Start a new project with technologies you are familiar with. Try new technologies on projects you are familiar with. Don't start a new project with new technologies.
i.e i learned some programming languages by implementing a simple binary Usenet reader/client. i know pretty well by now what it encompasses to build that thing why it is harder to do with some paradigms then others and immediately see value whenever something turns out to be more elegant then previously. and if the task gets unpleasant i can usually state if that is because of the task or the technology or in this case the language i am using....