Perfection and play
A leader I know was once approached by a direct report who was in a state of exasperation because he was unsure how to navigate a highly ambiguous situation. The direct report asked pleadingly: "What's the playbook here?" The leader responded by saying, "If this job were merely a matter of following a playbook, you should be paid only minimum wage."
It was a harsh response. It certainly could have been more humane. But it was essentially true.
In a complex world, judgment is what creates value, and judgment is context-specific. The right judgment is an approximation, not a formula. It's often a case of being equally committed to seemingly discordant ideas. It's almost always a case of mindset more than method.
Take the example of tennis superstar, Andre Agassi. On the one hand, he was obsessed with controlling what he could control, which is why he was so meticulous about the contents of his game bag. Perfectionism became the bedrock of his confidence in a sport that was wildly unpredictable and constantly up for grabs.
On the other hand, he was acutely aware of the limits of this mindset. Over time he learned that if you chase perfection, making it the ultimate goal, you end up pursuing something that doesn’t exist. You end up making yourself miserable, along with everyone around you. He learned to loosen up his playing style.
Perfectionism was the driver that propelled Agassi from amateur to professional. Playfulness was what got him to the top of the world. For him, and for many like him, perfection and play are the yin and yang of top-performer psychology.
Watching the best salespeople, you see a similar phenomenon. These sellers have a strong and systematic process. They are committed to recurring actions that maximize the probability of long-term success (research, prospecting, regular client engagement). They strive for completeness in downside protection and upside capture.
But they are forever experimenting with creative angles. They are always attentive to subtle shifts in market dynamics, company initiatives, and client psychology. They are not afraid to push the conversation in a different direction, proposing fresh and surprising sources of value to the partnership.
In Bird by Bird, Anne Lamott's wonderful guide to writing and life, she observes that "perfectionism is the voice of the oppressor, the enemy of the people. It will keep you cramped and insane your whole life, and it is the main obstacle between you and a shitty first draft."
An irresolvable tension between perfection and play is at the heart of ingenuity in many creative realms. There will never be a reliable playbook on how to balance the two.