Brilliant Mistakes: Creating Portals of Discovery

By Paul J. H. Schoemaker

“Mistakes are our portals of discovery.” James Joyce

If you have ever flown in an airplane, used electricity from a nuclear power plant, or taken an antibiotic, you have firsthand experience with the power of mistakes. Each one of those innovations resulted from a flash or two of brilliant insight, and many, many years of wrong answers, dead ends, and missteps. The ill-fated flight at Kitty-Hawk showed how an idea that is impossibly wrong can be achieved by two Wrights. Alexander Fleming’s accidental discovery of penicillin, the world’s first and most successful antibiotic, involved a sloppy lab, keen perception and an exceptionally well-prepared mind. Scientists labored for decades to harness nuclear power, beginning with Einstein’s landmark 1905 publication hypothesizing that mass (M) can be converted into energy (E=mc2). Einstein’s famous theory was itself the result of nearly a decade of errors and published mistakes, over 23 by one count with several necessary to sustain Einstein in his radical beliefs about time, space, energy and gravity.1 My new book, Brilliant Mistakes2, examines the beneficial side of error by considering mistakes as potentially power “portals of discovery.”

The mindset of noticing anomalies and learning from them is the essence of brilliant mistakes.

Think about the last time you tried something new – whether it was acquiring a language, learning a new sport, or starting a company. Did you make errors along the way? Did those errors help, or hinder, your eventual progress towards your goal? The path from insight to discovery is seldom a straight line. Most ground breaking achievements in science, technology, economics and the arts represent long, meandering paths of misjudgments and false turns. Indeed, our very existence as humans relies on the error mechanism of “random mutation”; we literally would not exist on the planet if our evolutionary process had not included a few hiccups and false turns. My case for brilliant mistakes draws mostly on behavioral decision theory and its close cousin, behavioral economics, but also portfolio theory or options thinking.

In Praise of Folly. Because humans suffer from bounded rationality and furthermore don’t know what they don’t know, the only way to overcome myopic frames, overconfidence, and incremental career progress is to innovate beyond the bounds of our self-limiting world views. There is a long list of past business mistakes – as judged by conventional wisdom at the time – that proved to be brilliant. It includes personal copiers, selling via pet stores, ATM machines, credit cards for students, organic food, fractional jet ownership, and tobacco-free cigarettes. Just as these ideas were ridiculed at the time, there are many silly ideas floating around today in business that will prove to be brilliant in the future. The challenge for managers is to recognize them, and this can only happen if leaders create sufficient space for productive mistakes to occur. As IBM founder Tom Watson famously observed, “If you want to succeed faster, make more mistakes.” In most companies, brilliant mistake may already have been made, but the brilliant part lies dormant because there is little appetite or capacity to mine the mistake. Since the tuition was paid, why not extract the lesson?

We overly emphasize the role of rational decision making and planning but in doing so may undervalue the power of accidental learning.

The field of science is the best in learning from surprise, with the arts running a close second. An especially brilliant mistake occurred when meteorology researcher Edward Lorenz rounded some numbers by tiny fractions when typing them into his computer. This caused some strange weather patterns in his computer simulation and eventually led him to discover the butterfly effect (the notion that small changes in complex systems can create major consequences, such as a butterfly’s wing flaps in Hong Kong causing a hurricane in the Gulf of Mexico). Lorenz is now considered the father of deterministic chaos theory. Another striking example, mentioned above, is Alexander Fleming who discovered the world’s most successful antibiotic ever by chance. Fleming embraced the principle of “limited sloppiness” in order to widen his range of observation. His highly prepared mind recognized aberrant growth in some petri dishes that he had forgotten to clean in a timely manner. Unwelcome spores had come in through the window and contaminated his cultures. The spores possessed hidden antibiotic properties that slowed the growth of bacteria near where the spores had fallen. Fleming’s eye keen spotted the tiny disturbances from the corner of his eye as he was tossing the contaminated glass plates in a bin for cleaning. Intrigued by what he saw by happenstance, the ever curious Fleming explored it further and discovered penicillin. This mindset of noticing anomalies and learning from them is the essence of brilliant mistakes.

Beyond Rationality. I argue in my book that it isn’t enough to just realize that mistakes can reveal surprising lessons and fuel progress. I feel that we should do better than simply relying on random error to eventually point the way. We should become much more strategic about the errors we allow. Unfortunately, the social systems that surround us make this a difficult proposition. Our schools and organizations are designed for efficiency and order – fine principles, but ones which rarely encourage mistakes (either brilliant or foolish ones) to be made. Students are graded on how much they know, not on the degree to which they learned from helpful errors. Similarly, companies strive for error elimination, hiring learned advisors and relying on sophisticated management tools such as Six Sigma. It’s little wonder, then, that most decision-making books follow suit, encouraging you to focus narrowly on mistake avoidance today, rather than provoking you to plan for the stream of decisions that you will face tomorrow. We overly emphasize the role of rational decision making and planning but in doing so may undervalue the power of accidental learning. We also need to encourage strategies that design for serendipity, even if they cannot always be analytically justified.

Designing for, and learning from, a mistake can make it “brilliant.”

Ironically, it was the University of Chicago – that bulwark of rational economic thinking propelled by Milton Friedman and other Nobel Laureates in economics – that launched the first academic center among business schools to study our less rational side. As a faculty member at the business school’s Center for Decision Research, I spent twelve years among colleagues doing research on subjects that seemed, at the time, rather esoteric and off-kilter. We would study why experienced executives could be blinded by their mental frames and examine the virtues of throwing perceived wisdom out the window at times. At first, our esteemed economic colleagues looked askance at these studies and findings. The field of behavioral economics was still in its infancy and decision psychology an emerging field that rarely ventured beyond the laboratory or ivory tower. It did not receive much credence in those days from Chicago’s Nobel Prize winning economists, who also heavily influenced the business school there.

Nonetheless, it turned out to be a “brilliant mistake” for the University of Chicago’s business school to encourage a small group of intellectually diverse scholars to challenge the deeper tenets of the rational economic model. The field of behavioral decision theory has now gained great momentum across multiple academic disciplines. The principles that underlie it – such as the idea that humans are error-prone, that consumers do not always behave rationally, or that markets are not always efficient – have gained wide attraction and infiltrated popular thought. In 2002, the Nobel Prize in economics was awarded to Daniel Kahneman, a psychologist who by then had joined Princeton University. Popular books drawing on the field now fill bookstore shelves, with such titles as Freakonomics, Predictably Irrational, and Nudge. The field is also embraced by politicians, including the Obama administration as it explores new approaches to healthcare, education and other thorny policy issues.

Deliberate Mistakes. The examples above are mostly about remarkable individuals who learned from mistakes that occurred at random. I cite them because they illustrate that success is enhanced if mistakes are viewed as gifts. The deeper lesson in my book is that it often pays to design for these gifts of learning, rather than waiting for them to occur by accident. This deliberate approach to making mistakes – in order to accelerate learning or achieve higher performance – plays a crucial role in music, especially jazz. When trumpet great Wynton Marsalis was asked during a goodwill music tour to Cuba how important and valuable mistakes are, he replied, “Very important, because if you’re not making mistakes, you’re not trying. That is the art of jazz. It’s an art of negotiation, of communication.” As one guide to jazz improvisation explains, “we must accept each idea that we present to the group as valid. If each idea that is presented is utilized in some way by that individual, the other people in the group can respond knowing full well that it will be included to some degree. One can say that no idea that is presented is faulty. There is no such thing as a mistake but only opportunity to explore a path that may not have been considered. Each idea presented can be used in a positive way.”

Jazz great Miles Davis would have agreed. He urged his followers “…not to fear mistakes – there are none.” Even classical music giants resonate to this theme. Igor Stravinsky said, “I have learned throughout my life as a composer chiefly through mistakes and pursuits of false assumptions, not my exposure to founts of wisdom and knowledge.”

Artists are especially adept at struggling with deliberate mistakes. Their very willingness to enter a field as uncertain and unstable as art means that they are, by nature, far less risk-averse than the rest of us. Artists are willing to live at the edge, embrace deviance and challenge bourgeois conventions. They accept that mistakes are vital as well as rather uncomfortable companions along the road to success. And for most artists, there is far more failure than success at first, a necessary condition it seems to have a decent chance of achieving something of note. The phenomenally successful British novelist J. K. Rowling emphasized this key point during her Commencement address at Harvard in 2008. She explained how mistakes and failures had taken her to a point of deep insight about herself, prior to her smashing success with the Harry Potter series. In her words:

By any conventional measure, a mere seven years after my graduation day, I had failed on an epic scale. An exceptionally short-lived marriage had imploded, and I was jobless, a lone parent and as poor as it is possible to be in modern Britain without being homeless. The fears my parents had had for me, and that I had had for myself, had both come to pass, and by every usual standard, I was the biggest failure I knew. Why do I talk about the benefits of failure? – simply because failure meant a stripping away of the inessential. I stopped pretending to myself that I was anything other than what I was, and began to direct all my energy into finishing the only work that mattered to me. Had I really succeeded at anything else, I might never have found the determination to succeed in the one arena I believed I truly belonged. I was set free, because my greatest fear had already been realized, and I was still alive, and I still had a daughter whom I adored, and I had an old typewriter and a big idea. And so rock bottom became the solid foundation on which I rebuilt my life.”

Besides being good at defying convention, hitting rock bottom and then rising to new creative heights, some artists are skilled at incorporating random errors into their creative process as well. Jackson Pollack, in a famous example, created his famous “drip technique” of painting because his constrained financial circumstances required him to use resin-based household paints, which were thinner and more liquid than the more expensive artist’s paints. In his path breaking 1922 novel Ulysses, Joyce comments that, “…a man of genius makes no mistakes. His errors are volitional and are the portals of discovery.” And Joyce adopted quite some random elements in his later writings, including a hall-way conversation that happened by accident Finnegans Wake.

Key Takeaways. In my book Brilliant Mistakes just published by Wharton Digital Press, I build on the strong foundation of decades of research in behavioral economics and decision psychology. I offer a practical plan for separating destructive from constructive mistakes, for learning to make more of the brilliant kind. I encourage leaders to embrace this quality, to milk it for all of its evolutionary and learning potential. For those rationalists who deem the notion of a Brilliant Mistake to be an oxymoron, I would recommend that they take a portfolio view. For a risk-averse decision maker, it may be worth putting some money in a project expected to yield a loss provided this investment offers a sufficient hedge in case other investments sour. Even though that seemingly inferior project will not raise profit expectations, it can help reduce losses in case bad scenarios happen. Similarly, a deliberate mistake can be viewed as a hedge against conventional wisdom, one that will have a high payoff when the majority view of the crowd happens to be wrong. My book provides the formal argument for those interested drawing on finance theory.

In conclusion, my Brilliant Mistake book emphasizes the following key messages:

1. It is important to embrace the learning potential of mistakes – first, by overcoming the shame and fear that lead us to overlook the covert messages they carry about how we make decisions.

2. To learn from a mistake, it’s critical to separate the decision process – the part that you own – from the outcomes, which are usually influenced by multiple factors.

3. There is a difference between silly errors and brilliant mistakes, and it all hinges on the relative costs and benefits of what is at stake. Designing for, and learning from, a mistake can make it “brilliant.”

4. In some cases, it’s advisable to allow room for mistakes to be made. Just as random mutations have advanced evolution, “clever,” well-designed mistakes can further human progress by opening new portals of discovery.

For most people, the problem is not that they make too many mistakes, but too few. When asking seasoned leaders about their areas of greatest regret, they mostly will recount errors of omission rather than commission – what they failed to do, rather than what they did. People are quick to agree that, in retrospect, one can learn much from mistakes, and that some mistakes therefore can have great value. When I ask experienced managers in executive programs what they learned from the most in life, they usually say mistakes. When I counter with “Since mistakes have been so valuable to you, why don’t you make a few more?” they tend to look back at me with puzzled faces. The idea of purposeful mistakes runs counter to the idea to good management – the “zero-tolerance” approach of reducing error whenever and wherever possible.


About the author

Paul J. H. Schoemaker just published Brilliant Mistakes: Finding Success at the Far Side of Failure (Wharton Digital Press). He serves as Research Director of Mack Center for Technological Innovation at the Wharton School of the University of Pennsylvania, where he teaches strategy and decision making. He was previously at the University of Chicago, from where he spent an extended sabbatical with the scenario planning group of Royal/Dutch Shell in London. Paul is also the founder and chairman of Decision Strategies International, Inc, a consulting and training firm specializing in strategic planning, executive development and technology solutions ( Schoemaker has written over 100 academic and applied papers, and is the (co)-author of numerous business books including Decision Traps, Decision Sciences, Wharton On Managing Emerging Technologies, Winning Decisions, Profiting from Uncertainty, Peripheral Vision, as well as Chips, Clones and Living Beyond 100.


The views expressed in this article are those of the authors and do not necessarily reflect the views or policies of The World Financial Review.