"I'd rather be lucky than good."
That is the genuinely humble refrain I've heard many times from the people we work with: successful entrepreneurs who ironically seem to frequently make their own luck.
The humility comes from a deep appreciation of the myth of the self-made [wo]man and an acceptance of the randomness inherent in leading a business and exposing themselves to the vagaries of market conditions. Luck, at least in the form of good timing, is a significant component of all good fortune. It's not just hard work, effort and self-reliance. Decisions matter. And we all have ours to make. Some set us up for the likelihood of good fortune; others for the reverse.
This is also different from the "lucky sperm club". Tania and I spent the week visiting a small cadre of our clients in Florida. While down there, we toured one of the most affluent areas of the country: Palm Beach (home to Mar-a-Lago). The level of wealth in the region is staggering and so is the wildly disparate distribution of that wealth.
Most of us have had some sort of significant head start in life–the kind of good fortune owing to the accident of one's birth. The blessings are different for all of us but I am interested more in what someone does with their endowment than where they are in absolute terms. It's the delta that's the measure of a person. What worthwhile thing did you do with what you were given at birth? How did you improve the human condition?
Being good increases the probability of good fortune.
Oliver Wendell Holmes famously said, “For the simplicity on this side of complexity, I wouldn't give you a fig. But for the simplicity on the other side of complexity, for that I would give you anything I have.”
The people who seem to make their own luck brave the wilds of simplicity on the other side. Markets and economies are complex and inherently unpredictable. Most people have a low tolerance for these difficulties and instinctively opt instead for the smaller game of lazy over-simplification. While linear, cause and effect narratives are perhaps safe and easy, and give the illusion of predictability, they rarely expose us to the possibility of anything truly great.
The people who make their own luck seem to be adept at two kinds of energy-intensive thinking. The first is statistical reasoning. This involves doing the work to understand the probabilities that various strategies have for working in a given context. Every problem offers some opportunity to leverage financial, human, social or intellectual capital; some strategies are more likely than others to bear fruit in uncertain times. This is a matter of education, experience and contact with wise people. The second is exponential reasoning. This involves understanding the compounding effect of certain levers over others and specifically how network effects accumulate through time. The network is a source of wisdom, insight and other informed people.
Fortune favours the bold. It also favours the humble and the disciplined. It's not about mindless effort, but better practices. Such work is in active and deliberate defiance of the evolutionary drive to take the easy way out and save metabolic energy and brain cycles. If you want a guarantee, buy a toaster; otherwise, there is no getting around developing the non-linear and very counter-intuitive capacities of your brain.