Ask HN: How and when do you cultivate new skills?

I'm not sure if this topic has been already covered. I've searched HN, didn't find any links, so posting it.

I'm a computer graduate good with Java, and now planning to move on to other languages like Python and Java script.

Every time I start a new project with Python, I feel it difficult to work because there is so much of Python out there. Stack Overflow questions do help me for the time being, But I'm still not getting a feeling that I'm good with the language.

So my question is, What is the best way to learn a new language? Is it directly getting your hands dirty working with it or you understand the language and then do your projects?

Also, How many hours do you spend learning a new language( I know this depends largely on IQ too)?

Thanks for all the inputs.