Photoshop version 1.0 for me, Illustrator 88 (c. 1990 - I think! lol…)
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I lived through that type of situation also. We had an 18’ Brown horizontal camera (a beast complete with carbon arc lamps, later replaced with halogen) and a turntable for cmyk separations - we tray developed everything, then eventually moved to a film processor. Our shop transition was more gradual with a progressive mix of outgoing old and incoming new technology. People who wanted to learn were given the opportunity to upgrade skills. Some of the more stubborn hang-ons were eventually laid off. It started in the creative department, then transitioned to production. We saw several orders go to output bureaus and film houses as production aligned itself with creative. (late 80s, early 90s)