A blog post on Perl 6 led me to the description of Worse is better philosophy.
I get the impression this idea is relatively famous, but I had not come across it before.
A summary might be, that successful systems often pass rough edges of the design to the user, in order to avoid complexity in implementation. This makes it harder for the user, but this is “better” because the system is simple to implement, and therefore, is more likely to reach the user’s computer in a state to do real work. The “worse” system gets greater mind-share, and so it gets more attention and support.