I was talking to one of my archivist colleagues about a collection he was processing and the challenges he was having identifying file types based on their extensions. The collection does go back several decades, but some of the file extensions were unrecognizable.
This was when I confessed: during a period of time in my life, I ignored files extensions, sometimes changing them to meet my own whims.
There were a few reasons for this. The very first computer that I owned was an original 1984 Macintosh. Since file extensions were not visible in the file browser, and my applications magically opened associated files, I didn’t really even know they existed. In my first work environment where we had DOS IBM PCs (prior to that I used terminals and mainframes), all my files were on a handful of single-sided 5.25″ floppy disks. I would insert the floppy into the drive and open the file from within the application, since that was the easiest method. I had no awareness of the registry or the existence of file format-application mapping at that time.
I had the misguided notion that it would be easiest to manage my files if I knew what type of content it was, not what type of file it was: .LET for letter, .MAN or .GDE for documentation, .ENV for envelope and so on. In some cases, the weird file extensions were created when I moved a Mac file with a long file name over to a DOS PC with its 8.3 character file naming restrictions. That’s how I ended up with files with names like “PHOTOLA.BEL” and “LJMCNEMA.ILI”.
But for the life of me, I cannot fathom what I meant by some of these file extensions 30 years later. What could I have meant by “.OB”? I can guess what my work process was when I created “.WK1” and “.CHG” files. I created them, and I don’t know what I meant. How would an archivist fare?
This definitely came back to haunt me when I needed to access and/or migrate both my Mac and PC files later. I kept my original files with their original names, migrated off their original media, including the original 1984 Mac floppy disk that came with my Mac. And yes, I do still also have the original media. I ran all the files through a commercial file conversion tool, making copies and converting to more recent versions with much (but not complete) success. In some cases the files _without_ any extension fared the best, because operating systems and conversion tool weren’t mislead by the extension, getting their information from the file itself. The files with the crazy extensions (a mix of mostly Word Perfect, MS Word, Aldus Pagemaker and Adobe Illustrator files) were a mixed bag. In some cases when it failed, I made educated guesses and changed the file extensions on the copied files and was at least able to read the content, even if it was not formatted 100% correctly. The biggest failure at the time? Mac Write 1.0 files, but that was a tool issue, not a file extension issue.
I did this circa 2003 before our community practices and tools had evolved to where they are now. I want to run this experiment again to see how successful it is. And I want to caution all content creators to carefully watch your use of file extensions, because you never know what the legacy of your files might be.