I think that if you get your organization scheme and your tools set up in advance, you can really expedite this process and make it a lot less painful.
As an example, in about 2 hours on Saturday night I sorted out over 1000 unfiled files I had accumulated. While my approach and circumstances are highly specific and unlikely to be directly applicable to your situation, the concepts may help you to think through your process.
I have been paperless for years, and everything is scanned or downloaded, including all bank statements and bills. However, I went through a period where I was just scanning but not sorting or collating, and wound up with >1500 unfiled files in a folder (of course called “to file”). With my new schema for file naming and sorting I decided to process the backlog. Here’s what I did.
My files eventually wind up in a folder tree under “ScannedDocuments.” (They are not all scans, but that’s just what I started with and never changed the top level folder name.) Under that I have subfolders, two of which are called Bills and BankStatements.
I have a folder called Dispatch, synced between laptop and desktop, where I now put things that need to be filed/processed.
I created a folder under ScannedDocuments called Process as a staging area.
I have also recently (documented elsewhere) created some custom python scripts that reformat filenames into the schema I am now using (date and filename embedded, words separated by underscore, no spaces) and a script that uses tags to move files to major sorting areas and into subfolders. To move to the ScannedDocuments folder a “#Doc” will do it, and a “:Process” tag will move into the Process subfolder. I have talked about this scheme elsewhere.
Hazel of course does the heavy lifting, with rules I have been creating on the Process folder to handle all different kind of files.
To sort my files, I went to the “to file” folder and just selected a particular group of files, let’s say “checking account .pdf”. After selecting all the files, I launched a Keyboard Maestro macro that pops up a palette of my renaming tools, and select the one to rename the files to the proper format. Once renamed in Finder they remain selected, so I can pop up another KM palette that lets me assign both of the tags with one click. I then drag them to the Dispatch folder, where a Hazel rule detects that there are sorting tags on the files and launches my filing by tag script which figures out they belong in the ScannedDocuments/Process folder and moves them there.
I then go over the Hazel again and create the proper rule for a file name of that format (eg filename matches xxxx-xxxx_text where x is a single digit. The rule then moves the file over to the corrected filing folder (in the tree I have been using for some time).
This process of creating the Hazel rules in the Process folder is very quick, and I can select large groups of files and with a few clicks and a drag have them renamed, tagged, and sorted.
As a result, I was able to process over 1000 of the files in a short period of time.
There are a few other files that will be amenable to this process, leaving behind the “one off” types of files that do not easily follow rules and will have to be hand-reviewed and sorted or trashed. (I don’t create Hazel rules for things that are one-off’s or very rare, as I don’t want Hazel to be chewing up processing time for things that won’t happen. For instance, if I have a credit card and then cancel it, and so there will be no further rules, I disable the associated Hazel rule so that it won’t enter into the processing loop.)
This is just one scheme that I used over this weekend that really helped me plow through a backlog of filing that I should not have accumulated in the first place. And, by getting all these rules and support automation in place, going forward it will be easy to look at the Dispatch folder weekly or more often as needed, rename and tag files and have them automatically go where they are supposed to go, so I won’t wind up with a mess again in the future (I hope).