Interesting you want to go ruby. Scala and Java are semi-interoperable. As is Clojure. At least they all tolerate the JVM and JVM related infrastructure (to various levels). Some of the frameworks interoperate more than the others. Ruby is a bigger leap than some other possible leaps.
Perhaps senior mgmt is micromanaging WRT language selection. Could be your boss micromanaging and he's throwing senior mgmt under the bus. Or maybe you're correct. Anyway the point is you need to make sure its merely the specific language you don't like. If you move to a new ruby using employer where everyone has to dress the same way and hold their coffee cup the same way, you might be really unhappy if its actually the micromanaging you don't like rather than mere language choice.
Finally aside from any micromanagement issue there's work style. I prefer nearly consultative, professional environments where deliverables matter and you don't tell someone 5 levels lower on the hierarchy how to tie their shoes. However its a perfectly valid business choice to run a place the other way, and have an unprofessional, general laborer, non-craftsman type environment. You need to explore your thoughts on this too, again, see above, if you think your dream job is ruby and they don't micromanage one particular aspect of your job, you may none the less hate the new job if what you really dislike about the current job is the general laborer / code monkey / unprofessional unskilled labor workplace.
Other people have already mentioned that language doesn't matter as much as architecture / design. A extremely rigid view of language likely implies an extremely rigid view of arch / design, yet another axis to think about. If your current employer is extremely rigid about language you may have not considered what it would be like to work at a place with more freedom, or even just a different set of equally rigid arch/design outlooks.
Interviews are a two way street and with little experience you need to learn more about a potential new employer than they need to learn about you especially WRT the above.
I think you're hitting the nail on the head with this not really being related to an issue with the language choice. I think I just came to a decision I don't want to develop for the web in Java. I kind of lead with the language argument, but really my issue is with mgmt and processes. Mostly with promises from mgmt, regarding a positive change in the way we do things. However, this has been a long long time coming. I have started to get to a bit of a too little too late predicament. This has been fuelled by my mentors who have all left my company for the same reasons. Leaving me without a mentor figure, which is something I am really striving to obtain again. I would like a mentor at least until my development confidence has been made more concrete. As mentioned above, my development career is still early days.
What you have said about architecture and design also rings true! Many other employees in my company are crying out for the development a more maintainable and stable product, coupled with selling this product to clients expectations. Which we seem to struggle to get right time and time again.
I will definitely take you advice as well with the interview process. I need to ground my wants from a future employer.
Really appreciate the detailed response! Helps put in to perspective what my priorities should be!
So reading between the lines the most experienced longest term dev has only 18 months experience. There's nothing wrong with any individual dev personally only having 18 months experience, obviously every dev with 19 or more months experience passed thru the same state. The disaster is solely at the company/mgmt level where you're now the senior technical lead.
One aspect of a company circling the drain, is you're better off finding another place on your own terms before it goes under, apparently soon. Once it crashes, if you're still there, you've gotta settle for anything just to pay the bills. Its hard to say how long you've got before they close, but assuming your last paycheck didn't bounce its longer than you'd have if you wait till the bitter end.
Getting stuck at a better run company that none the less is technologically a clone, complete with pure java etc is still going to be much better.
As a guy who had his 18 months in 1982, I'm just saying I've seen a lot of companies swirl around the drain and its not sounding good for the company regardless of all this "I have lost the java faith" or whatever.
Perhaps senior mgmt is micromanaging WRT language selection. Could be your boss micromanaging and he's throwing senior mgmt under the bus. Or maybe you're correct. Anyway the point is you need to make sure its merely the specific language you don't like. If you move to a new ruby using employer where everyone has to dress the same way and hold their coffee cup the same way, you might be really unhappy if its actually the micromanaging you don't like rather than mere language choice.
Finally aside from any micromanagement issue there's work style. I prefer nearly consultative, professional environments where deliverables matter and you don't tell someone 5 levels lower on the hierarchy how to tie their shoes. However its a perfectly valid business choice to run a place the other way, and have an unprofessional, general laborer, non-craftsman type environment. You need to explore your thoughts on this too, again, see above, if you think your dream job is ruby and they don't micromanage one particular aspect of your job, you may none the less hate the new job if what you really dislike about the current job is the general laborer / code monkey / unprofessional unskilled labor workplace.
Other people have already mentioned that language doesn't matter as much as architecture / design. A extremely rigid view of language likely implies an extremely rigid view of arch / design, yet another axis to think about. If your current employer is extremely rigid about language you may have not considered what it would be like to work at a place with more freedom, or even just a different set of equally rigid arch/design outlooks.
Interviews are a two way street and with little experience you need to learn more about a potential new employer than they need to learn about you especially WRT the above.
Good Luck and all that.