize. This doesn’t necessarily mean the relationship had a cataclysmic demise like an episode of The Bachelor. Many times these are the relationships where we simply found ourselves drifting apart, losing focus, and hesitating to reach out later due to the perceived risks involved. The universal law of inertia had its way with us.

While taking action may bring more immediate challenges, it is often the inaction that leads to long-lasting regrets. Inaction tends to illustrate our failure to live up to our own goals and aspirations. Those regrets can instantly replay in high-def on that flat screen tucked in the back of our brains.

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That internal flat screen can instantly recall technicolor memories from the major stages of life. They replay like a trailer for the sequel to Titanic.

So, what does exploring regret have to do with our happiness? Doesn’t reliving our biggest regrets lead to a lifetime of unhappiness? Not really.

It’s possible that the four core regrets (foundational, moral, boldness, and connection) hold the secrets to inner peace and tranquility. By revisiting our regrets, we can learn from our mistakes and do better in the future. (Assuming that we don’t get stuck in a cycle of ruminating over the past.) We can identify the things that truly bring us happiness and discover our core desires. Regrets provide a little instruction book for finding what will ultimately make us happy.

So, let’s review this together. Regret falls into four simple categories, three of which are caused by inaction and one by poor actions. The inaction regrets are foundational regrets (like if only I had made different decisions), boldness regrets (like wishing I had taken the risk when I had nothing to lose), and connection regrets (like friendships that I didn’t maximize when I had the chance). Moral regrets are based on poor actions (like regretting eating that delicious hot cheese and chili dog ten miles ago). Okay, that’s not really a moral regret, but you get the point.

I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.

So, what about you? Do you have any regrets that you’d like to get off your chest? Leave me a comment below and share what still keeps you awake at night—as long as it isn’t the hot cheese and chili you ate on the way home. Keep that to yourself, please.

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Four Things Regret Can Teach You About Yourself

© Tom Greene 2023. All Rights Reserved.