I have been working on Ruby since THE DAWN OF TIME! It certainly feels that long but in practice I discovered, and subsequently was fortunate enough to bag my first Ruby gig way back in 2007. We didn't tend to write tests in those days. But keep that to yourself!
Ruby changed my tolerance of what you might consider bad or unclean code. It'll do that to you.
I love Ruby for the community. I've been fortunate enough to meet so many people I have grown to respect over the years and universally they have been nothing but awesome, kind and sharing folks. Ruby would be nothing without its community, and long shall it remain so.
I hate Ruby for the DSL obsession. We're experiencing something of a backlash at the moment, but Ruby folk propensity to turn absolutely anything into a DSL is kinda grating for me, personally. What's wrong with plain old Ruby?! OK, rant over.
Most terrible architectural solution/code I have ever met is the code I wrote last week. But seriously, if you don't feel the same way about your own legacy code... You're a better engineer than me.
Life after Ruby is like being unplugged from the Matrix. I'm happy to knowingly exist in an entirely fabricated universe. Leave me plugged in please.
My dev environment contains tmux, vim, Ruby and not much else.
I enjoy the chattering of the various Rubyists I follow on twitter. Also I've found the Ruby rogues parley list to be particularly good although I tend to lurk there and not post too much.
I enjoy our various Ruby community events around London and the South of England. But also I try and attend events and gatherings for other languages and technologies.
I recommend Trailblazer by Nick Sutterer because he pays me a huge bonus for mentioning it and I'm on the cover. No, seriously - Nick is doing some really interesting and 'alternative' things with rails that would benefit us all. Plus he does a butt load of open source and is generally a pretty smart and cool dude. If you've not read it, give it a try.
My personal life hack is to be nice. Always assume the best in people. Your judgements are much more a reflection of you as they are of the person you are judging.
If you want to become an expert you should know that experts are just regular people that have experienced more pain and suffering than the average person, but have managed to translate that into experience. Although that said -- the real expert understands they are not an expert at all.