I performed a little experiment this month, to test my hypothesis that a number of useful files accumulate on the desktop and are worth saving for the long term.

The experiment was simple:

  • I allowed files and folders to accumulate on my desktop from October 1st to 30th, without organizing or filing any of them
  • On Oct. 30 I went through them and analyzed their contents to see whether the files were of long-term value
Oh god no

Here are the results:

  • 156 files and 5 folders accumulated, with a total size of 2.2 gigabytes
  • File types included:
    • 5 folders (from images I exported from slide presentations, since it creates a new folder with each export)
    • 2 design files
    • Text expander snippets file
    • 1 audio file
    • 5 html files
    • 135 image files
    • 1 slide presentation
    • 1 video file
    • 9 PDFs
    • 1 text file (because virtually all text I store directly in Evernote)
  • It took me 23 minutes to file all 161 items in my P.A.R.A. system in Evernote and my Documents folder (which syncs automatically with Google Drive).
How I arrange my windows for filing

As I filed each item, I added them to a list sorted by low, medium, and high value.

Low value

These items were low value mostly because I had other places I could find them if needed, such as my email, source files, websites, or cloud storage. They made up about 75% of the items, and I deleted them immediately in large groups using command-shift-click to select multiple items, and command-delete to send them to the trash.


  • PDF of academic paper I read and took notes on (already added as an attachment to an Evernote note)
  • Screenshots of PDF diagrams (already added to notes)
  • Images from online articles (already used)
  • Screenshots used for troubleshooting/email explanations (can find in email if needed)
  • Slide images/screenshots for book manuscript (added to Google Doc)
  • Screenshots taken for social media/blog posts (already published)
  • Photos for online photo galleries (already published)


Medium value

These items could probably be found elsewhere, but they were relatively important and I might need to reference them again. They made up most of the remaining items, and I filed them in my P.A.R.A. system, mostly under Areas.


  • Signed change of address form for tax prep service
  • 3 401k plan documents
  • ETF form for life insurance payments
  • Video + audio of recorded interviews (always good to save in case they disappear from online hosting)
  • Photos gathered and organized for blog post (which I may need to use again for followup articles)
  • PDF about info overload someone sent me (which I’d like to read)

High value

These two items either related to active projects that I needed to take action on (banner image) or took some effort to produce (Facebook data archive); I put some extra thought into how I labeled and filed them, one in a project and another in an area.


  • Banner image for promoting upcoming workshop (reminding me to promote it)
  • Facebook data archive export (downloaded to create a photo album of my 6 years in the Bay Area, and saved as a backup)


I’ve always made a habit of clearing my desktop and downloads folder on a weekly basis, since they are like the “inboxes” to my digital life. Because most files downloaded from websites, saved by software programs, or exported from source files tend to be saved here by default, a diverse mix of digital assets tends to accumulate quickly.

I think there are three primary benefits to doing this, and the actual storage of the file is the least important one:

  1. Reminds me of actions I need to take
  2. Keeps my workspace clear for incoming inputs
  3. Saves files for future reference

Only a tiny percentage of accumulated files remind me to take an action, since I’m pretty good at capturing open loops before this point. But even that tiny percentage can yield large benefits. In this case, I am flying to São Paulo in a few days to deliver a full-day workshop, and remembering to promote it to my audience could have a significant impact on its success.

Just as importantly, I noticed that having so many files lurking in the background produced a kind of psychological noise. Even though I rarely saw them behind the application windows, the effect was similar to having a messy desk. Often I went looking for a file I had saved to the desktop, and had to wade through the morass to do so.

My conclusion is that it is absolutely worth clearing your desktop and download folders on a semi-regular basis. A great way to do this is to make it part of a Weekly Review, so that you’re doing it in big batches, which saves time.

Aaaaah….like a cool glass of water in the desert

Downloads folder

For good measure, here’s the same experiment conducted for my downloads folder over the same time period.


  • 49 files and 12 folders accumulated, with a total size of 5.5 gigabytes
  • File types included:
    • 12 folders
    • 7 spreadsheet files
    • 2 disk images
    • 3 ePub files (exported as part of my editing process)
    • 16 images
    • 4 videos
    • 11 PDFs
    • 5 zip archives
    • 1 aborted video call download
  • It took me 13 minutes to file all 62 items in my P.A.R.A. system in Evernote and my Documents folder

And here is how I rated their value:

  • High value:
    • Personal tax returns
    • Quarterly business financial statements
  • Medium value:
    • Completed W9 form for virtual assistant
  • Low value
    • Slide images for book manuscript (already added)
    • Photos downloaded for Facebook album (already saved in Google Photos)
    • Spreadsheet of business expenses (already categorized and sent to bookeeper)
    • Videos for blog (already uploaded to Vimeo, and backed up via Google Drive)
    • Videos for book feedback (already reviewed)
    • Blank W9
    • Blank change of address form
    • PDFs made as bonus downloads (already uploaded to Google Drive)
    • Icons used in blog posts or slides

Follow us for the latest updates and insights around productivity and Building a Second Brain on Twitter, Facebook, Instagram, LinkedIn, and YouTube. And if you're ready to start building your Second Brain, get the book and learn the proven method to organize your digital life and unlock your creative potential.