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Obliquity: Why Our Goals Are Best Achieved Indirectly

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If you want to go in one direction, the best route may involve going in another. This is the concept of 'obliquity': paradoxical as it sounds, many goals are more likely to be achieved when pursued indirectly. Whether overcoming geographical obstacles, winning decisive battles or meeting sales targets, history shows that oblique approaches are the most successful, especially in difficult terrain.

Pre-eminent economist John Kay applies his provocative, universal theory to everything from international business to town planning and from football to managing forest fires. He shows why the most profitable companies are not always the most profit-oriented; why the richest men and women are not the most materialistic; and why the happiest people are not necessarily those who focus on happiness.

224 pages, Hardcover

First published May 1, 2010

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About the author

John Kay

55 books126 followers
I was born in Edinburgh, Scotland in 1948, and completed my schooling and undergraduate education in that city: I am fortunate to have lived most of my life in beautiful places. I went to the University of Edinburgh to study mathematics. But, after taking a subsidiary course in economics, I decided that I wanted to be an economist. The notion that one might understand society better through the application of rigorous and logical analysis excited me – and it still does. After graduating from Edinburgh, I went to Nuffield College, Oxford. I worked there under James Mirrlees, who was in due course to win the Nobel Prize for his contributions to economic theory.

On Mirrlees’s advice, I applied for and to my astonishment got a permanent teaching post in the University of Oxford at the embarrassingly early age of 21. Oxford is a collegiate university – members of the faculty generally have both University and College appointments. This post carried with it a fellowship at St John’s College, an association which I have maintained and enjoyed ever since. Through the 1970s I developed a conventional academic career, publishing in academic journals, and writing my first book Concentration in Modern Industry (with Leslie Hannah, an economic historian colleague). My particular interests were in public finance and industrial organisation.

But my rationale for studying economics had, from the beginning, been concerned for application. My career began to change direction when I was asked to join a group to review the structure of the British tax system. This group was established under the auspices of a newly established think tank, the Institute for Fiscal Studies, and was headed by James Meade, another economist who had achieved the ultimate distinction of a Nobel prize. Meade’s rigour was as demanding as that of Mirrlees, (both delivered it with extraordinary personal charm). But the most important effect of my experience with the Meade Committee was that I began to develop a taste for the popular exposition of economic concepts.

In this vein, I wrote (with Mervyn King, now Governor of the Bank of England) a more personal account of issues in taxation, The British Tax System which ran through five editions.

Pursuing these interests, I moved from Oxford and joined the Institute for Fiscal Studies as its first research director. Soon after I became Director of the Institute. IFS developed into (and remains) one of Britain’s leading think tanks, respected and feared by policymakers and journalists for its fiercely independent analysis of fiscal issues.

After seven years, I decided it was time to move on. The success of IFS had been built on serious economics accompanied by a commitment to popularisation and application. If this could be done for public policy issues, could the same be done in the area of business policy? This was the thinking that led me to accept a chair at the London Business School in 1986 and, at the same time, to establish a consulting company, London Economics.

Over the next few years, the application of economics to business issues became my intellectual focus. During this period, London Economics grew rapidly, largely on the back of the wave of privatisation and regulatory change in Britain in the 1980s. By 1991, managing the company had become a major responsibility. I revised my arrangements with London Business School. My new contract was as Visiting Professor but my job as executive chairman of London Economics took the larger part of my time. London Economics grew until, by its tenth anniversary, its annual turnover exceeded £10m with offices in three continents and assignments in over sixty countries.

London Economics gave me insights into the business world. These came both through consultancy work with major corporations and first hand observation of the growth and development of a small business. Other activities have enriched my more scholarly work by broadening the experi

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Profile Image for Ian "Marvin" Graye.
850 reviews2,086 followers
June 13, 2012
The Allure of the Oblique

I bought and read this book because of one word, which happened to be its title.

I was fascinated by the word “obliquity”. I wasn’t familiar with it. I didn’t even know whether it was a neologism created by the author, John Kay, a Professor of Economics and regular columnist for the Financial Times.

As it turns out, the word has been around since the fifteenth century. Naturally, it derives from the word “oblique", which means "slanting, sidelong, indirect".

As a noun, it is the quality or state of deviation or deviating from a line or direction.

Kay uses it to describe the process of achieving a goal indirectly rather than directly.

In Off the Black

Kay credits Nobel Prize Winner, Sir James Black, with the principle of obliquity, which asserts that “goals are often best achieved without intending them”.

This statement is pretty equivocal. It doesn’t purport to suggest that goals are always best achieved without intending them.

To the extent that a goal is an objective or something you intend to achieve, it doesn’t make sense to say that you can best achieve it without intending to.

It would cease to be a goal, if you no longer intended to achieve it by any means.

Black’s statement therefore can mean no more than that, sometimes, you can achieve a goal as an unintended or accidental outcome of trying to do or achieve something else, perhaps even another goal.

I could have lived with the implications of this statement, but I suppose my reaction would have been “So what? What else can you tell me?”

Indirect Achievement

Perhaps anticipating my skepticism, Kay takes Black’s principle and builds a whole new worldview on its foundation: “our goals are best achieved indirectly.”

Gone is the word “often”, absent is any reference to the lack of “intention”.

Instead, we now have a principle that states, effectively, that if you intend to achieve a goal, you should endeavour to achieve it indirectly, not directly.

Intention is still part of the methodology, only we have to strive to achieve our goal by a different route or path, indirectly rather than directly, perhaps by the road less travelled.

He promotes this as a new guide to personal problem-solving and economic and political decision-making.

Still, my skepticism was starting to grow, not retreat.

I dearly wanted Kay to prove his case, I wanted him to persuade me, I wanted to be convinced.

Yet, I can’t say that he succeeded. Ultimately, I feel that he did too little with his material. He didn’t live up to its potential. He overpromised and underdelivered.

I am still fascinated by the word "obliquity", but for me, at least, the case for obliquity remains to be proved.

Equally importantly, I felt that there were some dangerous overtones in his political philosophy.

The Pursuit of Happiness

Kay cites John Stuart Mill approvingly in Chapter 1:

”I never wavered in the conviction that happiness is the test of all rules of conduct, and the end of life. But I now thought that this end was only to be attained by not making it the direct end. Those only are happy…who have their minds fixed on some object other than their own happiness…aiming thus at something else, they find happiness by the way.”

There’s nothing in this statement that I disagree with.

However, I don’t accept that it was intended as an argument for the indirect path in all activities.

In Mill’s eyes, happiness remained the ultimate end. However, he concluded that it was an outcome of the pursuit of some other goal, rather than an outcome of the direct pursuit of happiness.

Perhaps happiness is so abstract and its causes so diverse, subjective and personal that we cannot say that there is any one method of achieving it directly for all people.

However, can the same be said with respect to a recipe for baking a cake, or a decision about the best location for a new highway between two cities, or a method by which a judge arrives at justice in a dispute?

The Pursuit of Profit

Kay also cites George Merck:

”We try never to forget that medicine is for the people. It is not for the profits. The profits follow, and if we have remembered that, they have never failed to appear. The better we have remembered it, the larger they have been.”

While profit is less abstract and more quantifiable than happiness, it is still an example of a goal that, while it might be the ultimate end of economic activity in capitalist society, it is still best achieved as an outcome of the pursuit of some other goal (e.g., meeting the needs of the public).

You do not achieve profit and wealth by being passionate about profit and money, you achieve it by being passionate about something else.

The Science of Muddling Through

Kay borrows the distinction between direct and oblique approaches to decision-making from Charles Lindblom:

”The root, rational, comprehensive method was direct and involved a single comprehensive evaluation of all options in the light of defined objectives.

“The oblique approach was characterized by what he called successive limited comparison…a process of ‘initially building out from the current situation, step-by-step and by small degrees’.”

Kay cautions against thinking that the oblique approach is unstructured and intuitive. It is actually a disciplined and ordered process. It involves constant improvisation, pragmatism and never-ending learning.

The distinction between means and ends is important to simple problem-solving, but less central to “practical decision-making”. (He doesn’t explain the distinction any better than this.)

Objectives, Goals and Actions

Kay uses the traditional distinction between objectives, goals and actions.

Objectives are fluid and imprecise, which impacts on the goals and actions required to achieve them:

”High-level objectives – living a fulfilling life, creating a successful business, producing a distinguished work of art, glorifying God – are almost always too imprecise for us to have any clear idea how to achieve them. That doesn’t imply that these goals lack meaning or the capacity for realization. We understand their meaning and realise them by translating them into intermediate goals and actions; we interpret and reinterpret them as we gain knowledge about the environment in which we operate. That is why successful approaches are oblique rather than direct.”

Kay uses Isaiah Berlin’s definition of “pluralism”, in essence, “the notion that there is more than one answer to a question”, in contrast to “monism”, “the ancient belief that there is a single harmony of truth into which everything, if it is genuine, must fit.”

Ironically, our objectives are subjective, and therefore fluid and open to change.

As a result, our goals and actions must also be flexible.

We must embrace negotiation, adaptation and compromise.

Different people will solve the same problems in different ways at different times.

Complexity and Incomplete Knowledge

Kay recognizes that the world has become so complex that we can never have complete information about any particular problem or situation.

To the extent that we make assumptions and simplify the world in order to fit it into patterns and models, we have to accept that our models and perceptions might be wrong.

There is no point in becoming despondent about the risk of error. We move step by step toward better decisions and greater knowledge by way of a process of trial and error. No error, no progress.

The Road to Serfdom

By this point in the book, I was starting to feel frustrated that there was no real explanation of the mechanics of oblique decision-making and how it might interface with direct decision-making.

Besides, I was starting to get uncomfortable with the implicit politics of what is effectively a management theory.

In the same section that Kay cites John Stuart Mill, he quotes Adam Smith:

”By pursuing his own interest, he frequently promotes that of society more effectually than when he really intends to promote it.”

Later, he quotes Friedrich von Hayek:

”Nobody has yet succeeded in deliberately arranging all the activities that go on in a complex society.”

At the heart of “Obliquity” (the book) is a war with modernism, as represented by the architect Le Corbusier and the Communist Vladimir Lenin.

Its purpose is to establish that the world is too complex to be designed or commanded from above.

No grand design should be allowed to prevail. No politician or executive should be allowed to dominate.

Instead, what emerges from the apparent chaos of human interaction and pragmatism, like the capitalist economy, led by an invisible hand, is right. Or, at least, on the way to being right over a period of time. Only, don’t interfere with the process, let it come about indirectly.

There is something fundamentally conservative, non-interventionist and anti-progressive about this approach.

Obliquity could very well be an adjunct or handmaiden to Ayn Rand’s Objectivism.

Ironic Relativism

Ironically, Kay embraces the language of pluralism, complexity and chaos theory.

These concepts seem to be at odds with traditional conservatism. They imply relativism in values.

I might be doing Kay an injustice. However, in my eyes, the adherence to pluralism comes across as tokenist.

There is an iniquity at work here. It made me feel deeply suspicious of obliquity, notwithstanding its superficial appeal.

Kay doesn't seem to mind that some of us might take the road less travelled (and get lost), as long as the majority takes the road most travelled.

There is a sense in which, left to our own obliquitous devices, stripped of intention and directness, ironically, we will end up conforming. Unintentionally. Indirectly.

Obliquity is just a new way to preserve the economic and social system that we've got. Intact. Exactly as it is.

There is an underlying confidence that, without interference or design or positive discrimination, nobody will be able to counter the invisible hand of conservatism.

Standard Deviation

Kay's version of obliquity is really about maintaining a straight line or direction.

It's about maintaining the standard, maintaining standards, the norm.

It isn't really about deviation at all, let alone deviance.

In its own right, it's actually quite devious.

The more things change, the more they stay the same.

Pluralism is tolerated only insofar as it doesn't alter the status quo and nobody rocks the boat.

So, ultimately, capitalism in its current form will be perpetuated by a (seven?) billion instances of pragmatic obliquity.
Profile Image for Bobby.
7 reviews3 followers
February 24, 2012
Good quick read about how the path to achievement is often obtained by "muddling through" with uncertain destinations as opposed to detailed planning, sterile objectives, and over-analysis. Some excellent perspectives, and well worth reading.

On the downside, the book comes across as almost anti-objective decision making. I don't think this was Kay's intent, but I hoped the book would at some point go further in highlighting the value of using objective decision frameworks - even in instances where the path chosen differs from the results of the decision making exercise. In other words, "the model says we should do x, but we're going to do y. after we've seen the results, lets revisit the model and see what worked or what didn't and why."

I also didn't like Kay's use of political figures and economists in the anecdotes. With political figures, there's too much likelihood that the reader will disagree with Kay's perspective on the success/failure of a politician's strategy or that the reader will have a different interpretation of what actually constituted the politician's strategy.
Profile Image for Mara Shaw.
125 reviews34 followers
May 14, 2012
Remember the Smurfs? How half the words in their conversations were replaced with the word "smurf" or "smurfy"? John Kay has done something similar with "obliquity" and "oblique". Decisions that are made iteratively, with trial and error, employing emotion or intuition, or from going for greatness and reaping a side benefit of profits -- these are all oblique according to Kay. Quickly in the book, I was frustrated with the repetition, much as the Smurfs made me cringe.

Chapters 1 - 4 and "Conclusions" were well worth reading. Indeed, the most profitable companies are not usually those out to make the most money, but to deliver the best computer, airplane or other product. Hence their route to profit can be viewed as oblique, but only if you consider profit their goal. Boeing certainly started with great aviation as their goal, not profit, so they were working directly. Profit earning was an oblique goal.

Yes, Le Corbusier did urban planning a disservice when he ignored the interplay between people and "ideal construction" and planned Brasilia and many housing projects in a vacuum that made them unsuccessful. Studying and incorporating how cities and neighbourhoods grow organically into urban planning is critical. Is this oblique? Does the fact that Beckham doesn't use a slide rule to plan his kicks make his goal scoring "oblique"?

Enough. The book is peppered with examples of good and poor decision-making that makes this worth a quick read, including the Stockdale Paradox, Franklin's Gambit, the rise and fall of many industrial giants including Merck, Sunbeam, Boeing, and Lehman Bros. when they lost sight of the primary goal of the company and focused only on shareholder profits. Similarly, when people focus only on trying to be happy in the short term, they often short-change their long-term happiness that derives more from living a meaningful life than one filled with instant pleasure.
Profile Image for Sabina.
120 reviews3 followers
September 14, 2019
In essence, John Kay showcases with various examples that there is no science to decision making. Most decisions are made obliquely.
Edit: I came back to change my rating to 5 stars because the echo of the book’s content resonated with me the longer I thought about it. We have very complex lives and assume that we know the direct path to success, when actually we’re just muddling through. The only way to prepare is to acquire and accumulate knowledge in the field of your pursuit. Acknowledging this is life changing and oddly soothing.
Profile Image for Laura Gembolis.
442 reviews42 followers
September 1, 2019
If you are looking for the short version, another Brit gave us the same message: No, you can't always get what you want
But if you try sometime, you just might find
You get what you need

For the most part, obliquity seems to be pursuing goals that come from the heart rather than the pursuit of fame or fortune.

The book's set up: if you follow obliquity, it will get you the true measure of success. So as long as you are doing it for the right reasons, you will get wealthy, which was really the goal all along.

In my mind, the first half of the book can be skipped. Then the book strings together some interesting ideas, but doesn't delve to deeply into any of them. One that organizations pay consultants to justify decisions they already made. This made a lot of sense to me. And I would say when this happens, the bigger the consultant's fee, the worse the news. The book is filled with these insights - interesting, but so what?

I appreciated was the idea that there are two types of problems: closed problems (like Sudoku or chess) and open problems (what's the best solution to global warming?). Again -- makes sense. But not a lot of guidance once you've identified what kind of problem you have on your hands. And I would imagine that all problems that involve people are open problems.

The second half of the book is better than the first. I would say that it gets exponentially better. In fact, if I was the editor, I would have cut the first half the book and explore the ideas in the second half of the book.

This is where the book begins to explore the ideas of what it means to set a larger goal and staying open to several ways to getting there. However, it doesn't go deep enough to really stand for a big idea. It still skirts around the idea of obliquity. I guess the book's message - to get there by going slant. But we never get there. Maybe the book is a practice in obliquity. But I was left thinking -- so what?
Profile Image for Jeffrey.
9 reviews2 followers
June 7, 2011
Recommended. However, like many business and conceptually-driven academic books, the provocative concepts in the book make enduring the repetition and lack of stark definition worthwhile.

I am annoyed at the publisher and whatever writer from the Financial Times placed and wrote, respectively, the quote saying Kay was an excellent writer on the book's front cover. Unfortunately, Kay is not a great writer, as he failed to solve the problem of having an absorbing book spring out of concept that are extremely engaging when presented in-person. For the dry world of economics and business academia (which he obliquely argues out of existence or to be changed dramatically), this may be a page-turner. For most, this is not, and this book is a good candidate for a speed-read instead of a deep read. I did the latter and didn't find any of the morsels I was hoping the extra attention would give me.

The gold here is an introduction of sorts to non-linear thinking, and another attempt to explain magic in a bottle that will resonate for some. In short, Kay tells us that concentrating on qualities, obliquely, instead of the measurable results of projects and enterprises creates sustainability, innovation and most likely the results you were after in the first place. For those of us hooked on finances, shareholder value and beating last year's numbers, these concepts come as a blessed relief and perhaps a confirmation of some concepts that have been in the background of our thinking for quite some time. If you've every been accused of "trying too hard", this book is the antidote.
Profile Image for Jason Carter.
271 reviews5 followers
February 8, 2020
"Read this book." -- Nassim Taleb, author of the Black Swan

That's on the cover, and it's as succinct a review as possible. I would agree with Taleb. I'd have given this book five stars for its content, except that a couple of chapters seemed repetitive and unnecessary.

Kay argues that the direct pursuit of a goal is often less likely to achieve its objectives than the indirect pursuit:

- An airplane manufacturer seeking to make excellent airplanes is more likely to maximize shareholder value than an airplane manufacturer with "maximize shareholder value" as its driving principle
- A pharmaceutical company seeking to serve humanity through its craft is more likely to succeed than one seeking to "maximize profits through drug manufacturing"

These examples may seem obvious, and Kay perhaps spends too much time recounting them. The most valuable parts of the book, though, are his observations on the decision-making processes that lead otherwise world-class organizations to fall into these types of traps.

His chapters along these lines are in the vein of Kanneman's Thinking Fast and Slow, Gardner and Tetlock's Superforecasting, and Silver's The Signal and the Noise. I would reach back much further and outside the world of business books to compare it to Bradford's A Better Guide than Reason -- one of the early formative books in my intellectual journey.

In a nutshell, rationalism, ideology and dogmatism are frequently the enemies of good decision-making. Observation, experience, experimentation, and wisdom often prove much friendlier.

Examples abound throughout. Read this book.
Profile Image for Taylor Pearson.
Author 3 books721 followers
January 28, 2019
A convincing argument against setting long-term goals. This book took many of the learning of complexity science over the past few years and showed how many companies and individuals ignore them, to their detriment.

Great companies and lives are built not from un an erring focus on a long-range goal as many commentators would have you believe, but on an indirect and oblique approach that realizes reality is more complex than our reductionist plans would admit.
Profile Image for Emanuela.
Author 4 books65 followers
November 27, 2011
Per spiegare il pensiero obliquo l'autore ricorre spesso a confronti con lo sport:

Ed Smith, giocatore di cricket e scrittore, esprime questo concetto molto bene: "Non dico che lo sviluppo personale sia più importante della vittoria; al contrario, dico che godere del viaggio alla scoperta di sé, rimuovendo parte della pressione e delle angosce associate alla vittoria a tutti i costi, aiuta a vincere più spesso".

Bob Rotella autore di 'Golf is not a Game of Perfect' spiega che si può riuscire a fare un buono swing soltanto se non ci si pensa. Rotella ha fatto carriera convincendo il pubblico che questo principio non vale solo per il golf, ma ha un'applicazione molto più ampia.

E così Beckam quando tira in porta non fa prima calcoli differenziali, tira perché ha inconsapevolmente fatto una serie di valutazioni, frutto della sua esperienza che gli fa presumere che probabilmente sarà un goal .

Ecco, questo è il pensiero obliquo. Processi decisionali che sono presi in modo eclettico e pragmatico perché le condizioni sono così complesse che un'analisi razionale non consente di avere tutte le variabili sotto controllo, anzi è questa presunzione di totale controllo che induce a fare errori madornali.

Kay ripropone in questo libro quello che già avevo trovato in Do The Work, ma con una forma un po' più attorcigliata anche se più analitica.
Ho ricopiato una tabella interessante che mette in parallelo il pensiero lineare con quello obliquo su alcuni punti chiave come: obiettivi e traguardi, interazione, complessità, problemi incompleti e pervasi da incertezza, astrazione, intenzionalità, confronto limitato, informazione, eclettismo, adattamento, esperienza, direzione, coerenza, razionalità del processo, che mostrano l'approccio diverso alla soluzione dei problemi. Potrebbe tornarmi utile.
Profile Image for Arup Guha.
64 reviews5 followers
November 14, 2021
This book makes an important point. You can’t deal with complex systems by planning your actions down to the last detail aimed at meeting simplified second or third level goals. The right way is to have high level goals and an iterative approach through incremental steps. Expertise comes from experience not from having all the answers. Lastly and most importantly, all simplified explanations and models are after the fact, created in hindsight and don’t have much value beyond confirmation of what was already known subconsciously. You know more than you realise you do.
Profile Image for Tim Hughes.
Author 3 books55 followers
April 21, 2018
In this book “Obliquity” John Kay points out that actually objectives are a waste of time, what do I mean?

If we go back to 1940, Prime Minister Churchill stood up in the UK Parliament and said that the United Kingdom would be victorious. Which was a goal, but Churchill had no idea how he would reach that goal.

Think about it, the Nazis had pushed back the whole of the Europe onto the beaches of Dunkirk, the UK hadn’t prepared itself for war and especially a war over a highly efficient and overwhelming Nazi army. The US was neutral and in fact passed laws which meant they could not arm the UK. In fact the US lent the UK to buy airplanes and then wouldn’t ship them; just as France was overwhelmed by Panzer tanks.

Back to Parliament and Churchill stood up and said we would be victorious. How? There are no objectives that you can set to achieve that goal.

That’s where the world of obliquity kicks in.

Churchill didn’t know that two things would happen.

The Nazis would invade the USSR, which would suck a massive amount of resources.
The Japanese would bomb Pearl Harbour bringing the neutral USA into the war.

This is obliquity! You simply cannot plan for everything in life and in fact planning can mean you have blinkers on and cannot see, what could actually be a better solution than whatever you could have planned for.
Profile Image for Andrew.
133 reviews
June 10, 2022
It’s been a while since I left McGilchrist’s book by the wayside. As a distraction, I thought I’d read another quick book just to get my mind off the book I’m writing at the minute, but the more you try to avoid him, the more you see McGilchrist in the shadows. Honestly, it might just be the best book I have ever read so far (along with Wilber’s) for its breath, depth, and impact. This review isn’t even about it and yet, here I am, mentioning it. Anyways, I thought Kays’ was a pretty good book that perfectly illustrated the difference between the left and right hemisphere approaches to life.

Obliquity describes the process of achieving complex objectives indirectly. I think a parable mentioned in the book helps to explain this notion. A visitor comes across three stonemasons at work. He asks the first one what he’s doing and he says that he’s cutting some stones. The second one says he’s building a magnificent cathedral. And the third says he’s working for the glory of God. Bear in mind that they’re all doing exactly the same thing (cutting stones) but describing it with different levels of abstraction, from the exalted abstract to the mundane concrete. Now, in order to pursue the most divine objectives, we need to translate them into concrete actions; the whole point of the book is that we cannot pursue these complex objectives directly because they tend to be imprecisely defined, contain values that conflict with one another, and they evolve as we take steps in the direction of their completion; they’re moving targets in other words. We need an iterative process of top-down assessment of the whole and bottom-up course correction to make sure what we’re aiming for makes sense in light of new information.

Happiness is not achieved through the pursuit of happiness is a good way to sum up what the author is getting at. The larger and complexer the problem, the more it requires an oblique approach. What is an oblique approach? It means to have in mind a high-level goal (Working for the glory of God) while leaving the actual accomplishment of that task open ended and undetermined. I think it helps to counter the oblique (right hemisphere) with the direct (left hemisphere) approaches.

The left perceives a direct connection between intention and outcomes; the right believes that the intention is neither necessary nor sufficient to secure the outcomes.

The left reviews all possible outcomes; the right chooses from a much more limited set.

The left assembles all available information; the right recognises the limits of its knowledge.

The left maximises its objectives; the right adapts continuously.

The left can always find an explanation for its choices; the right just tries to find the right answer.

The left believes that order is the product of a directing mind; the right recognises that order emerges spontaneously without anyone fully grasping it.

The left insists on consistency; the right never encounters exactly the same problem twice.

The left emphasises rationality; the right recognises the inherent subjectivity of each decision and emphasises good judgment.

The left thinks that everything can be automated; the right realises that experts can do things that others can’t, and they can’t fully explain themselves.
Profile Image for Ed.
333 reviews30 followers
May 29, 2011
Well I read this book in more or less one sitting today. Couldn't put it down. I guess it has profoundly shaken some of my ideas about how to make good decisions, and I will have to weave it into my conflict work.It is a well written and persuasively argued case for going about achieving things indirectly, in an exploratory, provisional way. And this is necessary in business, in our own personal lives, in our attempts to become happy. Life is way too complex for our goals to be always clearly stated and the author shows how the indirect approach allows ends and means to co-evolve and achieve better results. Clearly there cases where a direct approach works, but not in the more messy, complex problems that abound in our lives, in our world.

His account makes sense of a lot of my experience in the corporate world. The successful companies, the ones that consistently make money over decades, are the ones that do not make profit making their only over-arching goal. Instead the successful companies focus on a range of goals like making great aircraft or saving lives via new medication. And his examples from the pharmaceutical industry will please my friend Kate: J and J win for their indirection. :)

So don't read this book if you don't want your world view shaken up. I guess it is the perfect anti-dote to the sort of process discipline that I like; but in reality it is a call to use good process wisely, imaginatively, creatively rather than a call for anarchy or irrationality. It is consistent with the Japanese approach of Kaisen or continuous incremental improvement. And it is in a way a transcendence of the right/left dichotomy that seems to have lost its heuristic power.

Incidentally, the book is full of great quotes:

'Tell all the truth, but tell it slant. Success in circuit lies.' Emily Dickinson

'Visionary companies pursue a cluster of objectives, of which making money is only one - and not necessarily the primary one. Yes, they seek profits, but they are equally guided by a core ideology - core values and a sense of purpose beyond just making money. Yet paradoxically, the visionary companies, make more money than the purely profit driven companies. Jim Collins and Jerry Portas. Built to Last

And central to his view is Benjamin Franklin's:

'So convenient a thing it is to be a reasonable creature, since it enables one to find or make a reason for everything one had in mind to do.'
Profile Image for Choonghwan.
120 reviews6 followers
July 30, 2015

I found some western philosophers like this book’s author might have reached the concept of “Wu Wei (non-doing)”, which is the basis of Taoism, in oblique ways. The author argues we cannot pursue elusive and sublime goals, such as running a good company, winning a war, directly.  There are many reasons: we cannot fully understand and get enough information to make a perfect decision even with hindsight; environment and situation take turns and twist constantly; we cannot enforce our will unilaterally and, thus, need to adapt to opponents’ response continuously; we are human beings after all neither profit-maximizing nor soulless acolytes. 

There is an old saying in China. When the state was governed poorly, people complained their ruler; when governed relatively well, they acclaimed; when governed immaculately, they asked themselves “who cares about the sovereign anyway!”

Maybe that is the seed of human tragedy. We admire mediocre leaders and ignore supreme ones at our own peril. 

Profile Image for Joseph.
283 reviews23 followers
November 29, 2011
The book discusses on why an indirect/muddling through (or just oblique) way is better than a direct approach. For example, why paradoxically, the happiest people in the world arent pursuing happiness per se nor are the richest people on the world maximizing wealth per se...that happiness and wealth are often a by product of our passion/energy.

the book also advocates an present adaptive approach to achieving goals vs long term plan. I agree with this thinking. another thinking is to break down the things we want to achieve (either direct or oblique) into (a) high level objectives (2) goals - current state and desired states and (3) actions

the cons of the book (1) the author would have done a better job expanding the many ideas in the book. all too often, the details are too brief. More examples would certainly do the book more justice.
Profile Image for Robert Giddings.
29 reviews1 follower
April 27, 2016
This book starts off with an interesting idea, but then slaps it repeatedly across your face until you're just sick of it. In a way it's impressive that it manages to do this in less than 200 pages. The book also fails to be constructive, giving various examples of decisions made in the past which have gone wrong and why, but not giving any kind of decision making advice other than "if a plan isn't working then don't stick to it".

The style is similar to Malcolm Gladwell, but the book is not as well-written as Gladwell. The subject matter is similar to Nassim Nicholas Taleb, but the book is not as interesting or thought-provoking as Taleb's.

I generally agree with most of the arguments made by Kay, but feel he makes them too often, and the reader's response is too often "so what should we do instead?" and that question is rarely satisfactorily answered.
Profile Image for Carla.
583 reviews
September 28, 2011
I read this book in Dutch (for Managementboek.nl). I rated it as "okay" because the message is interesting, as are the examples but I didn't see the practicality of it. Even the chapter "Obliquity in practice" gave more arguments and not the "how to apply this" that I hoped for. Kay argues that often goals for success, happiness aren't reached directly but indirectly. People or companies that aim at being successful, often aren't so successful. I found the concept of Franklin's Gambit interesting. It's the "game" people play, according Kay, where they've already taken a decision and then rationalize it. The decision to attack Irak is one example. Franklin's Gambit can be disastrous. That made me think.
Profile Image for Rick.
91 reviews11 followers
August 4, 2015
I didn't think I would like this book as much as I did. I'm not sure if I want to become an urban planner anymore now, after Mr. Kay describes the failures of planned development to keep up with the demands and changes to a city. If you go after a complex problem, especially one that will affect many people, you must be able to pivot if necessary, instead of going full speed ahead with a single preconceived solution.
Profile Image for Mikedariano.
153 reviews23 followers
October 8, 2017
Suggested by Rory Sutherland this book would be five stars for someone unfamiliar with the ideas of bottom up/emergence, Nassim Taleb, complexity theory, or decision making. It's a great introduction to those ideas.
From the book, "If there is a one line explanation of the power of obliquity it would be - evolution is smarter than you are."
If that quote interests you - dive in.
217 reviews6 followers
July 20, 2020
Thought this was a good book. Although it took some time to get into the flow. The central theme of the book can be summarized as know the game you are really in. Many companies get caught up in the game of profits and winning. those are external outcomes that generally lead to disaster. I relate it to Simon Sinek's know the game you are really in..know your why. For example, for technology the game we are really in is convenience. Not in building cool technology or in making profits. If we remember our why, cool technology and profits will naturally follow. I think of Apple and Steve Jobs and how he was obsessed with UI, UX and excellence. It really wasnt a tech guy and was not driven by profits. He wanted to create great and beautiful products. The accommodates and money came after.
The author uses examples such as the airlines and how they stop caring about aviation and stated caring about stockholder profits. That led to their downfall. He tells us about another example in a health science company that loses sight of his why and this loses profitability.

In the end he mentions that many times the way to the end goal is not straight way but the obliquity way. He mentions people that taught outside the box. Those that diverted from the prescribed way of thinking or group thinking or society's thinking. Instead they looked at the problem from a different vantage point and got a better pathways and results. Thus the way to greatness and profits is not to look for greatness or profits but to love what you do.

We prefer to tell stories than to use analytic models, and the best and most helpful models are, at their root, narratives. This book presents its messages through stories because, as every teacher or consultant knows, that is the method through which we best absorb arguments and make sense of a complex world. But stories can mislead as well as inform; we must build our stories from the evidence—not, as in Franklin’s gambit, build our evidence to match narratives we have previously constructed.

I call it the principle of obliquity: Goals are often best achieved without intending them.

Visionary companies pursue a cluster of objectives, of which making money is only one—and not necessarily the primary one. Yes, they seek profits, but they’re equally guided by a core ideology—core values and sense of purpose beyond just making money. Yet paradoxically, the visionary companies make more money than the purely profit driven companies.

In obliquity there are no predictable connections between intentions and outcomes. Oblique problem solvers do not evaluate all available alternatives: they make successive choices from a narrow range of options. Effective decision makers are distinguished not so much by the superior extent of their knowledge as by their being aware of its limitations. Problem solving is iterative and adaptive rather than direct.

The difficulties of pursuing happiness begin with the difficulty of knowing what it is we pursue.

We don’t consider any man successful until he has died well.

An old story tells of a visitor who encounters three stonemasons working on a medieval cathedral and asks each what he is doing. “I am cutting this stone to shape,” says the first, describing his basic actions. “I am building a great cathedral,” says the second, describing his intermediate goal. “And I am working for the glory of God,” says the third, describing his high-level objective. The construction of architectural masterpieces required that high objectives be pursued through lesser, but nonetheless fulfilling, goals and actions.

I am not saying that personal development is more important than winning; on the contrary, I am saying that enjoying the journey of self-discovery, by removing some of the pressure and angst associated with winning at all costs, is one way of helping you to win more often

But the skill of the artist, like the talent of the poet, lies in the originality with which this goal is interpreted.

Obliquity is a process of experiment and discovery. Successes and failures and the expansion of knowledge lead to reassessment of our objectives and goals and the actions that result.

Teaching quality is defined as the relationship of the classroom experience to the intended learning outcomes.

The computer is an efficient decision-making aid, not an efficient decision maker.

The oblique decision maker, the fox, is not hung up on consistency and frequently holds contradictory ideas simultaneously.

With hindsight, I believe the right way to have formed an opinion would have been to say: “I do not trust the judgment of the people who are making this decision or their ability to handle the consequences.” That would have led to the right conclusion, and for the right reasons.
225 reviews10 followers
November 12, 2022
Obliquity is a Gladwell-style account of why "our goals are best achieved indirectly," with all the good and bad that entails.

The good: Kay is an engaging writer and the book is an easy read. He also does a good job of bringing together a diverse set of literatures, each of which shores up this idea that pursuing your goals can get you into trouble.

The simplest formulation of this might be the classic Boeing story: Boeing was a great company, building great planes, with great engineers, until it became too focused on pursuing profit and, well, 737MAX et al.

It's a decent hypothesis because, frankly, I think we can all relate to this. Working out to lose weight ends up being unsustainable for most people; rather it's important to find ways to build exercise into your life that you enjoy (and then health benefits come along). Being fixated on getting 100% in a class makes you blind to the more holistic, intrinsically-motivated learning you need to achieve real learning. So on and so forth.

The bad: "Your goal is best achieved indirectly" only makes sense some of the time. So, Boeing should ignore the goal of making money and achieve that indirectly by making good planes. But, if we were to apply the rule, it bungles us up: Boeing should ignore the goal of making good planes and achieve that indirectly by... _____?

See, the underlying lesson here is a bit more complex: you should be reflective about which goals you pursue, and pursue the ones you actually care about rather than the perverse incentives.

To use an example Kay draws on in the book that's squarely within my expertise, he points out how forest management gets messed up because of this: if we try to stop all wildfires, we build up fuels in the forest, and therefore get bigger fires. Quid pro quo, Kay says we stop the goal of "putting out fires" and instead practice healthier forest management.

Okay, but that just generates a new goal. Obviously, I like that goal better (e.g., "foster a healthy role ecologically, culturally, and societally for fire"). But, we need some sort of stopping criteria for when we have found the goal we should focus on achieving directly, rather than ending up on a treadmill of revising goal after goal after goal.

In any event, this is a three star book because I think it raises some good points - and is well written - but doesn't actually reveal the simple rule it claims to. The examples Kay gives are not so much about achieving your goal indirectly as being aware of easy solutions and perverse incentives and making sure you're directly pursuing the goal you actually care about.

But, hey, maybe the title was just meant to be oblique?
Profile Image for Samuel Mwangi.
10 reviews
January 21, 2020
Roosevelt, like Lincoln before him, understood that the scope of his authority was inescapably limited by the imprecision of his objectives, the complexity of his environment, the unpredictability of the reactions of others and the open-ended nature of the problems he faced. All these factors mean that even the most powerful men in the world must proceed by choosing opportunistically from a narrow range of options.


But Tetlock’s most striking discovery is that although the foxes perform better in terms of the quality of their judgments, the hedgehogs perform better in terms of public acclaim.




visionaries who project some current technological or geopolitical trend with exaggerated pace and to exaggerated extent. All lack the real imagination needed to understand the complexity of their environment. Hedgehogs, not foxes, they strive toward answers that were formed in their minds even before they encountered the problem.
Elon Musk is a prime example of this.


The hero is not the captain who sails obliquely round the storm but the captain who takes his ship through it.


empirically, Machiavelli understood that to be an effective decision maker it was wise not to seek public credit for the success of one’s decisions. Yet another of obliquity’s many paradoxes.


As the economists Ken Arrow and Frank Hahn put it, “The immediate ‘common sense’ answer to the question ‘What will an economy motivated by individual greed and controlled by a very large number of different agents look like?’ is probably ‘There will be chaos.’”1 But the outperformance of controlled and planned economies by decentralized, disorganized market systems is perhaps the greatest triumph of obliquity.
Screw central planners


Those who direct businesses must try to balance a multiplicity of objectives and meet the many and incompatible demands that individuals and other organizations make upon them. Any senior manager will tell you this is the reality of how his or her day is spent.
Difficulties of being a boss.


When you behave consistently, I label you an ideologue; when my behavior is inconsistent, I describe myself as a pragmatist.


The world is too complex and uncertain for consistency to be possible—or even a well-defined concept.


In a necessarily uncertain world, a good decision doesn’t necessarily lead to a good outcome, and a good outcome doesn’t necessarily imply a good decision or a capable decision maker.
Profile Image for Nick Carter.
48 reviews15 followers
August 20, 2021
The idea of "obliquity" - that it's better to reach for high level objectives and be flexible with the goals to get there - is extremely useful.

It's ironic - me, being a rambler by nature - that I prefer my nonfiction books to be straight to the point. How are we defining the terms that I'm potentially adding to my worldview? Why are they important? How are we proving that this is the case? I like knowing that what's being put forward is a cohesive view of a truth of the world.

With those standards the book felt a bit confused to me. I think the titular word "obliquity" was being used in more than one way, so it took work on my part to piece together what the gems were from this book. The use of real-world examples was also something that is normally a plus in this self-betterment / business-application genre of books, but it didn't have that oomph it should've had. Kay moves through a smorgasbord of examples with a quickness that would make the great Busta Rhymes sweat. So quick, sometimes it's not clear why our venture into example company X proved the flavor of obliquity Kay is explaining in a particular chapter. These are two things that affected the experience for me, even though the ultimate message was gold itself.

In the end, maybe I'm just being intellectually lazy, haha. The book has an extremely valuable message about how to attack (and explore) what you want to do in life. In the end, a message is a message, huh?
Profile Image for John Jacobi.
Author 2 books28 followers
May 8, 2017
Good ideas, bad writing: most of the book suffered from this unfortunate combination. It was also repetitive and could have been greatly condensed.

Still, the end of the book pulls everything together quite nicely, describing some of the principles of cultural evolution. To ask what a business is for, he says, might be comparable to asking what a tiger is for. Be forewarned, though, that these descriptions are not technical. For that other books on this topic are better: Cultural Evolution by Boyd and Richerson, The Evolution of Technology by Basalla, etc. And Matt Ridley's Evolution of Everything provides more facts on the evolutionary rather than decision-making side of things.

The best part of this book is the way Kay reappraises the human mind in the midst of sciences that degrade them for the sake of so-called rational ideals. He explains why human decisions are different from decision by computers, what they can do better, why the emotional will is necessary to make decisions, etc. I'm not how sure he knows it, but he gave insights good for those who favor a human ecology over a human economy.
Profile Image for Zak.
136 reviews2 followers
April 30, 2022
This was excellent.

Definitely made me want to read more of JK (not to be confused with Rowling).

The crux of the idea is JS Mill's thing about people wanting to be happy shouldn't aim at happiness but rather at other things for their own sake (i.e. friendship, work, etc.) and happiness will come with it. It was sort of about that but more about debunking the supposedly 'rational' approach to problems and projects in favour of a more organic 'muddling through'.

Best bits were about the folly of 'planned' cities/housing vs 'organic' developments, the reality of post-rationalisation over rational solution making and the best leaders having clear high level goals but being flexible in their realisation.

There was clearly a lot of overlap with Taleb's work but ironically Kay approached it in a more direct rather than meandering manner. Given the topic of the book, the fact that I prefered Kay's approach suggests I've got some work to do...
Profile Image for Alexej Gerstmaier.
172 reviews8 followers
December 31, 2022
"Our customers didn't really use our models for decision making either. They used them [...] to justify decisions that they had already made"

"Good decision makers are eclectic and tend to regard consistency as a mark of stubbornness, or ideological blindness, rather than a virtue"

"'maximize shareholder value' is not a useful guide to executive action. 'That's not a strategy that helps you know what to do when you come to work every day'"

"With hindsight, I believe the right way to have formed an opinion was to say: 'I do not trust the judgement of the people who are making this decision, or their ability to handle the consequences.' That would have led to the right conclusion, and for the right reasons. There is nothing wrong with using 'I trust him' or 'I don't trust him' as a basis for a decision"

Profile Image for r.
174 reviews23 followers
November 9, 2019
“If people are predictably irrational, perhaps they are not irrational at all: Perhaps the fault lies not with the world but with our concept of rationality. Perhaps we should think differently about how we really make decisions and solve problems.”

“Happiness is not achieved through the pursuit of happiness. The most profitable businesses are not the most profit oriented. The wealthiest people are not those most assertive in the pursuit of wealth. The greatest paintings are not the most accurate representations of their subjects; the forests most resistant to fires are not the ones whose foresters are the best at putting out fires.”
268 reviews
December 15, 2019
The ultimate book made out of a short magazine article, expanded but without really adding anything new. Discusses the idea that sometimes approaching a problem head on and having a well defined plan in advance of action is maybe not the best approach. Instead being open to change and taking alternative 'oblique' routes is more likely to lead to success. Suffers from the same problem of much of Thomas Friedman's work which presents a single anecdotal case and then extrapolates this in to a generalisation which could quite easily be refuted by any number of alternative examples. A lot of rather cliched stories and examples which made the book rather frustrating to read.
14 reviews6 followers
April 23, 2019
Obliquity starts out with a good presentation of oblique approaches to solving problems. However, as Mr. Kay goes on, it becomes more clear that he is asserting oblique approaches because that is how he sees all problems - the evidence is picked and the logic is adjusted to prove this point (which just further supports that progressing directly in a planned manner is incorrect, because he's already "obliquely" decided this was the correct approach).

I would recommend the first 50 pages or so of this book, but find that the remainder became dogmatic and "preaching".
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