Some years ago I was in a state that I now discover in many other people on the web, and which I term "PL anxiety". It is characterized by a constant insecurity about which PL is the best, which one to learn, how "fast" each one is, whether PG is really right, etc etc.
In retrospective, my way out of this was a four-pronged approach:
(1) The Breadwinner PL
What's important about the breadwinner PL is that you know its semantics and its standard library by heart.
(2) The C PL
Infinitely many good things come to you by learning C, because your OS is written in it. Studying C, you'll learn awesome stuff, like how to handle SIGSEGV, exploit your branch predictor, write a language runtime, and what a linker is, for example.
The more you learn about C, the more you'll learn about a wide array of services that are already provided to you by your OS and compiler. And C is fun and simple to boot, and will give you the warm fuzzy feeling that comes from building things (almost) from the ground up.
(3) The Romantic PLs
These are languages that you really like and if you're really lucky, might one day get paid for using. You don't have to make a choice - learn them all. They all have their pros and cons, and in the end you'll have to roll your own, anyhow.
(4) The Other Interesting PLs Out There
Also keep an eye on olden golden PLs and newcomers to the scene, even if you're never going to use them: they may blow your mind, and that's what you really should be looking for. Ωmega is a good example.
The Real World
I've come to start new non-hobby projects in my breadwinner language, because it's the most convenient, I know it by heart, all my problems have already been encountered and hopefully solved by somebody else, there are tons of libraries, and PLs seem to matter very little for many projects (and if they matter, you can always Greenspun it).
The thing that keeps me motivated learning more about PLs are PLs themselves. I learned C writing Lisp->C compilers, for example. I'm learning about dependent types because I'd like to implement a PL that has them. It's weird, but works for me.