At the end of the Thai massage, the therapist patted my back and gently said, “Relax your shoulders.” I tried to follow his instructions and release every muscle I could feel, but a moment later he asked again. At this point, I whispered a little embarrassment“It’s as quiet as it gets, I’m afraid.” He was disappointed. “Oh…if you can’t rest, it’s not good for you,” which is no wonder I need more rest.
As unfair as it may seem, the more we chase certain things, the more they slip away. Try to fall asleep and your mind suddenly starts racing. Try to sound interesting and you’ll just end up being awkward. Go search happiness and you may end up more dissatisfied than when you started.
People looking for new friends or romantic partners often report that they found them the moment they were looking. As soon as they stopped “chasing butterflies” and took up a hobby, dedicated themselves to a project, or just started walking, new connections seemed to emerge spontaneously.
Long before “chasing butterflies”. Social media motivational cliché, an idea coined by the 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 immediate happiness can even be the fastest way to become unhappy. Happiness, he discovered, comes only as a byproduct of treating something else as your primary goal.
“Only those are happy (I thought) whose minds are set on anything but their own happiness,” Mill wrote. “The goal of something else, they find in the way of happiness.”
Chain trading
You might expect the “paradox of search” to apply only to the emotional and impersonal parts of life. But we find countless examples of the same dynamic in the cold, hard world of media business and strategy.
In the summer of 2008, the founders of a then-small startup called AirBed & Breakfast were tough on the media. attention. They set clear goals: CNNto New York Timesand TechCrunchbut no one answered. And of course they didn’t. Why do national editors care about three unknown guys who tried to rent out air mattresses in strangers’ homes?
As Airbnb co-founder Brian Chesky later commented on Reid Hoffman Masters of scalethey finally decided to try something else. Instead of chasing national coverage, they emailed a bunch of obscure, hyperlocal bloggers in Denver, Colorado. The Democratic National Convention was about to flood the city with guests and fill all its hotels.
These small bloggers proved to be a better target than CNN. With thousands of stories vying for attention in a major national outlet, local writers are always hungry for stories that are literally on the street. Bloggers wrote about the startup, cutting the line for local Denver newspapers to pick up the story. Eventually, the national reporters covering the convention picked up on the local news, and suddenly, a small start that the national press had previously ignored was everywhere.
The way to the center, it turned out, went through the edges.
The search paradox
The economists’ name for this pattern is “oblique”. In his book Problem: Why our goals are best achieved indirectlyauthor John Kay examines companies that achieved high returns while achieving completely different immediate goals. They invariably focused on things like craftsmanship, engineering excellence, or prestige. Because the path to success in a complex market is rarely a straight line, they found that profit is more reliable as a side effect than a direct goal.
In a less commercial and perhaps more personal context, this tendency is something that philosophers have noted for decades, treating it as an enduring feature of human nature rather than a cognitive fallacy. British American writer Alan Watts often called it the “Law of Reversed Effort”. He observed that the conscious desire to achieve a state – complete peace, undisturbed sleep, spontaneous attraction – can reinforce its absence. Trying to force yourself to relax, Watts suggested, is a bit like trying to smooth running water with a flat iron; interference will only disturb its surface further.
Modern psychology was naturally interested in the science of why direct relationships often fail. In his 1994 article “Ironic Processes of Mental Control,” Harvard psychologist Daniel Wegner suggested that when you actively relax, sleep, or suppress a thought, the mind is doing two things at once. One of the processes tries to create the desired state, while the other “checks” whether it worked or not.
This monitoring process causes problems. Because the mind must be alert to signs of failure, it focuses on what we are trying to overcome: arousal, tension, forbidden thought. The more we push towards a goal, the more the mind wonders if we have succeeded and the more elusive the goal becomes.
Bad problem
None of this is to say that direct effort is always or completely useless. Some targets respond perfectly to direct search. Whether you want to learn a new language, train for a marathon, or assemble a piece of furniture, there is a clear path: set a goal, follow the instructions, and measure your progress along the way.
But not all problems work this way. In 1973, design theorists Horst Rittel and Melvin Webber published an important paper distinguishing between “tame” and “bad” problems. Taming problems can be clearly identified and solved step by step. Wicked problems have no single formula, no ultimate test of success, and no clear cut-off point.
While Rittel and Webber specifically studied public policy, the main lesson applies to how we approach our lives: We constantly confuse tame, mechanical tasks with problems that are inherently more fluid and unpredictable.
Some high-level goals—finding happiness, attracting attention, or shaping culture—behave exactly like these messy, open-ended tasks. They involve other people, change incentives, and feedback loops that change the rules in the medium. In such environments, direct prosecution often fails. Pushing harder for results reinforces the obstacles that stand in the way.
This is why the exact strategy that works for simple tasks often fails for complex ones. When something is unpredictable, the most effective strategy may not be to aim for the outcome itself, but to develop conditions that make that outcome more likely to occur. Focus on work, craft, relationships and small communities where ideas take root. Butterflies can come, but only if you take the time to cultivate the garden.
