Would you be embarrassed to show me your desktop? Or your downloads folder? While I certainly hope not, (because I try my hardest to create a shame-free environment) I find that lots of people aren’t so proud of the jumble of files and icons that they stare at every day.

And even more than that, your cluttered desktop might actually be increasing your stress. Studies show that digital clutter can have the same affect on our brains as physical clutter: cortisol, the stress hormone, increases.

And according to at least one study, we spend about 20% of our work time looking for information and documents. Think of all the time we could be saving if we had a system for our files and knew where to find things.

At this point, enough of my clients have asked how to manage digital files that I figured it’s about time to share my process. So, let’s get started

Know Your Filing Style

Are you a navigator or a searcher? Navigators like to have a place for every file, and their brain goes down that file-tree to find what they are looking for. Searchers search by first instinct.

If you’re a navigator, you want to make sure that you have a solid folder structure. Don’t make it too complex. My general rule is that you only want to add complexity where complexity is necessary and helps. If we make a complex file structure first, with lots of nested subfolders, when we go to actually file the stuff we need to file, we may find out that we didn’t create the right structure for what we have. And that will be frustrating.

Instead, start with basic categories (e.g. “finance”) and as you start adding files, you can create subfolders that make sense. So, you might add a subfolder called “taxes” once the main “finance” folder starts to contain bank statements and taxes. And then you might add folders for each year of taxes.

If you’re a searcher, well, don’t worry about creating a file structure because you won’t use it anyway.

What’s in a name?

Regardless of whether you are a searcher or a navigator, you’re gonna want to make sure that you have a solid naming schema for your files so that you can easily see them at a glance, or search for them because they are named something that makes sense to you.

If you don’t have a schema already, try the following:

  • CompanyOrName Document Title YYYY-MM-DD
  • Use INCOMPLETE if there is still some action that needs to happen on the document (needs to be completed and/or signed).
  • Use SIGNED to indicate a fully executed document.

For example:

  • Bank of America Checking Statement 2020-03-31
  • Crabtree_CindyLou Resume 2020-02-19
  • State Farm Insurance Application INCOMPLETE 2017-01-18
  • State Farm Insurance Application SIGNED 2017-01-19

Getting to “Desktop Zeroish”

Now, if your desktop is so cluttered you can barely see it, and your downloads folder is so bloated you’re regularly getting notifications that you need to clear up space, we’re not getting to “desktop zero” by actually going through all those old files. Unless you feel like taking a weekend to binge watch Netflix and tackle this project. (Which you might, because…pandemic.).

But let’s say you don’t feel like devoting hours to the backlog of your files.

In that case, we’re going to treat this process similarly to how we get to inbox 0. You’ll sort your files by date, and move everything older than a certain date into a folder on Drive, Dropbox or wherever you store your files. If you store files on your computer instead of using cloud storage, then move them to a folder called “old files”. (But if you do this, I highly recommend using a backup service as well.)

Once you’ve “archived” the majority of files, then you’ll review the remaining files one by one, rename them according to your naming schema and, if you are a navigator, file in the appropriate folders.


Yes! I find it useful to keep the following folders on my desktop:

  • Active
    • Just a few files I’m actively using/editing
  • To File
    • Holding tank for stuff that made it onto my desktop for some reason, and needs to be filed appropriately; see below for filing process.
  • Frequently Attached
    • For items I am constantly attaching
  • Screenshots to Review
    • Screenshots that will either be renamed, or filed, per the process below

Staying at Desktop Zeroish

If you’ve made it this far, you’re likely not gonna wanna do a repeat of cleaning all that stuff up. So, let’s not let it get messy again. And in order to avoid descending into chaos, you’ll need a strategy. A two part strategy:


To limit stuff getting onto your desktop in the first place, you can generally save docs to Google Drive, Dropbox or Box directly from your email. Gmail has a built-in “save to Drive” button, and there are Gmail and Outlook integrations for both Dropbox and Box.

It takes about 15 seconds in the moment to save that attachment to the right place and rename it something that makes sense to you, but it’ll save you minutes, maybe even hours, in the future of looking for it. It’s worth the time in the moment.


  • Daily, make sure anything on your desktop gets in one of the few folders I mentioned above to keep on your desktop, or the trash
  • Schedule time weekly to:
    1. Review downloads folder
      1. Move anything you don’t need to trash
      2. Move everything else to the “To File” folder; rename, if necessary
    2. Review the screenshots
      1. Rename the ones you need to keep and move them to the “to file” folder
      2. Move the rest to trash
    3. Review the “To File” folder
      1. Move everything to its rightful folder (hopefully in Drive, or somewhere else that’s backed up to the cloud).
    4. Empty the trash

Can this be automated?

Some of it can be! There are tools, like Hazel, that will allow you to set up rules to automatically move, tag and archive files. But for me, the simple process above keeps me in check.