OBLIQUITY

The average professional person plans, does, acts, and checks. It is the principle behind any decent management system (quality, environmental, health and safety). Planning is something professionals work on for the whole of their careers. It is something that is unique to the individual; it is affected by their style; it hopefully gets better as you age.
John Kay’s Obliquity (2012): Why Our Goals Are Best Achieved Indirectly, argues a deceptively simple idea: for many of the goals people care about most; happiness, business success, innovation, wealth, even good public policy; the best way to achieve them is often not to pursue them head-on. Instead, they are reached indirectly, through intermediate aims, good judgment, and practical adaptation to context. Kay calls this principle obliquity.
At the heart of the book is a challenge to a deeply modern assumption: that if you define an objective clearly, measure it precisely, and optimize relentlessly for it, you will get the result you want. Kay argues that this logic works well for simple, technical tasks but breaks down in complex human systems. In areas like business, politics, education, personal life, or financial markets, goals are often difficult to specify fully, environments change constantly, and the very act of chasing a target can distort behaviour. In these settings, direct maximization can be counterproductive. Success comes more often from building capable institutions, following coherent values, responding intelligently to feedback, and pursuing worthwhile activities for reasons larger than the target itself.

The central idea: indirect routes often work better than direct pursuit
Kay’s claim is not that goals are unimportant. It is that many important goals are complex objectives; they are hard to define, hard to measure, and shaped by many interacting variables. If someone tries to maximize such a goal directly, they often oversimplify it into a narrow metric. Once that happens, people start optimizing the metric instead of the real objective. The result can be failure disguised as success.
For example, a company that sets out simply to “maximize shareholder value” may end up making short-term financial decisions that damage its products, culture, reputation, or long-term competitive position. A person who tries too directly to “be happy” may become self-absorbed and disappointed, because happiness often emerges from relationships, meaningful work, and engagement rather than from monitoring one’s own emotional state. A government that tries to improve public services solely by imposing numerical performance targets may get gaming, bureaucracy, and box-ticking rather than genuine improvement.
Kay argues that the best outcomes often arise as by-products of other worthwhile activities. Profit comes from making products people value. Happiness comes from living meaningfully rather than chasing happiness itself. Great institutions are built by people focused on craft, service, mission, or excellence – not by people staring only at a dashboard of target metrics.

Why direct optimization fails in complex systems
One of Kay’s most important themes is that the world is too complex for simple optimization models to govern many human decisions. Economic theory often imagines decision-makers with stable preferences, clear objectives, and enough information to maximize utility or profit. Kay, who is an economist, does not reject rational thinking; rather, he criticizes the overextension of abstract optimization models into domains where they fit poorly.
Complex systems have several features that frustrate direct pursuit. Objectives are ambiguous, people and organizations rarely want just one thing. Businesses want profits, but also customer loyalty, employee commitment, innovation, legitimacy, and resilience. Individuals want money, but also love status, freedom, purpose, and peace of mind. These aims can conflict, and they cannot always be reduced to a single scale.
Information is incomplete, decision-makers never know everything they need to know. They act under uncertainty, often with delayed feedback and changing conditions. Means reshape ends, the process used to pursue a goal can change the environment itself. Measuring performance alters behaviour. Incentives produce side effects. Markets respond strategically. People react to being managed. Metrics are imperfect proxies, when organizations choose measurable indicators as substitutes for real goals, those indicators can become corrupted. If a school is judged by test scores alone, teaching narrows to the test. If a hospital is judged by waiting-time targets alone, effort may shift toward the measure rather than patient care.
Because of these problems, direct pursuit often leads to goal displacement, the measure takes over from the mission. Obliquity is Kay’s alternative. It does not mean drifting without purpose; it means recognizing that worthwhile ends are often reached through indirect, disciplined, context-sensitive strategies, rather than rigid optimization.
Happiness as the clearest example of obliquity, but happiness is elusive when treated as a consumable product to be maximized. It is more likely to arise when people are absorbed in meaningful work, relationships, commitments, and activities that take attention away from the self. This point links Kay to a long tradition of moral philosophy. Thinkers from Aristotle onward argued that flourishing is not a feeling that can be manufactured directly but a condition of living well—developing character, exercising judgment, participating in community, and pursuing worthwhile ends. Kay’s version is secular and practical rather than purely philosophical, but the structure is similar. Happiness is not a target you hit by aiming at it directly; it is a by-product of a life organized around things that matter.

Business obliquity
A major portion of the book applies obliquity to corporate life. Kay criticizes the doctrine, common in late twentieth-century management, that the sole purpose of business is to maximize shareholder value. His argument is not anti-profit; it is that shareholder value is usually the result of running a good business, not a reliable operational principle for running one.
Companies that endure tend to be organized around capabilities, reputation, customer service, innovation, and employee commitment. Their leaders often think in terms of products, mission, and institutional quality rather than purely financial extraction. When firms focus narrowly on quarterly earnings or stock price, they may underinvest in research, squeeze staff, manipulate accounts, pursue foolish acquisitions, or take hidden risks. These actions may flatter short-term metrics while destroying long-term value.
Kay’s argument here is subtle. A company must remain financially viable, but it creates that viability by doing many other things well. Managers should ask: What can we uniquely do for customers? What capabilities make us better than rivals? What kind of organization are we building? How do we earn trust? Those are oblique routes to profitability, but in practice they are often the only reliable routes.
This perspective also helps explain why some of the most admired companies have cultures centred on engineering excellence, design, service, or long-term stewardship rather than explicit maximization formulas. Their leaders may care deeply about returns, but they pursue returns through a richer conception of the firm. The best decision-makers know what cannot be quantified cleanly. They understand context, history, incentives, and human motivation. They use models as aids, not masters.
This is particularly important in finance. Kay is sharply critical of the belief that sophisticated quantitative systems can eliminate uncertainty or convert radical uncertainty into measurable risk. Financial actors who believe too strongly in their models may take catastrophic risks because they mistake what can be priced for what can be known. Obliquity, in this context, means humility: building robust institutions, diversifying exposures, preserving trust, and recognizing that survival and resilience matter more than elegant optimization.
Kay’s book is therefore both a critique of narrow managerial rationality and a defence of a richer, more humane understanding of success. It asks readers to abandon the fantasy that every important goal can be maximized directly through metrics and incentives. Instead, it proposes that the best route to many worthwhile ends is oblique: purposeful but indirect, disciplined but not mechanical, strategic but humble. The result is a thoughtful and highly applicable book about why wisdom often beats optimization when life becomes complicated.

References
Kay, J. 2011. Obliquity - why our goals are best achieved indirectly. Profile Books Ltd, London, United Kingdom.

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