A clearhat is someone who realizes there is an endless war between blackhats and whitehats that has been going on for centuries, even millennia, since the dawn of civilization itself: For every whitehat that appears on the scene, there is a blackhat out there, who is or becomes an equal. They create each other; as one develops a new skill, the other learns how to oppose or overcome that skill, and vice-versa. It's like an arms race, where each battle is won by the side that develops the best new weapon.
So a clearhat is someone who sees this, and realizes: "No matter how good I am, no matter how bad I am, no matter how skilled I am, whether I succeed or whether I fail, I'm contributing to an endless war between two opposing forces, which existed before I was born, and will exist long after I'm gone." A clearhat, then, aims at a different target than "one side or the other," and engages in a different game -- neither wholly white nor black. The color clear is a reference to staying out of that polarized game as much as possible, being invisible to it.
To those who play the whitehat and blackhat zero-sum game, the clearhat position is not looked upon kindly. It appears to be a betrayal. Or, in kinder terms, it is seen as incompetent, or immature. It is inferior, in one way or another.
This happens because there is an implicit "if you're not for us, you're against us" embedded within our culture and there is little tolerance for people in the middle who can't make up their minds, especially when there's a war going on. So that's all they see in a clearhat -- someone who won't make up their mind.
Inwardly, a clearhat is one who invents a path forward which is somehow both and neither, together, simultaneously, choosing to do those things "against which there is no law," walking in a forbidden land between giants who throw stones at each other every day. Their game is about things like structural clarity, simplicity, and elegance, not win vs lose. Beauty, not victory, because beauty is the victory.
The age-old black-white struggle may seem structurally simple, but it is a global game with many layers of redirection hiding an inherent logical weakness that, like the emperor's new clothes, no one dares admit. Its history reaches all the way back into evolution's grand struggle for survival as well as its continual ascendence theme. That continual ascendance is commonly understood as "survival of the fittest" which is, like so many things, a zero-sum way of seeing things. Note that evolution's grand journey is also an ascendance of a certain kind of elegant resilience... even beauty... In short, there are other ways of measuring evolution which are not so zero-sum.
Instead of inventing the next great weapon, or its antidote, the clearhat is inventing ways to get by without weapons altogether by replacing their need with other interesting things and ideas.
Clearhat simplicity must be a liveable one, not fake or academic, idealistic, theoretical, or extreme. Those are fragments of zero-sum pursuits, and we're talking about something more coherent. This is also not about going into the desert and living with nothing like a monk; this is about living in the midst of a polarized culture, blending in, being ordinary, joining the ordo ordinarium -- the order of the ordinary people -- being one with the common man, because here, in ordinariness, is where the idealistic extremes of black and white are most easily ignored in favor of the simple, and ordinary things which comprise the daily life of the simple, and ordinary.
Sound like your game? Have at it. Be ordinary -- not defensively, not offensively, but intentionally, thoughtfully, competently, and simply. Avoid defining yourself in the zero-sum games when you can. There is no initiation into the clearhat world. It's an idea you like or you don't, and if you like it, you do it, whether people notice or care or not.
That being said, this is the website of a software developer and lover of philosophy, mathematics, technology, and the ultimate elegant hacker, the Lord Jesus Christ, mostly stuff like Sagittarian INTJs might dig. The rest of you will probably find this all tedious, not charming, and you're probably right.