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The power of regret - book summary and d ...

The power of regret - book summary and discussion

Feb 12, 2022

Consider how many times in your life you’ve said some version of, “I have no regrets!” Perhaps you took a year off work to pursue a startup, and even though it failed, you're glad you bothered trying. Or maybe you bought a particular watch you thought you would love, but it ended up sitting in the safe and you eventually sold it for a loss. 

It would seem that we tend to be coached both directly and indirectly that we would be wise to live a life with no regrets, and so, we tend to reframe everything with a silver lining, so we can avoid regret altogether. Daniel H. Pink, author of the new book, The Power of Regret: How Looking Backward Moves Us Forward, reckons this is "dead wrong"! (Not sure I fully agree, but anyway!)

Leave "no room for regrets," counseled positive thinking pioneer Rev. Dr. Norman Vincent Peale, who shaped twentieth-century Christianity and mentored Richard Nixon and Donald Trump. "Waste no time on . . . regret," advised Justice Ruth Bader Ginsburg, the second woman to serve on the U.S. Supreme Court, who practiced Judaism and achieved late-in-life goddess status among American liberals.

Or take the word of celebrities if that's your jam. "I don't believe in regrets," says Angelina Jolie. "I don't believe in regrets," says Bob Dylan. "I don't believe in regrets," says John Travolta. And transgender star Laverne Cox. And fire-coal-walking motivation maestro Tony Robbins. And headbanging Guns N' Roses guitarist Slash. And, I'd bet, roughly half the volumes in the self-help section of your local bookstore. The U.S. Library of Congress contains more than fifty books in its collection with the title No Regrets.

Embedded in songs, emblazoned on skin, and embraced by sages, the anti-regret philosophy is so self-evidently true that it's more often asserted than argued. Why invite pain when we can avoid it? Why summon rain clouds when we can bathe in the sunny rays of positivity? Why rue what we did yesterday when we can dream of the limitless possibilities of tomorrow?

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-forgive the terminology, but the next word is carefully chosen-bullshit.

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.

The Power of Regret by Daniel Pink

Pink argues that to have regrets, is to be human, simply because they are functional. Regrets teach us, or clarify for us, what is important to us. Regrets tend to remind us what we really want in life, and they inspire us to make different choices in the future. According to Pink, the key is to ask ourselves how we can use our regrets as tools for living better.

As I have alluded to in this post about Social Psychology and Watches, Pink mentions how people overvalue positive emotions and undervalue negative ones. While positive emotions are undoubtedly good to have, exclusively positive emotions are not particularly good for our growth. We can use Negative emotions to teach us, but only if we can stop trying to ignore them, or wallow in them... because that would make them debilitating rather than useful.

Four core types of regret

Pink conducted research for his book collecting over 16,000 regrets from people spanning 105 countries. He also interviewed over 4500 people about their regrets. The American Regret Project, in connection with the World Regret Survey, form the largest pool of data ever collected about what humans regret. In doing this, Pink was able to distil the regrets into four 'core' types of regrets:

Foundational Regrets - these are cumulative regrets which inevitably lead to bad situations for ourselves in the future. As the name suggests, these are 'big ticket' regrets such as not exercising or not taking care of our bodies, not saving enough money or not studying hard enough in school.

The lesson: Think ahead. Do the work. Start now.

Boldness Regrets - these are regrets borne out of a point in your life where you were at some sort of juncture, usually faced with a 'safe' option and a 'risky' option. This can be things like a time when you didn't ask that crush out on a date, or you didn't take that risky job at a startup. He claims that people overwhelmingly regret playing it safe, even when they take a chance and it doesn't work out in their favour.

The lesson: Ask him/her out. Take the trip. Start the business. Buy the watch (lol!) 

Moral Regrets - these regrets also arise out of a juncture in your life, but the options are doing the 'right' thing or the 'wrong' thing. All the usual moral topics come into play here; It could be a time when one didn't stand up against bullying or it could be infidelity and so on. 

The lesson: When in doubt, take the high road.

Connection Regrets - these regrets happen when you neglect the people who matter to you and who help you establish a sense of wholeness. These regrets made up the largest category – humans have a massive amount of regret about fractured or unrealised relationships. The weird thing about this one is, all examples will be highly personal. I can think of one that comes immediately to mind... it isn't completely lost, but it is nearly there and this might just be the trigger I needed to reach out and try and save it. Fingers crossed.

The lesson: If it’s a closed door regret, do better next time. If it’s an open door regret, do something now. 

What do these core types of regret tell us?

Fundamentally, these categories outline what makes life worth living, right? Think about it; If you know what people regret the most, you essentially know what they value the most... and in this case, it boils down to: stability in the foundations of life (health, wealth etc), boldly doing things and in turn learning and growing (instead of passively letting life pass us by), doing right by others (and feeling bad when we don't) and connecting with or loving other people. That's it!

Jeff Bezos famously uses a “Regret Minimisation Framework,” in which he imagines himself at age 80 and tries to limit the number of regrets he has in life. Pink says that the problem with this approach, is that we can’t possibly minimise all our regrets; Instead, we should focus on the ones that are most important: 1) regrets about stability 2) regrets about boldness 3) regrets about morality and 4) regrets about connection. Turns out, in social psychology, maximisers tend to be miserable.

How should we deal with regrets?

In short, according to Pink, there are two stages. The first is to reframe the regret. The second is to disclose it. 

Reframing the regret - this is his way of saying we should normalise the regret. Pink suggests we look at our own regret and ask ourselves, “Am I the only one with this regret?” - odds are, the answer is going to be a resounding "No!" - we can then reframe this as part of the human condition, or something which other people have gone through as well... In this way, we can normalise it.

Disclosing the regret - by talking to others about our regrets, we relieve the burden of regret and start a process in our brain to make sense of what we're feeling. Additionally, Pink says, we need not fear that others will like us less when we disclose our vulnerabilities. In fact, the opposite is true: they like us more. People tend to empathise with you, and even admire your courage. As Pink says: "One of the things I found about regret is that if I talk about my regret, people inevitably want to talk about theirs."

For instance, when I exercise or run, until I read this research I would always lacerate myself if I was going too slow or not going far enough, and thinking that that’s really motivation. And it isn’t! Now, it’s not saying, “You’re running really slowly but you’re still an awesome person, Dan, you’re just so great.” That doesn’t work either. What works is saying, “OK, you’re running right now. Running is really hard. You’re maybe having a little bit of an off day, but you’re not the only person who’s had an off day, but focus on the fundamentals and keep moving.”

Dan Pink

Bottom line / Concluding thoughts

Pink's overall goal with this book, is to get people to normalise having regrets in the first place, rather than simply trying to convince ourselves we have no regrets (to learn and grow from). 

I guess the TL;DR version of this book is: talk about our regrets with other people in order to normalise and neutralise them, share the lessons we learn from each regret and aim to apply the lessons to the next decision we have to make.

So you're probably wondering what this has to do with watches... this book left me wondering the same thing! Given the book covers four core categories of regret... we can probably agree that watches hardly qualify as 'core' to anything! That being said, bear with me anyway... 

I would say that watches fit into the 'boldness' category... and most watch collectors will have faced a 'risky' and a 'safe' purchase juncture at one time. You can probably guess the' safe' option is usually a Rolex or similar... the 'risky' option would be an obscure independent who has yet to make a name for themselves... what did you pick? 

Even more interesting, is what you've currently got in your collection, and what this is causing you to miss out on. Say you have 5 steel Rolex sports watches... you've likely paid about £40-50k for these watches cumulatively, and you can likely sell them for £100k or more. Why don't you do it? Would you regret it?

Not sure how I feel about this either... I have watches which I bought at retail, which fall into this category of irrational (grey market) pricing - the economically optimal decision is to sell them if I would not pay the grey market price to acquire them... but I don't. I tell myself I like them, and I struggle to know for sure... I guess time will tell whether there's a regret to discuss!


Originally published at on February 12, 2022.

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