The Ruby aspect here is interesting. My gut feeling in my area is if you are coming to these jobs with a non-traditional background and don't have a CS degree

The Ruby aspect here is interesting. My gut feeling in my area is if you are coming to these jobs with a non-traditional background and don't have a CS degree you are better off studying Ruby or Python or something a little less traditional. If you are applying to places that use more popular languages you're competing in a sea of candidates with degrees and experience in those languages. I feel like the Ruby and Python shops are going to be more open minded about hiring someone without the expected degrees, and they are probably a bit more loose about some stuff. I have almost exclusively worked at Java shops, but I did work one job that was a Python shop. The team borderline hated Java/C++/C# in a political way and was militant about how great Python was. If you shared their feelings they would have a strong affinity with a candidate. Where I work now we have long had one oddball product that is built on Ruby on Rails. It had an equally passionate/weirdly political team that was really adamant Ruby was better than anything else and they also hired more people from non-traditional backgrounds. After I left the Python position for quite a few years I got recruiters who were strictly trying to find developers who would do Python.. as if it was going to be more important than what the product was or the team composition or corporate culture. If someone calls/writes me about a job where the team works in Java, C#, etc.. they don't emphasize the language, they emphasize something about the company, who is funding it, what the product is, etc..