As I’ve thought about the different things simplicity can mean, I realized there’s a big difference between making something simple for me and making something simple for someone else. Worse yet, if we only focus on making life simple for ourselves, that’s when some of the most complex things for others are made.
Suckbusters has a story about Notepad’s confirmation box. I’m not sure if it’s as bad as the author says, but the point is that the programmers weren’t thinking like a user. They were making things easy on themselves.
The trouble is knowing when it’s worth making my life a little more complex. Usually if I think in terms of how a feature should be, I realize it’s worth whatever technical hurdles there are to get there.
Joel Spolsky calls this bringing “the program model in line with the user model.” His book User Interface Design for Programmers is worth a read even if you aren’t a programmer.