On Digital Organization

We create and accumulate huge quantities information these days. I don’t think that makes us fundamentally different than our ancestors in terms of organization. What separates us is that it’s now possible to have our data completely disorganized in a way that is invisible to others. This requires an increase in awareness and intentionality to reap the inherent benefits of organization.1The title of this post is brought to you by Semicertain.

A huge portion of computer interface design comes from analogous situations in physical space. We organize our data into files and folders because that was the sensible choice in the days of manila envelopes and filing cabinets. We call the neutral main space of our computers the desktop because that’s what we called the slab of wood on which we’d place books and papers throughout the day. This skeuomorphism is inescapable.

Just as people existed (and continue to exist) on a spectrum of physical organization in their lives,2Luckily for me, my position on this spectrum changed drastically once I was in college and I finally decided that having a tidy living and work space was helpful. there’s a vast spread of ability and inclination to straighten up digital data. But with the active development of tools intended to render organization unnecessary, we’ve increasingly lost the desire to meaningfully and intentionally arrange our digital spaces.

For centuries, organization of data needed to be constantly updated by someone. A book’s index represented significant labor, as does a library catalog or even a filing cabinet for personal documents. A rudimentary system for filing was all but necessary because there were no alternatives except a stack of papers to be rifled through that were, at best, sorted by what we’d now call “Last Viewed”. No doubt there are people who handled — and still handle — their physical organization in this way, whether it’s papers or books, recipes or bills. But it’s a terrible system that fails to scale.

Contrast this with computers and phones, where the concept of search has allowed this lack of a system to become widespread. Many people, particularly current students, don’t know that folders exist on their devices because there is no obvious need for them. Why organize anything when searches for file names or keywords within a document bring us what we’re looking for nearly as quickly as someone who claims to have a process?3This is assuming people are naming files in any consistent fashion which, I would argue, is a perfectly reasonable system of organization compatible with modern search. But I’m fairly confident anyone not using folders probably isn’t renaming anything they download.

In specific cases, the search is even done for us. For example, both iOS and Android have a setting that will suggest a few apps you may be interested in opening next based on your previous usage patterns. I have no doubt this approach to digital assistance will become increasingly prevalent across other domains, such as suggesting to a student around 4:30 PM that they go to a specific website because that’s when they typically work on homework for a certain class.

These tools let users entirely disregard how their data is organized. While search tools are fantastic — I rely on them every day — their tangential effect on how people view data organization is problematic and requires additional effort to help users understand the utility of systems for sorting and structuring our information. Foremost among these is the subconscious impact of committing to a structure that allows us to properly utilize the data within.

I’m of the belief that how we think, and the way we represent the structure of our thinking, inform and complement each other. It’s analogous to “Look good, feel good”, where the effort of being intentional with our actions has an impact on our mentality, and a more confident mentality makes us (and others) see ourselves as looking better. The organization of our data adjusts how we view it, which can further inform new ways to gain insights from it. If there is no organization, it is difficult to know what information we do or do not have. A structure that is too granular can make approaching the data within overwhelming, while too broad a structure kicks the can down the road.4“I know, I’ll organize my files into both the Desktop and Downloads folders instead of just Desktop. That’ll fix it!” In fact, in the realm of files and folders the “Look good, feel good” mantra applies directly: a file system structure that looks pleasing will probably feel helpful.

For those who actually work with structured data, from CSVs to databases, nothing I’m saying is groundbreaking. It’s nearly tautological to say that it’s important to structure these pieces of data. Instead, let’s pivot to data everyone has and consider the impact of a structure there: photos.5For the young folks out there, this is a shortening of the word photograph, which you may have never heard spoken before.

Photos are a great test case because every online photo storage service has worked hard to make manual organization unnecessary. They take advantage of time, location, and facial data to power their search. There’s increasing use of OCR that allows for searching text within an image. With all those tools working in the background, why bother organizing photos into albums?

One reason is based on the edge cases of current technology. As good as they are, you can still find reports of auto-generated albums and photo spotlights that include pictures of potentially difficult memories such as ex-partners, deceased family members, or other triggering images that thematically belong but that the program lacks the context to exclude. While we expect these tools to become more capable and erase more and more edges, it’s not the same as controlling them yourself.

In a similar vein, an intentional theme across photos may be more abstract than “food” or “sports”. For example, a podcaster I listen to talks about his favorite photo album containing pictures of his wife that are uncomfortably close to her face. I’ve made albums that combine trips to the San Diego Zoo, or that split out wedding photos into very particular categories meant for sharing. This approach to compilation provides a grasp on the photos available to you before you go searching for them, and an easy spot to pull specific items from without needing to search, then manually gather them each time.6I’m not arguing this needs to be done manually. Tools like ChatGPT make it clear that we could query our searches to do this for us, but if we subsequently save the results of the search we’re admitting that the organization is useful, which is my entire point.

Structuring photos into albums (or some other form of organization that pleases you) lets you align how you imagine these visual snapshots of your life with how they are actually represented when you go look for them. Odds are you have some significant events that stick out in your mind, and there are particular memories from those events that you also have pictures of. If the collective whole of a trip is a single entity in your mind, it’s worthwhile to have that internal framework represented with the pictures themselves.

We have amazing tools available that allow the technology we use each day to reflect how our minds work. Whether you truly are a rather messy person, or you aspire to use a particular system, there’s software out there that will align with your how you think. If you’re unsure, a tool ill help guide you into a system that, yes, will still include search, but will also provide a framework for your information and thus a way of approaching it. With so many high-quality options, relying just on search is an ignorant choice. It’s okay to end up with something basic, but be intentional about your approach, know what your plan is, and realize that your choice will affect your ability to effectively find and use your data.

  • 1
    The title of this post is brought to you by Semicertain.
  • 2
    Luckily for me, my position on this spectrum changed drastically once I was in college and I finally decided that having a tidy living and work space was helpful.
  • 3
    This is assuming people are naming files in any consistent fashion which, I would argue, is a perfectly reasonable system of organization compatible with modern search. But I’m fairly confident anyone not using folders probably isn’t renaming anything they download.
  • 4
    “I know, I’ll organize my files into both the Desktop and Downloads folders instead of just Desktop. That’ll fix it!”
  • 5
    For the young folks out there, this is a shortening of the word photograph, which you may have never heard spoken before.
  • 6
    I’m not arguing this needs to be done manually. Tools like ChatGPT make it clear that we could query our searches to do this for us, but if we subsequently save the results of the search we’re admitting that the organization is useful, which is my entire point.

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