Luckiness and Playfulness in Entrepreneurial Thinking

Note: this post was originally written for and published on the 1388 Consulting blog.
My favorite successful entrepreneurs are those who have the humility to acknowledge what a big role “luck” has played in their success. Those who no matter how hard or how smart they worked, recognize that the same paths and opportunities available to them were simply not available to many others who worked just as hard and just as smart.
But our understanding of luck should not be simply about what external circumstances are — or are not — available. There is something about luckiness that requires us to look inwards as well. As the saying goes:
“luck is where opportunity meets preparation.”
But what is that preparation? I feel like a lot of people interpret this to mean hard work. Just a lot of very hard work. While that is certainly part of it, I’m afraid that it may not be the whole picture. Paradoxically, by focusing solely on working hard, we may find ourselves at times being too busy to get lucky.
Are you too busy to be lucky?
Dr. Richard Wiseman has done a lot of interesting research on luck. Consider this experiment that he describes:
“I gave both [self-described] lucky and unlucky people a newspaper, and asked them to look through it and tell me how many photographs were inside. On average, the unlucky people took about two minutes to count the photographs, whereas the lucky people took just seconds. Why? Because the second page of the newspaper contained the message: ‘Stop counting. There are 43 photographs in this newspaper.’ This message took up half of the page and was written in type that was more than 2 inches high. It was staring everyone straight in the face, but the unlucky people tended to miss it and the lucky people tended to spot it.”
“For fun, I placed a second large message halfway through the newspaper: ‘Stop counting. Tell the experimenter you have seen this and win £250.’ Again, the unlucky people missed the opportunity because they were still too busy looking for photographs.”
So what is this aspect of luckiness that we can sometimes miss because we are too busy preparing? I think it involves an element of playfulness. It seems to be the opposite of a single-minded, total, unflinching commitment to a specific goal pursued with compulsive vigor, which is incidentally often what entrepreneurs do and how they are described.
Instead, it seems to be more about flexibility, curiosity, openness, and imagination. It involves a certain readiness for serendipity and willingness to be surprised, to genuinely learn something new. It means opening one’s self to look at the world with a sense of awe and wonder, rather than a premise that there is not much else to learn, and all that remains is execution. I am reminded of the famous quote attributed to Albert Einstein:
“There are only two ways to live your life. One is as though nothing is a miracle. The other is as though everything is a miracle.”
Playful people often “tinker” with things, playing around with the various resources, tools and technologies they have access to, just to see what new possibilities they can uncover. They also tinker with ideas, playing imaginatively with connections and combinations of words, concepts, frameworks, models, theories, histories, and methodologies. Nineteenth century philosopher Charles S. Peirce, calls this a process of “musement” which follows no rules except “the very law of liberty.”
Entrepreneurial thinking involves intentional playfulness
Although scholars who study creative thinking often point to playfulness as a critical element, those who study entrepreneurship often miss this element as an aspect of entrepreneurial thinking or what makes people and organizations more entrepreneurial. Heidi Neck and colleagues at Babson College are among the few that emphasize playfulness in entrepreneurship education.
It is true that there are pitfalls to excessive openness and playfulness. One can become indecisive, and lose the focus and stamina necessary to carry out a project to fruition. In the end, playfulness is part of the exploratory mindset that must always be balanced with exploitation and implementation processes.
But I also don’t think playfulness is just something for the early phases of entrepreneurship, when you are looking for ideas, which is then to be discarded once you have settled on a path forward. The minute you lose your sense of playfulness is the minute you close yourself off from many potential opportunities, and possibilities to get lucky. This is as true for entrepreneurship as for life in general: the minute you assume you have nothing else to learn, is the minute you will stop learning.
As eloquently stated by Peirce:
“Upon this first, and in one sense this sole, rule of reason, that in order to learn you must desire to learn, and in so desiring not to be satisfied with what you are already inclined to think, there follows one corollary which itself deserves to be inscribed upon every wall of the city of philosophy:
Do not block the way of inquiry.”
