The best books on Living Prudently

Why have you suggested prudence as your theme? What do you mean by it, and how do we pursue it in our lives?

Prudence is a balance of caution and action. It incorporates creativity in thinking of options and tactics, along with a full awareness of the possibilities of deception, self-deception and ignorance. It is simply saying: Life is complicated, and just because I feel something I don’t necessarily know what’s best for me. We must be careful about the boundless ways in which we can delude ourselves – the boundless ways in which the heart can lie. The problem today, and the reason why prudence is my theme, is not that it’s so rare – it’s always been rare – but that imprudence is so honoured.

In practice so many life choices – especially in relationships – aren’t the products of calculated decision-making, they’re leaps of faith.

It’s fascinating that you use the word calculated. I think it is that word that gives the concept of prudence a bad reputation. People who are prudent are seen as being calculating, and calculation is the enemy of the heart, or so it appears to us.

Everyone wants to be spontaneous.

Precisely. In that sense we’re all prisoners of [18th century French philosopher Jean-Jacques] Rousseau. We are all living a dream that our hearts are pure tuning forks, and we simply have to tune out the noises around us and listen to the pure vibration coming from our hearts, and then – beyond all concern for evidence or the reality of the way things work – we will know what to do.

Even Hitler, another child of Romanticism, was a proponent of this romantic attitude. The Nazis were incredibly romantic. Hitler said: “I follow my course with the precision and security of a sleepwalker.” Meaning he trusted himself in the same way that a naive and romantic 21st century person will trust his or her heart to know what’s right. We know this often leads to terrible decisions but God forbid we should be calculating! So we continue to go forth blindly.

Is it especially hard to achieve prudence in today’s society and culture?

It’s always been hard to sift through the fog of possibilities and false whispers that flood us within and without. But it’s especially hard today in the face of an anti-prudence ideology. In action movies, there is a hero and a villain. The hero is usually a good-hearted but rather impulsive person. He trusts his instincts and goes by his heart. You always know the villain because he’s the most thinky character in the movie. He’s the one who plots, strategises and uses cunning. So we are caught in a culturally constructed contradiction between thought and the heart. By being thoughtful, we think we are being calculating and therefore at risk of being manipulating, deceitful and false. We don’t like that image of ourselves. We like the hero who is pure of heart, trusts his gut, flies forward and deals with whatever comes at him.

Instead, what we should be aiming at is a full awareness that when we’re faced with a decision – from what to do about my marriage, or my job or where I’m going to live – we have to listen to our hearts but also be aware of the possibility that we may be deceiving ourselves. We are too often creatures of attitude. The deepest truth of our hearts is often an attitude that we have picked up from groupthink or the culture around us, or it’s some past decision that we have an unthinking allegiance to.

The recent book I’ve worked on [with Mira Kirshenbaum] is I Love You But I Don’t Trust You. When there’s been a betrayal in a relationship, you’re deeply hurt and terrified. The dilemma we face is that we’re often torn between imprudent alternatives. If you’ve been terribly hurt, you can be a prisoner of past decisions, of attitude, of other people’s expectations or of fear. Until you go through a process of challenging your fears and feelings against what’s possible and what’s real, you’re not making the most prudent choice. So much of my work [as a therapist] has been about rescuing people from imprudence – the imprudence of their current situation, where they’re on the verge of making bad choices, or the destructive cost of past imprudence.

You advise on decision making, and wrote a book about it. What are the essentials to keep in mind about making the right decisions?

In that book I was building on the Harvard Business School model of quantitative decision making, and looking at what I call the fuzzy decisions. In other words the decisions without data, which are the most vexing ones in our lives. For example, should I marry this person? I wanted to see what good decision makers did that bad decision makers didn’t.

I uncovered 30 rules of thumb that good decision makers follow that the rest of us too often don’t.  The most distinctive rule was asking themselves: What is the one most important thing here? Bad decision makers piled up options and priorities – they wanted to somehow satisfy every single priority they had. This led to paralysis, or to being so overwhelmed by the possibilities that they picked any old option, like when you’re at the supermarket and there are so many choices that you just pick the item in front of you. The best decision makers think: What’s the one thing here that’s most important? If you’re marrying someone, is it that they have a pretty face or a good character? It can be hard to figure out what the one most important thing is, but you certainly make better decisions if you do that exercise than if you don’t. And that is an example of prudence.

It’s just stunning when you look at the decisions individuals – and nations – make when they never thought about what the most important thing was. When Donald Rumsfeld started the Iraq war and said “you go to war with the army you have”, he was acting like the most important thing was to go to war. Well if you’re fighting a defensive war, sure. But if you’re making war on another country, I think the most important thing is to be prepared for the war you know you’re going to fight.

So Iraq is another lesson for prudent action?

I think so. Don’t you? Just ask the relatives of servicemen and women killed in poorly armoured troop carriers. It’s a textbook case of imprudence.

This is a good point to begin on your book selection with The Odyssey.

Yes, speaking of war. Here we have the introduction in Western literature to the concept of prudence, embodied in the character of Odysseus. You could even conceive of The Iliad and The Odyssey as a two-volume study of the nature of prudence and imprudence, because it begins with the imprudence of Achilles. Achilles has a fit about something that in the context of war is an extremely low priority. He’s pissed off because he doesn’t get some slave girl as a prize. He makes a low priority a top priority, which is one of the hallmarks of imprudence. And he does so in service of self, which is another.

And let’s not forget Paris’s act of monumental imprudence in stealing Helen.

There you go. And then you have Odysseus, in contrast. The epithets about Odysseus are always about his cunning and his prudence. In the first book of The Odyssey he is referred to as a “master tactician”. He’s always careful, and we see that most of all in his return to Ithaca and his wife. He doesn’t just waltz in, he comes in disguise. There’s no equivalent of a Western hero in modern times who would do the same. They would walk in with guns blazing. But Odysseus is careful. Why? Because he doesn’t know what he’s going to find.

Odysseus is the great hero of prudence in all of our literature. He thinks before he acts, and bases that action on caution. And his wife, Penelope, is the heroine of prudence in literature. She’s a single mother, she doesn’t know if her husband is coming back or not, and she has all of these suitors. She’s in an extremely vulnerable position – how can she say “yes” to one of the suitors when her husband might come home, but how can she say “no” and possibly invoke their wrath – so her best option is to keep them hanging on. That’s why she weaves and unweaves her tapestry at the loom every night. She says she will choose one of her suitors as husband when she finishes her tapestry, but she has no plan ever to finish it.

And then devises an impossible test with a bow that the suitors are meant to string.

Exactly. All in the service of delaying them. In my book on decision making, one of the guidelines that comes through very strongly is: Don’t decide until you have to. That’s what Penelope does. Let me read to you a short passage of hers that captures that note of prudence. This is in Book 19, and she’s talking about a dream. She hasn’t acknowledged that Odysseus is Odysseus yet. She wants to test him first. He tells her about a dream and she says:

“Friend, many and many a dream is mere confusion, a cobweb of no consequence at all. Two gates for ghostly dreams there are: One gateway of honest horn, and one of ivory. Issuing by the ivory gate are dreams of glimmering illusion, fantasies, but those that come through solid polished horn may be borne out, if mortals only know them.”

These are not the words of a foolish woman. This is the voice of someone who knows that you have to test the promptings of your heart. That the dreams that come from you, or seem to be given to you, might be given by good or bad forces, might be helpful or destructive. They have to be tested by thought and experience. And that is essential to prudence.

Yet so many other Greek heroes are exemplars of imprudence and hubris.

The impulsiveness of Greek heroes is legendary. Just look at Oedipus. Here is a man who was given a prophecy that he was going to kill his father and sleep with his mother. A minimally prudent person, hearing that prophecy and believing it as a good Greek of his day should have, would not then kill an older man and sleep with an older woman. Yet he did, and that was his downfall. Antigone, on the other hand, was faced with a tragic choice about whether to bury her brother with the honour he deserved in spite of the king having forbidden it. She was prudent because she did what she felt was best, with full and thoughtful awareness of the terrible consequences of her action.

Your second choice is King Lear. What can we learn about prudence from Shakespeare?

You see the same dichotomies, and beginnings of discomfort with prudence, in Shakespeare that you see throughout our culture ever since. Edmund is prudent – evil and calculating. That is the danger we think we face. And on the other hand we worship Cordelia, but she is an utter fool. She is absolutely sincere, horrified by the phoniness of her sisters, only tells Lear “I love you according to my bond” and is cast out by him as a result. She could have been true instead of being silly. Tragically, she was both true and silly.

But let’s not forget that the mainspring of the tragedy was Lear’s imprudence in giving away his kingdom without, at a minimum, thinking to whom he was giving it. How could he have been so blind as to who his daughters were? But this is evidently not their first experience of his imprudence. Regan says: “He has ever but slenderly known himself.” That lack of self-knowledge runs through the history of imprudence.

One way of reading King Lear is that through the process of his imprudence and suffering, Lear learns to know himself and emerges, finally, a better man – even if he dies.

Psychologists ask the same question: Do we learn from our mistakes? Or in other words: Do we get wiser as we grow older? Perhaps not on a Learian scale but on a more mundane scale, do we learn from our imprudence? And the answer is no. The answer is people do not get wiser as they grow older, rather they become more entrenched in the attitudes they started out with. Because you can only learn from experience with the mental furniture you have at the moment. And that mental furniture consists too often of those attitudes you began with. So a lot of what people “learn” is just a confirmation of their attitudes. Contemporary psychology is filled with lessons like that, where people at the end of the journey get what they started with. Life, instead of being filled with lessons, is too often a cracked mirror reflecting us back to ourselves.

If Lear learns, he learns because Shakespeare wanted him to. And he learns because he had therapists along with him, in Edgar and the Fool, and later Cordelia. You have three to one therapist-patient ratio, so how could he not have learned?!

Going back to Cordelia, are you saying she should have lied, and spouted sugary words like Goneril and Regan? Because that would be false to herself.

I’m not trying to re-write Shakespeare, but a prudent version of Cordelia could have said: My Lord, you asked me to describe how much I love you. Let’s talk about all the times we’ve had together, all the moments we’ve shared, the conversations we’ve had and the ways I’ve accompanied you. When have I ever been anything other than a devoted and loving daughter?

She was rather blunt in saying “Nothing”.

She stabbed herself in the heart, and she’s not the only Shakespearian heroine to have done that – only she did it with her words.

You also wanted to mention Hamlet in the context of prudence.

Hamlet is conceived of as the poster child for indecision. I think that’s a bad rap. He is faced with the difficult question of what the best thing to do is. It’s easy to make fun of him for thinking about it so carefully because he’s a graduate student in philosophy – so he was always going to be wrapped up in the coils of thought. But his dilemma is really a practical one: Can I trust the ghost of my father? Should I kill my uncle and take vengeance and the consequences of vengeance? If I do kill him, what is the best moment to do it? Do I really want revenge if he confesses, and so I end up sending him straight to heaven? Hamlet struggles with all of that. More than indecision, he really represents someone who is trying to be prudent, as best he can. Like Antigone.

He is certainly contrasted with Ophelia, who deals with overwhelming difficulty by throwing herself in a river – the height of imprudence. Ophelia is Lear without his team of therapists. Hamlet is simply trying to be as thoughtful as possible about what the best thing to do is under incredibly difficult circumstances. And we know, for example from the World War II literature of people in the resistance, that sometimes in difficult circumstances you can be boundlessly prudent but in the end you’re still dragged under.

Tell us about your third selection, a biography of the 18th and 19th century French diplomat Talleyrand. First will you remind our readers who Talleyrand was?

Well, who wasn’t Talleyrand? He was a statesman in France before, during and after the French revolution. He was able to be foreign minister under a number of different regimes when people who were deviating from the orthodoxy of the moment were getting their heads chopped off left and right. He is the poster child for landing on your feet no matter what. Because he was so thoughtful, careful and obeisant, and always took care of himself, he was deeply distrusted by everyone. And yet he was also trusted by everyone, because he was given top posts and top assignments which he always handled well and made a bundle to boot.

This was a time of cruelty and chaos when many people died for having principles. Napoleon had principles, and he brought tremendous destruction. All of the people of the Terror – Robespierre and others – were people of tremendous principle. Having principle is no guarantee against evil and destruction. When times are turbulent, sometimes survival is the best principle. One woman who knew Talleyrand at the time said of him: “One of the first things that struck me when I first talked with him was his complete lack of any illusion or of any enthusiasm.” I think what she meant was that he saw things as they were, not as he wanted them to be and not as other people saw them. That is another hallmark of prudence. But it’s always lonely.

Another word to think about prudence with in the context of Talleyrand is adaptability. Surely in everyday life, even if you’re not a French revolution-era politician, adaptability is essential.

I’m grateful that you brought that word up. I did a study many years ago of various modalities of therapy, from Freudianism all the way through to cognitive behavioural therapy. My question was about their models of mental health rather than mental illness. In other words, what is the cure designed to bring about? The interesting thing was that despite the divergence and conflict among these modalities of understanding illness, they all had the exact same model of mental health. It was exactly what you just said: Adaptability. Mental illness was seen as a rigidity of response.

Flexibility is another word for it. Flexibility means that when you have no illusions about reality then you can see what’s real. And when you can see what’s real, you can respond to it not in a stereotyped way but in a way that best serves your goals in the context of your circumstances. This is talked about all the time in the psychology of investing – poor investors have emotional relationships with their investments. They feel a tender connection to something because they own it, rather than seeing the reality that it’s just a pile of money with a label on it. Research shows that people get caught up in financial bubbles – even when they are knowledgeable about the danger of them – precisely because, unlike Talleyrand, they have a rigid and supine response to their own illusions.

Let’s move onto Lionel Trilling’s Sincerity and Authenticity.

This is a must read for anybody to break free of the chains with which we live in our obsession with sincerity and authenticity, which have unfortunately become enemies of prudence. Trilling shows where these notions come from and how we have been formed today by those origins. Another source for this idea of listening to your heart is Ralph Waldo Emerson’s Self Reliance. But life isn’t like that. What Trilling explores is the difficulty of that enterprise and the contradictions you fall into. For example, if you believe in the unconscious – Trilling was of course tied to Freud – then how do you trust your impulses when your impulses are creations of God knows what faulty process? So then what material, of what murky and suspicious provenance, are you being sincere and authentic about?

Will you define sincerity and authenticity as he uses them, and explain his thesis?

Sincerity is simply that you mean what you say. It’s Cordelia again, making telling the truth and making sure you are seen to be a truth teller your most important priority. Authenticity is a more complex notion of being real with respect to who you are, or who you or others think you should be. But this leads to all kinds of difficulties. For example, authenticity is promoted in rap music, which is all about cred. You’re credible because you walk the talk and because of the life you live. You come from the streets and you represent the life of the streets. But there are dilemmas of authenticity within the black community, because the life and the style to which you’re being authentic came from a ghetto created to a large degree by white people – so to a very real degree you’re being authentic to a form of slavery. Then authenticity quickly becomes a style. Once authenticity is codified, and it always becomes codified, nothing becomes easier to counterfeit.

The forms of life to which we conform by being authentic are too often not who we really are, and our subservience to them becomes an enemy of prudence – a codified, handed-down version of the self becomes our agenda, not what is actually prudent. To take another example, many women have hurt themselves by being enslaved to the need to be nice, partly in service of the idea that authenticity for a woman means being nice. Femininity has been perceived as being nurturing and nice and sweet and soft. Well it’s lovely to have nice people around, but that perception of niceness and cooperation as a hallmark of womanly authenticity was created by a patriarchy that wanted to disempower women. So the niceness which is seen by many women as a mark of their authenticity can just as easily be seen as a mark of their disempowerment. It’s a pretty cool trick when you can not only oppress someone and get them to use on themselves the tools of their own oppression, but to actually claim those tools as marks of their truest selves. The point is that when you start talking about authenticity you’re walking into a hall of mirrors.

Trilling uses the maxim “stay true to oneself”, which has now become a bit of a cliché. How useful is that phrase?

It’s terrible when you think that it’s easy – just a matter of following the promptings of the heart. It’s wonderful to stay true to yourself if you can do so without all of the crap – all the illusion, deception, self-deception, ignorance and other things that clutter up the self like a junk shop. Then of course you should be true to yourself. If you like chocolate, chocolate is what you like. There’s not a lot of opportunity for self-deception when it comes to what flavour of dessert you like. But there is when it comes to what wine you like, because we know from tests that people’s preference for the more expensive wine with the famous label is completely at odds with what they prefer in blind tastings. If people don’t even know what wine they like, how are they going to be true to themselves? This is a segue in a sense to my final book.

I’m curious to hear why you picked this one.

This may be a surprising choice. This is a book for religious people, in the Christian tradition, about discernment – which Thomas Green usefully defines as “where prayer and action meet”. Discernment is, for example, a young man or woman believing they have a religious vocation and wondering if this feeling is real. To question “is this feeling real?” is a heresy in a world which worships feelings, where feelings are the very touchstone of reality. Yet questioning them is a tradition that goes back to Plato. The analogy of Plato’s cave already tells us that we can’t trust our perceptions – that we have to accept the possibility that the world we see is in reality shadows, and that there might be another reality that requires prudence to think about.

Weeds Among the Wheat – and you don’t have to be religious to appreciate this book – is saying that to make a life-changing decision you have to be extremely thoughtful about where the promptings of the heart come from, and that feelings have to be tested in community with people who are wise and experienced, and know how the heart can deceive us. Decision-making studies are filled with the ways in which we deceive ourselves. Green says that not deciding is just as imprudent as impetuously deciding. He wants us to sift through the deceptions and see if we can feel our way towards the truth. If you transpose his religious mode into a more secular mode, you find a model for prudence.

Presumably the title comes from the parable of the wheat and the weeds?

The double meaning is that the weeds of ignorance, deception, self-deception and habit can choke out the nourishing grains of wheat, but on the other hand amidst all these weeds there is healthy, valuable wheat that needs to be strengthened and brought to life. In other words, there is a truth of action that can be figured out. But it’s not going to be figured out by simply saying: This is what’s in my heart, therefore I know it’s right.

To sum up, what should we take away from this conversation in terms of taking prudence as a guideline for our lives, relationships and decisions?

Let me run through some points. Number one: Prudence does not mean cunning, trickery and knavery. Number two: Imprudence destroys lives. When I look at bad marriages, people often tell me they knew they were making a mistake when they were walking down the aisle. When I ask why they didn’t stop it, they say they had paid for it and everyone was invited and sitting in the church. So they make a lifelong commitment and raise three children in a context that they already know is a terrible mistake. Lives are destroyed because careers are chosen imprudently, or investments are made imprudently. It goes on and on. The current housing bubble is a crisis of imprudence. Without prudence lives are ruined.

Number three: Prudence requires going beyond the promptings of the heart. What one feels is evidence only of what one feels. Those feelings may be valid and useful, and they’re always worth paying attention to, but they’re not the end of the story. To be prudent means to go through a process – with a wise adviser or friend, and not someone who is just reciting the party line of current attitudes – and to be thoughtful, careful, patient and test everything. Test everything you think you know that may not be true. It’s not the things we don’t know that hurt us, it’s the things we think we know that are wrong.