As one of the original members of Apple's Macintosh team, Susan Kare played an integral role in determining the look and feel for the original Mac OS. Recently, Priceonomics ran an extensive and informative interview with Kare wherein she details some behind the scenes info regarding the design of some of her most famous icons and fonts.
First, it's interesting to note how Kare -- who holds a Ph.D in design -- got involved with the Macintosh team in the first place. As it turns out, Kare was friends with Andy Hertzfeld who tipped her off that the then burgeoning team needed some graphic art expertise.
By remaining friendly with Andy after high school, I knew he obviously was really interested in computers. He showed me a very rudimentary Macintosh, and mentioned that he needed some graphics for it. He knew I was interested in art and graphics, and that if I got some graph paper I could make small images out of the squares, which he could then transfer onto the computer screen. That sounded to me like a great project. I did it in exchange for an Apple II, although I didn't actually use the Apple II for Mac graphics.
Once on-board, Kare went to work where she would go on to design icons and fonts that are familiar to multitudes of computer users even to this day. From the Happy Mac to the dreaded "bomb" icon, Kare's work certainly evokes feelings of nostalgia for anyone who spent a fair amount of time on the Mac back in the 80s and 90s.
The entire article is well worth a read as it provides interesting tidbits regarding the Apple command key, how Kare dealt with Steve Jobs, how the infamous Dogcow icon came to be, and why Kare never viewed icon design as a new artistic endeavor unto itself.
I still joke that there's nothing new under the sun, and bitmap graphics are like mosaics and needlepoint and other pseudo-digital art forms, all of which I had practiced before going to Apple. I didn't have any computer experience, but I had experience in graphic design.
As for what Kare has been up to after leaving Apple, well, she joined Steve Jobs at NeXT and subsequently went off on her own in 1997, going on to to perform freelance work at companies like Facebook, Paypal, and Microsoft.
She also sells prints of some her most well-known icon designs on her website.