Why More Effort Doesn't Always Equal Better Results

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Toward the end of a Thai massage, the therapist twisted my back and said, gently, “Relax your shoulders.” I attempted to follow her instruction by consciously releasing every muscle I could sense, but a moment later she asked again. At this point, I whispered back with slight embarrassment, “This is as relaxed as it’s going to get, I’m afraid.” She sounded disappointed. “Oh... if you can’t relax, that’s not good for you,” which, unsurprisingly, did not help me relax any further.

Unfair as it sounds, the harder we chase certain things, the more they slip away. Try to fall asleep and your mind suddenly starts racing. Try too hard to appear charming and you'll just become awkward. Go looking for happiness and you may end up more dissatisfied than when you started.

People who look for friends or new romantic partners often report that they found them the moment they stopped looking. As soon as they stopped "chasing butterflies" and picked up a hobby, dedicated themselves to a project, or simply started going for walks, new connections seemed to have appeared on their own.

Long before “chasing butterflies” became a social media motivational cliché, the idea was articulated by 19th-century philosopher John Stuart Mill. In his autobiography, Mill wrote about what we now call the “paradox of hedonism.” He realized that measuring and pursuing happiness directly might even be the fastest way to become miserable. Happiness, he discovered, appears only as a byproduct of treating something else as your primary goal.

"Those only are happy (I thought) who have their minds fixed on some object other than their own happiness," Mill wrote. "Aiming thus at something else, they find happiness by the way."

Trading up the chain

You might expect the “paradox of pursuit” to only apply to the emotional, unquantifiable parts of life. But we find countless examples of the exact same dynamic in the cold, hard world of business and media strategy.

In the summer of 2008, the founders of a then-tiny startup called AirBed & Breakfast were desperate for media attention. They pitched the obvious targets: CNN, the New York Times, and TechCrunch, but no one responded. And of course they didn't. Why would national editors care about three unknown guys trying to rent out air mattresses in strangers’ apartments?

As Airbnb co-founder Brian Chesky later explained on Reid Hoffman’s Masters of Scale, they eventually decided to try something else. Instead of chasing national coverage, they emailed a handful of obscure, hyper-local bloggers in Denver, Colorado. The Democratic National Convention was about to flood the city with visitors, overwhelming all of its hotels.

These small bloggers proved to be a much better target than CNN. While thousands of stories compete for attention at a large national outlet, local writers are constantly hungry for stories that are, quite literally, right up the street. The bloggers wrote about the startup, which lowered the bar for the local Denver newspapers to pick up the story. Finally, national reporters covering the convention noticed the local coverage, and suddenly, the tiny startup that the national press had previously ignored was appearing everywhere.

The path to the center, it turned out, ran through the edges.

Paradox of pursuit

The name economists have for this pattern is "obliquity". In his book Obliquity: Why Our Goals Are Best Achieved Indirectly, author John Kay examines companies that became highly profitable while pursuing entirely different immediate goals. They focused relentlessly on things like craftsmanship, engineering excellence, or reputation. Because the path to success in a complex market is rarely a straight line, they found that profit arrived more reliably as a side effect than as a direct target.

In a less business-like and perhaps more personal context, this tendency is something that philosophers have noted for decades, framing it as a persistent feature of human nature rather than a cognitive glitch. The British American writer Alan Watts often referred to it as the “Law of Reversed Effort.” He observed that the conscious desire to achieve a state—perfect calm, effortless sleep, spontaneous charm—can reinforce its very absence. Trying to force yourself to relax, Watts suggested, is a bit like trying to smooth rippled water with a flat iron; the intervention only disturbs the surface further.

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Modern psychology was naturally interested in the science behind why the direct approach so often fails. In his 1994 paper “Ironic Processes of Mental Control,” the late Harvard psychologist Daniel Wegner proposed that when you actively try to relax, fall asleep, or suppress a thought, the mind engages two processes at once. One process tries to create the desired state while the other one “monitors” whether it has worked.

That monitoring process turns out to be the troublemaker. Because the mind must remain vigilant for signs of failure, it keeps attention fixed on the very thing we are trying to eliminate: the wakefulness, tension, the forbidden thought. The harder we push toward the goal, the more the mind checks whether we have succeeded, and the more elusive the goal becomes.

Wicked problems

None of this means that direct effort is always or completely useless. Some goals respond perfectly well to straightforward pursuit. If you want to learn a new language, train for a marathon, or assemble a piece of furniture, there is a clear path: define the objective, follow the instructions, and measure your progress along the way.

But not every problem works like that. In 1973, design theorists Horst Rittel and Melvin Webber published a landmark paper distinguishing between “tame” and “wicked” problems. Tame problems can be clearly defined and solved step by step. Wicked problems have no single formulation, no final test of success, and no clear stopping point.

While Rittel and Webber were specifically studying public policy, the underlying lesson applies to how we approach our own lives: We constantly confuse tame, mechanical tasks with problems that are inherently more fluid and less predictable.

Some high-level goals—finding happiness, attracting attention, or shaping culture—behave exactly like these messy, open-ended tasks. They involve other people, shifting incentives, and feedback loops that change the rules midway through. In such environments, direct pursuit often backfires. Pushing harder on the outcome simply reinforces the obstacles standing in the way.

This is why the exact strategy that works for simple tasks so often fails for complex ones. When something is unpredictable, the most effective strategy may not be to target the outcome itself, but to cultivate the conditions from which that outcome is most likely to emerge. Focus on the work, the craft, the relationships, and the small communities where ideas take root. The butterflies may come—but only if you spend your time growing the garden.