How long have you been using Photoshop?
For me, 3.0 is when it starts to look familiar, which makes it mid-90s. I was working at Tri-Met then and did most of the maps in Corel Draw. Illustrator wasn’t available on the PC for a long time and Corel had a great set of tools. I still am a big fan of the early Corel Draw interface.
Aldus Pagemaker was the page layout program of choice on the PC in the early to mid 90s, until it was bought by Adobe. But my first page layout program was Ready Set Go in the late 80s on one of those cute little original Macs with the tiny screen.
What tools were the ones you learned to design with?