I haven't had a chance to look through it in-depth yet, but this looks pretty interesting: https://github.com/donnemartin/system-design-primer
As far as things that have had an important impact in my learning path, I do have a few Ruby books I really like (the key here is to get your hands dirty with code as you read along): - https://www.amazon.com/Ruby-Under-Microscope-Illustrated-Int... - https://www.amazon.com/Metaprogramming-Ruby-Program-Like-Fac... - https://gumroad.com/l/rebuilding_rails
I think reading about (and looking at the code) for things you use and trying to understand how they work under the hood has been super useful: http://aosabook.org/en/index.html
Having smart people around to learn from is extremely helpful too.
Happy to chat more if you'd like. Just drop me a line: connor[at]opendoor[dot]com
Check out Pat Shaughnessy's Ruby Under a Microscope [0].
It gives a nice overview of the internals of MRI. It doesn't cover a who lot of the C code, but references plenty of it and where it can be found in the source code of MRI. Grab the book, the source for MRI, and do some digging.
[0] https://www.amazon.com/Ruby-Under-Microscope-Illustrated-Int...
http://patshaughnessy.net/ruby-under-a-microscope
http://www.amazon.com/Ruby-Under-Microscope-Illustrated-Inte...
"Ruby Under a Microscope" does something fairly ambitious. It attempts to write a system internals book in a language that non computer scientists can readily understand. While there are numerous code snippets and examples to try and examine, the ability to look at the various Ruby internals and systems and see how they fit together can be accomplished by someone with general skills and basic familiarity with programming at the script level (which for many of us is as far as we typically get). An old saying says you can’t tell where yo hare going if you don’t know where you’ve been. Similarly, we can’t expect to get the most out of languages like ruby without having a more clear idea what’s happening under the hood. It’s entirely possible to work with Ruby and never learn some of this stuff, but having a guide like "Ruby Under a Microscope” opens up a variety of avenues, and does so in a way that will make the journey interesting and, dare I say it, even a little fun.
[1] https://www.amazon.com/Ruby-Under-Microscope-Illustrated-Int...