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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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Brooks Duncan

I love taking technical topics and translating them so that they make sense to non-nerds. I'm a Chartered Professional Accountant and have been a software developer and have run software support in very small startups and extremely large public corporations. I strive to be relentlessly helpful in everything that I do. I live in Vancouver, Canada and insert extra u's in many of my words.

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  1. I tried the bulk renaming feature in Windows – it works great! I hadn't tried it before.
    Have downloaded Filejuggler – I've done so before, but hadn't actually USED it, and I recently got a new computer so time to try again.
    I downloaded DuplicateCleaner and since I transferred files from my old computer to this new one, I am excited to get rid of duplicates.

  2. Thank you for information about hidden renaming feature in Windows, I didn't know you could edit multiple filenames like that.

  3. For bulk renaming, I'll use the built-in Windows feature. For automating files, I'll try File Juggler. For duplicates, I'll try Duplicate Finder free first and then buy Pro if I like it. Thanks for the suggestions!

  4. I had no idea you could RENAME files in bulk! So I picked up an app called CleanMyMac and it seems to be doing a great job of clearing out dupes and freeing up space. I've tried Hazel in the past but have struggled with it. I guess I just need to read the HAZEL TUTORIAL next time! These tips have been very helpful. You can use applications for years and not be aware of these hidden treasures.

  5. This is the best day so far!! I've tweaked my existing practices the previous 4 days, but this one is the one I've most been struggling with: previously 'filed' items! Thank you for the tools!!!

  6. I use Hazel a lot but I know I can do more with it. I just need to dive deeper into it.
    I have Gemini, but I haven't been using it because I'm afraid I'll delete the copies I have on purpose: my backup files! I need to get over that and check it out again. I'm sure there's a way to exclude my backup files from being compared.
    As for bulk renaming: so far I'm not really sure what I should use it for. Most of my files are single files, not groups of files.
    Thanks for the suggestions, I'm definitely going to look into these again later today!

  7. Wow. I wasn't familiar with Gemini, and it looks really helpful. I downloaded the trial and had it scan my home directory. It found about 76 GB. It identified about 14 GB that were duplicate folders and copied documents or photos. There were many of the same folders that appeared in Downloads and _DATA (old external drive contents), plus others, including many books, videos, articles, and sample code. I have already started removing the duplicates and ensuring that they are now only in my DropZone (for now), although that's not where they really belong. It's critical to think of the DropZone as temporary storage for incoming stuff so it doesn't just become another Downloads dumping ground.

    I also tried out the Finder bulk renaming, as well as the Renamer tool to see what they can do, but initially I think I need about what needs to be renamed and deal with the folders first and where they really belong. All the books, videos, and courses need to be organized so they are more accessible.

    I really need to think about Triple-A top-level structure, especially what belongs in under _ACTIVE. Right now, there's nothing in there because it's scattered all over the place, and that must change. Also, I have to review my ARCHIVE and make sure it's organized appropriately for long-term storage. And I should probably align my _ASSETS structure to be similar to _ARCHIVE.

    First I must absolutely deal with my backlog and get stuff out of Downloads and _DATA by moving its folders and files to _ASSETS. Then I should identify and move what really should be under _ACTIVE, and that should be aligned with my OminiFocus projects and areas. My DEVONthink databases need similar tweaking and refinement. For example, should I have ACTIVE, ASSETS, and ARCHIVE database like in my file system folder structure?

    Also, I should examine note-taking and writing apps like Drafts, Ulysses, Scrivener, Obsidian, etc. to see preferences and locations need changing. Also I need to review all my other apps and tools to determine how they need to be adjusted for this new organization system. Right now my Projects directory is getting very cluttered with all the various tools, frameworks, and languages so that needs some thought too.

    In any case, this challenge has really helped me get rolling with something I have been putting off for some time. This gets me started, and that's important.

  8. I using the built in windows renamer function under file exporer and have download file juggler to explore it.
    Thanks for sharing for the past 5 days.

  9. I currently use 2 different bulk renamer tools on my Mac. NameChanger is a really simple one that I use for quick replacement changes, For example changing spaces to _

    The other one I use is A Better Finder Rename 10 for when I want to do complex changes using various rules and adding in things more easily.

    Both work wel

  10. I managed to get the renaming done with the built in app. It is somewhat course. I downloaded the trial version of Renamer and will see how I go.
    Although I used Hazel in the past successfully, I got hopelessly lost in trying to create rules for renaming, tagging and filing automatically with the APP. I will have to start from scratch as I noted that the last version I used was. version 3. We are now Version 5. Well, live and learn I guess…

  11. I use Hazel and Gemini Duplicate finder through Setapp. Both programs have been very helpful. I ended up with a lot of duplicate photos trying to merge my photos from iCloud and Google photos. It will take a while to get those extra 5,000 photos under control, but Gemini does make it easier by finding all the duplicates and similar photos for me and allowing me to choose which one I want to keep. I think it is certainly easier than trying to go through all the photos without any help.

  12. I tried Dropit once, which is similar to File Juggler. I didn't have a system like this in place though, so it never ended up doing anything. That will be much different this time!

  13. I’ve used the macOS Finder to rename files that I’ve separated into the different folders, Gemini to get rid of duplicates, and Hazel to automate the filing of a number of files based on keywords in my naming convention.

    This has been very helpful.

  14. I downloaded Gemini and spent the evening searching all my files for duplicates, including 45,000 photos. Bulk renamed many files and will try out Hazel this weekend sometime.

  15. *mind…blown*

    This is amazing. I literally got rid of SO MANY THINGS in just a few clicks!!! This is amazing!

    I've also downloaded Hazel and I'm looking forward to using it!

  16. Wow! I ran the duplicate cleaner for Windows and I'm blown away by how many duplicate files I have. And the built in bulk renaming tool is great. It'll make it so much easier as I go thru and start re-organizing all these files. I'll admit, I wasn't sure there'd be much for me to use in this little challenge, but I'm thrilled at what I've learned this week. Thank you!

  17. I'll definitely be trying the built-in tools first. I always try those first so I don't fill my machine with software I won't use. I can't wait to try a duplicate finder. I have backups of backups of photos. So freaked out about losing any, I have copies everywhere. I had a job for 13 years and due to the job, was able to store things on my work computer. When I left, I made backups, more than once just to be sure. I've been casually manually getting out the duplicates just because I wanted to look at some of them! But that's not productive in the least. I've been kind of paranoid about duplicate finders but I think that's just mild paranoia:) Thanks for this challenge. It's lit a fire!

  18. I just ran the trial version of Duplicate Cleaner Pro – 4,449 duplicate files – "ugh" and "yay" at the same time. Once I start working with my back photos, I may use Bulk Rename or FileJuggler if it allows it to sequentially label photos from the same period of time/trip.
    I also just dropped off a full 20 gal tub of physical papers in the schools recycling dumpster. A lot of work – I have stuff from 2004/2005 and up! But as I am seeing the progress, it is worth it. Still building my large pile of shredding. So far I think I have easily purged 1 – 1 1/2 drawers of a 4 drawer filing cabinet!

  19. I have used a duplicate finder, but will check out zgemini and I was already planning to use Hazel from one of your other trainings, but I haven’t – so now is the deadline!! Can’t wait to streamline my digital files!!

  20. I love and frequently use Duplicate Cleaner and Bulk Rename Utility, ironically, for newer files. But sometimes the sheer amount of duplicate files found in backlog is too much. Too many groups to go through, so if anyone has some advice besides "buckle up", it would be very much appreciated.
    Also, I recently found out from a power user of Total Commander (talk about "…much", but I low-key love it) – TC has bunch of things it can do (besides view files), like Compare directories, bulk rename, and such. :) Now all that is needed is for me to go through the mess.

  21. Well, Gemini is amazing! I think I have to buy a subscription for a year–I can easily clear a ton of junk from my computer. Reading the Hazel guide and I think I'm going to have to give that a test run, too.

  22. I used to be much more organized when file storage was limited to cassette tapes or those 8" and 5" floppy disks. As the storage space and drive options increased, I got super lazy about data cleanup and organized storage. I purchased the tools mentioned long ago, applied them to individual areas or groups, then neglected to continue to use them when I got super busy elsewhere. It is only in retrospect that I see how continued use of these tools would have saved me SO much time over the years! I will be reacquainting myself with the tool's updated versions and setting aside time to work on each of my storage areas to rename files I have missed (or make the names more consistent), get rid of duplicates and consolidate my MANY areas of storage.

    Thank you for this challenge! It hit a sore spot in my processes that needed attention. My biggest takeaway? I bypassed simplicity and made things complicated by treating my systems (e.g., databases and programs) as separate areas. When I used the tools and rules on each area/system, I did not notice inconsistencies across all systems (naming convention, for example) and did backups and maintenance separately. Result: more time spent & lots more disk archives, probably with duplicate files. Simplicity would have shown me the similarities between all of the systems so I could have been using a version of the Triple-A Method long ago.

  23. I didn't realize that Windows rename function works across groups of files! Working on standardizing and applying File Juggler now.

  24. I have Setapp, but did not have Gemini nor Renamer. I do have Hazel though and have been using it a little bit, but want to go deeper with that app as its power is amazing. Thanks for the pointers to Gemini and Renamer. The former already helping with my HUGE photo library and the latter adding to the power I have seen with the Mac built in Renaming tool that I began to use a couple of months ago. Thanks for this 5 day "challenge". Much appreciated. Looking forward to joining you on 17th May for more training in this area.

  25. Used File Explorer to rename lots of Scan# files, then moved them to their corresponding folders. Realized I don't need to include the bank name in the file's name if I'm putting all the files in the bank folder.

  26. I have my dropzones and my folders in my favorites and sidebars for easy access. I have my naming protocols set and my three email inboxes are down to only what has come in since I checked email earlier today. I am now working for one hour in ridding myself of duplicates. Tomorrow I have an hour scheduled to work on dropzone filing!! I am feeling much more confident about using my time efficiently and keeping the digital inflow manageable. Thank you.

  27. I know that somehow I have duplicate and quadruplicate files, so I am definitely going to give the duplicate finder a try – especially on my thumb drive

  28. At our work, we can’t download 3rd party apps so I’ll have to leverage windows explorer to do bulk renaming. But I plan to give it a try and see how it works.

  29. I love Hazel and use it quite often. Also to move files into DEVONthink where they are further processed with rules. Tried Gemini once but because I am well organised I don't have duplicate files. ;-) The Finder rename function is usually sufficient for renaming multiple files.

    Great challenge! Thanks a lot AE team!

  30. I'm going to give Gemini a try. Sounds like a great utility. I'm a big fan of Hazel and barely scratch the surface of what it's capable of, so looking forward to digging more.

  31. I didn't know about the bulk file renaming in Windows. Awesome! I was able to mass-rename a bunch of old files and then cut-paste them into the correct Archive section of my folders. Thanks!

  32. I never even considered the possibility of a bulk renaming tool. I plan to use the Bulk Rename Utility this afternoon as I have two "assets" folders and really could use a better file name structure.

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