“Anxiety is the dizziness of freedom.” ¹

Kirkegaard summed up the bittersweet dilemma of modern existence nearly 200 years ago. If anything, life today is even more dizzying – and anxiety-inducing – now that we’re freer than ever to choose where to live, where to travel, who to spend our lives with, and what to read, watch, listen to, do for work, and do for fun before we die. 

The two insidious little words at the root of all anxiety are “what if.” Unlike dolphins, katydids, and all other sentient beings, humans can imagine a scenario other than what is, opening the door to one of the most dreaded emotions in existence: regret. 

Regret is unpleasant at best and gutting at worst. We’re wired to make choices that minimize regret as much as possible, whether that means the safer or riskier option. We hate putting ourselves in peril but also missing out on a stroke of good fortune or “a good deal.” ² Lotteries, insurance plans, and the stock market are all examples of how our fear of regret has become a multi-trillion-dollar global system. The Nobel prize-winning psychologist Daniel Kahneman sums it up well when he says regret is “a punishment we administer to ourselves.” ³

We can try to ignore regret, laugh at it, or deny that it exists for us, to varying degrees of success. Yet regret, like anxiety, is baked into the human condition. There’s no question whether we can escape regret during our lifetimes; we can’t. A better question is, how much should the fear of regret affect our decisions?”

This is one of the tougher existential riddles I don’t think we appreciate enough. Anticipatory regret – regret we imagine we’ll feel – is very effective for high-risk, low-reward choices. It’s not hard to imagine we’ll regret driving 60 miles an hour through a school zone to shorten our trip to the grocery store. But what about hiking Mount Kilimanjaro, getting married, or starting a bakery? The same reasoning that protects us from harm can also cut us off from the greatest joys and satisfactions in life. How do we get around this?

Embrace the Possibility of Regret 

One of the strongest arguments against thinking about regret is that focusing on either the past or the future takes us out of the present. “Keep hold of this alone and remember it,” advises the Stoic philosopher-emperor Marcus Aurelius: “Each of us lives only now, this brief instant. The rest has been lived already, or is impossible to see.” ⁴ Nietzsche posed an even more radical argument against regret with his embrace of “amor fati”: love your fate, no matter what comes, and don’t wish it for it to be any different.

There is a lot of wisdom in loving and accepting what is, especially since there are no controls in life to see what could have been, and that’s a good thing; we’d go insane otherwise. But the past and the future are real in their own way and they require our attention to make any meaningful decisions. As wonderful as it would be to live in the moment every moment, that pleasure is reserved for all the other animals. We can savor an ice cream sundae while we’re eating it, but life is composed of more than ice cream sundaes.

Janet Landman does a beautiful job showcasing the positive side of regret in her book Regret: the Persistence of the Possible.  Regret can be good, Landman argues:

“It is a good thing that the human mind is not limited by what actually exists. It is in this capacity to care enough about the particularities of experience to bother to imagine alternatives to reality that we accomplish the task of becoming fully human.”  ⁵

Here’s another way to think of this: rather than seeing regret as a punishment for being human, look at it as an acceptable side effect. Yes, being human means we will feel anxiety and occasional regret, but it also means we have the ability to progress and achieve and accomplish. Since there is no getting away from this double-edged sword, why not focus on the positive side?

Only by embracing the possibility that some of our decisions may lead to regret will we free ourselves from the mire of anxiety. Anxiety will always hover in the background, but it won’t be in the driver’s seat. It will take its rightful place as a reminder that to be human means to care, to love, to imagine, to try to do the best thing with the information we have on hand. ⁶

A Useful Heuristic for “Will I Regret This?” 

Life is messy no matter how careful or wise we are but it’s fair (and only human) to ask, “Is there a cheat code to help us make choices we don’t regret later?” I think there is. But it starts by understanding that regret comes in different categories.

The journalist David Pink conducted what is to date the largest survey ever done on regret. He made a discovery that’s been corroborated by research: we tend to regret the things we didn’t do more than the things we did. To complicate the matter, Kahneman (the guy who described regret as “a punishment”) and others have found that regrets of action hurt more than those of inaction in the short term. Could the latter be responsible for the former?  

Here’s an example: you don’t want to regret saying something nasty to a person who is behaving offensively. But in being so careful not to, you end up never saying or doing anything at all, leading you to later regret that you weren’t more courageous. Of course, there is a middle ground: you can be courageous without being mean or petty. But the middle ground does not make for easy landing, so many of us default to inaction.

A choice that requires you to go out of your way for something meaningful is probably a choice you won’t regret.

If there is any shorthand I can think of for avoiding this pitfall, it’s this: A choice that requires you to go out of your way for something meaningful is probably a choice you won’t regret.

Standing up to a bully, hopping onto a plane to see your friend in the cancer ward, going to Iceland with your toddler now instead of wondering if you’ll have another chance later: it’s hard to imagine regretting any of these. Even if the outcomes are not as warm and fuzzy as you’d hoped, you acted out of courage and faith. The sting of “what if” is not nearly as strong as it would be if you hadn’t done the proactive thing.

And for all other choices that don’t fall into this category? Maybe it doesn’t matter so much. Our anxiety tells us it does matter, all of it matters, but with some wisdom, you can discern the difference. Staying home and watching TV instead of going to Europe with your family may be a choice you come to regret. But should you go to Germany or France? Should you take a river cruise or go by train? Those are minor details in comparison. 

At its worst, anxiety keeps us so paralyzed by the fear of choice and regret that we never get around to truly living. The unknown – the great and dreaded “what if” – will always be lurking there, but it need not be a serious concern if we are always in motion and awake to the possibilities around us, ours for the taking if we simply reach out.

Perhaps the real superpower in life is not getting rid of anxiety, but harnessing it to our advantage by making choices that can be scary, and embracing whatever comes as a result. Or in the more memorable words of Kirkegaard: “Whoever has learned to be anxious in the right way has learned the ultimate.”

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1. Kierkegaard, S. (2014). The concept of anxiety: A simple psychologically oriented deliberation in view of the dogmatic problem of hereditary sin (A. Hannay, Trans.). Liveright.
2. Zeelenberg, M. (1999). Anticipated regret, expected feedback, and behavioral decision making. Journal of Behavioral Decision Making, 12(2), 93–106. Read here.
3. Kahneman, D. (2011). Thinking, fast and slow. Farrar, Straus and Giroux.
4. From Meditations, Book 3.10
5. Landman, J. (1993). Regret: The Persistence of the Possible. Oxford University Press. 
6. You’ll find a beautiful (and quite literal) example of this in the Disney film Inside Out 2.  Anxiety, one of the principal characters, discovers that she is more empowered when she takes a supportive role rather than an executive one. Likewise, Joy discovers that getting rid of Anxiety is not an option; they need to work together.