Your mess is perfect when it reaches the point at which, if you spent any more or any less time organizing, you would become inefficient.

When we see a perfectly clean, organized office, with it’s sleek glass-topped desk and a white MacBook centered perfectly atop the desk’s vast emptiness, we might find it cold, sterile, oppressive even. It’s not a coincidence that the Death Star’s halls are clean, white — and cold!

On the flip side, when we see an office with a desk buried under mountains of paperwork, with trash bins overflowing and computer cables snaking haphazardly across the room, we often find it overwhelming, disgusting even — and rarely think well of its owner!

For most of us, there’s a “sweet spot”, somewhere between the Death Star and the garbage dump, where everything we need (and nothing we don’t) is close at hand, where the minimal amount of work yields the maximum gain. Where that sweet spot is will, naturally, be different for each of us — and finding it is often made difficult by confusing clutter with messy perfection, or by confusing laziness with efficiency.

The Oppression of Organization

Too much organization, especially for creative people, can be stifling. One reason is that organization often stems not from our particular workspace needs but from moral and social judgments imposed on us (and internalized) externally. That is, we feel the need to organize to meet social standards that may not have anything to do with our own needs.

Messiness in Western society is associated with a lot of negative things. Clutter, disorder, messiness is associated with dirt, disease, and filth. Messiness is considered inhuman, uncivilized — remember Mom telling you your room was a “pig sty”?

It’s also associated with laziness, the greatest of sins in a Western mindset guided by the Protestant work ethic. While we might feel that our work takes priority over cleaning up, there’s a part of us that will always feel that we should be doing it all — that not cleaning up is a sign of sloth, no matter how much other work we’re getting done in the meantime.

Messiness is also a class issue. Middle-class reformers have always advocated lives of zen-like simplicity to their working-class charges. (In the 1910’s and ’20s, they would set up model homes in poor tenements showing workers and immigrants how a “proper” home should be kept — plain furniture, no curtains, open cupboards, hardwood floors, and bare walls were the norm, in contrast to the mish-mash of overstuffed furniture, cheap posters and wall calendars, heavy curtains, and multiple rugs the immigrants and workers preferred.) Wealthy people look down on the nouveau riche who stuff their homes with Baroque furniture, Persian rugs, and glod-trimmed everything. Non-clutter is the foundation of Apple’s success — among well-off, professional, upper-middle-class social elites (and their emulators).

But there’s a cost for this kind of neatness, a point of diminishing returns beyond which more time spent organizing and cleaning means less time spent getting work done. This is especially true when workers (and I’m including the work of family, home life, and hobbies here as well as the work we do for our jobs) “borrow” systems that are advocated by professionals as “gospel” but do not truly reflect the individual’s working life or personality. As it happens, a great many highly organized people are no more able — and even less able — to find the things they need, when they need them, than the chronically messy.

The Cluttered Mind

On the other hand, keeping up some kind of order is not without value. As every craftsperson knows, tools and supplies that are tossed around haphazardly become broken or damaged, which means they aren’t able to do their work even when they can find their equipment. Spending time looking for some item you need right now is no fun, and surely inefficient.

Messiness can also indicate underlying psychological blocks. People who refuse to clean up after themselves or to put things “in their place” might well be acting out retained resistances to an overbearing parent or schoolteacher whose daily involvement in their lives is long past. Or they may be using their mess as an excuse to not get things done — because they don’t know what to do with themselves if they finish. Or they may act out of the unconscious fear that if they got everything in order, they’d have to start dealing with more troubling aspects of their lives.

And messiness can be anti-social. Having a messy office can keep you from working well with others, even if you have no trouble working in it. Having a messy home can prevent you from inviting others into it — or others from accepting such invitations. Our mess can become a barrier to — or, in some cases, insulation from — interacting with the rest of the world.

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Making the Perfect Mess

The trick, then, is to find the balance point between too much organization and too little. Where, exactly, that balancing point is will differ for each person, depending on their personality, their career, their family life, who they interact with, and a variety of other factors. There are, though, a few questions you can ask yourself to figure out where that balance point is for you and what kind of work you might need to do to reach it. You might want to think them through a few times for different contexts (e.g. office, kitchen, living area, garage/toolshed, etc.)

What are your organizing strengths? What do you do extremely well? Are there areas where you’re very organized, maybe related to a hobby or other specific activity? For instance, I play guitar, and all my musical equipment is always in one of two places, everything gets put back when I’m done, everything is well-maintained. 

What are your organizing weaknesses? In what part of your life are you always scrambling? What activities are the least efficient for you? In my case, I’m a bad filer — there’s something in me that says I can only file when I’m done with something, so if there’s a chance I might use it, it needs to stay out. 

        * What do you like most about whatever space you’re thinking of? 

        * What do you like least about that space? 

        * How would you feel if the space was completely clean? How would you feel if it were in complete disarray 

        * What three things do you regularly need that you can’t find? 

        * What could you do to make those three things more findable? 

        * What in your life do you have no problem finding? What is it that you always put back in an assigned place, or always know where it is even if it’s in a cluttered place? What is it about that thing or those things that make knowing its/their whereabouts important to you? 

        * What are the first three things you would clean if you knew an employer or client would be visiting you tomorrow? 

        * What piece of cleaning have you been putting off for a while? Why do you think you’ve resisted cleaning up just that one area? 

        * What are the tools you always need to have within arm’s reach? 

        * What else is within arm’s reach that you rarely or never use? 

        * How would you describe your space to someone you’d hired to help you get organized? 

        *  How would you organize your space if you had been hired to organize it? 

Like I said, there are no right or wrong answers, here. The idea is to help you find that comfortable medium, where the things you need are at hand and the things you don’t need are out of the way but still findable. I think most of us spend a lot of energy maintaining a “mental map” of our space, and I strongly believe in “off-loading” some of that work to well-designed systems — but there’s no use in doing that if you end up spending the same amount of mental energy maintaining your mental map of how the system works!

Instead, if you can figure out the “sweet spot”, you can focus on “nudging” your system back towards it. This is far preferable to the kind of worry and anxiety the prospect of a “clean sweep” can create in us. Don’t, however, confuse comfort with effectiveness — we humans can get used to just about anything (there are people who mentally collapse when removed from prison, hostage situations, even concentration camps!) but that doesn’t mean that it’s the most effective way for us to live.

Take some time to ask — and answer — the hard questions to produce an organizational system that works most effectively for you. That means that it does the most it can do with the least amount of energy — both in physical labor and in mental anguish.