I recall a little sign which was sometimes spotted on desks, back in the before-times when everyone had a desk and papers and ring-binders and books and a telephone that also sat upon that desk. The sign was: “A messy desk is a sign of genius.” (And sometimes it said, “…of a creative mind.” )

I’ve had a lot of desks. In every case, I’ve always swerved repeatedly between messy and organized. I get to a point where—sometimes with a literal scream—I stop working and reorganize everything. For a long time, I hoped that one day I would manage to be just comfortable enough, with just the right amount of clutter and chaos, to be able to reach a steady state.

One detail that drives me bonkers is in the digital realm, computers are perfectly organized. I use a tool (called Reeder) to manage a read-this-later collection. It’s a big collection often reaching 500 different things marked as possibly interesting. (Some are interesting enough to spend a few minutes on, some are interesting enough to spend hours on.) Sometimes I’ll randomly shuffle things in a digital list. But sometimes… the list is just ordered the way you assemble it. And you can look at the list in forward or reverse order. This gets to me. If it’s a big list, neither forwards or backwards is best. So instead, I do both: I read the item off one end (the thing that’s been in the list longest) and then the other (the newest), and I just alternate in a reading session.

Perhaps this seems like a silly or trivial thing to point out. But there’s a bigger lesson: Where do I have some specific structure (organization, ordering, etc.) that I didn’t actually intend? …is that structure holding me back or keeping me from experiencing something I’d prefer?

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