Taming a Hundred Files

Part 4 of 7: Documents in the Wild

Dev is a freelance consultant with five clients at once, and Dev's problem is not writing documents. Dev's problem is that after a busy quarter there are a hundred of them: kickoff notes, brand guides, meeting recaps, invoices-in-prose, three different "final scope" docs per client. One document is a joy to write. A hundred loose ones is a search problem you gave yourself.

I used to think folders were clutter, honestly. I have changed my mind. A shallow folder tree is the cheapest organization you can buy, and Documents has one built for exactly this.

The tree in the sidebar

Every document lives either at the root or inside a folder, and folders nest as deep as you care to go. Dev's setup is boring in the best way: one folder per client at the top, a couple of subfolders inside each (one for notes, one for deliverables), and the documents filed under those. The whole thing renders as a tree down the left side of the workspace, and it stays put as you move between documents, so it is always there to navigate from.

The Documents sidebar tree showing a nested hierarchy: Client Work containing Acme Rebrand, which contains two documents, alongside a Globex Retainer folder

A nested tree: Client Work, then Acme Rebrand, then the actual documents. Expand what you need, collapse what you do not.

Nesting is checked so you cannot do anything absurd, like make a folder its own grandparent (the code walks the parent chain and refuses a circular reference). You get the depth without the ways depth usually goes wrong.

Moving things after the fact

Here is the thing nobody admits about organization: you never get it right the first time. You file a document under the wrong client, or a folder that made sense in January is wrong by March. So documents move. Every document has a Move control in its header, folders can be reparented, and the file just relocates in the tree. Its path (that .md filename from Part 1) travels with it. You are not locked into wherever you first dropped a thing, which is what makes it safe to just drop things and sort them later.

That is the workflow I actually recommend: do not agonize over where a new document goes. Put it down, keep writing, and reshuffle the tree when the shape of the work becomes obvious. Cheap to move means cheap to be wrong.

Nothing you delete is really gone (yet)

The other quiet reassurance is delete. When you remove a document or a folder, it is a soft delete: the row is marked with a deletedAt timestamp and drops out of your tree, but it is not shredded on the spot. That is the difference between "I cleaned up my workspace" and "I panicked at 2 a.m. because I nuked the wrong client folder." Deleting is supposed to feel safe, and here it mostly does.

Folders, moving, and a delete that does not bite. That is enough to keep a hundred documents from becoming a hundred problems. Next up is where it gets social: handing one of these documents to someone else without the usual chaos of permissions.

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