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  • Bradley James Davies

Quick, Crucial Read About Regret by Daniel Pink

Updated: May 24, 2023

Wow. What a transformative read. I've struggled with regret for too long. Pink's new book helped me take some significant steps forward in this area of my life. I've laid down lots of regret baggage as a result, and being freed of the weight has been life-changing.


Out of all of the books I've summarized and shared, this is at the top of the list. I hope you find it helpful.


p.s. a friendly reminder that the words are all Pink's.


p.p.s. have a good read or listen to share with me? Please do! This Pink book was a recommendation, and what a gift it proved to be.



Summary of The Power of Regret: How Looking Backward Moves Us Forward by Daniel H. Pink


“No Regrets!” Few credos blare more loudly than the doctrine that regret is foolish—that it wastes our time and sabotages our well-being…This worldview makes intuitive sense. It seems right. It feels convincing. But it has one not insignificant flaw.


It is dead wrong…What the anti-regret brigades are proposing is not a blueprint for a life well lived. What they are proposing is—bullshit.


Regret is not dangerous or abnormal…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…


Seventy years of research distill to two simple yet urgent conclusions: Regret makes us human. Regret makes us better.


The purpose of this book is to reclaim regret as an indispensable emotion—and to show you how to use its many strengths to make better decisions, perform better at work and school, and bring greater meaning to your life. You’ll learn how to undo and reframe some regrets to adjust the present. You’ll also learn a straightforward, three-step process for transforming other regrets in ways that prepare you for the future.


I hope you’ll see regret in a fresh and more accurate light, and learn to enlist its shape-shifting powers as a force for good.


THE PARADOX OF PAIN AND THE PAIN OF PARADOX


A look at the research shows that regret, handled correctly, offers three broad benefits. It can sharpen our decision-making skills. It can elevate our performance on a range of tasks. And it can strengthen our sense of meaning and connectedness.

Leaning into regret improves our decision-making process—because the stab of negativity slows us down. We collect more information. We consider a wider range of options. We take more time to reach a conclusion. Because we step more carefully, we’re less likely to fall through cognitive trapdoors like confirmation bias.


To be sure, regret doesn’t always elevate performance. Lingering on a regret for too long, or replaying the failure over and over in your head, can have the opposite effect. Selecting the wrong target for your regret—say, that you wore a red baseball cap at the blackjack table rather than that you took another card when you were holding a ten and a king—offers no improvement.


Conducting a “midlife review” focused on regrets can prompt us to revise our life goals and aim to live afresh.


When we handle it properly, regret can make us better.


Thinking is for doing. We act in order to survive. We think in order to act.


If thinking is for doing, what is feeling for?


Stashing negativity in your emotional basement merely delays the moment when you must open the door and face the mess you’ve stored inside…Consistently diminishing negative emotions isn’t a sound strategy either.


Too much regret is dangerous, sometimes devastating. It can lead to rumination, which severely degrades well-being, and to the regurgitation of past mistakes, which can inhibit forward progress…Repetitive thought can worsen regret, and regret can exacerbate repetitive thought, creating a descending spiral of pain. Rumination doesn’t clarify and instruct. It muddies and distracts.


When it comes to regret, a third view is healthier: Feeling is for thinking.


Don’t dodge emotions. Don’t wallow in them either. Confront them. Use them as a catalyst for future behavior. If thinking is for doing, feeling can help us think.


Ample research shows that people who accept, rather than judge, their negative experiences end up faring better. Framing regret as an opportunity rather than a threat helps us transform it.


The key is to use regret to catalyze a chain reaction: the heart signals the head, the head initiates action.


All regrets aggravate. Productive regrets aggravate, then activate…your response determines your result.


When you feel the spear of regret, you have three possible responses.

  • You can conclude that feeling is for ignoring—and bury or minimize it. That leads to delusion.

  • You can conclude that feeling is for feeling—and wallow in it. That leads to despair.

  • Or you can conclude that feeling is for thinking—and address it. What does this regret tell you? What instructions does it offer for making better decisions? For improving your performance? For deepening your sense of meaning?

Kintsugi (which translates to “golden joinery”) considers the breaks and the subsequent repairs part of the vessel’s history, fundamental elements of its being. The bowls aren’t beautiful despite the imperfections. They’re beautiful because of the imperfections. The cracks make them better. What’s true for ceramics can also be true for people.


“You have a broken heart, it means you have done something big enough and important enough and valuable enough to have broken your heart.”

Four categories of human regret:


Boldness regrets…over time we are much more likely to regret the chances we didn’t take than the chances we did….What haunts us is the inaction itself. Forgone opportunities to leave our hometown or launch a business or chase a true love or see the world all linger in the same way.


Moral regrets…When we behave poorly, or compromise our belief in our own goodness, regret can build and then persist.


Connection regrets…Fractured or unrealized relationships with spouses, partners, parents, children, siblings, friends, classmates, and colleagues constitute the largest deep structure category of regret. Connection regrets arise any time we neglect the people who help establish our own sense of wholeness. When those relationships fray or disappear or never develop, we feel an abiding loss.


Foundation regrets…sound like this: If only I’d done the work…Foundation regrets begin with an irresistible lure and end with an inexorable logic…To identify a foundation regret in yourself or in others, listen for the words “too much”—whether they attach to consuming alcohol, playing video games, watching television, spending money, or any other activity whose immediate lure exceeds its lasting value…Then listen for the words “too little”—whether they describe studying in school, setting aside cash, practicing a sport or musical instrument, or any other undertaking that requires steady commitment…Foundation regrets are not just difficult to avoid. They are also difficult to undo.


Embedded in each of these regrets is a solution…which is contained in a hoary Chinese proverb: The best time to plant a tree is twenty years ago. The second-best time is today.


BOLDNESS REGRETS


Play it safe or take a chance?...With boldness regrets, we choose to play it safe…Boldness regrets sound like this: If only I’d taken that risk….the pain of boldness regrets is the pain of “What if?”


“Regrettable failures to act . . . have a longer half-life than regrettable actions”...Inaction regrets outnumbered action regrets by nearly two to one…At the heart of all boldness regrets is the thwarted possibility of growth. The failure to become the person— happier, braver, more evolved—one could have been.


Many of those who did play it safe in their careers look at their choices from the vantage of midlife and wish they hadn’t.


Boldness regrets are often about exploration. And some of the most significant exploration, respondents said, is inward. Authenticity requires boldness. And when authenticity is thwarted, so is growth. The most telling demonstration of this point came from several dozen people from all over the world who described their regret—their failure to be bold—with the same five words: “Not being true to myself.”


With boldness regrets, the human need is growth—to expand as a person, to enjoy the richness of the world, to experience more than an ordinary life. The lesson is plain: Speak up. Ask him out. Take that trip. Start that business. Step off the train.


MORAL REGRETS


Moral regrets sound like this: If only I’d done the right thing.”


Acccording to Haidt’s research, when we consider what’s moral, we have an instantaneous, visceral, emotional response about right or wrong—and then we use reason to justify that intuition. The rational mind isn’t a black-robed jurist rendering unbiased pronouncements, as I’d thought. It’s the press secretary for our intuitions. Its job is to defend the boss.

In both the American Regret Project and the World Regret Survey, people reported more harm-related moral regrets than any other kind. And the most common harm was bullying. Even decades later, hundreds of respondents deeply regretted mistreating their peers.


There is something heartening about grown women and men waking up at night despairing over incidents decades earlier in their lives in which they hurt others, acted unfairly, or compromised the values of their community. It suggests that stamped somewhere in our DNA and buried deep in our souls is the desire to be good.


With moral regrets, the need is goodness. The lesson, which we’ve heard in religious texts, philosophy tracts, and parental admonitions, is this: when in doubt, do the right thing.


CONNECTION REGRETS


Connection regrets are the largest category in the deep structure of human regret. Connection regrets sound like this: If only I’d reached out.


Closed door regrets distress us because we can’t do anything about them. Open door regrets bother us because we can, though it requires effort.


While the connection regrets that people reported in the surveys numbered well into the thousands, the specific ways their relationships ended numbered only two: rifts and drifts.

Rifts are more dramatic. But drifts are more common.


The Harvard Medical School Grant Study had audacious goal was to try to determine why some people flourished in work and life and others floundered…The combined conclusions of these efforts are considered serious, instructive, and probably universal…


As the Harvard Gazette summarized in 2017: Close relationships, more than money or fame, are what keep people happy throughout their lives. . . . Those ties protect people from life’s discontents, help to delay mental and physical decline, and are better predictors of long and happy lives than social class, IQ, or even genes.


Men who’d had warm childhood relationships with their parents earned more as adults than men whose parent-child bonds were more strained. They were also happier and less likely to suffer dementia in old age. People with strong marriages suffered less physical pain and emotional distress over the course of their lives. Individuals’ close friendships were more accurate predictors of healthy aging than their cholesterol levels. Social support and connections to a community helped insulate people against disease and depression.


Meanwhile, loneliness and disconnection, in some cases, were fatal.


In 2017, Robert Waldinger, a psychiatrist and the current director of the study, described to a journalist the core insight of the Harvard research: “Taking care of your body is important, but tending to your relationships is a form of self-care too. That, I think, is the revelation.”


George Vaillant, another Harvard psychiatrist, headed the Grant Study for more than thirty years. In an unpublished 2012 manuscript, he reflected on what he’d learned from the experience. After eight decades, hundreds of subjects, thousands of interviews, and millions of data points, he said he could summarize the conclusion of the longest-running examination of human flourishing in five words:


“Happiness is love. Full stop.”


In the end, the problem we contend with as people is remarkably simple. What gives our lives significance and satisfaction are meaningful relationships.


With connection regrets, the human need is love. Not love only in the romantic sense—but a broader version of love that includes attachment, devotion, and community and that encompasses parents, children, siblings, and friends…The lesson of closed doors is to do better next time. The lesson of open doors is to do something now. If a relationship you care about has come undone, place the call. Make that visit. Say what you feel. Push past the awkwardness and reach out.


Each time you look in the mirror, you see one person. But if you squint a little harder, you might see three selves…Higgins argued that we all have an “actual self,” an “ideal self,” and an “ought self.”


Our actual self is the bundle of attributes that we currently possess. Our ideal self is the self we believe we could be—our hopes, wishes, and dreams. And our ought self is the self we believe we should be—our duties, commitments, and responsibilities.


However, when we don’t make these efforts, when a discrepancy persists between who we are and who we could or should be, unpleasant feelings flood the gap…Over time, people regret inactions more than actions, they conducted six studies that reached a single conclusion: people regret their failures to live up to their ideal selves more than their failures to live up to their ought selves. Regrets of “coulda” outnumbered regrets of “shoulda” by about three to one.


“Couldas” bug us longer than “shouldas,” because we end up fixing many of the “shouldas.”


The result is that opportunity and obligation sit at the center of regret, but opportunity has the more prominent seat. This also helps explain why we’re more likely to regret what we didn’t do than what we did.


We regret foregone opportunities more often than unfulfilled obligations. Yet we also know that a wholly realized life involves a mix of both dreams and duties…A life of obligation and no opportunity is crimped. A life of opportunity and no obligation is hollow. A life that fuses opportunity and obligation is true.


How to build that life by transforming your existing regrets and anticipating your future regrets is the subject of the rest of this book.


What do we do with our regrets? If regrets make us human, how do we enlist them to make us better, more satisfied people?


The starting point is to revisit one of the key distinctions in the architecture of regret: the difference between regrets of action and regrets of inaction—between regretting what we did and regretting what we didn’t do.

For action regrets, your initial goal should be to change the immediate situation for the better…


People are much more likely to undo regrets of action than regrets of inaction. We’re more apt to repair what we did than what we didn’t do…So, to address regrets of action, begin by asking yourself these questions:

  • If I’ve harmed others, as is often the case with moral regrets and sometimes the case with connection regrets, can I make amends through an apology or some form of emotional or material restitution?

  • If I’ve harmed myself, as is the case for many foundation regrets and some connection regrets, can I fix the mistake? For example, can I begin paying down debt or logging a few more hours at work? Can I reach out immediately to someone whose connection I severed?

We can also respond to action regrets by using At Leasts to help us feel better about our circumstances. At Leasts don’t alter our behavior or boost our performance in the future, but they do help us reassess the present…At Leasts can turn regret into relief…because At Leasts spring to mind naturally far less often than If Onlys, we must summon them ourselves at the right time…At Leasts work like antibiotics…If we use these antibiotics too often, their efficacy will wane. If we use them intelligently, they can aid in healthy functioning.


So, with action regrets that are bringing you down, ask yourself: How could the decision I now regret have turned out worse? What is one silver lining in this regret? How would I complete the following sentence? “At least….


If we look backward with the specific intent of moving forward, we can convert our regrets into fuel for progress…They can propel us toward smarter choices, higher performance, and greater meaning.


Rather than ignoring the negative emotion of regret—or worse, wallowing in it—we can remember that feeling is for thinking and that thinking is for doing.


Following a straightforward three-step process, we can disclose the regret, reframe the way we view it and ourselves, and extract a lesson from the experience to remake our subsequent decisions.


STEP 1. SELF-DISCLOSURE: RELIVE AND RELIEVE


The first step in reckoning with all regrets, whether regrets of action or inaction, is self-disclosure.


But an enormous body of literature makes clear that disclosing our thoughts, feelings, and actions—by telling others or simply by writing about them—brings an array of physical, mental, and professional benefits. Such self-revelation is linked to reduced blood pressure, higher grades, better coping skills, and more.”


In this research, writing about negative experiences like regret, and even talking into a tape recorder about them, for fifteen minutes a day substantially increased people’s overall life satisfaction and improved their physical and mental well-being in ways that merely thinking about those experiences did not. Yet the reverse was true for positive experiences: writing and talking about triumphs and good times drained some of their positivity.


The explanation—and the reason self-disclosure is so crucial for handling regret—is that language, whether written or spoken, forces us to organize and integrate our thoughts…It converts blobby mental abstractions into concrete linguistic units.


When feeling is for thinking, and thinking is for doing, regret can perform its decision-enhancing, performance- boosting, meaning-deepening magic…Writing about regret or revealing a regret to another person moves the experience from the realm of emotion into the realm of cognition…Instead of those unpleasant feelings fluttering around uncontrollably, language helps us capture them in our net, pin them down, and begin analyzing them.


Merely writing about emotional difficulties, even solely for your own consumption, can be powerful…The initial step in dealing with all forms of regret is to disclose the regret.

So, to begin to harness your regrets to improve in the future, try any of the following: Write about your regret for fifteen minutes for three consecutive days. Talk about your regret into a voice recorder for fifteen minutes for three consecutive days. Tell someone else about the regret in person or by phone. Include sufficient detail about what happened, but establish a time limit (perhaps a half hour) to avoid the possibilities of repetition and brooding.


STEP 2. SELF-COMPASSION: NORMALIZE AND NEUTRALIZE


Self-criticism…It projects toughness and ambition, but often leads to rumination and hopelessness instead of productive action…The most powerful and promising alternative is called “self-compassion.”


Self-compassion begins by replacing searing judgment with basic kindness…“being imperfect, making mistakes, and encountering life difficulties is part of the s

hared human experience.” By normalizing negative experiences, we neutralize them.


Self-compassion delivers the benefits of self-esteem without its drawbacks. It can insulate us from the debilitating consequences of self-criticism, while short-circuiting self-esteem’s need to feel good through vanity and comparison.


Self-compassion…prompts people to confront their difficulties head-on and take responsibility for them…self-compassion pushes us forward—and for the right reasons.

So, drawing on the science of self-compassion, the second step in transforming our regrets is to ask ourselves three questions:

  • If a friend or relative came to you with the same regret as yours, would you treat that person with kindness or contempt? If your answer is kindness, use that approach on yourself. If your answer is contempt, try a different answer.

  • Is this type of regret something that other people might have endured, or are you the only person ever to have experienced it? If you believe your stumble is part of our common humanity, reflect on that belief, as it’s almost always true…

  • Does this regret represent an unpleasant moment in your life, or does it define your life? Again, if you believe it’s worth being aware of the regret but not overidentifying with it, you’re on your way. If you believe this regret fully constitutes who you are, ask someone else what they think.

STEP 3. SELF-DISTANCING: ANALYZE AND STRATEGIZE


Talking about ourselves in the third person is one variety of what social psychologists call “self-distancing.”...But immersion can catch us in an undertow of rumination. A better, more effective, and longer-lasting approach is…not to plunge in, but to zoom out and gaze upon our situation as a detached observer, much as a movie director pulls back the camera.


After self-disclosure relieves the burden of carrying a regret, and self-compassion reframes the regret as a human imperfection rather than an incapacitating flaw, self-distancing helps you analyze and strategize—to examine the regret dispassionately without shame or rancor and to extract from it a lesson that can guide your future behavior.


Shifting from the immersive act of recounting to the more distanced act of reconstruing regulates our emotions and redirects behavior. As a result, self-distancing strengthens thinking, enhances problem-solving skills, deepens wisdom, and even reduces the elevated blood pressure that often accompanies stressful situations.


Equally important, the fly-on-the-wall technique helps us withstand and learn from criticism—it makes it easier not to take it personally—which is essential in transforming regrets into instruments for improvement.


The second way to self-distance is through time…one study showed that prompting people to consider how they might feel about a negative situation in ten years reduced their stress and enhanced their problem-solving capabilities compared to contemplating what the situation would be like in a week.


Mentally visiting the future—and then examining the regret retrospectively—activates a similar type of detached, big-picture perspective as the fly-on-the-wall technique.

The third method of self-distancing is through language…When we abandon the first person in talking to ourselves, the distance that creates can help us recast threats as challenges and replace distress with meaning…getting people to write about their challenges using third-person pronouns like “she,” “him,” and “they” rather than first-person pronouns like “I,” “me,” and “my” increased their intellectual humility and sharpened the way they reasoned through difficulties…Addressing regrets in the second person—referring to oneself as “you” rather than “I”—also strengthens people’s behavior and deepens their commitment to improving future behavior.


So, to gain the benefits of self-distancing, try any of the following:

  • Imagine your best friend is confronting the same regret that you’re dealing with. What is the lesson that the regret teaches them? What would you tell them to do next? Be as specific as you can. Now follow your own advice.

  • Imagine that you are a neutral expert—a doctor of regret sciences—analyzing your regret in a clean, pristine examination room. What is your diagnosis? Explain in clinical terms what went wrong. Next, what is your prescription? Now write an email to yourself— using your first name and the pronoun “you”—outlining the small steps you need to learn from the regret.

  • Imagine it is ten years from now and you’re looking back with pride on how you responded to this regret. What did you do?

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.


It’s also possible to move forward by looking forward—by foreseeing regrets before they occur.


OTHER TECHNIQUES YOU WON’T REGRET


1. Start a regret circle. Think of regret circles as close cousins of book clubs. Gather five or six friends over coffee, tea, or drinks. Ask two of them to come prepared with a significant regret. Let them tell the story of their regrets. Have the others respond to each regret first by categorizing it. (Is it action or inaction? Into which, if any, of the four deep structure categories does it fall?) Then, for each regret, the group works through the Disclosure-Compassion-Distance process. When the gathering ends, the two people commit to adopting a specific behavior (for example, speaking up to an unpleasant boss or asking out a crush). At the next meeting, the others hold the regretters accountable for that promise—and two new people share their regrets.


2. Create a failure résumé. Most of us have a résumé—a written compendium of jobs, experiences, and credentials that demonstrate to prospective employers and clients how qualified, adept, and generally awesome we are. Tina Seelig, a professor of practice at Stanford University, says we also need a “failure résumé,” a detailed and thorough inventory of our flops. A failure résumé offers another method for addressing our regrets. The very act of creating one is a form of disclosure. And by eyeing your failure résumé not as its protagonist, but as an observer, you can learn from it without feeling diminished by your mistakes.


3. Study self-compassion. I’ve been reading social science research and attempting to make sense of it for twenty years now, but few subjects have spoken to me as powerfully as the research on self- compassion. Understanding self-compassion helped me curb excessive self-criticism because I became convinced that berating myself, while masochistically enjoyable, just wasn’t effective. Self-compassion similarly helped me see my idiosyncratic struggles as both common and solvable. I encourage you to look more deeply into this topic. One place to begin is Kristin Neff’s website (https://self-compassion.org), where you can measure your own levels of self-compassion. Her book Self-Compassion: The Proven Power of Being Kind to Yourself is also excellent.


4. Pair New Year’s resolutions with Old Year’s regrets. A core point of this chapter— of this entire book—is that looking backward can move us forward. One way to imprint this principle onto your life is to establish a ritual. In late December, the temporal landmark of January 1 stirs us to make New Year’s resolutions. But as a precursor to that practice, try what I call “Old Year’s regrets.” Look back on the year that’s about to end and list three regrets. Do you regret not reconnecting with a relative or former colleague? Or never getting around to launching that side business? Or telling a lie that compromised your values? Write down these regrets. And make undoing the action regrets and transforming the inaction regrets your top resolutions for the new year.


5. Mentally subtract positive events. To take the hurt out of a regret, try a mental trick made famous in the 1946 movie It’s a Wonderful Life. On Christmas Eve, George Bailey stands on the brink of suicide when he’s visited by Clarence, an angel who shows George what life in Bedford Falls would be like had he never been born. Clarence’s technique is called “mentally subtracting positive events.” Think of something good in your life—a close friendship, a career achievement, one of your children. Consider all the decisions and indecisions, mistakes and triumphs, that led to that happy situation. Now take them away. To use an example from the last chapter, I could mentally subtract having met my wife. The result is misery and gloom. But, as happened with George Bailey, the subtraction deepens my gratitude and casts my regrets in a new light.


6. Adopt a journey mindset. Achieving our goals can insulate us from regret. But if we don’t sustain our behavior after reaching those goals—by continuing to exercise regularly or by maintaining the good work habits that led to the completion of a project—regret quickly finds its way into our minds. One antidote to this problem comes from the work of Stanford University professors Szu-chi Huang and Jennifer Aaker, who recommend what they call a “journey mindset.”


“Live as if you were living already for the second time and as if you had acted the first time as wrongly as you are about to act now!” Viktor Frankl, 1946


THE UPSIDE OF ANTICIPATION


In general, we find the pain of losing something greater than the pleasure of gaining the equivalent thing—so we go to extraordinary (and often irrational) lengths to avoid losses.

Anticipated regret is particularly useful in overcoming regrets of inaction…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 situations where you’re unsure of your next move, ask yourself, “In the future, will I regret this decision if I don’t do X?” Answer the question. Apply that answer to your current situation. This approach underlies the (small but growing) popularity of “obituary parties”—in which people channel their inner Alfred Nobel, draft their own obits, and use the written pieces to inform their remaining years.


Our goal should not be to always minimize regret. Our goal should be to optimize it.


WHAT TO DO WITH YOUR REGRETS: A RECAP


For an Action Regret, Undo it. Apologize, make amends, or try to repair the damage. At Least It. Find the silver lining: think about how the situation could have turned out worse and appreciate that it didn’t.

For Any Regret (Action or Inaction) Self-disclosure. Relive and relieve the regret by telling others about it—admission clears the air—or by writing about it privately. Self-compassion. Normalize and neutralize the regret by treating yourself the way you’d treat a friend. Self-distancing. Analyze and strategize about the lessons you’ve learned from the regret by zooming out in time, in space, or through language. To Use Anticipated Regrets in Your Decision Making: Satisfice on most decisions. If you are not dealing with one of the four core regrets, make a choice, don’t second-guess yourself, and move on. Maximize on the most crucial decisions. If you are dealing with one of the four core regrets, project yourself to a specific point in the future and ask yourself which choice will most help you build a solid foundation, take a sensible risk, do the right thing, or connect with others.


Open the hood of regret, and you’ll see that the engine powering it is storytelling…Our very ability to experience regret depends on our imagination’s capacity to travel backward in time, rewrite events, and fashion a happier ending than in the original draft.


Regret depends on storytelling. And that raises a question: In these stories, are we the creator or the character, the playwright or the performer?


We are both.


We live at the intersection of free will and circumstance.


McAdams has found that people whose identities involve contamination narratives tend to be unhappy with their personal lives and unimpressive in their professional contributions. But people with narratives rooted in redemption are the opposite. They are generally more satisfied and accomplished—and they rate their lives as meaningful.


If we think about regret like this—looking backward to move forward, seizing what we can control and putting aside what we cannot, crafting our own redemption stories—it can be liberating.



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