Perfectionism is a double-edged sword. The problem is that striving for perfection is not always appropriate. I touched on this earlier in my musings about “parallel focus”, where the key to having multiple priorities is knowing which of them need perfection and which don’t. My friend Mischa Hildebrand also has a good article about perfectionism, which I recommend if you want to dive deeper into the two sides of it. Today, I want to talk about one specific area where perfectionism may not just be unnecessary but an unattainable goal - organizing your digital creations and possessions.

Jim McGee, who I met in a Zoom breakout room in Anne-Laure LeCunff’s “Collector to Creator” course, wrote an article called “Embrace the mess if you want to do better knowledge work”. He reminds us of the argument between “neats and scruffies” that was part of early Artificial Intelligence research discourse and is coming up again in the knowledge management space. The “neat” philosophy believes in transparent, elegant, and orderly systems, whereas “scruffies” assume that the real world is inherently too messy for these systems, and it’s okay to hack your way into approximate solutions.

There’s a famous German figure of speech called “Ordnung ist das halbe Leben”. Its literal translation is “tidiness is one half of life”. Interestingly, Linguee provides “A tidy house, a tidy mind” as the English equivalent. On the other hand, if a cluttered desk was a sign of a cluttered mind, isn’t an empty desk a sign of an empty mind? Does creativity even demand a bit of chaos?

If you look at computing, you’ll see that neat structures adopted from the physical realm like files and folders are increasingly getting replaced or overlaid with things like tagging and full-text search. Knowledge work relies on networked thinking, which is incompatible with hierarchical structures. It also includes ideas that exist in different stages, some of which will never be fully-formed.

My point, and the one Jim McGee tried to make, is that the answer is: Yes, creative knowledge work relies on a certain level of chaos. Things will never be in perfect order. The sooner you accept that the happier and more productive you’ll be.

Proverbs like those I quoted earlier come from a time where the order was necessary because there were no devices that could help you make sense of it. We have thus learned that it is a value and virtue of its own. I still agree with physical objects, but I don’t think the same applies in the virtual world. The ability to find the data you need when you need it is more important than it being part of an elegant and consistent structure. The systems you design and implement to organize your life must optimize for the former, not the latter.

I tend to obsess over small details in the consistency of the data and information I collect, which aren’t necessarily valuable. I also feel that every unpolished thought and every information ever collected is a to-do item, which is equally wrong because some ideas that seemed important once are not worth following up. Sure, there might be joy in organizing and cleaning stuff, but that’s probably not where I create a lot of value. I fear that the belief in the “neat” philosophy is just the digital equivalent of “procrasti-cleaning”.

If I wanted to name one realization from the past year (although I’ve been thinking about it for much longer), it would be that. Building a perfect and clean system of thoughts isn’t a prerequisite for achieving something meaningful. And neither for being a happy and well-rounded person. It’s not that I necessarily spend a lot of time trying to build that system, but it’s that I feel like a failure for not doing so, even though it’s impossible. And I’m pretty sure that’s holding me back. One of my resolutions for the coming year is to try and be more lenient about this. As long as I am doing creative and intellectual work, my mind garden and its implementation won’t be a zen garden, and that’s okay.