I started using the Ruby programming in around 2003 or 2004, but stopped at some point later, perhaps around 2008. At the time I was frustrated with the approach the Ruby community took for managing packages of Ruby software: Ruby Gems. They interact really badly with distribution packaging and made the jobs of organisations like Debian more difficult. This was around the time that Ruby on Rails was making a big splash for web application development (I think version 2.0 had just come out). I did fork out for the predominant Ruby on Rails book to try it out. Unfortunately the software was evolving so quickly that the very first examples in the book no longer worked with the latest versions of Rails. I wasn't doing a lot of web development that at the time anyway, so I put the book, Rails and Ruby itself on the shelf and moved on to looking at the Python programming language instead.
Since then I've written lots of Python, both professionally and personally. Whenever it looked like a job was best solved with scripting, I'd pick up Python. I hadn't stopped to reflect on the experience much at all, beyond being glad I wasn't writing Perl any more (the first language I had any real traction with, 20 years ago).
I'm still writing Python on most work days, and there are bits of it that I do really like, but there are also aspects I really don't. Some of the stuff I work on needs to work in both Python 2 and 3, and that can be painful. The whole 2-versus-3 situation is awkward: I'd much rather just focus on 3, but Python 3 didn't ship in (at least) RHEL 7, although it looks like it will in 8.
Recently I dusted off some 12-year old Ruby code and had a pleasant experience interacting with Ruby again. It made me wonder, had I perhaps backed the wrong horse? In some respects, clearly not: being proficient with Python was immediately helpful when I started my current job (and may have had a hand in getting me hired). But in other respects, I wonder how much time I've wasted wrestling with e.g. Python's verbose, rigid regular expression library when Ruby has nice language-native regular expression operators (taken straight from Perl), or the really awkward support for Unicode in Python 2 (this reminds me of Perl for all the wrong reasons)
Next time I have a computing problem to solve where it looks like a script is the right approach, I'm going to give Ruby another try. Assuming I don't go for Haskell instead, of course. Or, perhaps I should try something completely different? One piece of advice that resonated with me from the excellent book The Pragmatic Programmer was "Learn a new (programming) language every year". It was only recently that I reflected that I haven't learned a completely new language for a very long time. I tried Go in 2013 but my attempt petered out. Should I pick that back up? It has a lot of traction in the stuff I do in my day job (Kubernetes, Docker, Openshift, etc.). "Rust" looks interesting, but a bit impenetrable at first glance. Idris? Lua? Something else?