Tech Support Stories Part 2
In short order I learned troubleshooting Windows was a waste of time. Even if you knew why 98 was doing something, you rarely could fix it. So I would just run assembly lines of re-installs, backing up all the users files to a file-share and then clicking through the 98 install screen a thousand times. It sounds boring now but I was thrilled by the work, even though copying lots of files off of bogged down Windows 98 machines was painfully, hilariously slow.
Since Bill believed in telling people they were (effectively) stupid and had broken their machines through an inability to understand simple instructions, I took over the delicate act of lying to users. A lot of Windows IT work is lying to people on the phone trying to walk a delicate line. You can't blame the software too much because we still want them to continue buying computers, but at the same time you don't want to tell the truth which was almost always "you did something wrong and broke it". I felt the lying in this case was practically a public service.
It wasn't until one of the schools offered me a full-time job that I realized my time in IT was coming to a close. The automation and writing AppleScript was so much more fun than anything I was doing related to Active Directory or printers. It had started to become more clear with the changes Apple was making that they were less and less interested in the creative professional space, which was my bread and butter. This school was super nice, but I knew if I started working here I would be here forever and it was too boring to do forever.
That's when I started transitioning to more traditional Linux sysadmin work. But I still think back fondly of a lot of those trips around Chicago.