My Photo Organizing System

This is a method of organizing photos for the average human with thousands of camera phone photos that would like them decently organized on a computer. It is not for professionals shooting 30 MP raw imags. Though honestly it would probably work for them, too, with slight modifications.

This system is Mac+iOS-focused but the important philosophies are just as applicable to Windows and Android.

Principles and philosophies behind my photo organizing system:

  • I don’t want to use a browser cloud interface. It’s okay if the photos are backed up to the cloud, but I don’t want to have to interact with my photos in a wonky browser app
  • I want my photos in folders, on my computer. They can be on a home server (or Networked Attatched Storage, or NAS), or on an external hard drive, that’s okay. But I want to be able to browse them on my computer, in folders. That’s because, to me, this is by far the quickest way to find a photo. In my case, I have 250,000 photos. They take up 525GB. They fit on my internal drive. This is ideal because you can then use Spotlight for quick-searching of folder names.

My solution:

  • My big epiphany is that I realized that naming photos takes too much time, and it is quicker to throw a photo into a named folder than it is to rename the photo. I do occasionally try and rename photos but it is clear to me that this is one of the largest stumbling blocks of any photo organization system: naming photos takes too long.
  • The same can be said for tags. Tags require special software to work. Maybe that software is your OS, maybe it’s iPhoto or Lightroom or something, but they do not migrate and they may break. Choose folders over tagging or naming files.
  • The secret is copying photos into folders. Folders for everything. And it is okay to have multiple copies of photos. Put a copy everywhere you think you might look for it. If a photo shows Jane and Lisa at Susan’s wedding, put a copy in the Jane folder, the Lisa folder and in the Susan’s wedding folder. This takes up more room, yes, but hard drives are big and cheap and camera photos are small. Make copies. Everywhere you would ever look.
  • The solution, then, is to develop a comprehensive folder structure, and copy photos into that folder structure. My top-level folder structure has folders for friends, locations, jobs, trips, rock shows, weddings, parties, etc. Each folder has a folder structure underneath it. Everything is nested. Everything is organized.
  • You can then point photo organizing or backup software at the folder structure, if you like. For example, you could have (as I do) Adobe Lightroom, Apple Photos, Plex and Dropbox all pointing at the same folder structure. I suspect you’ll find (as I have), however, that working directly with the folders and the photos in them is far easier and quicker than working with Lightroom or Apple photos.
  • Sorting photos works best with two monitors, so I will describe the approach to sorting with two monitors in mind, but it can work with a single monitor. More on this in a bit.
  • It is important to make use of what is called “spaces” on the Mac and “multiple desktops” on windows: the ability to have multiple screens of windows that you can swipe through. Become familiar with this feature. Learn the gestures to swipe between spaces (a three-fingered left-right swipe on a Mac trackpad, for example) and how to drag files from one space to the next (click and drag the file, then, while holding down the drag, swipe to the next space with two more fingers).
  • The trick then is to make a space or multiple spaces of all of your most commonly used folders, leaving them open and sized small enough to act as dropzones for rapid file sorting. For example, here is my main photo-sorting space:
  • You can have as many of these as you need: I have a second one (one quick swipe to the right) for job-related stuff, and a third for extended family/childhood/geneology stuff, for example.
  • I use Dropbox to automatically copy my photos from my phone to my computer. You can also use other software, including the “Image capture” software built into Mac OS (it is in your Applications folder). Do not use Apple Music/iTunes for this or dot Mac or whatever. Get the images copied, in bulk, onto your computer into a single folder
  • Open up a window of your camera uploads on another monitor (or, if having one monitor, make space for it on the main monitor but, again, it is MUCH faster with two monitors). Mine is on the vertical monitor on the left.
  • Now it is simply a matter of dragging the photos into their appropriate folders. Hold down the Option key to make a copy of a photos. For example, if you want two copies of a photo, one in a folder called “cats” and one called “funny,” hold down the Option key while moving the photo to the “cats” folder, then, the second time, drag the photo to the “funny” folder without the option key. You’ll now have copies in both places, and it will be removed from your Camera Uploads folder. One photo down.
  • You can also do this with multiple photos using the Shift or Command key. They each behave slightly differently, but you’ll get the hang of it quickly.
  • Pro tip: On the mac, use Command-L or Command-R to rotate the image to the right or left, right in the folder. Do this before you copy the images.
  • If you are going to rename photos, do so right now, before dragging them to the folders. You can also make use of the multiple-rename function built-in to Mac OS by selecting a bunch of photos, control-clicking and selecting “Rename…”
  • You will want to use the “format” setting, and leave the “Start numbers at” set to 1. Make sure you end your name with a space or some other method of separating the file name from the number. (See why renaming takes so much time?)
  • When I was doing my huge, first initial photo sort of thousands of photos, I renamed a lot. These days, I don’t do it much. If I get to a batch of photos I shot at a wedding, maybe I’ll select them all and rename them “Bob’s wedding” or something, but I usually just throw them in a folder named “Bob’s wedding” in the wedding folder. The renaming can be nice, though, so if you have a folder named “Becky” and there’s a photo in there that you like and you’re wondering where it came from, if it’s named “Bob’s Wedding 6” you can quickly get an idea. However, if you really cared, you could also just quickly search your computer for the file name and see where else you stored it to determine the event. In the end, file naming is, at best, nice-to-have and totally not mandatory.
  • Again, this system does not preclude the use of a photo organizing software. See this note for more info on how to do this with Apple Photos, for example. When I first took this step, this was important to me, but it has literally been years since I’ve felt compelled to open up a photo organizing app. I do quick edits in preview, more detailed ones in Photoshop.
  • With this method I am able to sort right around 1,000 photos an hour. It may take a little practice to get up to that speed, but I am unaware of any system that can approach anything like that. And this is with full “tagging” (via folders). The lego beekeeper photo, for example, may go into my Lego folder, my Beekeeping folder, and my Doug folder, since he looks like my friend Doug. It would take just 3–4 seconds to do that.
  • I do this with videos too, though they are stored in a separate folder structure, on a NAS. You could do them integrated or separate. The imae above of my main folder drop areas has two folders that are video folders, resting on a NAS.
  • Important hack: Make a folder, on your desktop. Within this folder, make aliases to all of the folders you want to appear on your screen into which you will drop photos. Now, whenever you need to reopen all of the windows (because the Mac closed them, or you restarted, perhaps), you can simply select all of these aliases and Command-click on them. The windows will open up in the same order which you last had them. This is immensely time-saving.

That’s it! I know it can seem scary to not bother titling photos, but the titling is what makes the task insurmountable. It’s why you have thousands of unsorted photos. Facial recognition is creepy and still mostly sucks. Third-party photo management apps breed lock-in and will eventually disappear. Only folders last the test of time.

Good luck and happy sorting! May you find it, under this system, as deeply a relaxing activity as I do.

Update: I forgot to mention one of the best benefits! It’s future proof! Make a new friend? Add a new folder? Get a new hobby? Make a new folder, and keep going. You can always go back and add more photos to it later. Want to do a big reorg? Go for it. Nothing will break.

author, @agencythebook, @mannupbook. writing an ad economics book. reformed angel investor, record label owner, native alaskan. co-founded @barbariangroup.

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