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The Most Effective Way of Organizing Your Files, Folders and Documents

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Stack of Files

One of the simplest and most overlooked aspects of being organized is getting your computer files organized. Every time you have to dig around for a document you can’t find or have to do unnecessary clicks to access a folder, you are not as productive as you could be. Let’s look at some good practices for keeping your files and documents neat, in folders and easily searchable and accessible.

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.


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.

Sample Folder Structure
Sample Folder Structure

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.

If you want more articles and tips like these, let us know where we can send them to:

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Posted by Moana  | August 5, 2018 at 9:55PM | Reply

I have thought about it long & hard about what to do to limit paper trials in my home….. I have a four drawer filing cabinet, which gets overfilled before the EOFYs even get halfway. I have SO many product manuals, school reports, utility bills, invoices, receipts, study certificates, award certificates, medical informations, insurance details, statements, etc…. & that is just home stuff!
So I want to condense the amount of paperwork I have & get, by scanning & or saving everything online to make it digital filing from now on.
So, I am thinking of opening a separate email account specifically for digital filing. I thought I would use the email account to save all scanned & saved document paperworks into folder files, shred the physical paperworks, donate the shreds to pet stores etc (all ID related informations would be security stamp blocked out before shredded, of course) & only keeping any signature based paperwork in it’s physical form for the filing cabinet. I was just going to use a hotmail or gmail accounts.
I would use my iClouds accounts, but it’s limited storage…. & I only have less than 500MB left for some unknown reason, lol.
I am concerned that using those recommended in the posts, as my digital filing system, that when either the company goes under, or no longer functions for whatever reason, or new idea comes up, making the previous programs scrapped of existence, then I’d lose everything I had on it.
Also a little concerned that, in the end, finding out that everything I have done up to that point, transferring it all from old to new or updated apps/programs, won’t happen because of some old system’s glitch etc…. like the StoCard app when my mobile phone was stolen, at the time I installed the app, it was only accessible by that device it originated on….. so I lost access to ALL cards & had to redo the entire set up, this time, another app connected to individual ID access.
Unless someone can tell me something that is highly reputable & easiest route to do in transferring from physical filing to digital filing?
I want to make it an easy system, for myself, but I’m a bit overwhelmed by it all really.

Posted by Shellie Johnsey  | December 21, 2017 at 6:42AM | Reply

Nice Share this is awesome

Posted by Adam  | September 17, 2017 at 5:55AM | Reply


Here is nice program for organizing files:

Posted by Lyan  | June 29, 2017 at 4:49AM | Reply

I was just reading through the guide and this “chunking” just made me far more confused. It’s not the definition I have a trouble with but the actual operation you do as the follower of this guide. Outright, I certain the guide does not suggesto to Right Click and select Chunk Up/Sideways/Down.

So what is it exactly that is being suggested to be done and how?

Posted by Ed Ende  | June 20, 2017 at 1:06PM | Reply

I found out what TED notes are. I have also learned that it would be better for me to use something like Dropbox (which I have chosen) rather than rely on USB’s I have also began to create my document tree and scan my personal papers and photos.

Posted by Ed Ende  | June 13, 2017 at 9:48AM | Reply

What are TED notes? Also, I am 76 years old. I am beginning to scan almost all of the photos and papers I have accumulated over the years so that those after me won’t have to wade through items of questionable interest to them. I plan to back up my work with two USB’s (in case one fails.) What do you think of this idea? Thank you.

Posted by Ed Ende - "Never Too Old to Learn"  | May 27, 2017 at 10:51AM | Reply

Thank you. I have discovered worthwhile information I should have learned, mastered and applied 35 years ago. My intention now is to read everything at least twice. I purchased an inexpensive ($400.) Windows-based computer and intend not to load such applications as iTunes and Picasa 3. I will use this computer for my files and the Internet. I will soon begin to organize my work on the computer as soon as I outline everything on a test document. Thank you again.

Posted by Rob Crombie  | March 17, 2017 at 9:06AM | Reply

If you email me, I can offer assistance (free)
robhp AT iprimus DOT com DOT au

I am 75, was a qualified ACA, and then spent 20 years in IT as a senior analyst (and programmer).

Posted by Val  | February 24, 2017 at 7:51AM | Reply

i need to start from ground zero and learn everything. My husband managed our computer and set things up initially. I have saved documents by title rather than in folders because I didn’t know how to set them up initially. Now I know I need to go back and organize. Which will take forever.

That said, is there a good book out there that will teach me everything I need to know from creating folders, storing info, backing up documents, photos, videos, etc, uploading, downloading, dragging dropping and anything else basic for Windows operating system?

My husband is no longer here and while we each did things for one another we didn’t teach the other what to do so I find myself at square one.

Can you recommend a book to keep on hand for quick reference that’s not complicated for Windows operating system, organization and understanding the basics operations of a PC?

Any input would be appreciated.

Posted by Alexandra  | January 4, 2017 at 8:48AM | Reply

I can always tell how busy I am by how messy my desktop and download folder get. Your article is great, nice to see you are keeping it up to date!

Posted by JB  | December 14, 2016 at 5:55PM | Reply

My desktop is clean and files and organized. Creating folder efficiently for where it properly belongs.

I used dropbox for my files storage online and since I have a licensed Microsoft office I do have 1 terabyte for Onedrive.

Posted by Ken  | December 9, 2016 at 4:28PM | Reply

Do you know of any professional providers courses that offer online or in-person courses on this topic? If so, please share their contact information and/or website. Our organization may be looking for such a course in the near future.

Thank You,

Posted by Mitch  | December 3, 2016 at 3:34PM | Reply

I am still looking for a way, a software that is able to sort and organize the hundreds or thousands of files that I have for the many projects that I have in my computer. I can’t use online service so I am trying to find a software that I can give search criteria and then the software will quarantine or sort these files for me. Then I will create a new folder for these files that are all over the place . Is there such a dream software? Not online service please. Thank you all.

Posted by James Bergman  | October 26, 2016 at 5:37PM | Reply

Effectively storing my files on my desktop is all about using proper folders and then being consistent in using them. I normally save my files using the same kind of system I use when storing hard copies. Yes, I still use hard copies as well as digital versions. It is my backup in case anything goes wrong with my computer.

Posted by Delilah  | August 3, 2016 at 10:40PM | Reply

What’s the difference between Google Drive and Dropbox? Why so much emphasis on Dropbox? This is not the first time I’ve seen praise to Dropbox.

Posted by somebody  | April 5, 2016 at 2:09PM | Reply

just dump it all in

Posted by Dalia  | February 9, 2016 at 4:44AM | Reply

I am in the process of reorganizing my computer files based on your advice, but one point isn’t clear – What is your advice for the /archive folder? Does it retain the same structure as /business and /personal or do you just dump everything in?

Posted by MELANIE CHEW  | December 10, 2015 at 12:25AM | Reply

Nice work! Thanks for the info, super helpful. Merging files is super easy with AltoMerge. Try it on your own here AltoMergealso here and you’ll make sure how it’s simple.

Posted by A. M Julius  | December 6, 2015 at 10:41AM | Reply

Hello, i am a teacher in collage, and i like your idael so much, look forward to have more of it.

Posted by Josh  | September 4, 2015 at 11:32PM | Reply

Hello, I am a remote entrepreneur but mostly work at home on my imac. I have a 10tb NAS server, Gdrive and several computers (2 pcs, 1 mac) and a laptop that I work on. I run several businesses and I do freelance work including video editing, photography, graphic design and web developing as well. I like your idea of using a standard business folder alongside personal to separate documents but should I then organize businesses separately in there or outside the business folder or something different entirely? Currently, I have 1 master folder for each business/trade on my desktop and I don’t frequent Documents or Downloads folder much. My desktop gets cluttered with current work but I will be implementing Hazel soon. My questions are how do you recommend I organize my business folders and do you have any other multitasking techniques that I could implement considering I dabble in a lot of different areas? Thanks so much! This is one of the most helpful articles I’ve seen.

Posted by Dhruv  | August 24, 2015 at 3:54AM | Reply

Desktop and My Documents / Documents folder should be empty or redirected to drive other than C: So that in case of OS crash C: can be fixed without any mess.

Posted by EvertVd  | July 5, 2015 at 6:17PM | Reply

I’m not sure I agree with the statement that the desktop should remain empty. It is there for a reason, and it is the main thing you return to everytime you leave a program (or start up your computer). In my philosophy the desktop is the place where you put everything you work on. Be it a project folder or downloads. Whenever you return to your desktop you instantly see what you need to do, no need to search for files burried deep on some drive.
Once a project is finished it can be transferred as a whole to a place of permanent archive. Same applies to downloads, once finished with them, either delete or archive them. So your desktop is the place where you work from and your “goal” is to make it empty (but it never will be as long as you keep working on stuff).
My only problem with this started a few years ago as I tried to integrate cloud based services into my workflow. I am still trying to figure out how to incorporate google documents in my projects as they are firmly located ‘in the cloud’.

Posted by Janet Butler  | December 29, 2014 at 6:17PM | Reply

Thanks for this post. I do IT at my local insurance company, and I was given the task of updating our storage system, so this was super helpful.

Posted by Organizing my records  | November 3, 2014 at 6:19PM | Reply

Great post! My company has been really busy lately, and as a result our files and records have gotten quite cluttered. This was a huge help. Thanks for sharing!

Posted by zak  | July 13, 2014 at 1:37AM | Reply

I am not very computer savvy. is it possible to hire a computer assistant who could help me organize my files?
The help does not need to be on site. after some initial discussion of how best to organize the information the help could be by remote access to my computer.
Are there such services available that are reliable?

Posted by Lorne Fade  | May 10, 2014 at 7:49AM | Reply

Great overview on how to get organized in business with file structure. I use google drive and dropbox religiously for this and it makes like a breeze. Thanks for sharing the insights!

Posted by Ryan  | March 13, 2014 at 6:49PM | Reply

Sir, where would you file things like software installers or app preference files under personal? I’m basically using your organizing files and folders and documents article as a starting point. Thanks for actually posting what I was looking for– there should be more of this.

Posted by Aaron Lynn  | March 17, 2014 at 6:03AM

I keep my app installers in /Downloads/apps with a backup set on an external hard disk. I have about 20gb of installers, and they’re readily available online so I don’t feel the need to take up unnecessary Dropbox space with them.

For preference files and backups and stuff I put them in Dropbox.

Posted by Shai  | January 25, 2014 at 4:04PM | Reply

This is a great article for presenting the basics, foundations, and mindset for setting up and effective folder hierarchy.

I’m mainly a Windows user and here are some comments that I though worth adding:
1) I completely agree that the Desktop should be empty. Windows Search is a good way to launch one’s regular applications, but I recommend using application launcher such as Find and Run Robot or Launchy that are far more customizable and powerful.

2) I agree with Senile Citizen that searching for a file with a meaningful name does not contradict filing it properly in an appropriate folder hierarchy. I (try my best) to give all files a meaningful name and then use Everything Search to find it near instantaneously. Everything also allows the user to open the containing folder if more actions should be taken. Everything uses the NTFS journal so its search is very fast (but it searches for file names only and not for their content). It is specifically useful for locating that odd invoice or other document that you don’t quite remember what was its date; much faster then sorting through the right folders that could hold a lot of other files as well.

3) It is quite disappointing that in this day and age the file system are so lacking with it comes to storing metadata. The lack of simple mechanism for adding tags to files conisderabbly hinders the ability to “file” documents that fit several categories or folders. I have redundancy (except for physical data storage) and I don’t want to create several copies of the same file (e.g. an invoice for multiple projects). To avoid this I use shortcuts. Not the ideal solution because they break quite easily (and Everything is very useful in finding their new locations and updating the shortcut in such cases), but they at least serve a remainder or a note.
I also use shortcuts for easy access. I use a master archive folder and instead the physical folder-specific one I have a shortcut pointing to the relevant sub-folder of the main Archive folder. Ultimately it achieves pretty much the same thing.

4) Because Windows doesn’t allow the user to move the entire user folder, and in light of the rise of SSDs, I find it counterproductive to waste the limited storage space and writing cycle of the SSD for storing using documents. There are several solutions (like mounting a specific partition from another drive as the C:\Users\ folder) but all of them as one shortcoming or another. What I prefer to do is just relocate all the date containing folders (Documents, Music, Pictures, etc.) to a separate home folder via the Windows properties dialog window. Not the best or ideal solution, but the benefits often outweigh the disadvantages. For a single user machine there is no further concerns, but for a multi-user system that Home folder could be further divided to hold the data of all users and by adjusting the security settings an unauthorized access could be prevented.

Posted by Steph  | January 15, 2014 at 10:07AM | Reply


I am a fairly new dropbox user and have a question regarding hierarchy of folders. I cannot find this answer anywhere so far. If I create a shared folder and then create a folder one level down, but within that shared folder, is the new folder within the shared folder hierarchy automatically shared?


Posted by Thanh Pham  | January 16, 2014 at 3:24AM

Yes – everything within the shared folder will be accessible by others.

Posted by Chris  | December 13, 2013 at 10:05AM | Reply

Query: What do you think of Dropit as a file organizer manager? I have used it extensively for storing various file types, e.g., software installation applications,*.exe, and zip files.

Posted by Thanh Pham  | December 13, 2013 at 1:57PM

None of us use Windows so we can’t comment on its effectiveness.

Posted by sunnymoon16  | March 4, 2013 at 3:49PM | Reply

This article was a great read! Thank you!

Posted by Ryan  | February 28, 2013 at 4:13PM | Reply

Are there any companies that will come in and organize shared computer drives? If so, what company is rated the best?

Posted by ann sarimo  | January 8, 2013 at 4:14PM | Reply

Hi Aaron, I love when I’m doing random online surfing and stumble across a great blog like yours. Fun to read and super useful information. Love the post about super foods that help you lose weight and boost productivity. Need to find out where I can get Chia Seeds in Helsinki. Anyhow, while I’m here visiting and learning, I thought I should also take a moment to introduce you to a new service that I started using a few months ago but became such an avid user that I decided I must join the company. The service is called Arkkeo and I’m not going to give you a marketing pitch (well maybe a little one) but since it’s relevant to your blog, you should check it out if you have some time. I was a DropBox user but dropped DropBox in favor of Arkkeo’s great categorization and tagging system and the mobile app which has helped me to reduce my junk drawer to only junk and no more piles of receipts waiting to be filed. Cheers to a productive 2013. Nice blog indeed. Ann Sarimo

Posted by Senile Citizen  | November 19, 2012 at 11:52PM | Reply

Aaron does an excellent job of describing folder hierarchies. But as a retired college library director I will have to emphatically disagree with the following comment that Aaron makes.

He said, “My personal test for organization is this: you should be able to find the majority of your documents without using Spotlight or Windows Search. If you can’t, you’ve got some housecleaning to do.” His statement shows a fundamental misunderstanding of the difference between browsing and searching.

Let’s take a look at the way libraries have traditionally worked. Although libraries house books, magazines, newspapers, CDs, DVDs, etc., etc., I’ll limit this explanation to a comparison between digital files and physical books. We’re all familiar with those.

Every major library will shelve its books in such a way that documents on similar topics are shelved together. This facilitates browsing because, whenever you have successfully found one book that is of interest to you, you may find that an even better book is shelved nearby. This is especially helpful when you are trying to master a field of knowledge that is totally unfamiliar to you.

There are two different major shelving hierarchies that have developed for use in large libraries. Most, but not all, academic libraries will use the Library of Congress system; and most, but not all, public libraries will use the Dewey Decimal system. Each of these systems is constantly being fine tuned to adjust to changes in the world of knowledge.

These subject schemes can be compared to the hierarchy of digital folders that Aaron has described. Because a major library must meet the needs of large numbers of people, they use these standardized subject schemes that have been found to work well for the largest number of people. You, on the other hand, are not bound by such restrictions when developing a folder scheme for your personal use. You can develop the scheme that works best for you.

Having said all this, there is a major problem with ALL of these hierarchies. The problem is that almost any book (or file) deals with more than one subject. So into which area of the subject hierarchy should you file it? No matter which area of the hierarchy you choose, the item could almost certainly be just as logically placed in any one of several other locations.

But the item can only physically sit in one place. So what happens if you search for an item in a perfectly logical place, but the item has actually been stored in a different, but also perfectly logical place? In this case, the hierarchy fails you.

For over a hundred years, libraries have used subject headings within card catalogs to solve this problem. Card catalogs have, of course, now been replaced with electronic catalogs; but the process is still similar.

While a book (or file) resides in only one place, multiple subject headings (or keywords) can be assigned to that item. The effect is the same as if multiple copies of the book or file were in existence. It does not matter which of those subject headings or keywords you use in your search; you will still find a pointer to the actual physical location of the item.

I try to file every item as soon as I create or receive it. I file it in TWO ways. I file it within my personal hierarchy of folders. But I also assign keywords. By doing so, I am prepared for both browsing and searching.

Aaron has done a great job of explaining subject hierarchies, so I won’t add to what he has said. Instead, let me talk about keywords.

I store my keywords in the “Spotlight Comments” field of each file on my Macintosh. I try to assign at least one keyword for every subject that is an important part of the document. I use every keyword that I can imagine myself searching for the next time I want to call up this file.

Not only that, but I also try to cover all of the various forms of the same word. For example, I might use “Investing,” “Investment,” and “Investor.” I might include both the terms “Finances” and “Financial.”

When dates are involved, I enter them in the format, Year-Month-Date (2012-11-19). When dates are included as parts of the filenames, dates in that format will be sorted in chronological sequence.

When it comes time to search, I enter my search keys into Spotlight. Sorry about that, Aaron. I almost always find the exact file within seconds. I don’t have to wade down through the file hierarchy.

Oh, I must say that Apple didn’t realize what they had created when “Tiger” (System 10.4) came out. They had developed the most sophisticated filing system ever created, but since they didn’t know what they had, they allowed “Leopard” (System 10.5), and again “Snow Leopard” (System 10.6) to blow that excellent filing system out of the water. Those two systems were money down the drain as far as I’m concerned. The Spotlight in those two systems cannot be trusted to consistently search the “Spotlight Comments” field. Furthermore, they both tend to actually DELETE some of your comments. Apple’s technical support couldn’t find a solution.

I went back to “Tiger” (System 10.4) for almost everything I do so as to preserve my hard-worked-for filing system. I created a small separate partition on my hard drive for “Snow Leopard” (System 10.6), but it just sits there unused. I have years of work in my filing system, and there is nothing in either of those operating systems that is as precious to me as my filing system. Therefore, I haven’t even tried Lion and I don’t care to.

Posted by Amy  | December 9, 2012 at 8:50AM

I am so glad you decided to comment on this, because you did a far better job of explaining things than I ever could have. I agree with you that there is a difference between browsing and searching. I find your methods of organizing files to be fascinating– and certainly a reason to get into Spotlight and poke around with some things.

When it comes to documents and digital files, I think things are changing and we have to get away from strict hierarchies. And though this article talks about personal document organization, could we benefit from document sharing or storage on platforms? Full disclosure: I work for, a document discovery and sharing platform. With machine learning as well as crowdsourced knowledge, it’s becoming increasingly easier to become more hands off with organization of documents– spending less time sorting and more time tagging.

Also, I think your comment showcases how much there is still to learn from information science when it comes to digital information and the WWW, even when it comes to things as “simple” as how to organize your own local store of documents.

Posted by Thiago  | December 31, 2012 at 10:16AM

Your explanation was wonderful. I too have developed a system for “tags” or keywords, but since I work from a Mac AND a windows machine, in sync with dropbox, spotlights comments wouldn’t work. What I do is put tags right in the filename. So a filename with a layout for a client will be called “layout-homepage-client-name-20121230.psd” the numbers in the end are the date of the filename creation, in the year-month-day format. They are needed as my “tags” would sometimes overlap like “wallpaper-nature-brazil-beach” (I have 4 files that match this description). This numbers are printed by a snippet in TypeIt4Me app. Textexpander would achieve the same result, but it is more expensive than Typeit4me.

Posted by Patrick  | November 5, 2012 at 7:50PM | Reply

Hey! I love your post! Could you please recommend some great wallpapers and/or post your desktop screen? That would be great

Posted by Will  | October 31, 2012 at 2:17PM | Reply

Although I keep certain areas clean like my desktop, it’s almost impossible to find what I need when it comes to anything else. I usually use my desktop to put things that are high priority that I want to see each time I turn on my computer.

I have done tidy up sessions before with my pc, and I’ve noticed increased productivity and less mental clutter, but sometimes I forget the importance of not only having an organized workspace, but an organized digital workspace. These are excellent tips and I’m going to start doing this on my next scheduled break.

Posted by Thanh Pham  | November 2, 2012 at 1:59PM

Yeah it will take some time to get used too. Also, the initial set up will take some time. However, once you have it all set up you’ll be really fast. So the payoff is definitely worth it.

Posted by Chris  | October 26, 2012 at 10:09AM | Reply

Have you guys played around with Sugarsync? I used to use Dropbox and enjoyed it but found that Sugarsync was even better (in my opinion) because you don’t have to move folders or files into a Dropbox folder to sync. Plus, Sugarsync gives you 2G of more free space when using the free version.

Posted by Thanh Pham  | October 29, 2012 at 10:15PM

Hi Chris I personally haven’t. I really like Dropbox so I haven’t looked elsewhere for software.

Posted by Vincent van Andel  | October 25, 2012 at 5:05PM | Reply


When does the Devonthink article/series come out? I’m waiting a long time for it, want it so badly.
Maybe interesting, the MacPowerUsers are gonna do an episode about it (and also about academic workflow). Can’t wait for it!


Posted by Thanh Pham  | October 25, 2012 at 5:37PM

Hi Vincent I have a post lined up for this in November. That’s all I can reveal :-)

Posted by Vitali Roberts  | October 24, 2012 at 8:29PM | Reply

I’ve been struggling with this for years. Just when I think I have a solution, technology evoles and I am left with a bit of a mess. So now I have left over bits from pre Evernote, Dropbox and Google Apps, not to mention personal stuff, like migrating from Windows based to iOS. So Thanh, can you look in your crystal ball and let me know what to do now?

Posted by Aaron Lynn  | October 25, 2012 at 12:36AM

Take a day out and consolidate everything into a neat hierarchy. It’ll be a PITA to do, but once it’s done moving to future platforms will be a lot easier.

(Un)fortunately I only see technology, tools and apps as changing faster and faster in the near future. Setting up a solid foundation now for getting organised and understanding why and how you have all your files organised will make it easier though!

Posted by Nicole  | October 24, 2012 at 10:01AM | Reply

More tips that worked for me (on a PC) to help me clean up my desktop and minimize the time spent opening applications, folders, and files:

–Put applications that you normally open every time you turn on your computer in the Startup folder. At my work PC, this is Outlook and Evernote. At home, it’s Gmail and Evernote.
–Use an application like Auto Hotkey to open applications, folders, or files. At work I have a script for opening certain folders on shared drives and specific web pages, with two keystrokes. (The reason I don’t have a browser open at start up is because I could be working in any number of web pages, so it makes more sense to hand-pick which opens up.)
-Minimize the toolbar and shuffle through programs using Alt+Tab. Pretty.

Posted by Thanh Pham  | October 24, 2012 at 2:27PM

Great tips Nicole! I like the idea of putting programs in your start up folder. Mac users should do this too.

Posted by Arsarn  | October 22, 2012 at 5:00AM | Reply

Hi AE guys,

What do you think about importing all the documents (except for clouding services) to DT Pro. I’m thinking about doing this as it’s much easier to find and track documents.


Posted by Thanh Pham  | October 22, 2012 at 3:06PM

You could do that, although I wouldn’t do a complete import but a reference. DevonThink Pro can import documents in two ways: 1) copy and store document in DT 2) Copy file reference into DT. With (2), whenever you change something about a file, it will also be reflected in the actual file. With (1) that’s not the case because it’s only reflected within DT.

If you want DT to manage your files, make sure to use option 2. You can set this before you import documents. I only do this for very select files and folders – definitely not everything.

Posted by Miranda  | October 21, 2012 at 4:23PM | Reply

Hi There!
I have Evernote and Dropbox and a Flash Drive. What do you recommend for maximizing the use of each and not duplicating efforts or causing confusion as to where my files are under these three systems? I was thinking that I could use Dropbox more for documents that I share with others or that need to be updated by me regularly. And I was thinking to use Evernote for more stationary files (those that I do not have to share or edit/update/revise often). I seem to rely most on my flash drive; but those can get lost or damaged. Not sure how to harness these three things to create something that is logical and efficient. Do you have any suggestions?

Posted by Thanh Pham  | October 21, 2012 at 7:14PM

Hi Miranda,

Some might disagree with my approach, but here’s my take on this.

Dropbox – use this as your primary storage location.
Evernote – don’t use this for storing files (use it for storing notes)
Flash drive – Assuming you mean the smaller ones (storage size < 16 GB), use this to have backups of frequently used files or very big files that can't be downloaded quickly. When you setup Dropbox as your primary storage location, it becomes very easy to share document with others (and to revoke access). You'll also have access to your documents through the web or any computer where you can install Dropbox. If you're someone who wants to share documents with people, Dropbox is the way to go. Designate one folder for this such as the /public folder that comes with Dropbox. Evernote is not really meant to be used for storing files. It definitely can, but I think it's a little clunky to use it for that purpose. For storing and sharing notes it's great, but not for files. When you set up Dropbox correctly for sharing, then you'll find that you'll avoid using a flash drive. I only use a flash drive when someone needs something from me and they can't be online for a reason. Or another reason to use a flash drive is to have big files on there (such as videos) because it's faster to transfer it via USB than over the Internet.

Posted by Ciaran Antur  | February 13, 2013 at 6:25AM

Thanh, Miranda,

I would not forget to mention Google Drive (which works quite the same as Dropbox), Twindocs (very appropriate for stationary documents and focused on document organization) or Box (somehow between these two), among others.

It is true, though, that Evernote is not so focused in documents, but it does great with notes and web clips. So, you can give a try to any of the three above (or any other alternative services) for your stationary documents, as Dropbox could do better with sharing or backup features.

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