Web sites don't behave like nature on the back end, but the experiences we find most pleasing on the Web conform to a natural order: in the grids we use to constrain information; in the "weather" of how content flows into and out of a visual presentation; through each tiny interaction we initiate with the system and the expected reaction. As designers, we attempt to control as many of these variables as possible in order to ensure a consistent, desired effect on the user.
But sometimes it's just as valuable to let users follow a more chaotic, yet finite path. Elegant Web experiences walk a fine line separating simplicity (yawn) from chaos (huh?). And the rules that govern the quality of the attempt are derived from considerations of natural organization. This can still be elegant -- as long as the chaos is modulated within a stable container, constrained by a well-designed illusion of natural order.
Great Web sites have feel -- what Leonard Koren had called "heartfelt intelligence." And there’s a certain logic to how they manifest. When I was in high school, one of my fellow students devised a computer program that could write symphonies. The program followed "the rules" of how a symphony should be composed, and it turned out somewhat turgid music. That is, until the student devised a scheme in which the program randomly broke those rules. It turned out that there was a point of natural order between too few rules broken (rigidity) and too many rules broken (cacophony). When his program was dialed in, it composed an infinite number of superlative symphonies.
I have fond memories of playing drums for the first time with a top-flight band and record producer. The engineer would cue up the metronome and the entire band would play through the song again and again, attempting to finish a clean take. When we'd thought we perfected every single note on the Nth run-through, a curious thing happened. The producer said into the talk-back mic: "That was perfect. Now, could you do it again?"
Several more attempts at the material followed. Soon, we began to relax into the song again. Musical flubs and jokes passed between the performers. The song began to gain new life. After the session, I went into the control booth and asked the producer what he was aiming for -- and his answer was bold. While we'd performed the song exactly how we'd envisioned it, the arrangement had suffered because it was lacking feel. Feel only comes about when you tear away the illusion of perfection.
What does abandoning perfection truly mean?
Let's chip away the very ideal of perfection itself -- not just on an aesthetic and surface level, but in how we perceive the unique qualities of an online experience.
Perfection can be appreciated by individuals, but all things tend towards imperfection. No matter whether you're creating a print design or a Web site, over time, it will decay. The artifacts that result from our design process are contingent on the same limitations as human beings: decay, disorder, chaos, and death. Perhaps we should call this the second law of Web site thermodynamics: after your work is released into the wild, it will always tend towards entropy.
Perfection is a moment in time, while consideration of imperfection is rooted in the flow of time. I call things perfect all the time. Imagining a fine, dry sake I had a few days ago -- it was absolutely perfect. But that's a subjective description abstracted from a slice of my experience. Words are merely the leavings of our intellect, strung together into a story. The same goes for designed artifacts. The more imperfect the artifact, the more they tell of the passage of time, and the more human they become.
Perfectionist tendencies foster dualism, which is a logical construct -- not emotional. When I'm talking with my peers at work about the quality of an experience, I've asked them to stop saying that a proposed headline or a UI design is merely good or bad. Things tend towards or away from a desired result, and we use our critical apparatus as a wedge. Instead of perfection, a more useful word would be the nature of a design. Our impulse to clutch at perfection is denying the nature required to make meaning through design. Meaning can be expressed through refinement, but it can be an antiseptic kind of meaning.
Thinkers like Alan Cooper have beaten into us that Web sites and apps should behave like "considerate human beings." That’s because people often treat these constructs like living beings. It's inevitable that as we craft more and more Web sites that escape their logical roots in computer technology, we will relate to them better.
So a postulate I'd like to put forth is that when the proper amount of imperfection is present in a designed Web experience, it feels more human. A Web site that is more human becomes more useful, right? Here, we have to be careful. A web site is only more useful if it is elegant in its imperfection.
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This is a bonus scene from ”The Elegance of Perfection” in A List Apart.

As usual, a very well thought out meditation. Can you give some examples of what kinds of imperfections give the character you are talking about? Or a website with a quirk you find charming?
Posted by: Jennifer | April 19, 2009 at 07:43 AM
Perfect squares are just boring. That's why we perfer rectangles
Posted by: Mipovia | April 19, 2009 at 10:36 AM