In an unpredictable world, achieving complex goals through direct methods often fails. Traditional, rigid planning can fall apart under changing circumstances. Embracing obliquity—an indirect, adaptive approach—leads to success by allowing flexibility, learning from failures, and focusing on meaningful pursuits.
Obliquity is a concept that challenges the conventional wisdom about how to achieve success and reach our goals. Economist John Kay popularized the term in his 2010 book “Obliquity: Why Our Goals Are Best Achieved Indirectly.”
The central idea behind obliquity is that complex goals are often best achieved indirectly rather than through meticulous planning and a laser focus on the end objective. Kay argues that in a complex, unpredictable, and ever-changing world, taking an indirect, iterative, and adaptive approach is frequently more effective rather than charting a straight line to the target.
There are numerous examples of obliquity in action. Many successful companies did not start with a grand vision of what they would ultimately become. Instead, they solved a specific problem and iteratively evolved their products, strategy, and business model based on feedback and changing circumstances. For instance, Google started as a PhD research project to improve online search. Only later, almost as a byproduct, did advertising and other business opportunities emerge.
Similarly, achieving happiness is a common goal in our personal lives. However, research shows that people who pursue happiness as their primary aim often end up less happy. Fulfillment tends to come obliquely—as a side effect of engaging in meaningful pursuits, cultivating relationships, experiencing personal growth, and contributing to something larger than oneself. The happiest people are often not focused on happiness but on living according to their values and ideals.
The theory of obliquity does not imply that goals are unimportant or that planning is pointless. Quite the contrary, Kay emphasizes that having high-level directional clarity about where you want to go is critical. The distinction is that with complex goals in an uncertain world, the path is often winding, and the final destination may look different than originally envisioned. Rigid plans tend to fall apart upon contact with reality. Openness to serendipity, iteration, and adaptation is essential.
This oblique approach requires a certain level of humility and a recognition that we cannot predict or control everything. It means holding our assumptions and strategies loosely while remaining firmly committed to our underlying values and vision. With obliquity, we embrace uncertainty, see failures as learning opportunities, and trust that as long as we keep putting one foot in front of the other in the right general direction, we will eventually arrive at a worthwhile destination, even if it’s not exactly the one we originally had in mind.
The idea of obliquity can feel counterintuitive in a world that celebrates people who seem to achieve wild success by pursuing their dreams with relentless, direct focus. However, an indirect adaptive approach is a more realistic path to success for many complex endeavors. As the aphorism goes, “Life is what happens to us while we are making other plans.” Often, it is only by letting go of our narrow attachment to specific outcomes that we can achieve the most significant breakthroughs. Obliquity reminds us to embrace the journey and trust that our ultimate destination will be all the more fulfilling, given that we have been shaped by unpredictable currents along the way.
Embracing obliquity can guide us through the uncertainties of the future. Focusing on flexible, adaptive approaches can help us better navigate complex goals. As we learn from our experiences and remain open to change, we move closer to fulfilling our ambitions in ways we might not have initially imagined.
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