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Welcome to Day 5 of the 5-Day Digital Organization Challenge!

During the past few days, you’ve been setting yourself up for success by creating your consistent and descriptive naming convention, and you’ve been setting up your simple organization system using the “Triple-A” method.


Of course, creating your organization system isn’t enough; you need to actually use it to organize your files, notes and photos.

If you think of it, there are two separate issues:

  • How do we get started with the new items coming in?
  • What the HECK do I do about all this old stuff I had before I started this project? Especially when there are tons of duplicates, tons of things to rename, and just… tons of stuff to deal with.

The new stuff is the easiest. As new files, notes, and photos come in, you can use the strategies we’ve covered in the Challenge so far:

  • Use your Dropzone to collect
  • Apply your simple naming convention
  • Have your frequently-used folders like your Dropzone and your “Triple-As” accessible from the Sidebar
  • File things away to your easy organization system

But what about your existing information, which may or may not be a complete mess? (No judgement either way.)

We’ll share a resource at the end of this article that will help you get started, but in the meantime, some tools can help take a lot of the heavy lifting out of dealing with your backlog:

Duplicate Finders

Somehow, we all have a bunch of duplicate files and photos and other types of information everywhere. It can be a pain to deal with them one by one (and who has the time?)

Fortunately, there are some helpful apps!

One class of app is a duplicate finder – they can search folders, your Home directory, your photo library, your music library, and almost anywhere else you point them to. Then, they automatically or with confirmation highlight and remove duplicates for you.

This can make getting organized so much easier — there’s nothing less productive than taking the time to organize something that is an unneeded duplicate!

Here are some suggestions:

Bulk Renamers

How do you apply your new naming convention to your older files?

In some cases, you may be able to do it to groups of files instead of having to do each one one-by-one.

Built-In Bulk Renaming

You may not know this, but both Mac and Windows have built-in bulk renaming features. They’re just a little hidden.

  • On Windows, in File Explorer, select a group of files and choose Rename. When you type in a name, all files will be renamed to that new name, numbered sequentially.
  • On Mac, in the Finder, select a group of files and choose Rename…. You can then replace text, add text, or change the re-format the name to whatever you’d like for that group of files.

Third Party Renaming Tools

There are also many, many third-party bulk renaming tools:

  • On Mac, a popular tool is Renamer, also available in Setapp.
  • On Windows, a popular tool that has been around forever is Bulk Rename Utility, though the interface is a little… much. If you can get past that, it can handle pretty much any renaming situation.

File Automation Tools

Some tools will automatically do the heavy lifting of renaming, moving, and other file-manipulation tasks. They’re great for new items coming in but can also be used in some cases to handle your existing files.

If you’re interested, you can read more in our Hazel tutorial. Most of the examples work for both Mac and Windows.


Don’t let the volume of your existing backlog hold you back! There are tools to make getting organized much more painless.

If you missed them, here are the other days of the Challenge:

For today’s lesson, here are your exercises:

  • Try using the built-in bulk renaming features of Mac or Windows to rename some files to see how they work.
  • If you think it would be helpful, try one of the third-party helper tools. They all have free trials.
  • Let us know in the comments which helper you’re going to use (if any!).

Check Back Tomorrow

This 5-Day challenge has given you some tools and strategies to organize your files, notes, and photos the easy way. When we announced the Digital Organization Challenge, we mentioned there are prizes. We haven’t forgotten!

Check back tomorrow on the blog, and we’ll share more details for how to win and what your digital organization next steps are.

We will also be hosting a series of live, interactive, free trainings to help you get organized. Click here to register your spot. We hope to see you there!

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  1. I finished programming and fine tuning and tweaking my Digital Declutter Shortcuts using some of the advices shared.

    I am thinking about to share them if anyone is interested in the Dojo.

    Regarding Bank statements I have programmed a specific path in my Rename File shortcut as it’s specific, recurring and needs to be saved to specific location.

    I have performed some mass renaming on very old files just to test the function.

  2. Downloaded Gemini; it’s chugging away in the background as we speak doing it’s first sweep for duplicates.

    Also downloaded PhotoSweeper to sort out all those very similar photos you take of the same people in the same place at the same time.

  3. I am behind in reviewing my duplicate files, even though Gemini has been reminding me to do so. That task is on my calendar for early next week.

  4. For duplicates I am using NeoFinder which is also excellent for cataloguing all my files on all drives and in the cloud. I can see everything in one place (even offline and with nothing plugged in. And it finds and deals with duplicates.

    I use the Renaming feature in Finder for bulk name adjustments

    I use Hazel for automation

  5. I have renamed ca. 20.000 files of photos with on Mac in the Finder by changing the format of the names and added numbers.
    This will help me to find faster and easier photos based on years and events or places.

  6. ✅Already use Gemini ♊Good de-duplication suggestion 👌🏼

    As the article stated, macOS has a native bulk-renaming functionality that I regularly use ✅In addition, since I've tweaked out my Finder.app with XtraFinder modifications, it has a whole bunch of additional functionality built-in (ability to "cut" instead of just copy/pasting files, dual-pane mode, etc etc) and one of these additional features is a significantly souped-up version of the native file-renaming function 🏷I don't use this as often as the default option, but there are occasions where having additional control over various variables and tweaking the logic of a custom-designed naming template is useful. Best benefit is all of this gets baked into the native UI

    I mean, XtraFinder is also a 3rd party app, just like the 3rd party Renamer.app suggested in this article – but as opposed to flipping back-and-forth between a separate and external app vs the Finder window you get a much more seamless experience. 🪡🧵By the way, if XtraFinder isn't to your taste, TotalFinder is a nearly identical alternative as far as features go, just with a different aesthetic 🎨

    For Windows 10, I used to use a free + open-source software called QTTabBar to also mod the File Explorer in a similar manner. Likewise, in addition to tabs and colored labels and all sorts of other fancy features, one of the benefits afforded by the QT mod was a significantly more powerful and versatile "renamer" function (advanced logic, adjustable variables, the whole nine yards)🔖 I don't use Windows anymore, so I'm not sure if it's still supported now on Windows 11, but if so that'd be my recommendation as I can vouch from personal experience it integrates seamlessly with the native windows and workflows and it works like a charm 💯

    Of course, if you'd rather just stick with separate/dedicated renamer apps for Finder or File Explorer, that's entirely your prerogative 👍🏼

    As for file-automation, I can't recommend Hazel.app wholeheartedly enough alongside the article's suggestion, it's a very solid solution where you can set up robust rules per-folder that can be nested in their logic, has a plethora of naming template variables to boot, can even run further automations it may not natively support based on applescript integration, etc etc… it's just an incredibly well rounded utility that I use all the time and can definitely give a stamp of approval on without hesitation ✅

    That said, on the off chance anyone is interested, I made an interesting discovery on day #1 of the challenge when re-assessing my "dropzone" workflow. One of the "shelves" I settled on testing was Spotless.app from lightpillar.com/spotless.html and the reason why I liked it so much (aside from the UI that animates into view when dragging and dropping files similar to the one I described for Dropzone.app and Unclutter.app as well) was the additional benefits it brings to the table when it came to very hazel-esque rules and workflow. If anything, it's a bit more proactive than Hazel in that Hazel is **always** and **only** ever something that runs in the background (once you set up rules for a folder, it watches that folder, and only if any new changes occur does it run those rules) whereas in addition to monitoring some of my folders for changes + running certain rules on a customizable daily or weekly schedule + Spotless can also just be triggered to initiate at any given time, ad-hoc, on a whim.

    For example, let's say I have a folder whose contents are static, but I want. to make changes. Using Hazel, I'd have to approach this "back-to-front" so-to-speak, by creating a new rule first based on what behavior I want to occur and then letting it run live (possibly even creating a new file or dragging and dropping something new etc for it to "detect from the background" that some new change has occurred in your foreground Finder window) before it reassess the folder contents, reads the newly created rules, applies them, etc etc.. whereas with Spotless, even without having to stop and pause and think of the appropriate structure and logic of the rules I need to employ here up-front, and also without the need for making arbitrary changes in order to trigger said rules, I just… drag those files to the shelf that animates into view. That's it. Far less mental overhead. And as soon as I do, Spotless notifications and prompts interact with me further as I decide "oh okay well all PNG images can go over here, but wait how about those with an extension of .jpg and .jpeg get sorted in this other manner and collated over there. Okay now what's this next interactive display Spotless is showing me? An identical excel file? Let me quickly compare any changes in closer detail… they don't seem to be different in any crucial aspect, so let's keep the former and toss the duplicate one with the newer creation date into the trash. Oh what's this? Spotless just suggested I take this opportunity to set a rule for taking such similar actions each time in the future? Well isn't that helpful! And while I appreciate the thoughtful gesture, I think I'll adjust this to continue interactively prompting me each time so I can make a visual assessment between duplicates on a case-by-case basis…" and so on and so forth.

    Of course, you can always open up the Spotless app itself and peek behind the rules you created and adjust them — just like how Hazel functions (and the ONLY mode in which Hazel operates) — but the fact that you have "up-front interactions" with notifications and prompts and even that shelf-UI to trigger automations at any given time, or that menu-bar drop-down/pop-up/whatever-that-window-is-called which even shows you a history of changes which you can either click "undo" on en-masse or rather than bulk-operations just selectively restore individual file changes on an as-needed basis, et cetera, et cetera… it's just a whole different vibe that feels proactive and helpful in a way that Hazel doesn't.

    Now, I'm NOT gonna be replacing anytime soon, if even at all. It's the crowned king, IMHO, and for good reason. But while the underlying rules of filtering/sorting criteria seems to be powered by the very same sort of / same logic-engine that Hazel itself uses as well, Spotless is a different beast altogether in the thoughtful way it's designed and the manner in which it "stays out of sight and out of the way **right up until** it comes to the fore like a helpful assistant right when you need it to" is a novel behavior that feels far more unique to Spotless and outright incomparable (if not borderline antithetical) to the modus-operandi of Hazel.

    Simply put in a (perhaps silly, but sincere) analogy: Hazel is a ninja. A ninja isn't seen. It isn't heard. It doesn't get a ticker-tape parade or public spotlight for it's heroic deeds. It just does it's job, faithfully, loyally, in the shadows, without seeking fame or gratitude or reward. And it does a damn fine job it it too! Whereas Spotless is more akin to a knight in shining armor! It always stays one-step behind you and to the side… right up until you cast an order or are in need, at which point it swoops in to carry out it's duty with honorable service. As master swordsman, it's just as much of a capable warrior as it's ninja elder, slaying your enemies and vanquishing your foes until the path before you is once more… spotless!

    Okay, maybe I got a bit carried away with that analogy lol. But yeah, that's why I like automating with Hazel but am also currently in a trial attempting to integrate Spotless too, as I find them both to be reliable – and even filling different niches despite the overlap in their core purpose and function 🗂+ ⚙️= ✅

    Anyway, those are my 2 meager cents, for whatever it's worth ¯\_(ツ)_/¯

    #AllChallengesCompleted! 😤

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