The idea of organizing files and documents goes back to the good-old-days of filing cabinets and paper.

The advantage of the original paper-based cabinets was that you really had to think about where to put documents so that you could locate them easily when they were needed. With digital documents, since you can’t see or touch them, it becomes too easy to have files scattered all over your computer.

Since this is a digital mess and not a physical mess, often you don’t realize you have a problem — until you have a problem! You don’t feel the pain of a disorganized system until you can’t find a document you need.

Even though search is a powerful tool, and there is a training course in The Dojo taking you through searching for files, you still want to have a basic organizational structure so that you don’t have to rely solely on search.

Note: We’ll be talking about folders and directories on your hard disk in this article. The same general concepts will apply if you use a system like DevonThink, Evernote, or OneNote.

We’ll do our best to cover both macOS and Windows in this article. For the most part, the user directory structure is the same, and the strategies should apply to both Mac and Windows.

The Goals of Your Organizational System

There are three overarching goals for your file organization system:

1. Easy to File– You don’t want your system to be a huge, hierarchical maze. You want it to be fast and easy to save files so your system does not cause friction.
2. Easy to Find – You want your system to make it easy to find the file or folder you need, either by poking through folders or using search.
3. Reusable – Where possible, you want to use re-usable templates and naming conventions, both of which support the previous two goals.

Some Simple Rules

Let’s start with some simple rules for managing your files and folders.

1. Don’t put files on the desktop

Your desktop is supposed to be clean and display that gorgeous high-resolution wallpaper you’ve got going on. It should contain your trash/recycle bin, and that’s about it.

On occasion, it can be handy to put a file or two on your desktop for temporary storage if you’re referring to it regularly and don’t need to file it just yet.

If you want to make sure to keep your desktop clear, check out our Hazel tutorial. There is a rule to automatically clean off your desktop. While Hazel is a Mac application, you can do the same thing with DropIt on Windows.

2. Limit folder creation

When you’re creating folders, think minimal. Most files and documents can fit somewhere in your hierarchy if you’ve done a good job of initially mapping it out.

In general, only create new folders (especially top-level folders in Documents) if you find yourself repeatedly coming back to save similar files in the same place, only to find that it doesn’t exist yet. You’ll know when it is time to create another level in the hierarchy rather than creating a vast extensive multi-layered tree before you need it.

You want your structure to be as simple as you can get away with. I have always liked this quote from David Sparks in Mac Power Users episode 99:

“You don’t want to spend any more time on the input side than necessary to find it on the output side.”

3. Name your files and folders strategically

One of our goals for organizing our files is “Easy to Find.” A key way to accomplish this is by putting some thought into how you name your folders and files.

It doesn’t have to be anything complicated. Friend-of-AE Brett Kelly likes to talk about the concept of naming your data by keeping in mind your “Future You”. Here’s what he means by that:

…try to imagine the circumstance in which you’ll need it and which words you’re likely to use when trying to find it.

Think about saving a phone bill. Do you think phone bill.pdf is a good name? Probably not. July phone bill.pdf is not any better.

So when you’re naming that phone bill, think about how you might look for it. Probably:

• By date (I want the July 2017 phone bill)
• By company (I want the XYZCorp phone bill)
• By type of document (I want a phone bill)

So a good name would allow you to look at the files in a folder and right away see what each file is without opening it. It would give you things you can use to search.

So a good file name, in this case, could be 2017-07 XYZCorp Bill.pdf

The same concept applies to folders. It is not helpful to have a bunch of folders called Invoices inside other folders. It would be better to call the folder ABCCorp Invoices (even if it is inside a master ABCCorp folder) so that you can use that name to search on later. It makes it much faster and easier to get to with the keyboard.

Dropbox and File Sync

Before we get into the nitty-gritty of directory organization, I want to give a mention to Dropbox and other similar services.

Sync services (including those built into macOS and Windows 10) are amazing tools for having access to your documents between different devices and being able to be productive wherever you are. They’re also great for sharing documents with others.

We use Dropbox extensively, but many people use iCloud Drive or OneDrive, and Box and Google Drive are also popular.

The structures and strategies we talk about here can be used on your local file system, or can be synced to the cloud if you place the folder structure in the special folder for your service of choice.

Documents

Let’s take a look at your personal documents. Whether you use Windows or Mac, you will likely use the /username/Documents folder on your computer to hold your personal documents. (Of course, if you use Windows, the slash is a \ instead of a /.)

If you happen to do both work and personal tasks on your computer, you should create two folders to separate out your personal and business items.

If you’re using Dropbox, it could look like this:

• /Dropbox/Business
• /Dropbox/Personal

If you’re not using Dropbox, you can similarly do:

• /Documents/Business
• /Documents/Personal

Now how you divide up your personal documents is mostly a matter of how you mentally divide up your life. A very basic split could be Education, Employers, Family, Finance, Health, Home, Purchases, Travel, and Vehicle.

There could then be a moderate amount of subfolders under these. For example, if you have kids and have documents related to your parents, you may want to split up Family:

• /Documents/Family/Duncans (My parents)
• /Documents/Family/Yeungs (My wife’s)
• Kids

If your mind goes this way, you could also do a split by life areas, like:

• /Documents/finances
• /Documents/social
• /Documents/play
• /Documents/mind
• /Documents/health

The general rule to follow is to pick a folder structure that matches how you mentally organize things. If you use a task management system, it’s probably not a bad idea to mimic the structure that you use in there too.

Business Documents

Similar to your personal documents, your business documents and how you organize them will largely depend on your occupation, industry, company and job position.

If you are in a large organization, you will likely be working from a shared drive, in which case the directory structure will usually be pretty set, so you don’t have to worry about it too much.

If you are a small team or organization and are building your structure, it can be helpful to get the people together who will be working with these documents and come up with the structure together. You’ll be more likely to have buy-in if the people who are most familiar with the documents have a say in how they’re structured.

If you decide to store some documents locally or if you’re not working from a shared drive, it largely comes down to what you do. For example, say you’re a business analyst doing project work. Your directory structure could look something like this:

• /project name 1
• /project name 1/wip
• /project name 1/brainstorming
• /project name 1/output
• /project name 2
• /project name 3
• /archive

Each project would then have subfolders related to logical units of organization, like the type of work, stakeholders or who you’re reporting to. /archive is where you would move your completed projects when they’re done. In contrast, say you’re an online marketer working from your laptop on the beaches of Bali, you may have something more like this set up:

• /finances
• /legal
• /marketing
• /products
• /projects
• /planning
• /systems
• /technology

This is actually pretty similar to what we have set up at Asian Efficiency (sadly, I am not writing this from the beaches of Bali). How you organize your business-related directories comes down to how you decide to divide up your business or job into logical units. An easy way to do this is to grab a sheet of paper or a whiteboard and map out your company/enterprise in detail, based on what it is you do day-to-day. Then group related activities into logical groupings – think of it as an organization chart for your job/company, minus the positions.

Sample Folder Structure

To get started, here’s a sample folder structure. You could start with this and tailor it to your needs.

Folder Templates

Once you start analyzing how you work with files and folders, you may notice that you have certain folders and subfolders that you use over and over.

This is especially true for financial documents, client work, and project work.

It can be very helpful to pre-create a folder template with the structure you want to use. Then every time you come to a new financial period, onboard a new client, or start a new project, you can just copy over that folder template.

This has two benefits:

1. It saves time. With a few mouse clicks or keystrokes, you have your whole folder tree created.
2. It enforces consistency. You know your folders will be named the same way every time, which means it is more likely that you will save things in the right place, and it makes it much easier to quickly find things with search.

To create a folder template, just set up your sample folder structure. Then when you need it, you can copy it in Finder on macOS or File Explorer on Windows and paste it into your new client or project folder.

To be extra Asian Efficient, you can use a tool like Keyboard Maestro or Alfred and have your folder template created with a few keystrokes. No mousing needed.

Shortcuts, Favorites, and Launchers Are Your Friends

Do you have specific folders that you access all the time? Instead of always digging through your file structure to get to it, you can drag the folder to the Finder or File Explorer sidebar. This will create a shortcut directly to that folder, giving you 1-click access.

Pro-tip: This feature is great for those folders you permanently need access to, but it is also excellent when you are working on a project. Drag your project folder(s) to the sidebar while the project is going on and you want quick access to the folder, and then when you’re done, you can just remove it. Shortcuts can be temporary!

If you are a keyboard type (which we highly recommend), learn to use an app launcher like Alfred or LaunchBar on Mac or Listary on Windows. You can start typing the name of the folder you want, and with a few keystrokes jump right there. Once you get the hang of it, it will probably become your preferred way to go to a folder.

Automated Organizing

We touched on this earlier in the article, but once you have your folder structure set up, you can gain a huge productivity boost by setting up an automated organization tool like Hazel on Mac or DropIt on Windows.

If you have files that are recurring (for example bills or statements) and you can think of a way to build rules for them (for example “always named xyz” or “always contain the text abc”), you can use these tools to auto-file the documents for you. All you need to do is scan or download the document, and your tool will rename it and whisk it away to the appropriate folder.

Here is our Hazel tutorial (the same general concepts apply to DropIt), and here is a tutorial for going paperless using an automated organizer.

In Closing

We hope you’ve picked up some ideas from this article that will help you better organize your documents and files. As long as you follow the rules in the beginning and set up an effective hierarchy, file and directory organization is a breeze.

For more in-depth training on file organization and file search, make sure to check out our training courses inside The Dojo, our exclusive members-only community that is jam-packed with trainings, courses, masterclasses, podcasts, coaching calls, action plans, and productivity-focused individuals just like you.