I was still working as a Unix administrator when I started with Ruby. I knew I wanted to start building things, and it was clear to me that web development was the only good place to do that at that time. I jumped on Ruby on Rails as the only language and framework that seemed focused on helping me get things done as opposed to endless architecting. I started with the pragmatic books - Agile Development with Rails, and Programming Ruby. They were great places to start, but nothing teaches like doing. My time at Thoughtbot is what really helped me grow from a beginning Rubiest to an expert.
Right now, I'm mostly interested in cloud technologies, which is why I'm working at Engine Yard. Just like before, I'm focused on helping developers get stuff done as quickly as possible. Having a platform to deploy to which takes care of all of the sysadmin stuff I used to have to worry about is a huge win for developers.
I started with Ruby at the same time I started with Rails. My background had been in PHP, Perl and Java/J2EE. I knew it was time to dedicate myself to Ruby and Rails when after working on a Rails app I had to go back to maintain something in Perl.
Honestly, the most improvement have come from the work I've done and the people I've done it with.