You study, you learn, but you guard the original naivete. It has to be within you as love is within the lover.
Henri Matisse
How many times have you heard someone say this: “If I had known then what I know now, I would never have (fill in this blank with a great story).” As a rule, the story filling in the blank will be about some unexpected success, or some particularly spectacular failure, or just an interesting narrative. But successful or not, it is almost always a story that is profoundly important to the teller, a treasured memory, and most likely something that made a big difference in the life of the person telling it. What makes an “I-would-never-have” story so poignant is the knowledge that something has been lost. Just behind the narrative there is more than a touch of nostalgia and yearning for that time when “I didn’t know," a return to times that were somehow more immediate, more fulfilling and perhaps more productive. Even so, an “I-would-never-have” story is almost always positive in some way, and there’s an important reason for this.
Naivete is a powerful, powerful state of being.
For the entrepreneur, nothing is more precious – and more at risk – than a sense of wonder and a sense of possibility. And these states are enriched by naievete. The true entrepreneur (or the true intrapreneur, for that matter) is almost always characterized by an inability to see negatives, a certain blindness to obstacles, a disregard for barriers. For them, it is almost as if they are unaware of limitations. And being blind to obstacles, they will tend to run straight at them – and often right on through them – while calmer, more practical heads hold back. Oftentimes this is not so much a function of courage, or intent but is simply naivete about obstacles and consequences.
“If I had known then . . .”
A naïve state is what keeps the entrepreneur alive, optimistic, energized and in the game. Without naivete, there is more caution and less experimentation; more management, and less leadership. Probably, there is also less real success. Naivete is the power behind risk, and without it, the entrepreneur is in danger of becoming the jaded manager.
That’s because time, experience and miles tend to make even the most imaginative and visionary entrepreneur less naïve, and more aware of negative consequences. And when that happens, caution – the Kryptonite of the entrepreneur -- takes over. That risk-taking, innovative visionary who started a business with little more than a napkin sketch, a notepad and a coffee shop is replaced by the cautious bean-counter, intent on nailing that second round of funding. That near-Quixotic adventurer is replaced by an office-inhabiting financier. The entrepreneur becomes the manager, and, more than likely, will be going to a party soon, where the story will be told: “If I had known then . . .” And all those those listening will feel just a little sad and a little disheartened, because they will know that something powerful and wonderful is gone.
Naivete is a powerful state, but it must be distinguished from a simple lack of self-awareness, or simple ignorance. Naive is not the same as dumb. A naïve visionary is ambitious; an un-self-aware visionary is foolish. A naïve leader brings others along on a mission; an un-self-aware leader takes lemmings to the cliff. A naïve entrepreneur will prevail; an un-self-aware entrepreneur will just consume resources.
The difference lies in intentionality, because it is quite possible to intentionally cultivate and enrich naivete. The painter Matisse was a great painter because, as he said, he held on to his naivete. That did not mean that he didn’t study technique, that he didn’t practice his art, that he didn’t learn from mistakes, that he didn’t fail, and fail often. What he meant was that he kept alive an unrestrained sense of possibility, something he would not allow to fall prey to experience.
The entrepreneur would be well-served to do the same. Naivete is the lens through which possibility is magnified. It is a healing balm for failure. It is a source of energy. Cultivated, enriched, treasured, and understood, naivete powers up a sense of wonder and excitement. With it, the entrepreneur is always engaged, active and growing something; without it, the entrepreneur may be limited, afraid, and holding back.
So, the next time you hear someone start a conversation with “If I had known then,” remind yourself of how important it is to keep and enrich your own naivete. And do your very best to not know now, what you know now.
Henry Doss is a student, musician, venture capitalist and volunteer in higher education. His firm, T2VC, builds startups and the ecosystems that grow them. His university is UNC Charlotte.
