My girlfriend creates large, complex mandalas, which are impossible to draw freehand. Because of their complexity, they require a lot of planning. She can spend days just drawing guides, measuring angles, and sketching in fills to make sure everything will fit.

At first, I thought this was very unartistic, as if the act of planning made them less creative. I always envisioned art as something that was intuitive and spontaneous. I had the view that creative people just pulled their craft from their head, and if you had to outline it, you weren’t the real deal. That’s probably why I resisted outlining my novels for so long.

As she developed as an artist, not only were her mandalas becoming more complex, the frameworks she was using were evolving also. She was invested in improving her planning methods, not just the results of her work.

From that, I learned that the frameworks we use (and whether we allow ourselves to use frameworks at all) are directly connected to our ability to create meaningful, creative, and useful work in the world.

When I began to look for other kinds of art in which arrangement was key to the creation of beauty and meaning, I discovered it was harder to find creative work that didn’t require this kind of meticulous planning:

  • Music is the arrangement of tones into meaningful ‘songs’ (even the song 4’33”, the silent composition by John Cage, imposes arrangement by specifying the duration and context of the piece). Improvisational folk music relies on preexisting frameworks and agreed-upon conventions, so it is still highly arranged.
  • Photography is arrangement through composition and exclusion. By framing a photo, you provide the viewer with some basis for deriving meaning.
  • Novel writing is the arrangement of events into meaningful ‘stories’.
  • Dance is the arrangement of movement in a way that connects with the song and the dancer’s expression.

Meaning and Art

To me, art is anything that gives meaning to ‘stuff’–materials, knowledge, events, sounds, ideas, information, etc–turning it from its raw state into something that is relate-able to humans. Good art is well-arranged, and bad art is poorly arranged, at least in relation to its meaning.

For example, a beautiful car is perfectly and efficiently arranged in a way that is in agreement with its significance, whether that’s driving fast or hauling. An ugly car is not, and makes concessions to things like profit, planned-obsolescence, or convenience. It is closer to being meaningless in terms of what it was meant to do.

The meaning can even be indecipherable or non-explainable, as in the case of some modern art; the very act of putting something in a gallery can give it meaning, as many modern artists have demonstrated, even if that meaning is not something we can put our fingers on.

But if all art requires arrangement to some degree, then arrangement, meaning-making, and art are basically the same thing–arrangement of the world into something meaningful–and the more masterful someone is at their craft, the better they are at organizing knowledge so that it can be interacted with in a meaningful way.


Humans as Arrangers and Meaning Makers

However, I think this ability to arrange-into-significance is not just important for art, but for any and all creative work.

We humans have always placed a premium on the ability to organize complex information into meaningful patterns. In prehistory, priests and tribal elders who could make important decisions were at the top of the hierarchy. As we moved to a more status-based society, kings were on top, but the most valuable (and often powerful) men and women were those who could organize complex information for the king to make useful decisions. In modern times, entrepreneurs arrange resources, knowledge, and people in relation to a market to create an economically-productive arrangement we call a business.

And teachers, one of the most highly-esteemed (though worst paid) jobs not only organize information to be meaningful to those they teach, but they also show students how to do that same task themselves.

We pay a lot for information meaningfully organized. Think tanks, consultancies, coaches, gurus, and internet experts are testament to this.

Highly trained professions also involve the collection and arrangement of information so that it can be meaningfully acted upon. Doctors engage with large quantities of complex but dry information–lists of symptoms–and present it as a meaningful diagnosis, which can then be acted upon.

Humans are meaning makers, and we do that by arranging the things in our world to express the meanings we want. The ability of a person to arrange the world is directly tied to the societal value of that work.

One of the greatest contributions of science has been to allow us to strip meaning from things in-the-world so that we can add new meaning to them. Prior to objective observation, anything encountered already came with lots of baggage, which could be useful at times, but didn’t allow for new meaning to be added.

The areas where I first was exposed to the value of information arrangement were chess–where organizing complex information into meaningful positions is the basis of winning–and novel writing–where my inability to organize information kept me from ever finishing.


When I first began playing chess, the pieces and their positions didn’t mean anything to me. I could tell there were many layers of information present–threats, potential tactics, strategic positioning, etc–but I wasn’t able to encompass all of it so that I could actually act on it.

As my skill level grew, I was able to see information and actually derive meaning from it. My brain was able to organize the patterns on the board into something that had meaning for the game I was playing. From there, it was just a matter of understanding what I wanted to do with that information.

By playing a lot of games and studying theory, I was able to learn the significance of different chess positions and to fit them into an overall understanding of the game.

I simply began focusing on acquiring frameworks for organizing the information the board was presenting me, instead of thinking expertise was some nebulous intuition that would magically materialize.

Novel writing

I always thought that writing a novel was an intuitive endeavor. After a few stalled attempts, however, I realized that my biggest obstacle wasn’t the imagination or the perseverance to write; it was the lack of organization. My plot threads would get so convoluted I couldn’t keep track of them, or they would just peter out into dead ends. I couldn’t see how to get from my middle to my glorious ending.

Then I read two books by KM Weiland, How to Structure Your Novel and How to Outline Your Novel, and it became clear to me that the vast majority of the work in writing a long-form story is in the organizing of the ideas.

A story, as opposed to an account of an event, is basically the organization of an event or experience into a meaningful telling. That’s why storytelling is an art: it requires the author to organize events, which would otherwise be context-less happenings, in a particular way that gives them meaning.

Weiland’s books simply provide a framework for organizing your ideas in a way that is story-able. Once I adopted her suggestions my stories started to come together. The sense of pointless struggling dissipated, and I was able to start writing again.

Caveat: You also need the ability to act on your insights

In chess, ability to execute isn’t really a limiting factor. If you can organize the board position, you can get meaning from it and act. In others arenas, that’s not always the case.

In Jiu-Jitsu, for example, my coach has explained to me what threats to look out for when I’m in the middle of a sparring session. But just because I notice that my opponent is trying to get past my guard, and I know the technical way to prevent that, doesn’t always mean I’m capable of doing it. I might be too slow in comparison to my opponent, or I might be too tired or too weak in relation.

A novelist might have a good grasp on the structure of her novel and the overarching meaning she wishes to convey, but lack the language skills to pull off the nuance she imagines.

And even a chess player might recognize he is falling into a trap but not be able to visualize far enough ahead to determine what exactly it is.

So, you also need the ability to act on your insights, but for the most part, except where insight and experience are very closely matched, simply having a more organized and meaningful perspective gives you a distinct advantage.


The whole point of this post is this: organizing the information you deal with is non-trivial, and one of the best ways to acquire expertise and mastery of anything is to acquire, develop, and utilize frameworks for arranging information in a way that allows you to interact with it.

The more efficient your frameworks, the better.

This flies directly in the face of the mindset that organization shouldn’t take up too much of your time. I agree that you can waste time putting stuff away and tidying up, but that’s not really the same thing as investing in good tools that either scaffold mental frameworks or are themselves useful ways to organize information. These help you engage with the information you work with.

For example, one of my good friends, who is a programmer, constantly amazes me with the way his mind is able to organize the various informational realms in his life, keeping them distinct but also drawing meaningful connections between them. He has put a lot of effort into being able to meaningfully organize and interact with his ideas and his work. Many of his tools are digital, but what is interesting to me is that the tools don’t do the important work for him, they just empower him to manage more complex and efficient organizations. They are reflections of his own mental processes, ultimately extensions of his mind, adjuncts to it, rather than alternatives to well-organized thinking.

And that’s what a framework ultimately allows: the extension and expansion of your mind beyond just what you can contain in your brain.

Notes: Consciousness and the Myth of the Myth of Multi-tasking

There are a few reasons I think the ability to more easily organize information is at the heart of great art. The main one is that the more I learn about conscious thinking, the more I realize just how limited it is in scope, but how powerful it is in intensity. It’s like a laser rather than a flood light.

The problem is that conscious thinking doesn’t seem able to handle a lot of information at once, so to really make use of conscious thinking, you need to support it with a system of organizing information that lets conscious thought focus on just one thing at a time.

People cannot multi-task: this oft-heard myth-buster is itself a myth. People can multi-task, depending on your definition of a task and their prior training. It would be absurd to suggest that a professional basketball player cannot take the ball down the court while avoiding opponents while simultaneously scanning her teammates for an opening.

However, only one of those activities requires her conscious mind. She has trained her unconscious mind to handle all the others, so she gets to be masterful in the things that matter: setting up a shot and coordinating with her team.

People cannot consciously multi-task because the conscious mind really can only do a single thing at a time.

We can task-switch, sometimes very fast, which gives the illusion of multi-tasking, but that’s how people get into car accidents while texting. Pilot training involves learning to task-switch efficiently, moving conscious thought from one instrument to the other and making good decisions about what you learn, but aviation also has a lot of systems in place to support this.

So, if you suck at organizing complex information, your conscious mind is left doing very surface-level thinking: “Can I move my knight here? Are there any immediate threats?” But if you take much of the organizational load off your conscious processing, either into unconscious processing through training or other heuristics, your conscious mind gets to deal with much more interesting problems: “How can I apply pressure to my opponent and begin to shift the position to the one I want?”

For an artist, good frameworks–visual guides, conventions, templates–allow his conscious mind to get really creative and explore exciting avenues that it couldn’t if it was worrying about keeping all the pieces together.

Notes: Digital Reliance

In a world where computers do a lot of the informational heavy-lifting for us, and Google has kindly offered to organize all the world’s information, I worry that we humble meatbags have neglected the importance of keeping our thoughts organized and meaningful. After all, any information we come across is already stored and categorized on some server. If we need it, we can just go and get it.

But I think something is lost when we approach our lives like a Gmail account, simply tossing everything into an Archive pile and relying on a good search bar to find it. Information stored that way loses its connections to other information. By throwing everything into the same pot, it all become indistinct and essentially meaningless.

Taking the time to relate new ideas to old ones, to structure our thinking, and most of all, to plan how we intend to proceed so that we have a skeleton already in place when we try to fill in the details is important. I’m a big fan of notebooks and journaling for this reason: it forces me to organize my thoughts into some meaningful arrangement of words.

I can then go back and conect those thoughts with new ones and come up with new ideas.


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