Obliquity: Why our goals are best achieved indirectly by John Kay
Summary
In Obliquity, economist John Kay argues that the most important goals in life and business are best achieved indirectly. Whether aiming for happiness or profit, those who pursue these ends obliquely, by focusing on values and meaningful work, often succeed where those pursuing them directly fail.
Kay challenges the reductionist thinking of conventional business strategy, where goals are assumed to be clearly defined and solvable like a Sudoku puzzle. Real life, he argues, is far more complicated. We’re not sure what our objectives are. Our options are often limited. The environment we operate in is uncertain. In this context, genuine success stems from commitment to deeper values, not narrow targets or calculations.
Key Insights
- We rationalise after the fact – We often decide first, then construct justifications later.
- Happiness comes obliquely – It can emerge from hard work, exhaustion, and even danger—not from seeking comfort directly.
- Early Boeing – Focused on building excellent aircraft, not on return on investment.
- Early Sony – Aimed to create beautiful, reliable, and useful products—not just profit.
- Profit is a by-product – “Maximising shareholder value” is not a reliable path to success. Kay argues this goal:
- Encourages short-termism and financial manipulation
- Undermines intrinsic motivation
- Misunderstands what makes great companies thrive
- Is based on unstable measures (e.g. fluctuating market value, variable accounting standards)
- Leads to goal distortion (Goodhart’s Law in action)
- Misplaced metrics – We often equate income with worth and bonuses with merit.
- Most people are intrinsically motivated – They want to do good work, not just earn money.
- The Cathedral parable – Describes three ways of framing work:
- “I am cutting stone” – Action-level focus
- “I am building a cathedral” – Project-level goal
- “I am working for the glory of God” – Purpose-driven mission
- Resilience through disturbance – Just as small forest fires prevent catastrophic ones, small setbacks can prevent bigger crises.
- Preparation matters – Pasteur: “Fortune favours the prepared mind.”
- Real life ≠ Chess – Unlike games, real-world decisions:
- Have poorly defined goals
- Offer limited, unclear options
- Happen in uncertain environments
- Bogus quantification – Metrics like the UN’s Human Development Index oversimplify complexity.
- Even profit isn’t objective – Different accounting standards (IFRS vs. GAAP) yield different results.
- Act from values, not forecasts – The best decisions stem from principle, not predicted consequences.
- Goodhart’s Law – When a measure becomes a target, it ceases to be useful.
- Churchill’s warning – “History, with its flickering lamp,” reminds us that clarity is elusive and hindsight deceptive.
Strengths
- Challenges the simplistic thinking behind modern management dogma.
- Rich in examples—from Boeing and Sony to Pasteur and Churchill.
- Philosophically grounded but highly readable.
- Encourages a values-first approach to decision-making.
Weaknesses
This book may frustrate readers looking for step-by-step frameworks or “action plans”, and some examples are anecdotal rather than factual, but these are minor quips.
Reflections
Obliquity struck a deep chord with me. In both business and personal life, I’ve seen how chasing the wrong metrics, like deadlines, profit, or approval, can backfire. Kay’s insights on how real-world goals are rarely clear or stable resonate strongly, especially in domains like software, policy, and ethics.
His view that good decisions arise from values, not predictions, aligns with many philosophical traditions, yet feels refreshingly radical in today’s data-obsessed world.
Kay quotes Churchill’s evocative phrase, “History, with its flickering lamp,” to illustrate that our understanding of the past is never complete or definitive. Even hindsight, often treated as a source of clarity, is dim, uncertain, and open to interpretation. This reinforces the book’s central theme: that navigating life’s complexities requires humility,
Conclusion
John Kay’s Obliquity is an interesting read, though at times he rather over-eggs the pudding. Success is not always found by following the most obvious path, but neither is it always gained by roundabout means. Sometimes a carefully planned, tightly executed project succeeds handsomely; at other times, the oblique approach proves wiser. It reminds me of the old biblical story of King David: in his first battle, he attacked the enemy in a straightforward frontal assault, but in the next, he waited until the sound of marching in the mulberry trees signalled his ambush from behind. The lesson is simple: adjust your tactics to your battle.
Book Details
Title: Obliquity: Why our goals are best achieved indirectly
Author: John Kay
Publication Year: 2011
Genre: Careers, Job Hunting