Personal Development

Digital Organization Challenge Day 5: Tools To Help You

Gardening tools

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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