Organizing Your Digital Vacation Photos Series: Step 1 (3 Steps to Creating Powerful, Searchable Folders)


Today you’ll begin a journey that will change your life. This statement might seem a bit bold, but if you’re drowning in photos and the stress of it all has you teetering on the brink of photo insanity, then it is a very accurate statement.  Disorganized photos can make you feel overwhelmed, confused, stressed, anxious, and even inadequate because you can’t keep up with it all. Today is the day all those feelings can stop.

I like to keep things simple. So don’t worry about it being too complicated. I like to find ways to get the job done right using the least amount of effort. Who doesn’t want that, right? Discovering how to do that might take a little time, but in the long run it really pays off. I can then accomplish what I want with the least amount of time, effort and financial investment.

What you’ll learn here is how I and many other photo organizers organize their own photos and that of their clients. How we do it right with the least amount of effort and time. So don’t get stressed out thinking about all you have to do to get them organized.

Follow this series and only concentrate on the one step I’m covering at that time. Don’t think about what’s ahead. Don’t look behind. The mess you have now is irrelevant. It’s manageable. With each step it’s evolving into photo nirvana.

Let’s get started!

Create New Folders

Creating new folders seems like a simple enough task. You’ve created hundreds of folders over the years either on your personal computer or at work. And it is a simple act to create a folder. However, the trick to a great folder structure is knowing what to name your folders and files so they make sense now and in the future for you–or anyone else that might need to retrieve some photos from your files.

Too often we name folders and files haphazardly and then we can’t find what we’re looking for. It’s so frustrating. But taking a little extra time to think the process through on the front end will save you tons of time later when you need to search for a file.

I’m going old school here by sticking with the operating system’s native file system (File Explorer; Finder) to organize photos. Why? Because the foundation of it hasn’t changed, except for some interface tweaking here and there just to confuse us and drive us a bit crazy. But the ability to create a folder structure in which we store all of our images, music, documents and videos is still there and is not going away.

There are many photo organizing programs available that can do powerful and amazing things. The one main issue with them is the learning curve involved. It takes time to try some out to see what benefits they offer, how difficult they are to learn, and if they do more than you’d ever need, or don’t have enough of what you need. If you decide on one, then you’ve got a lot of learning ahead of you before you can gain any speed with it. They also have a price tag that can get pretty hefty. If you have thousands upon thousands of photos, and cost isn’t a concern, then you might want to consider this option. It could be worth the time investment as well to learn it if it will help you get your photo collection organized faster.

For the purpose of this series though I’ll stick with the operating system’s filing structure. Microsoft doesn’t have a built-in photo organizing program (although I think Windows 10 does now) so creating folders in File Explorer is easy and familiar. Apple approaches photo organization a bit differently. They want you to use their photo organizing program rather than the native filing system. The reason, I believe, is because the program organizes the photos for you in all sorts of creative ways. It’s attempting to do the work for you. Maybe this works well for people in the short-term, and it’s definitely a fun and easy way to view them. However, when you back up your photos to an external drive or DVD, share with others, back up to the cloud, or transfer them to another computer with a different operating system, the original file names won’t make any sense. Plus, the organization is gone as it’s only available when used with their program. In the newest operating system, Apple did make it a bit easier to rename photos in bulk using Finder by including a simple yet limited way to do it through a pop-up menu.

Regardless of which operating system you use, sticking with the native filing system will help guarantee the work you do today will still serve you well 10 years from now and beyond. You won’t have to stress about cross-platform compatibility or a company going out of business leaving you to find a new renaming and organizing tool. Programs come and go but the operating system’s filing structure is here to stay.

The steps covered here will help you create a folder structure for your vacation photos that will put you on solid ground, but the principles can be applied as well to any other group of photos or files.

3 Steps to Creating Powerful, Searchable Folders

  1. Create a [Year] folder using File Explorer (or Finder for Mac), if you don’t already have one created for your photos. You can create this wherever you like such as under the Pictures or Documents folder.

Pictures folder example: 2016 Photos (or 2016 Pictures, whichever you prefer)

For example: Pictures > 2016 Photos

Documents folder example: Create a “My Photos” top-level folder; then create the “2016 Photos” folder under it.

For example: Documents > My Photos > 2016 Photos


With photos, always place the date first when naming folders and files. By placing the date first, the folders will sort in chronological order. This will help when you need to sort to find a specific year quickly. Plus, we tend to think in terms of years so it’s easy on the brain to go with this naming convention.

Including “Photos” in the folder name alerts you to exactly what is included in that folder. If you simply name it “2016,” you, or anyone else, won’t have a clue what’s in it if it is moved or copied elsewhere. For example, if you back up that folder to a portable drive, you’ll have a folder that says 2016 but you won’t know what’s in it unless you open it. If you share that folder with someone else, they’ll have the same issue. And what if you have a “2016” folder under the Videos folder? Try to back up both “2016” folders and it won’t work because they both have the same name! Not good.

When naming folders and files, always think what it will look like if it stands alone. If you can’t tell what the folder/file contains by looking at the name, then you need to be more descriptive. But keep it short. (File name limitations will be explained in a future Step.)

And always use words you’d use to perform a search for that particular folder/file. For example, if I want to find all my Viking river cruise photos, then I’d want to put “Viking river cruise” in the folder name, as you’ll see in Step 3.

Tip: Never use a symbol in the folder or file name. This can cause issues saving and transferring the file to another drive, platform, cloud service, etc.

2. Create a subfolder under the “2016 Photos” folder that will be a temporary holding place for all the photos you’ll be copying from your devices such as from a phone, tablet, camera, SD card, flash drive, etc.

Naming Example: 2016 Photos-Devices (or 2016 Photos-Temporary)


This holding place folder is to ensure you have your original photos saved before you start moving them and changing their filenames. In case something goes wrong or you want to start over, you have the originals saved. More about that in an upcoming Step.

3. Create another subfolder under the “2016 Photos” folder.

Follow this naming convention: [Year-Month] [Vacation Description].

Naming example: 2016-03 Viking River Cruise


Including the date and numerical month first will keep the folders in chronological order. The description identifies its specific contents. As you can see, the naming convention clearly identifies the folder’s contents, even if it’s separated from its top folder.

Here’s what your folder structure should look similar to:

Vacations Folder Structure_1-2
All Photos for 2016 Organized Under the 2016 Photos Folder

Optional folder structure:

If you take several vacations a year and want to keep the vacation pictures together, you might want to create a “2016 Vacations” folder first, and then create the “Year-Month Vacation Description” folders under it. This is a theme-based approach to organizing. You can then create folders for other themes such as Birthdays, Weddings, Landscapes and Johnnys Art Projects. You can also create a folder structure by month or season.

Here’s what your folder structure should look similar to if using this approach:

Vacations Folder Structure_2
Theme-based Approach: A Separate Folder for 2016 Vacation Photos

TIP: You can keep the “2016 Photos-Devices” folder directly under the “2016 Photos” instead of creating it under the “2016 Vacations” folder. Basically, the idea for this folder is a temporary holding place for your photos. You can move this folder around as needed to make it most convenient for you to copy your photos from this folder into a new one.

Take a little time to think about your folder structure and decide what approach works for you. Play around with the structure a bit based on the type of photos you already have. Try out a themes-based, people, seasons or month approach. Or a combination of two of them. But don’t stress too much about it. Decide on a structure and go with it. Creating relevant folder/file names using words you’d search with to find a particular group of photos is the key to great organizing. It means you can use those words to perform a search and find what you need quickly, even when your folder structure isn’t perfect!

So how am I organizing mine? I already had a 2016 Photos folder, so I created the 2016-03 Viking River Cruise folder as shown in the examples. That’s where all my 2000+ vacation photos will go.

What works for me is more of a chronological/theme-based system. I start with a Year folder, such as “2016 Photos.” Then I’ll create folders under that for 2016 Christmas, 2016 Easter, 2016 Weddings, 2016 Mallory, etc. I’ll create a person folder if I have photos for that individual that’s not associated with any specific event. However, even if I didn’t want to create separate folders for different events or people, it wouldn’t hurt my ability to find a photo quickly. I could actually have a “2016 Photos” folder that holds the whole years’ worth of photos and I’d be able to find what I want when I want by using a simple trick I’ll share with you later. But it’s just a lot easier to organize as I go along if I separate the photos into different folders.

If you have questions or run into issues, ask away. If I don’t know the answer, I’ll do my best to find it out for you. Have suggestions? Share them. And if I’ve forgotten to share something with you in this post that I think you’ll really benefit from, I’ll be sure to update it.

Pat yourself on the back or give yourself a big hug when you get your folder structure done. You deserve it. You accomplished something big. You tackled a problem that caused you stress, confusion or anxiety. You’re definitely on your way to great things.

Stay tuned for Step 2.

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