Our brains favor familiar patterns and solutions, a tendency rooted in our evolutionary preference for efficiency and energy conservation. This cognitive conservatism guides us to make choices that seem good enough rather than optimal. These fast and frugal mental shortcuts are beneficial most of the time. However, when we cannot overcome a problem head on, when we need to come at it from a new angle, conventional framing confines our perception. Like a sailor tacking against the wind, we too can navigate our cognitive landscapes by zigzagging—systematically challenging our usual approaches and deliberately thinking from alternate perspectives. When we employ this iterative mindset, we’re more likely to circumvent obstacles and uncover solutions that direct approaches miss.
Rory Sutherland, an expert in contrarian thinking within advertising, frequently challenges the status quo with his unconventional insights. I’m particularly struck by his claim that the opposite of a good idea can be another good idea. In his book, Alchemy: The Surprising Power of Ideas That Don't Make Sense he asserts that “While in physics the opposite of a good idea is generally a bad idea, in psychology the opposite of a good idea can be a very good idea indeed: both opposites often work.”
Paradoxical patterns
To understand this paradox, consider the Veblen effect in pricing strategies (something we’ve all experienced, though the term may be unfamiliar). According to the law of demand, higher prices should decrease demand. Yet, paradoxically, raising prices can enhance perceived value and status, thereby boosting demand. This is why luxury brands like Rolex, Rolls-Royce, and The Row can slap exorbitant price tags on their products; the high price itself becomes a marker of quality and exclusivity, enticing those who can afford what Thorstein Veblen called “conspicuous consumption.” It’s a phenomenon that flies in the face of traditional economic logic, illustrating how our decisions are shaped by psychological and social factors, not just the cool, rational calculus of homo economicus.
Another radical pricing strategy leverages our social instincts. Fixed pricing often creates an adversarial dynamic where neither buyer nor seller feels fully satisfied. A counterintuitive solution is to allow customers to pay what they want. Radiohead’s release of their album In Rainbows exemplifies this approach. By letting fans set their own price, Radiohead expanded their market, maximizing reach without losing out on higher-paying customers. Ultimately, the pay-what-you-want sales of In Rainbows outperformed the digital revenue of all their previous albums combined.
Surprising solutions that defy common sense are not confined to pricing strategies. The Braess Paradox provides a compelling contradiction to conventional thinking in urban planning. It suggests that adding more roads to a congested network can actually worsen congestion rather than alleviate it. This paradox, reminiscent of the anomalies in classical economic theories, sheds light on the complex interdependencies and feedback loops that define networks. Counterintuitively, by removing roads we can actually streamline traffic flow, achieving efficiency by subtraction rather than addition.
Break the binary
When we challenge ourselves to move beyond binary thinking, we open up possibilities that can lead to innovative and more effective solutions. Our habitual reliance on simplistic binaries—true/false, yes/no, stop/go—often restricts our understanding and limits our ability to fully grasp the complexities of any given situation. By expanding our perspective and considering multiple dimensions, especially psychological ones, we can discover novel approaches that might otherwise remain hidden.
Take, for instance, the concept of fragility. The opposite of fragile is unbreakable, right? But Nassim Taleb expands this spectrum with the notion of “antifragility,” a quality that allows systems to benefit and grow from volatility and stress. He explains, “Some things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder, and stressors…Antifragility is beyond resilience or robustness. The resilient resists shocks and stays the same; the antifragile gets better.” Once you start looking, you can find examples of antifragility everywhere. Taleb, a former derivatives trader and hedge fund manager, applies antifragility in the context of investing. Asymmetric bets not only withstand market volatility but also capitalize on it.
Time management is another domain where binary thinking proves insufficient. Either you say yes or no to a task. Take it or leave it. But this mindset is, as Leidy Klotz points out in a deceptively simple yet profound assertion, fundamentally flawed. “Saying no,” Klotz contends, “is not subtracting.” This may sound tautological, like some Zen koan that both makes perfect sense and none at all, but it’s a crucial distinction. Simply declining new engagements doesn’t equate to the deliberate act of subtraction. The idea of stopping, of just cutting things loose, feels taboo, yet it’s essential. Anything that doesn't align with your core mission—what you’re passionate about, what you can be the best at, and what drives your success—should be on your “stop-doing list.” Place this list next to your “to-do list” and review both daily, ensuring you’re not just adding tasks but also removing non-essential ones. And while you’re at it, consider pushing towards another edge by crafting a “done list” to record completed tasks. Over time, small wins accumulate, generating momentum towards larger goals. It’s the psychological equivalent of compound interest.
By adopting these expanded spectrums of thought, we can uncover profound insights and develop robust solutions to the challenges we face. The opposite of a good idea, therefore, can indeed be another good idea—one that we might not have considered if we remained confined to conventional framing.
Break the mold
Investor Howard Marks wrote that “You can't do the same things others do and expect to outperform. Unconventionality shouldn't be a goal in itself, but rather a way of thinking. In order to distinguish yourself from others, it helps to have ideas that are different and to process those ideas differently.” He conceptualizes the situation as a simple two-by-two matrix. Essentially, on one dimension you can either be right or wrong. On the other you can be conventional or unconventional. Obviously you don’t make money if you’re wrong, but most people don’t realize you don’t make money if you’re right and acting conventionally because the opportunity is too obvious and all the returns get arbitraged away. As Sutherland puts it, “The fatal issue is that logic always leads to the same place as your competitors.” The only way to generate outstanding results is to be unconventional and right. This principle applies broadly to innovation in any domain. Of course, this is hard to do because, at the start, you can only know if you’re unconventional. You don’t know if you’re right. And this is where the risk comes in.
Risk is scary. We’re instinctively risk-averse, gravitating toward the predictable. Consider a corporate expression of the 1970s and 80s: “Nobody gets fired for buying IBM.” At the time, IBM's strong reputation and market dominance made them a fortress of justification, allowing employees to sleep soundly, knowing that their logical, if uninspired, decision would not be questioned by higher management. In situations where decisions undergo rigorous scrutiny, taking the well-trodden path provides a shield against blame. It’s easier to rationalize such choices to others. As a result, the risk-averse maintain their positions within the protective confines of convention, while the risk-takers achieve success from what was initially perceived as imprudent or even irrational. The willingness to take calculated risks, to venture beyond the familiar, is one of the main differences between people who consistently generate breakthroughs—and everyone else.
Think sideways
Having explored the benefits of embracing unconventional strategies and the courage to differ from the norm, here are a few thoughts about how you might apply these concepts. Thinking sideways isn't just about choosing a different path—it's about understanding the deeper principles that govern successful outcomes and leveraging those insights in novel ways.
First, if you want to optimize for failure, simply do the opposite of the norm without understanding underlying principles. In tandem with nudging us towards non-consensus, Marks warned that “you should not aim for contrarianism for its own sake, but only when the reasons are good and the actions of the crowd look particularly foolish.” Conventional wisdom exists for a reason; it’s often built on a foundation of tried-and-true principles that withstood the test of time. Effective contrarians don’t just reject the status quo—they deeply understand it. The most important thing about being “unconventional and right” is the part about being right. In the end, getting it right really matters.
Second, when it comes to intelligent people trying to solve hard problems, there’s no shortage of rational, consensus thinking. To get an edge, you have to consider the irrational non-consensus too. Dare to look stupid. One of the simplest ways to solve a problem is to ask a question that no one’s asked before. Take a wild guess and test unconventional ideas that no one else will. This can unlock a competitive advantage since others are too risk-averse to try something seemingly irrational. In many ways, finding a viable approach that others are not using is a hallmark of a great strategy. As Kevin Kelly, founding executive editor of Wired magazine says, “Don't aim to be the best. Be the only.”
Lastly, value perception as much as reality. All human problems have a psychological dimension. Changing how people perceive something can be more powerful than objectively improving it. If you want someone to overvalue something, give it to them. If you want their wait time to feel shorter, hang a mirror in front of them. And if you want to improve their experience of a painful procedure, you can actually do so by prolonging their discomfort. Humans are wonderfully strange. Because of this, the opposite of a good idea can truly be another good idea. Embracing our complexity and contradiction can uncover remarkable solutions often overlooked by conventional logic.
Herbert A. Simon, the Nobel-prize-winning economist, believed that decision-making was about achieving outcomes that were “good enough” based on an individual’s limited information rather than expending effort finding the best possible or optimal choice. Simon called this “satisficing”—a combination of the words “satisfy” and “suffice.”
I believe Sutherland is expanding on an idea by Niels Bohr who supposedly expressed that “The opposite of a correct statement is a false statement. But the opposite of a profound truth may well be another profound truth.”
Homo economicus, or “economic man,” is a theoretical abstraction that some economists use to describe a rational human being. In certain neoclassical economic theories, people are portrayed as ideal decision-makers with complete rationality, perfect access to information, and consistent, self-interested goals. This construct traces its origins to an essay on political economy by John Stuart Mill. Modern behavioral economists have shown that human beings are, in fact, not rational in their decision-making. We are, instead, profoundly irrational, swayed by a myriad of biases, emotions, and social influences that Homo economicus would find utterly baffling.
Antifragile: Things That Gain from Disorder by Nassim Nicholas Taleb
Subtract: The Untapped Science of Less by Leidy Klotz
Through natural selection, species adapt and evolve in response to environmental pressures and random mutations, becoming evermore suited to their habitats over time. Our immune system becomes more robust by being exposed to pathogens, learning to combat future infections more effectively. And environmental stressors in natural ecosystems are critical for healthy growth and resilience. A striking example of antifragility is the Biosphere 2 project, which found that trees grown in a controlled environment without wind grew quickly but collapsed before maturing. The absence of wind prevented the development of the stress wood needed for trees to grow strong and stable enough to support their own weight.
The concept of a “stop-doing list” was popularized by Jim Collins, in his book Good to Great which emphasize the importance of not just focusing on what to do but also identifying activities and behaviors that should be discontinued to improve productivity.
Howard Marks wrote this in his “Dare to Be Great” memo to Oaktree Capital Management clients on September 7th, 2006.
People attach higher value to things merely because they own them. This endowment effect (coined by the Nobel prize-winning economist Richard Thaler) leads to an irrational overvaluation of owned objects compared to their market value, stemming from loss aversion and a sense of psychological ownership.
Unoccupied time feels longer than occupied time. By giving people something to look at or do (like checking their appearance), mirrors make the wait time feel shorter and less tedious. Also, solo waits feel longer than group waits. Mirrors allow people to observe others around them, creating more of a shared group experience rather than a solitary wait.
In a study by Daniel Kahneman, Donald Redelmeier, and Joel Katz, colonoscopy patients were randomly divided into two groups. One underwent a colonoscopy procedure wherein the scope was left in for three extra minutes, but not moved, creating a sensation that was uncomfortable, but not painful. The other group underwent a typical colonoscopy procedure. The findings revealed that those who experienced the prolonged, yet static discomfort rated their overall experience as less unpleasant than those who underwent the regular procedure. This is attributed to the “peak-end rule,” a psychological heuristic where people judge an experience largely based on how they felt at its peak and at its end, rather than based on the total sum or average of every moment of the experience. The less painful ending in the extended procedure influenced their memory of the event, making them more likely to return for future procedures.