Last summer, I took a course for solopreneurs that ended up being incredibly useful for getting a lot of the pieces of Backwoods Consulting out of my head and into actual documents. I worked through my branding and voice, nailed down my services and pricing, started building out products, and created SOPs and templates for the things I knew I’d need again. By the time I was done, I had accumulated a pretty substantial collection of resources for my own business.

And I organized them. Of course I organized them. I had folders. I had subfolders. Things had names. I knew where everything went, and when I put each document in its carefully chosen home, I’m sure I had a perfectly reasonable explanation for why it belonged there. And then I didn’t need most of it for several months.

When I finally went looking for something again, whatever brilliant organizational logic I’d been operating under the previous summer had apparently left the building. I knew the document existed. I knew roughly when I’d created it. I could picture the thing in my brain. What I could not figure out was why in the world I had named it whatever I’d named it or which one of several perfectly plausible folders I’d decided was its home.

Was it in my main Backwoods folder? Was it somewhere in the course materials (because I’d created it while taking the course)? Was it buried inside another folder that apparently made perfect sense to me at the time?

I searched for the words I thought I’d used. Nothing. I opened folders. Then subfolders. Then documents that looked vaguely promising just to see if maybe they were related to the thing I was actually looking for. Eventually, I found what I needed. So…technically…my system worked…If your definition of “worked” includes spending considerably longer than planned wandering through a filing system you personally created while repeatedly asking yourself, Why in the world would I put it THERE?

I eventually pulled everything into one Backwoods Resources folder, and this spring I went back through the whole thing properly. By then, enough had changed in the business that some of the documents needed updating anyway, so I reorganized the resources, updated what was outdated, and gave things names that would hopefully make sense to someone who hadn’t been inside my brain on the exact afternoon I created them. Which, as it turns out, includes me nine months later.

I run into a different version of this with bookkeeping clients all the time. A client can give me everything I’ve asked for. I’ve got access to their books. I’ve pulled the reports. I’ve got the bank statements, credit card statements, receipts and whatever else I need to work through the problem in front of me. Technically, I have all the information. But that doesn’t necessarily mean I can see the answer.

Sometimes I’m sitting there with multiple reports open, bouncing between bank and credit card statements, trying to match transactions while also figuring out who the vendor or customer actually was so I can determine whether everything has been categorized correctly. The information is there, but there’s no rhyme or reason to how it was organized or named before it got to me. Before I can fix anything, I have to figure out what I’m actually looking at and how all the pieces relate to each other. It’s a very different problem from simply not having enough information.

I’ve seen the same thing on a much larger scale too. Years ago, when I was tasked with reviewing and reorganizing a legal department’s shared drive, my first look at the thing was…well, it was a hot mess. There were folders inside folders inside more folders. Identical copies of documents were stored in multiple places. A single file might appear under Commercial, under the customer company’s folder, and again with the regulatory matter it had eventually been used for. The file names weren’t particularly helpful either, which meant I couldn’t just look at three similarly named documents and know which was the original, which had been edited, or which was the final version that had actually gone out the door.

So before I could decide how to reorganize anything, I had to figure out what the heck was actually hidden in there. I did what anyone else would do…I built what can only reasonably be described as an uber-spreadsheet. I tracked every folder, every subfolder, and every item inside them. When I found duplicate documents, I looked at the metadata to see when they’d been created or edited. Then I still opened the files to verify what was actually inside because the names couldn’t reliably tell me.

Somewhere in the middle of peeling back all those layers, something interesting happened. The filing system started making sense. Not good sense for the department as it existed by then, but I could finally see why the original attorney had done what she’d done. If she was working on something commercial, it made sense to put the document in Commercial. If it belonged to a particular customer, putting another copy under that customer made sense. If a regulator requested it later, putting it with the regulatory matter made sense too.

When she was the only person regularly working in those files, she didn’t need the system to explain itself to anybody else. She already knew why things were where they were. The problem showed up when other people needed to navigate it. That’s the part I couldn’t see when I first opened the shared drive. All I could see was the mess. Once I had the hierarchy sitting in front of me, I wasn’t guessing anymore. I could see what the original system had been trying to accomplish, where it was creating problems, and which parts of its logic were actually worth keeping.

Only then could I decide what the new system should look like. And I didn’t completely reinvent it. I used what I’d learned from the old system and changed the pieces that were causing the confusion. We established one naming convention that worked across almost everything. Regulatory inquiries had their own tracking process so we knew where documents originated, who created them, and which version was being worked on. We established a cutoff date so we weren’t wasting time reorganizing years of historical material just for the sake of making old folders look pretty. Anything before that date went into the archive, original folder and all. Anything after it went into the new system.

Those decisions were fairly easy to make once I could actually see the problem. Getting to that point was the hard part. And I think that’s something I forget sometimes when I’m staring at a mess, whether it’s someone else’s bookkeeping, an old filing system, or the Backwoods Resources folder I apparently designed specifically to hide documents from myself. My first instinct is usually to start fixing things. Rename this. Move that. Create a new folder. Reconcile the transaction. Clean up the report. Get everything where it belongs so I can move on.

But sometimes I don’t understand the mess well enough to fix it yet. Having all the information isn’t the same thing as being able to see what it’s telling me. And organizing information isn’t particularly useful if the organization only makes sense while all of the context is still fresh in my head.

Sometimes the better first move is to stop moving things around and figure out what I’m actually looking at. Where did this come from? Why is it here? Is this actually a duplicate, or is it a different version? What was the person who created this trying to accomplish? Is the information wrong, or is it simply presented in a way that makes it difficult to understand?

Once I can answer those questions, the next decision usually gets a whole lot easier. Maybe that’s reorganizing an entire shared drive. Maybe it’s correcting something in a client’s books. Maybe it’s creating a naming convention so six people don’t have to ask one person where she put something. Or maybe it’s admitting that Past Lettie apparently had some very specific ideas about where business resources belonged and Present Lettie would appreciate it if she’d stop being so darn creative.

The mess doesn’t always need to be fixed first. Sometimes I just need to see enough of it to understand what I’m dealing with. Then I can decide what the heck to do with it.