THE LESSONS OF REGRET
What is regret?
Regret is an often unexplored and, consequently, poorly understood emotion. I mean, is it an emotion? Unlike sadness, anger, and joy, it’s complex. It is an emotional experience, but it’s also intellectual. Inherent to regret is the recognition that something in our past didn’t go how we would have liked, that there is some hypothetical past (and present) we would have preferred. When we experience regret, we experience the contrast between reality and an imagined alternative, a fantasy.
If you search for a definition of regret, you’ll likely find something simple like “a feeling of sadness, disappointment, or repentance about something.” While that’s correct, it also seems to miss regret's dynamic, multi-faceted nature.
Live each day so as to have no regrets
One of the most common approaches to regret in our culture is to just refuse to have it. The phrase “no regrets” is often used, but does everyone who uses it simply mean that they literally don’t have regrets? Is that even humanly possible?
Sam Harris offers a more nuanced and helpful take: Live so that at the end of every day, you have no regrets about what you’ve done that day. I’ve adopted this approach and now act with the end of the day in mind, asking myself, “Tonight, will future me feel good about how I’m spending my time right now?”
Instead of taking an overarching view of one’s life, this is a low-pressure, practical approach to regret. We wipe the slate clean and begin anew every day.
Immediate regret vs gradual regret
We seem to experience regret one of two ways: immediately or long after the fact.
Delayed regret happens after we’ve grown and matured. With enough time and accumulated wisdom, we look back on our past actions and wish we’d acted differently. We notice our younger self’s blind spots or mistaken beliefs and wonder what might have been if we could go back and do things differently.
Immediate regret, on the other hand, is like a slap in the face. We say the wrong thing, lash out, make a stupid split-second decision, and immediately feel the regret set in. Our mistake is clear and obvious, and that split second of realization presents us with a powerful growth opportunity.
What does each kind of regret have to teach us?
Delayed regret is often the kind that slowly eats at us over the years. It’s the college major we actually wanted, the girl/guy that got away, the trip you never took. And it often comes with the belief that “It’s too late to do it now.” But is it? Maybe the exact opportunity is gone, but how can you act today to correct for your younger, immature self’s mistake?
Working 65-hour weeks, you missed your first son’s childhood, so you take your “oops” baby as a second chance to show up and be a dad.
You dated people casually, one thing led to another, and you’ve since married and divorced. Now, you're back to dating, but this time, you're looking for people whose values, personalities, and long-term goals match yours.
Your parents are getting old, and you’ve only seen them a couple of times each year for the last decade. Make it a point to spend more time with them in the coming decade. It could be their last.
Immediate regret is an opportunity to practice humility and integrity. It challenges us to set our ego aside and immediately make amends. Instead of doubling down on our mistake, we walk it back, regardless of how embarrassing it is. Even if it feels like admitting defeat, apologizing or correcting ourselves in the moment of immediate regret reinforces our integrity.
Regrets at the very end
Bonnie Ware interviewed people in palliative care and compiled a list of the five most common regrets of the dying.
I wish I’d had the courage to live a life true to myself, not the life others expected of me.
I wish I hadn’t worked so hard.
I wish I’d had the courage to express my feelings.
I wish I had stayed in touch with my friends.
I wish that I had let myself be happier.
Four of these five regrets are regrets of inaction, of things left undone and missed opportunities. Only one is a regret about something done and later regretted. This is often the case with regret; we regret the opportunities we didn’t take more often than the mistakes we made.
If you want to look back on a life well-lived, it is better to have acted and failed than not to have tried at all.
Whether it’s something as simple as getting a pedicure or as life-altering as changing careers, if you’ve been kicking that can down the road, there will never be a convenient time to do it. If it’s important, start now.
The philosophy and psychology of regret
It’s important to remember that when we regret the past, we make a faulty comparison between reality and an imagined fantasy. It’s an apples-to-oranges comparison in which it’s easy to pretend everything is apples. So how does this apples-to-oranges comparison fall apart?
In Stumbling On Happiness, Dan Gilbert explains that we misjudge how happy imagined scenarios would make us. Our imagined alternative lives are based on flawed memories and simplistic, overly optimistic assumptions. When we regret the past and imagine what might have been, we fail to imagine all of the ways things could be worse or consider the good things in our real lives that would be lost.
Impact Bias leads us to overestimate how events would have affected us emotionally, both positively and negatively. Big life events often have less impact on our happiness than we expect. Each of us has our own emotional baseline. Whether we’re typically grumpy, joyful, or somewhere in the middle, our emotional adaptability and resilience lead us back to that baseline in the long run.
The fundamental difference between reality and imagination, discounting the long-term impacts of big life events, and our emotional adaptability are just three of the ways we may mislead ourselves into simplistic thinking driven by regret.
So what’s the big takeaway?
Regret is complex. It’s both an emotion and a story about what might have been, comparing reality and a fantasy. If we’re not careful, regret can lead us to devalue our life, with its messiness, unexpected turns, and failures.
But regret is also an opportunity to learn from our past and make better choices on the road ahead. The key is not to avoid regret but to meet it with curiosity.
