This is an oldie-but-goodie: Guy Steele’s “Growing a Language” talk from OOPSLA 1998.
It is amazing to me that Guy, whose is something of a legend in language design, and who thinks so clearly about what makes a good language, was also key in designing Java. Java has been extremely slow to grow in the sense described in this talk, because for many years Sun resisted such growth. Only the rise of C# and the growing popularity of dynamic languages generated enough pressure to get Java unstuck… and in the last few year Java has become somewhat growable in the sense Guy describes.