Greetings, data-tamers!
I'll tell you about my Q4 2025 Consistency Challenge project down below near the end of this post. But fist, want to do some eye-opening math with me for a second?
If you spend just 5 minutes a day looking for documents (optimistic, perhaps), and then another 3 minutes doing the "Save As" dance to for new documents, that's 48 hours a year.
That's an entire work week, and then some.
I made a short quiz for document management. Sometimes, a little introspection helps drive the point home. Give yourself a point for every "yes" here:
- Do you have at least three files named some variation of "New Document" or "Untitled"?
- Have you ever opened multiple Word files trying to find that one paragraph you know you wrote somewhere?
- Do you use "Save As..." to create versions because you're afraid of losing something important?
- Have you ever searched your entire computer for a keyword because you can't remember which file contains it?
- Do you have a folder called "Old" or "Archive" that's basically a digital junk drawer?
- Have you ever emailed yourself a document just to have another backup?
- Do you keep important information in documents named things like "Misc Notes" or "Random Thoughts"?
- Have you spent ten minutes trying to figure out which folder to save your document in, since it fits in five of them reasonably enough?
- Do you have documents that mix meeting notes, to-do lists, and random research all in one file?
- Have you ever spent more than 5 minutes trying to figure out which file has the most recent version of something?
Let's see how you scored:
- 0-3 Points: You're Doing Pretty Well. You've got a system that mostly works. Maybe you have the occasional "wait, where did I put that?" moment, but nothing that derails your day.
- 4-6 Points: The Cracks Are Showing. You're in that frustrating middle ground where things work just well enough that you haven't hit the breaking point. But those little friction moments add up. You probably think "I should really organize this" at least once a week, but when would you find the time?
- 7-10 Points: Welcome to the Club. Friend, you and I need to talk. You're not disorganized; you're drowning in a system that was never meant to handle how we work today. Every time you need to find something, it's an archaeological expedition. And I bet you've thought more than once: "There has to be a better way."
You're in luck: there is a better way.
It Isn't Exactly Your Fault
Word was born in 1983. Reagan was president. The internet as we know it didn't exist. Documents had one job: look good when printed.
And Word is great at that job. If you need a resume that looks professional, a report for your boss, or basically anything written that needs to physically exist on paper, Word has long been the go-to app for that task. (For the Mac users not using Microsoft's stuff, pretend I'm talking about Pages) instead; the concepts still apply. For Linux users working with something besides either of these two software packages...I'm not sure what to say. You're probably nerdy enough not to suffer from this particular problem. Let me know.)
Despite its more focused, humble beginnings, here's what some of us are actually doing with Word in 2025:
- Jotting down quick thoughts during meetings
- Building personal knowledge bases we'll search through for years
- Collecting research from twelve different sources
- Keeping running notes that evolve over months
- Creating documents we'll literally never print
This is using a printing tool as a thinking tool. No wonder it feels like fighting with your computer every day.
I know some of you are thinking "but I should be better at organizing" or "other people seem to manage fine" or my personal favorite: "I just need to be more disciplined."
Stop.
You are not bad at technology. You are not disorganized. You are not lacking discipline. (Well, okay, you might be, but this particular struggle is not what proves it.)
Trying to build a personal knowledge system using a tool designed for creating print documents is like driving in a screw with a hammer. Sure, if you hit it hard enough and at just the right angle, you can kind of make it work. But wouldn't it be nice to just have a screwdriver?
Every time you've created another "FINAL_FINAL" version, or given your document an incredibly detailed filename to help differentiate it from everything else, or lost track of which document contains what, or wished you could just search everything at once...you were bumping into the fundamental design limitations of the tool.
The Evolution of Writing Digitally
Those of us who have been writing stuff down with computers since before the explosion of Personal Knowledge Management apps have gotten stuck in habits that developed around software limitations that no longer exist. Not everything has to be managed by hand using files and folders. Sometimes this approach makes sense, but definitely not always.
The good news is that there's a whole category of tools designed for how we actually work with information today. Tools that understand we want to:
- Search everything at once
- Connect related ideas without copying and pasting
- Never lose a previous version
- Find things based on vague memories ("that thing I wrote about last Tuesday")
- Identify entries based on key aspects of their content, not one single filename
In fact, not only do these tools exist, but there are many excellent options available, each focused on different handy features that make it likely that anyone can find a version that fits with your brain type and desired workflow. Of course, that also means that finding the "best" tool for you can feel like an insurmountable challenge all by itself.
I'm not going to tell you what you should do, but I hope to provide some guideposts along the way to help you determine what might be worth trying as an alternative. And, later this month, I'll talk through one specific tool and a migration process that should be instructive no matter what you decide to do.
Also, for those of you on the fence or already starting to panic: you don't have to abandon Word completely. There are still certainly valid use cases for it, and you can even keep using it for the arguably invalid use cases while you dip your toe in the water of something new and different.
If You're Up For It...
Before we dive into solutions next week, I have one small request. It might be painful, but it'll be worth it.
Look at your Documents folder. Right now. Don't clean it up first. Don't delete the obvious duplicates. Just observe it as it is. If you know how easily, count how many files and folders are in it. On Windows, you can use File Explorer and right-click on the "Documents" folder, then choose "Properties" from the bottom of the menu that pops up. On a Mac, you do basically the same thing with Finder, but choose "Get Info" from the pop-up menu.
Here's mine:
See those numbers? That's a lot of stuff.
Now, having big numbers here isn't automatically a problem. In my case, most of these are not individual Word documents that should be stored in a cleaner system. Rather, they're mainly application-specific work files that are at least not-too-terribly organized by program and by project. But I've still got a lot of files carried through the years that would become instantly more useful to me if I migrated them into the notetaking app I use regularly. (And don't even think about peeking at my 30-year archive, where you'd find thousands more.)
But in any case, step back for a moment, and consider your document situation from another perspective: it's not a mess. It's evidence of all the thinking, working, creating, and trying you've been doing despite using a tool that wasn't built for it. You should be proud you've made it work this long.
Next week, we'll explore how you can bring about a gentle transition from "document archeologist" to "library curator" for your document management. You can look forward to exploring:
- An easy rule of thumb for knowing whether or not to use Word when you want to write something new
- Three different migration approaches ranging from "barely any change" to "let's fix everything!"
- How to create a balanced document organization structure that works for your brain
- Clever ways to relate (and later retrieve) documents and notes based on what they are about
And yes, we'll talk about specific tools, but more importantly, we'll talk about the thinking behind making this shift without losing your mind or your data.
Q4 2025 Consistency Challenge Update
As promised, here's the part where I tell you all what I decided to do for the last quarter of this year's Consistency Challenge: I'm going to help my mom migrate her documents into a system that works for her. There are multiple reasons for this choice, but let's just say it's going to be a mutually beneficial project. I know her current document situation causes a lot of stress, and this will be a great hands-on test of what I've been recommending to you all.
Now, in light of the whole "give a man a fish" proverb, I'm not going to do it for her; I'm going to do it with her, seeing together what works and what doesn't, until she's comfortable enough to do the rest herself. (She's not an uber-nerd like me, but I'm sure she's capable enough with some introductory hand-holding.) The goal will be to get to this point--comfortable self-management--before Christmas...because who wants to be doing data organization around Christmas?
(Me. Probably. Because I'm that weird.)
What's your relationship with Word documents right now? Are you in the "it's fine" camp, the "help me" camp, or somewhere in between? Or is this a non-issue for you because you're already using a note-taking app or you simply never write stuff on your computer?
Until next Tuesday, happy data-taming!