John Kay's 'Obliquity: Why Our Goals Are Best Achieved Indirectly' explores the paradox that some of our most important objectives are accomplished not by direct pursuit but through indirect means. Drawing on examples from business, science, and personal life, Kay argues that complex problems often resist straightforward solutions. Instead, success comes from flexibility, adaptation, and a willingness to pursue values beyond immediate self-interest. The book challenges conventional wisdom on goal-setting and presents a nuanced understanding of achievement and motivation.
Success is often achieved indirectly, requiring flexibility and adaptation instead of rigid planning.
Pursuing broader values and purposes can lead to greater achievement than simply aiming for material or narrow personal goals.
Complex problems are best navigated through experimentation, learning, and acknowledging uncertainty.
The book was published in: 2010
AI Rating (from 0 to 100): 90
When facing the Tylenol poisoning crisis, Johnson & Johnson didn’t directly fixate on short-term profits; instead, they prioritized customer safety and trust, which ultimately saved the brand and led to long-term profit.
ICI focused on scientific and engineering excellence rather than profit maximization. Their indirect approach led to industry leadership and strong financial results, as opposed to rivals who obsessively chased profits and failed.
Trees in Oregon flourished best when foresters allowed nature to take its course rather than rigidly trying to optimize timber yield. Attempts to control and simplify the forest ecosystem led to poorer results than more hands-off, adaptive strategies.
Kay uses personal happiness as an example, arguing that people who consciously try to make themselves happy rarely succeed. Instead, happiness is often a byproduct of pursuing meaningful work, relationships, and activities.
Many successful entrepreneurs, such as Steve Jobs, achieved outstanding results not by chasing money but by focusing on creating excellent products and experiences. This indirect approach led to the reward of financial success.
Countries that tried to copy other countries’ constitutions directly often failed to achieve stability. Those that adapted institutions to fit their own culture and circumstances, like the United States, were more successful.
Kay uses the scientific principle that leverage works best indirectly to illustrate a broader point: indirect approaches often unlock solutions when direct methods stall.
Kay highlights how discoveries like penicillin and Teflon were the outcomes of pursuing different goals or open-ended inquiry, showing that major breakthroughs often come obliquely.
by Daniel Kahneman
AI Rating: 95
AI Review: Kahneman explores how we think and make decisions, exposing the biases and heuristics that shape our actions. Like 'Obliquity,' it reveals that rational, direct planning is often unreliable. The book is a foundational text for understanding complexity and indirectness in human reasoning.
View Insightsby David Epstein
AI Rating: 90
AI Review: Epstein argues that broad experience and flexible thinking often lead to greater success than narrow specialization, aligning closely with Kay’s message about indirect routes to achievement. Anecdotes from sports, science, and business support his thesis.
View Insightsby Nassim Nicholas Taleb
AI Rating: 92
AI Review: Taleb's work delves into the unpredictable nature of complex systems, emphasizing the significance of rare, unforeseen events. The book complements 'Obliquity' by advocating humility and indirectness in strategy.
View Insightsby Nassim Nicholas Taleb
AI Rating: 88
AI Review: Taleb expands on how systems can benefit from volatility and unpredictable environments. The book suggests embracing uncertainty and complexity—key themes in Kay’s advocacy for indirect strategies.
View Insightsby Richard Rumelt
AI Rating: 87
AI Review: Rumelt demonstrates that strong strategies often arise from flexibility, focus on core issues, and adaptability, rather than rigid adherence to plans. This practical book reinforces many of Kay's arguments about the limits of direct goal pursuit.
View Insightsby Clayton Christensen
AI Rating: 90
AI Review: Christensen examines how indirect pursuits—such as nurturing relationships and pursuing purpose—lead to fulfillment and success. The book draws on business and life experience to argue that indirect approaches often yield the most meaningful outcomes.
View Insightsby Daniel H. Pink
AI Rating: 85
AI Review: Pink reveals that intrinsic motivation—like autonomy, mastery, and purpose—leads to better performance and satisfaction than external rewards. This reinforces Kay's point about the power of pursuing meaning over immediate goals.
View Insightsby Tim Harford
AI Rating: 89
AI Review: Harford contends that learning, experimentation, and adaptation are crucial to thriving in an unpredictable world. His practical examples mirror Kay’s thesis that indirect paths often work better than direct ones.
View Insightsby Rosamund Stone Zander & Benjamin Zander
AI Rating: 86
AI Review: Through stories and actionable advice, the authors promote a mindset of creativity, learning, and openness to unexpected outcomes. The emphasis on seeing broader possibilities fits Kay’s philosophy of obliquity.
View Insightsby Ray Dalio
AI Rating: 82
AI Review: Dalio’s reflections on the necessity of radical open-mindedness, adaptation, and learning from failure resonate with Kay’s central ideas. He provides a practical framework for navigating complex, unpredictable challenges.
View Insightsby James Surowiecki
AI Rating: 84
AI Review: Surowiecki demonstrates how collective intelligence often solves problems more effectively than top-down, direct control. Many of his examples reinforce oblique approaches to solving complex issues.
View Insightsby Eric Ries
AI Rating: 82
AI Review: Ries advocates for rapid iteration, experimentation, and adaptation instead of strictly following business plans. The book is foundational in entrepreneurship, supporting Kay’s points on indirect success.
View Insightsby Avinash K. Dixit and Barry J. Nalebuff
AI Rating: 80
AI Review: This primer on game theory reveals how indirect tactics and anticipation of complexity often outperform linear thinking, aligning well with themes in 'Obliquity.'
View Insightsby Charles Duhigg
AI Rating: 85
AI Review: Duhigg explains how habits shape personal and organizational outcomes, often in ways that are not directly controlled. He shows that change comes through indirect, systemic interventions.
View Insightsby Angela Duckworth
AI Rating: 80
AI Review: Duckworth’s study of perseverance emphasizes that consistent effort, directed by values rather than immediate success, is key to achievement. Her findings support Kay’s ideas about indirect pursuit of goals.
View Insightsby Chip Heath & Dan Heath
AI Rating: 82
AI Review: The Heath brothers illustrate how effective change comes from shifting existing systems and behaviors rather than simple force of will. Their stories echo the value of indirect, nuanced interventions.
View Insightsby Adam Grant
AI Rating: 83
AI Review: Grant chronicles how creative, indirect approaches by non-conformists drive innovation. His examples reinforce Kay’s thesis that the best results come from seeing and acting off the beaten path.
View Insightsby Douglas W. Hubbard
AI Rating: 81
AI Review: Hubbard dispels modeling myths and shows how measurement often brings surprising, indirect insights into decision-making, much like the lessons found in 'Obliquity.'
View Insightsby Philip E. Tetlock and Dan Gardner
AI Rating: 87
AI Review: Tetlock and Gardner explore why some people make better predictions and how adaptability and indirect reasoning more often lead to accurate foresight. Their data-driven conclusions back up Kay's advocacy for flexible, indirect thinking.
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