The Perfectionist Dilemma

Why the Pursuit of Perfection Results in Failure


As artists, designers, entrepreneurs, and engineers, we are all creators and makers of one ilk or another. Some practice in paint, some in Xcode, and some in steel and concrete. But how we create, regardless of the medium, tool, or skill applied, is much less important than what we create.

That what is value.

A perfectionist for most of my life, my greatest obstacle to being the best creator possible has been none other than myself. For years, I toiled as a musician, marketer, and entrepreneur, carefully creating, crafting, and calculating just about everything. If I spent a minute, I spent an hour. The finished products were always exactly how I had envisioned them, but I made so few in certain settings that it hardly mattered. In hindsight, this kind of approach, though well-intentioned, was slow, obsessive, and often resulted in unfinished products that never saw the light of day. A creation that doesn’t create value for an audience, after all, is essentially meaningless.

Part of my personal objective in joining Tradecraft has been to learn how to move faster, disregard that which isn’t essential, and force myself into making mistakes. Mistakes that I’d so seldom made in the past and had been fearful to make. The kind that would inevitably make me better in the future.

Creators and The Creative Process

The creative process has been largely misunderstood by many. And it’s been misunderstood because we’ve glorified those who practiced it well. It’s convenient to call an idea or artwork ingenious in hindsight, like Edison’s phonograph cylinder, Picasso’s paintings, or even Page and Brin’s Google. All of these creations were made by visionaries, those who saw a future audience for their creations long before they were completed. But it’s important to remember that these inventions weren’t the result of endless brooding or even prolific visions. Rather, they were all the result of action and refinement over and over again until a desired outcome was achieved. Each has much more to do with the scientific method and applying new concepts than with a preordination for popularity. And this is where the pursuit of perfection fails its creators each and every time.

The Dilemma

As the name implies, the perfectionist dilemma is when a creator values the quality of a finished product such to the extent that it inhibits their ability to iterate, change, and even produce. For many, it’s the ultimate writer’s block, invoking a fear that the finished product isn’t or won’t be as originally intended. This in turn pushes the creator to distort the creative process into a problem solving scenario that demands a “right” answer for a “right” audience. Even renowned creators can experience the perfectionist dilemma in some way, creating products that are only for approval and applause rather than artistry, exploration, or creativity.

Creativity and innovation exist because they defy correctness and convention, and instead rely on something much more instinctual that might require several approaches. Creation is a process after all, not a single question waiting to be answered.

The world is full of creations that eventually catered to an unintentional audience, ranging from the remarkable, like Teflon, which was originally intended for military purposes, to the everyday, like Instagram, which started life as a different product altogether called Burbn. In the end, the “right” audience will find the creation, but only if the creator makes it available to them.

Measure Twice. Cut Once.

For many, there is an inherent fear in producing that which isn’t considered “right.” It’s rooted in our history of manufacturing and standardization during the industrial revolution. It’s rooted in our upbringing, awarding poor grades and handing out punishments to students that fail to grasp concepts and memorize as we intend them to. As a result, we’ve learned to disdain flaws, a point that former marketer turned best selling author and entrepreneur, Seth Godin, makes time and again throughout his works, and especially in his book “The Icarus Deception”:

“We have been brainwashed by school, indoctrinated by industrial propaganda, and mesmerized by the popular media into believing that compliance is not only safe but right and necessary.”

It’s also where we developed phrases like “Measure twice. Cut once.” These four words say so much about a perfectionist’s approach. It’s cautious, measured, exacting, and time-consuming, all of things that many of us can no longer afford to be because we now live in a largely digital economy instead of a physical one. In the physical world, there are consequences for not producing “to spec,” especially in an industrial setting, where glass must be able to withstand a certain amount of vibration, concrete must have a certain consistency, and oil must be of a certain viscosity.

But in the digital world, a finished product can always be changed. It’s another reason why phrases like “Measure twice. Cut once.” are being replaced by “Move fast and break things.”

The Key to Value Creation

And so the question begs. How do we produce that which has the most value for a given audience?

The key to quality just so happens to be quantity.

This is not simply to say that “practice makes perfect.” Rather, producing a finished product, even if it’s not as intended is the first step to creating something that is of value. Otherwise, a week, a month, a year, or a lifetime could be spent polishing and perfecting that which isn’t worth polishing or perfecting.

After a finished product has been produced, no matter its quality, produce another finished product, again and again and again. Ruminating over the quality of those products does more harm than good for both the creator, who never shares their ideas and the audience, which never gets to experience them. Imagine, for a moment, if some of the greatest minds of our time never shared their respective inventions.

Eventually, we have to learn that as creators we have everything to lose if our creations never exist. In the end, perfection just might be the willingness to fail, the willingness to not be…perfect.