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The Power of Regret, by Daniel H. Pink
“This is one of the central findings on regret: it can deepen persistence, which almost always elevates performance."
Matt Karamazov
October 30, 2023 • Estimated Reading Time: 25 minutes
YOUTUBE đź“š THE COMPETITIVE ADVANTAGE đź“š PATREON
đź“š Hey, good evening!
Editing this YouTube video is taking a bit longer than I expected, but it’s an extension of an idea that struck a chord with thousands of people on my other social media channels, so I decided to make a whole video about it.
The working title is “The Only 2 Places on Earth Where Everybody is Welcome.”
I’ll try to come up with a little better video title than that, but it’ll be going up on my YouTube channel as soon as it’s done. Hopefully tonight!
Right now, though, we’ve got my latest in-depth book breakdown of The Power of Regret, by Daniel H. Pink.
Regret may be our most misunderstood - and yet also our most valuable - emotion. In the book, Pink explores how we can tap into its power and wisdom and use it to help us live differently, and better, from this day forward.
The breakdown itself is about 10,800 words, covering all the Key Ideas, Book Notes, Action Steps, and more.
It’s also free, by the way.
It’ll only take you about 41 minutes to read the whole thing, and in it, you’ll learn about how to think differently about regret and transform it to help you approach the rest of your life more positively from now on.
Virtually everyone has at least a few regrets about how they’ve lived their lives so far, but your past doesn’t have to define your future.
You can read the full breakdown here, but I’ll give you a little preview in this email so you can decide whether to check out the full one later.
Again, totally free.
I should actually say “free for right NOW,” because it’s going back behind the paywall very shortly.
Then it’s just for members only at the Stairway to Wisdom.
Alright now, let’s learn how to apply…
This Book is For:
*Everyone who is interested in learning how to utilize our most misunderstood emotion both to make better decisions in the future and to tell ourselves a different story about our past.
*People who are curious about how the human mind can somehow take the pain of regret and turn it into the balm of wisdom.
*Individuals who tend to be overly self-critical or engage in unhealthy rumination, and who want to be set free by learning how to process regret and turn it to our advantage.
*Anyone who has ever been stung by regrets large or small, and has ever sat awake at night wondering what might have been.
Summary:
"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. Regret is also valuable. It clarifies. It instructs. Done right, it needn't drag us down; it can lift us up."
I'm going to open this Very Serious book breakdown with one of my favorite jokes: "I took the road less traveled, and then I had to eat bugs until the park rangers rescued me." Hold for Laughter
Jokes aside, it's more or less a universal human experience to look back on the path we never followed and feel a nagging, painful, sometimes sinking, sickening feeling that we've somehow missed our chance, that we've traded our many unlived lives for this one, real life, and that it could have been so much better had we simply acted differently.
Virtually everyone has experienced something to the same effect, ranging from the "that might have been nice," to the "damn, I really should have done that," all the way to the "I've thrown it all away and I'll never, ever recover from this."
Anyone who says that they have no regrets is also usually viewed with suspicion by most people who have taken the time to reflect on their own personal history.
In this book, The Power of Regret, Daniel Pink refers to regret as our most misunderstood emotion and shows how it can potentially be transformed, transmuted into something extraordinarily valuable. We can reflect on our regret, reorganize it in our minds, reconceptualize it, and then use it to live better with all the time we have left.
While philosophers like Friedrich Nietzsche took a different view of regrets (we'll get to him later), Pink believes that they are a universal and healthy part of being human. He supports his arguments by offering evidence from the largest sampling of American attitudes about regret ever conducted - including his own World Regret Survey - which has collected regrets from more than 15,000 people in 105 countries.
What he found was that the most important, nagging, and painful regrets often fall into one of four categories: foundation, boldness, moral, and connection regrets, all of which we'll discuss later on.
But he also mentions how people tend to overvalue positive emotions and undervalue negative ones. Everyone wants to feel good, be happy, and avoid pain and discomfort, but ignoring and suppressing our negative feelings and emotions - including regret - cuts us off from a key source of potential growth and self-knowledge.
Importantly, if you know what people regret the most, you also know what they value the most. In terms of the core four regrets, human beings tend to value stability (health, wealth, etc.), with a dash of adventure (taking chances, making bold moves, learning, and growing), doing the right thing (and experiencing hurt when we stray from the moral path), and connecting with others (forming and deepening relationships of all kinds: social, economic, and romantic).
As you can see, however, by valuing such a wide range of important human experiences, we also open ourselves up to profound regret from multitudinous sources. There are so many ways that one single person can go wrong. Against the emotion of regret, it turns out, we never really stood a chance.
What's more, navigating regret (and life) is always an ongoing process of closing certain opportunities while at the same time opening new ones. Every action we take determines the possibilities that are available to us in the next moment, and we are always choosing, even when we do nothing.
But we are not helpless against regret, as Daniel Pink argues in this book. We can enlist this misunderstood, potentially painful emotion in service of living a larger life, gaining redemption, and reclaiming at least a portion of our remaining unlived lives.
Key Ideas:
#1: One Look Back, Two Steps Forward
“Regret is the quintessential upward counterfactual - the ultimate If Only. The source of its power, scientists are discovering, is that it muddles the conventional pain-pleasure calculus. Its very purpose is to make us feel worse - because by making us feel worse today, regret helps us do better tomorrow."
Regret is a useful gift that nobody wants. Its purpose is to use psychological pain to motivate us to analyze our past, sit with our mistakes, and use the knowledge we gain to make better decisions in the future. Regret helps us live better, but not necessarily while we're experiencing it.
Sometimes we have to look back to see how we can move forward, and the emotion of regret is perfect for this task. It would be useless if we didn't do anything with it, but the very fact that we can extract meaningful lessons from the experience of regret is an extremely valuable gift.
The mechanism that it uses is psychological pain, that awful, stomach-dropping sensation of missing some precious, fleeting, irretrievable chance we'll never get again. Regret makes us feel horrible - so horrible that we resolve, however possible, never to reexperience it, and we take drastic action to avoid feeling that way ever again. It uses pain to motivate us to make progress.
You can think of it almost like the "hot stove" of our emotional arsenal, meaning that, after placing our hands on the hot stove of regret and feeling its gut-wrenching pain once, we'll hopefully never do it again.
Some people keep making the same mistakes over and over again, but for most of us, if it hurts enough, we'll go the rest of our lives avoiding the surface of that stove. This is how regret can make us better, how it can improve our lives.
The fact is that if your life isn't bad enough, you won't be all that motivated to change it. I've been there. I was doing "fine," but I wasn't loving how my life was going. It's easy to stay in that place of "good enough" for years on end, decades even, and then at the end of your life look back and get rocked by regret.
In that sense, experiencing regret early on is one of the best things that can ever happen to you, because then you have the whole rest of your life to make sure you never feel that way again (to the extent that that's possible).
More often than not, it's regret that can most effectively turn up the temperature of our emotional stoves, motivating us to work harder, for longer, think more deeply, and live more intentional lives:
“This is one of the central findings on regret: it can deepen persistence, which almost always elevates performance."
When the pain of regret is strong enough, we work so much harder than we would if we just "kinda" wanted things to be a little bit better. What happens is that we never want to feel that way again - we're desperate to avoid that sinking feeling tearing out the bottom of our soul - and so we keep going. We persist.
#2: The Four Types of Regret
"When we envision how awful we might feel in the future if we don't act appropriately now, that negative emotion - which we simulate rather than experience - can improve our behavior."
In the next few Key Ideas, I examine each of the four types of regret in more detail, but they include Foundation, Boldness, Moral, and Connection regrets, each of them associated with various human needs and possible lessons we can learn.
Fully experiencing each regret and leaning into what they have to teach us can help us lay out a roadmap for exactly what we need to do to avoid re-experiencing that type of regret in the future.
The truly amazing thing about our brains, though, is that they have the power to simulate these regrets in our minds so that we can learn how to avoid them before they even happen. Experience is probably the best teacher, but simulated experience can serve the exact same function.
For example, boldness regrets have to do with missing the chance to grow, evolve, or pursue some opportunity by taking action in the here and now. It's failing to speak up when you have an idea that can help your team achieve its goals, failing to offer your phone number to that attractive stranger, or not accepting that exciting job offer halfway across the country and forever wondering what might have been.
When you simulate these feelings in your mind, you can go part of the way toward feeling how you would feel if you didn't take that chance. If you let that woman leave the coffee shop without saying hello to her, how would that make you feel? If that simulated regret hurts enough, it will motivate you to put potential embarrassment aside and just go say hello already!
Human nature being what it is, however, virtually no one gets to move through life without experiencing any regrets at all. It usually takes at least one dark night of the soul per regret type (sometimes hundreds) before we actually get it.
#3: Foundation Regrets
"All deep structure regrets reveal a need and yield a lesson.
With foundation regrets, the human need it lays bare is stability: we all require a basic infrastructure of educational, financial, and physical well-being that reduces psychological uncertainty and frees time and mental energy to pursue opportunity and meaning.
The lesson reaches back two and a half millennia. Think ahead. Do the work. Start now."
The first category of regret that we'll take a closer look at is what Daniel Pink calls "Foundation" regrets, which can be thought of as all that "base of the pyramid" stuff that places us on a secure footing from which we can venture forth and attack life.
Regrets here concern things like not getting an education, not saving enough money for the future, not reading enough, often enough - that type of thing. While not necessarily as painful as something like moral regrets, where we may have done something awful when we were younger and spent the rest of our lives hating ourselves for it, foundation regrets can still be quite difficult to live with.
What makes them even more acutely painful is the realization that it may be too late to do anything about them. You only get one shot at your twenties, you can only enroll in university courses for the first time once, and compound interest is much less powerful when you chop off the first ten years.
That being said, unlike connection regrets that take a relatively long time to manifest, foundation regrets can be somewhat ameliorated by attacking them early.
If you take a proactive stance toward foundation regrets when you're young, and you take immediate, effective action in order to reduce the probability of experiencing these types of regret when you're older, it can help protect yourself from this type of regret.
It's always easiest to stop a fire when it's still small, and even if you didn't plant a tree twenty years ago, you can still plant one today.
Book Notes:
“In fact, I have yet to uncover a study disconfirming the ubiquity of this emotion. (And believe me, I've looked hard.) Scholars in every field, approaching the subject from different directions and using a variety of methodologies, arrive at the same conclusion: 'To live, it seems, is to accumulate at least some regrets.'"
“I regret that I didn’t appreciate reading earlier in life. Now I see the value of reading and often wonder what the compounding effect would have been if I had started ten to fifteen years earlier."
“People often talk about regret in terms of doors. Amy has a 'closed door' regret. As she told me, the opportunity to restore her connection with Deepa is gone. Cheryl has an 'open door' regret. The opportunity to reconnect with her college friend remains."
“We seek a measure of stability - a reasonably sturdy foundation of material, physical, and mental well-being.
We hope to use some of our limited time to explore the grow - by pursuing novelty and being bold.
We aspire to do the right thing - to be, and to be seen as, good people who honor our moral commitments.
We yearn to connect with others - to forge friendships and family relationships bonded by love.
A solid foundation. A little boldness. Basic morality. Meaningful connections. The negative emotion of regret reveals the positive path for living."
"Live as if you were living for the second time and as if you had acted the first time as wrongly as you are about to act now!"
Action Steps:
So you've finished reading. What do you do now?
Reading for pleasure is great, and I wholeheartedly support it. However, I am intensely practical when I'm reading for a particular purpose. I want a result. I want to take what I've learned and apply it to my one and only life to make it better!
Because that's really what the Great Books all say. They all say: "You must change your life!" So here, below, are some suggestions for how you can apply the wisdom found in this breakdown to improve your actual life.
Please commit to taking massive action on this immediately! Acting on what you've learned here today will also help you solidify it in your long-term memory. So there's a double benefit! Let's begin...
#1: Reverse Your Old Year's Regrets
Most people spend the last few days of the year thinking about all the new positive changes they want to make in the coming year. But how many people look backward at the previous year, and try to identify where they made the wrong choice and how they can make different choices the following year?
That's what Old Year's Regrets are all about, and you can use them to learn from the mistakes you've made during the last 365 days and chart a different course for the 365 days ahead.
This doesn't have to take a lot of time; just spend a few minutes to an hour looking back at the last year, and try to identify 3-5 specific regrets that you can work on undoing or coming to terms with going forward. Make transforming these regrets into something positive your top resolutions for the next year.
#2: Self-Compassion, Self-Disclosure, and Self-Distancing
“Looking backward can move us, but only if we do it right. The sequence of self-disclosure, self-compassion, and self-distancing offers a simple yet systematic way to transform regret into a powerful force for stability, achievement, and purpose."
According to Pink, we can begin to transform our regret by traveling through three distinct phases. The first is self-compassion, where we replace hostile (and often unhelpful) self-judgment and criticism with compassion and basic kindness, as though we were talking to a really good friend for whom we wanted the best.
Of course, this doesn't mean that we ignore the mistakes we've made or neglect our weaknesses. It just means that we take a constructive attitude toward them, recognize that they are part of the universally shared human experience, and treat ourselves more kindly.
Next, we practice self-disclosure, which means opening up to others about the sources of our regret and letting them help us relieve the burden of our regret.
Recognize also that most people will not think less of you for doing this. They won't think that you're a horrible person, or weak, or anything like that. I mean, some people might, but the people you want to build a future with definitely will not. They will support you no matter what, and disclosing your regrets to them (and remaining open to hearing about theirs) can serve to deepen your relationship with them.
Lastly, we move on to self-distancing, which is where we zoom out and look upon our regrets as a detached observer might see them. This will help you reframe the regret in question, seeing the situation as it really is, and helping you plan, strategize, and extract a useful lesson from your regret that can guide and support your future behavior.
#3: Undoing and At-Leasting
Regrets sting, but we are not defenseless against them, as we've seen. Two effective ways of alleviating the pain of regret are to undo the regret (to the extent that that's possible), and/or "at-least" our regret, which is to find some kind of silver lining, some positive that we can hold onto from the experience.
Sometimes all it takes to undo a regret is to offer a sincere apology. If you have a regret that can be solved with a simple, sincere apology, then you probably should just apologize! Other times, however, it's not so easy, in cases where you've lost touch with the person you need to apologize to, etc. As always, just do the best you can.
Alternatively, you can "at-least" the regret, and make sure that you take something positive away from an otherwise negative experience. As Mark Manson says in The Subtle Art of Not Giving a F*ck, wanting a positive experience is actually a negative experience (because the desire itself is a kind of psychological pain), but accepting a negative experience is actually a positive experience. That's kind of the idea here.
Sure, you lost your job, but in your 4 years at the company, you gained essential skills that you can take with you for the rest of your life. Your relationship fell apart, but you learned to clearly identify your own romantic boundaries and now you can bring that self-knowledge into all future relationships.
"The path to success is to take massive, determined action."
-Tony Robbins
About the Author:
Daniel H. Pink is the #1 New York Times bestselling author of seven books – including his latest, The Power of Regret: How Looking Backward Moves Us Forward. His books have sold millions of copies around the world, been translated into forty-two languages, and have won multiple awards. He lives with his family in Washington, DC.
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OK, that’s it for now…
More excellent book recommendations coming your way soon!
Again, the rest of the above breakdown is absolutely free (for now!), and you can find it right here.
What you see in this email is less than half of what you get at the Stairway to Wisdom. I left out most of the Book Notes, all the Questions to Stimulate Your Thinking, several of the Key Ideas, etc.
So there’s a lot more for you left to read if you enjoyed what you read in this email!
With that said, I hope you enjoyed this edition of The Reading Life, and enjoy the rest of your week!
All the best,
Matt Karamazov
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