How do you handle repetitive file organization around Lightroom Classic?

Agree with the other responders here. Just don’t manipulate the files outside of Classic. I import into a dated folder structure (year/month/date) and use keywords and collections to organize them internally. Selects and such are just done by flags and color labels and (smart) collections. You really don’t want to do any of this in your disk’s folder and filename structure. If I need space on a drive that the images are stored, I move entire months or years to external storage usually inside Lightroom or I move them in finder and reconnect the folder inside Lightroom Classic to the new location. Both methods work fine. I never rename files but if I did, I would do that inside Lightroom Classic (hit F2), because otherwise you will lose the connection to your images in Classic.

If you are doing things within the operating system, in a simple word: Dont. I agree with ​@dj_paige that this should not be done. If you move files around in the OS and not within LRC, it messes up the database and it will not know where the images are.

As far as how do people use LRC, there are as many ways as there are users. It’s like a giant Venn diagram with mostly overlapping circles. 

For the top, I do not leave my images within dated folders. It may be because, as my wife says, I am chronologically challenged. So, if you asked me when I went to such-and-such event, I’d have no clue. 

For me, what I’ve done is I rely upon the the place, not the date. So, for example, next week my wife and I are travelling to England to see North Yorkshire. This will be our eighth trip to the UK. So, I have a folder called United Kingdon. Within that folder is each trip we’ve done, and they are named “2014 - SW” or “2107 - Scotland.” Within each of those folder is a folder of the place(s) we went that day. So, for example, “9-11-17-Evesham,” and “9-12-17-Sticklepath.” Thus, I do show the date and the place, and if we went to more places than one on a day, they each get their separate folder. On top of this, I also create Keywords to help me find specific items. So, for example, at Sticklepath is a metal foundry where they show how a metal smithing was done before automation and power tools. So, I have a Keyword for Metal Foundry in Keywords. Since we’ve been to other foundrys, all of them would show up via the keyword. 

Let me take this a few steps further. A friend of mine was going to the UK, to an area where we had just been. I offered to send him photos that I took in the area. I pulled the photos into the Collection area in LRC, and sent that off. He replied “these are great photos, but where are they?” Since then, I create organized Catalog versions of my trip where I go into each folder, and select the representative image, and (if necessary) change the time of the image to pull that one in front. Then I send the image off to Photoshop where I state what the images are (Sticklepath), and where it’s located. I then put a 50% white layer inbetween the text and the image and send it back to LRC. I then remove that image from the stack that was just created, set the time a few seconds before the original image and move that folder into that collection in the Collections. After I’m done, I can send the travel images to anyone intersested. These become a photographic diary of our trip.

As far as moving images around in folders, rarely. One exception might be The Hill House, (East by Northeast of Glasgow). When were first there in 2014, we could view the outside, but not the inside. When we returned in 2024, there was this giant “box” around the entire house to limit the environment access because when it was built, around 1902-4, Charles Rennie Mackintosh and other inovative archetects were eager to use this new material, cement for construction. Others, like Frank Lloyd Wright were building these great building, and later were finding out they leaked and were deteriorating. I bring this up because I did move a copy of one photo from one trip the later trip’s photos to show the house, and the house in a box. Plus, we could now go inside to view and admire Mackintosh’s great design features.

So, about the only thing I change is the date of some of the photos so that I can order them into the order that gives the story I wish to tell. Despite constant requests for being able to save a custom order, that has failed on every request. 

Oh, one other reson I do not rely solely on dated folders is that I may visit one location more than one day. For those events, I certainly do move images around from folder to folder.

I’m sure most people reading what I do would scratch their heads for all the work I put into each trip. If it weren’t for the fact that I really enjoy the process, I might not do it myself.

Oh, here are the images of the Hill House with and without a box.

 

After culling/editing/exporting, do you still end up doing things manually outside Lightroom — renaming files, moving images between folders, separating selects/exports, preparing files for another tool, etc.?

I never do any of this. If I must move from folder to folder … well, I don’t. The photos come out of the camera and are imported into the folder that they will live in, no moving of photos needed. Almost all organization is done via keywords and other metadata. The is also no need to separate selects and exports outside of LrC, this can all be done inside LrC.

My workflow (greatly simplified)

1. Import into folders based on capture date (note: since folders are based on capture date, there is never a need to move photos to another folder)
2. Add keywords and other metadata as needed
3. Edit
4. Export as need to a temporary folder (not 100% of my photos are exported)

Why don’t I use operating system tools to organize? Because for my photos, which are all travels and people and events in my life, the hierarchy forced upon my photos by the operating system is one-dimensional, and my photos have numerous dimensions of identification (who, what, where, when and other slices as well). Your situation may be different.