I have been working on Ruby since 2009.
Ruby changed my way of thinking about meta-programming.
I love Ruby for offering you a great power. Great responsibilities come as well, but we all are very responsible right? Also I like it for large toolbox in both: ruby core and gems.
I hate Ruby for being slow. Sometimes I feel like it wastes my life.
Most terrible architectural solution/code I have ever met is Rails Callbacks design before version 4.0. Take a look and this crap and be ashamed if you've run this code in production once: https://github.com/rails/rails/blob/733bfa63f5d8d3b963202b6d3e9f00b4db070b91/activesupport/lib/active_support/callbacks.rb#L326 You would need some time to understand, but as you go deeper you'll find out how shocking terrible this code is.
The most spectacular Ruby news in 2014 was Ruby 2.2.0 release. I like the speed. It gives me hope that ruby will be fast one day. But this is just our cloudy dream.
Life after Ruby I would try to build my own JS framework or connect as core developer to existing one. They all suck terribly and there is a big opportunity to improve. Also I have an idea to write a revolution text editor that will have a significant difference from all existing ones and can change the world.
Currently I am working on Security Audit performed by a big fat company to make another big fat company think that our company is sexy. Sometimes we need to do such things... When you've started to make a real value, there are too many bad guys that want to steal it.
My dev environment contains a $5 chair, a table and Mac Book Pro. As for dev machine: it is pretty much limited with Browser, Editor, Console and Messenger: Chrome, gVim, iTerm and Skype. I like to keep it clean and simple. Also there is my notepad made of a paper. I don't know why I am using it, but when I feel lost I take away the laptop, taking a pen and start to write things. Computers are still not as good as a pen sometimes.
My favorite Ruby blogs\communities\websites are github.com is probably the best community. Discussions there are so well focused around getting things done. I like to participate in ruby developers's meetings in Kiev. They are always friendly and fun.
I haven't read a lot of ruby related books. I can't recommend to follow my example to anyone. I don't read books because I cannot contact author in real time and ask my questions. As for life books: I recommend Generation-P by Victor Pelevin. This book gives advices how to remain a free-thinking person in a world of consumption slaves.
My personal life hack is learning many human languages (being a polyglot). It lets you see the world as richer and wider place and understand things you would never realize when you are limited to what your native language has.
If you want to become an expert you should know you should forget what is easier for you right now and do things that bring the best result.