Unf:)ck Your Digital File System

In 2018, I was on a 30 hour flight from Florida to Viet Nam and I had exhausted all the movie options in the first third of the trip. With 20 hours left to go, I needed something to occupy my mind, something that I normally wouldn’t put as high priority. I started thinking about organization. Not tidying up my workspace or redoing a closet at home, but organizing my digital file system.

My profession requires me to work with files and folders 90% of time. PDFs, XLSXs, DWGs, PSDs, STEPs, SCHs, PCBs, DIPs, just to name a few. After years of files piling up and ending up on a cluster fucked desktop or everything filed away in a “Craig” folder, I decided on that plane ride to give this some thought and get organized.

Cloud Storage is Magical

One of my issues was that I was balancing too many computers and didn’t know which file was where. I had a computer at the office, one at home, a laptop, and my phone of course. The solution to this problem was to use Google Drive as my main file storage, damn the amount of space that I need. I opted for the largest amount of storage at 2TB which was more than enough for my needs. With this approach, I can now sync across all my computers and have web access to everything, even on my phone. This can also be done with Dropbox or similar but I already lived in the Google ecosystem so why not give them more of my money?

Top-Level Folder Structure on Google Drive

Folder Structure That Doesn’t Suck

Above you’ll see how I structured my folder with, what I think, are the more top-level categories I can think of. YMMV but these work for my situation. Notice that there is NOT a Miscellaneous folder. Miscellaneous folders are where files go to die.

Everything has a place, every folder has a purpose. Some of these are obvious but I’m going to run through my thought process for each.

  • \Business — Between my wife and I, we run a few businesses, so all business related items go here but there’s more inside that I’ll get to.
  • \Finance — This is personal finance stuff. A place for documents and info about taxes, budgets, loans, investments, etc.
  • \Media — A place for any sort of digital media; pictures, video, audio.
  • \Medical — Anything medical related for my entire family, including the dog. Mostly medical records all in one place vs. how the current medical record system works where your primary doc has to request from the hospital via Owl Postal Service.
  • \Projects — Everything that you do in your life whether for business or pleasure can be categorized as a project. Some examples of “projects” are vacation planning, home renovations, woodworking, car shopping, research, etc. This particular Project folder is for personal projects whereas the Business projects are filed under their respective business project folder. More on that later.
  • \Reference — The projects folder is meant to store living/breathing projects that have a beginning and an end. The project folder remains in projects to reference later. The Reference folder is for items that don’t get edited but need a home. Items in here include product license keys, manuals, licenses, Photoshop plugins, guides, etc.

Let’s Dive a Little Deeper

I think it’ll be best if I show the entire file tree for each folder to give you an understanding on how things are organized.

For my situation, I probably use the Business folder most often. It’s similar to the top-level folder but only has folders for Finance, Projects, and Reference. The Finance folder includes the financial side of the business activities. Invoices that need paying, invoices that I need to pay, financial statements, and any tax documents go here, organized in folders by year. When an invoice is paid, it moves to its respective project/client folder.

The projects under business have a particular structure. For my business, I do some heavy engineering design work and I will detail that folder below. The name of the project can be the client name or the project name itself. I usually start with securing a contract which goes in the Contracts folder. Then I start doing some intensive research and all that collected data goes in the Brainstorm & Research folder.

Finance is where paid invoices live for my records and also receipts that are pertinent to the project. Manufacturing is pretty specific to what I do but it’s where I stage files before I send them to get them manufactured so I have exactly what I sent over. Media is any photo/video pertaining to the project. Software is pretty specific as well, I create a software project inside of this folder if the project calls for it. Finally, Reference is where I might keep items that pertain to the product that I need a home but don’t need any updating.

The Design Files folder (Skip this if you’re not an engineer)

This one is very engineering-heavy. This includes all the CAD files for the entire product as well as the Bill of Materials. This is where all the version control happens. I’m still waiting for the GIT equivalent for CAD files for version control. I won’t go into too much detail with this one because it will be somewhat self-explanatory for you engineering types. Contact me if you really want to talk more about version control.

Personal finance lives here. For the Budget folder, I usually just download transactions from my checking account every quarter to see how things are shaping up. Am I spending too much? Don’t do that. What can I get rid of? Etc. I also use Mint.com. The rest of it is self-explanatory and I start collecting all tax docs throughout the year for my account and drop them into the respective year. The final tax returns live here too.

I subscribe to Envato Elements and Epidemic Sound where I get most of the stuff that fill these folder. I used to have a plethora of .mp3s in the Napster days that would fill the Music folder but…why? Spotify has everything I need. Personal photos go up on Google Photos so this Photos folder is mostly filled with stock photos to use in future projects. When I make videos, I love sound effects. Envato Elements have the best library of sound effects so those go in the Sounds folder for later use.

All medical records, invoices, receipts go here, for each person in a folder. I usually add sub-folders with each incident and get as many medical records from the docs and hospital as I can to file them away myself. I once had an MRI of my head and made it into an animated GIF. Found that one super quick because it was in my Medical folder.

Turns out, I do have a brain.

To give you an example of what I consider a project, here are some examples.

  • Trip Planning — In 2012 I planned a Euro trip with my wife and two friends. Everything from what to do, to where we’re staying, and cost spreadsheets went here, all in one place. I was even able to share the Google Sheet I used so we could all see it.
  • Home Projects — I have a project folder that is named the address of my current home. Inside there are sub-project folders with major renovations, categorized by date. I keep before/after photos in there, invoices, quotes, etc.
  • Medium Blog Posts — This is another project folder and inside there I have sub-folders for each blog I’ve written on media, including this one.
  • Glass Clock — This was the folder where I kept everything I did for my Glass Clock project. It involved a lot to not only make the clock but I also have all the video clips and final project files here.


The Reference folder usually doesn’t get touched much. As mentioned before I keep things such as product license keys, manuals, licenses, Photoshop plugins, guides, records, etc. For example, I have a scanned copy of my Scuba Diving Certification in there in case I forget my card when I go diving, which has happened before and the digital version got me in.

A Word About File Naming

Those are the folders, I try not to go too deep with folder but sometimes it’s impossible to avoid. Sometimes it’s best to just name your files in a particular manner to where they are super quick to find so you don’t have to go too deep in the folder structure. One important naming convention I follow is giving all files a date in the following format:

[YYYY-MM-DD]_[Descriptive Name].whatever

I use Windows and Windows automatically sorts files by name so when you provide a date in this format, files end up in chronological order by default. Easy to find.

This folder structure has forced me to be more organized and I’m always finding ways to improve it and make it more efficient. For now, this will do donkey.

Eats club sandwiches, not even in the club. Most active at craigrettew.com.

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