Ahh, to be young and in IT. In my younger days I was full of big dreams of being like the tech guys in action movies. You know, opening a socket to download a protocol so I can run a core dump on the secret agent's wristwatch.
As a "trainee programmer," Robert B. was enduring the typical crushing of his dreams that most of us went through early in our careers. He was responsible for technical tasks such as making tea and coffee, picking up sandwiches, ordering printer cables, and sending software update disks to customers. Robert was working at a successful company in the UK that built software for managing vehicle fleets. Customers ranged from leasing companies with thousands of vehicles to tracking lawnmowers at Clem's Lawnmower Rentporium.
One day Robert was asked to send out a disk to a client company's maintenance division. Brian, the company's transport manager, was running a Commodore PET with a 5.25" floppy drive. Robert copied the files on a disk, put a label on it, and put it in a mailer. With the disk, Robert included a note asking Brian to call him when the package arrived. The next day, Brian called.
Brian: OK, I got the disk, what do I do now?
Robert: Take the disk out of the mailer and place it in the drive.
(several minutes pass)
Brian: OK, which side goes up in the drive?
Robert (resisting the temptation to scream): You see the label that I put on it? That one goes up, then close the door on the drive.
Robert: Is something wrong?
Brian: It's just... there are no labels on this disk.
Robert: Are you sure? I'm almost positive that I put one on.
Brian: Yeah, positive.
Robert: Well, could you describe the disk to me?
Brian: Sure. It's round, shiny, and brown with a big hole in the middle. No labels.
Have you found the WTF yet?
When Robert explained to Brian that he'd ripped off the disk's casing, rendering the disk useless, Brian replied "I thought you'd wrapped it well."