So I've done this recently with Hugo. What I did for that was find out the bare minimum that I need to be able to build something with it (in this case, ensure that both Go and the hugo cli app are installed).
The next thing that I do is figure out a project that I can get some use out of, and start building it with the new technology. In the case of Hugo, I started recreating the Waffling Taylors website with it, implementing a new design as I went along.
Once I've scratched the surface enough, I'll go back and look into how the technology actually works. That way, I can better understand the inner workings and the design decisions for the technology.
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