Obliquity: Why our goals are best achieved indirectly by John Kay.
Who should read this book?
This book is meant for business leaders, strategists & policy makers.
Why you should read this book (or not)?
If you enjoy thought-provoking ideas and challenging conventional wisdom, Obliquity might catch your interest. The book’s main idea is that complex goals are often best achieved indirectly through what the author calls “oblique approaches.” While this concept is meaningful, the book doesn’t provide much in the way of practical advice or tools to apply these ideas effectively.
The introduction is the strongest part of the book. Kay reflects on his career as a consultant and raises some intriguing points about the paradoxes of happiness and success. However, these reflections aren’t explored in depth, leaving you wanting more.
The book relies heavily on a few anecdotal stories to support its ideas, but these don’t offer strong evidence. This overreliance on stories weakens the book’s overall credibility.
The writing itself can also be hard to follow, with dense sentences and overly complicated ideas. This makes it less accessible for readers looking for clarity or actionable insights.
One missed opportunity is that the book doesn’t help readers understand when to take a direct approach versus when an oblique one is better. It could have included useful examples or frameworks, such as the Stacey Model, to help distinguish between these situations. Kay’s suggestion to “start somewhere small” feels too vague without concrete examples or guidance.
Although the book introduces an interesting concept, it left me feeling unsatisfied.
If you’re curious about the idea of obliquity, you might find these books more practical and insightful:
- Working with Source by Tom Nixon
- How to Measure Anything by Douglas Hubbard
- The Joy of Agility by Joshua Kerievsky
- Range by David Epstein
These books provide clear frameworks, practical advice, and actionable examples that you can apply in business, strategy, or personal growth.
Interesting extracts
“For of over ten years, I built and ran an economic consultancy business, and much of our revenue was derived from selling models to large corporate clients. One day, I asked myself a question: if these models were helpful, why did we not build similar models for our own decision making? The answer, I realised, was that our customers didn’t really use these models for their decision making either. They used them internally or externally to justify decisions that they had already made.
They were playing what I now call Franklin’s Gambit, after the American polymath Benjamin Franklin. He wrote: ‘so convenient a thing is it to be a reasonable creature, since it enables one to find or make a reason for everything one had a mind to do. Franklin’s remark about hindsight rationalisation is particularly significant, not just because he was a clever man.
(…) Like many economists we believed that if our models did not describe the world, the fault lay with the world, not the model. But it isn’t just economists who make that mistake. Politicians, investors, bankers and business people believe that although they don’t solve problems according to a standard model of rational decision making, they ought to. So they pretend that they do – to others, and perhaps to themselves.
“The best route is the Panama Canal. Ships go eastwards in order to reach their western destination more quickly and economically. They follow a trajectory that is oblique. Obliquity describes the process of achieving complex objectives indirectly.”
“The environment social, commercial, natural in which we operate changes over time and as we interact with it. Our knowledge of that complex environment is necessarily piecemeal and imperfect. And so objectives are generally best accomplished obliquely rather than directly.
(…) 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 most successful in extinguishing fires. Soviet planners managed the economy far less successfully than the adaptive, disorganised processes of market economies.”
“But a more likely explanation is that people who say that bringing up their children has made them very happy are telling the truth. And when the same people say that much of the time they spent with their children was not happy, they are also telling the truth. Mountaineers like Messner do not say that being cold, starved of oxygen and at frequent risk of injury or death makes them happy. They confirm the common-sense assumption that such experiences are unpleasant. But the experience of having accomplished a difficult climb makes them immensely happy. They are not contradicting themselves, because happiness is not simply the aggregate of happy moments.”
“We frequently learn how to solve problems by tackling them. The National Park Service, US Department of the Interior, has learned to protect America’s natural environment in the hundred years since it was established. One of the responsibilities of the service is forest management. We might agree, roughly, on the meaning of the objective of good forest management. That objective needs to be translated into inter. mediate goals necessary for the achievement of that high-level Objective. A good forest is beautiful and accessible, and it has healthy trees.
One desirable intermediate state that contributes to these goals and objectives is the absence of destructive fires. From the early twentieth century, the policy of the NPS was one of zero tolerance. Every outbreak of fire, however small, would be extinguished – the basic-level action. But the incidence of fire did not fall: it increased.
Computer simulation of fire control policies suggests the explanation. Most forest fires are small and burn themselves out. In doing so, they remove combustible undergrowth, and create firebreaks that limit the spread of future fires. So the best way to reduce fire is not to extinguish all fires. The Service adopted a different view of the goals that would achieve its higher level objective: controlled burning replaced zero tolerance. But what actions does this goal require? In 1972 the Service decreed a new policy: it would put out man-made fires but allow natural ones to burn.
Sixteen years later, the largest fire in American history swept through Yellowstone National Park. In extremely dry conditions, several fires joined together. Lightning was probably the original cause, though perhaps some fires were lit deliberately by arsonists. By the time the blaze was controlled by a force of 25,000 fire-fighters at a cost of over $100 million, almost half the vegetation of the park had been destroyed. Today’s guidelines allow experienced forest rangers to use their judgement in deciding which fires should be tackled and which left to burn. Experience has shown that too much effort devoted to fire extinction is counter-productive. But some fire-control activity is essential. Time demonstrates, but only slowly, whether policy has gone too far in one direction or the other – whether actions are appropriate to states, whether goals are appropriate to objectives.”
“What is true of art is also true of other areas of human endeavour. What made Henry Ford or Walt Disney or Steve Jobs great businessmen was that they modified the rules by which their success, and the success of others in their industry, were measured. They changed our appreciation of what is good and bad in personal transport, in children’s entertainment and in computing. They sold us products we had not imagined. What we mean today by a good means of personal transport is very different from what we would have meant by the same phrase a hundred and fifty years ago, as a result of people who conceived vehicles quite different from those that had already existed. The criteria of achievement are constantly redefined by great achievers.”
“Marks and Spencer was famous for decades for the breadth of its staff welfare programme. The company gave its employees high-quality meals at low prices. But the policy did not originate in any direct calculation of costs and benefits; it was adopted when Simon Marks was making one of his legendary store visits. Marks discovered that the husband of the assistant serving him was unemployed and the family had not enough to eat. Marks was not engaged in philanthropy: he did not offer to feed his employee’s family. But nor had he calculated how the policy might enhance shareholder value. (…) Since participation can only be stimulated ‘by signs of personal trust’, how the company behaved in its interactions with staff was particularly important. The statement ‘We look after employees because we care’ is not the same as the statement ‘We have introduced new compensation arrangements because, having calculated the relative costs of benefits enhancements and staff turnover, and commissioned a consultant’s report on the policies of competitors, we believe our policy will produce a net enhancement of shareholder value.’ Even if the pensions and healthcare benefits that result are the same, the response to the oblique approach is very different to the response to the direct one. That is why companies often describe their purposes in their board papers and investor presentations in different terms from the language they use in press releases and in communications to employees. But people who work in a business generally know its nature well enough to see instrumentality at work.”
“In the nineteenth century German foresters rejected unplanned evolution in favour of design. You can still see such planned forests in many countries of Europe and North America: the trees are identical and evenly spaced. The foresters have calculated the most suitable crop and the optimal planting distances.
These forests are generally ugly, but were not very successful in economic terms, far more prone to accident and disease than the planters had anticipated. The foresters saw the trees, but not the wood. You cannot necessarily deduce the properties of the whole by adding up the properties of the individual parts.
This is true of many biological systems and of all social, political and economic systems. Monocultures are vulnerable to both economic and natural hazards. Worse, they may breed such hazards. The Irish potato famine is the most famous example. (…) Ireland starved because of the counter-productive interaction between the goals of individuals and the needs of society.
The planned, centralised solution failed in the forest because the planners did not possess the local knowledge held in communities which had nourished trees for thousands of years. The unplanned, decentralised solution failed in the Irish famine because the local communities did not possess the global knowledge required to anticipate, or protect against, potato blight. While decentralisation of the solution of complex problems in society and in organisations is essential, the successful management of such decentralisation is a complex process of iteration between central and local goals and central and local knowledge.”
“One of Klein’s experiments involved showing videos of paramedics in action some novice, some expert – to various groups of observers. He discovered that both experienced paramedics and lay people were more successful at distinguishing the novices from the professionals than were teachers of paramedic skills. Paramedic teachers monitored adherence to the rules they taught and saw such adherence more often in the novices. They looked knowledgeably for directness and could not recognise the success of obliquity from a short video. That doesn’t mean the teachers were bad teachers, or that novice paramedics should not pay close attention to the rules the teachers prescribe. The key point is that only when you know the rules so well that they are second nature can you do without them. When you have learned the direct solution, you begin to learn more oblique approaches.
The general public, by contrast, didn’t know or care whether the practitioners they observed were following the rules or not. The qualities the general public tended to value were confidence and decisiveness – and, most of all, results – and these were the qualities they generally saw in the most successful paramedics. When Klein interviewed these practitioners, he concluded that pattern recognition rather than calculation was the key to their success. They used successive limited comparison, they made an assessment – and if evidence seemed inconsistent with that assessment, they adopted an alternative.”
“An anecdote tells of the Russian planner who visited the United States after the collapse of the Soviet Union. He asked his hosts: ‘Who is in charge of the supply of bread to New York?’ Yet with no one responsible, no directing mind, New York was more reliably supplied with bread than Moscow had been with a planner in charge. The blind watchmaker outperformed the sighted craftsman. The outcome would be hard to believe if it were not our everyday experience.”
“Today, people who deplore the activities of modern business and those who applaud these activities both agree that business is distinguished from other forms of organisation by having profit as its defining purpose. Yet this agreement covers evident nonsense. Who would want to work for a corporation whose defining purpose was profit, and why would society allow such an organisation to exist? People would join that corporation, and society would allow it to function, only if the business met their needs – the needs of the workers for rewarding employment, the needs of the community for goods and services that people want to buy. Needs that change over time, and require that business adapt constantly to meet them. Business exists to serve social purposes and enjoys legitimacy in the short term and survival in the long term only to the extent that such business meets these purposes. Profit cannot then be the ‘defining purpose’ of a business.
Yet for years I struggled with the idea that if profit could not be the defining purpose of a corporation, there must be something else that was its defining purpose. If business did not maximise profit, what did it maximise? I was making the same mistake as those victims of the teleological fallacy who struggled for centuries with questions like ‘What is a tiger for?” Tigers, we now understand, are not the product of any purposive design. Tigers are the creature you would design if you were more skilful and knowledgeable than you could ever be, to do the sorts of things that tigers do. But that is not how they came into existence. Tigers are good at being tigers because adaptation has honed them to be well adapted to the daily life of tigerdom. There is no more, or less, to it than that.
A good oil company is good at being an oil company, just as a good university is good at being a university, a good harpist is good at playing the harp and a good dentist is good at filling teeth. There is no defining purpose of these activities distinct from the activities themselves. Those who direct businesses must try to balance a multiplicity of objectives and meet the many and incompatible demands that individuals and other organisations make upon them. Any senior manager will tell you this is the reality of how his or her day is spent.”
“When faced with a task that daunts you, a project that you find difficult, begin by doing something. Choose a small component that seems potentially relevant to the task. While it seems to make sense to plan everything before you start, mostly you can’t: objectives are not clearly enough defined, the nature of the problem keeps shifting, it is too complex, and you lack sufficient information. The direct approach is simply impossible. Every writer has experience of sitting at a blank page, waiting for inspiration. The wait is often lengthy. Get it down. That is how this book was written, and it couldn’t have been done in any other way. Only an oblique approach could have worked.”
“Good decision making is pragmatic and eclectic. Oblique approaches rely on a toolkit of models and narratives rather than any simple or single account. To fit the world into a single model or narrative fails to acknowledge the universality of uncertainty and complexity.”