Back in my late 20s, I got stuck on maintaining a legacy software system written in Ada95 (I was unemployed in 2008 and it was the only work I could find).

When that job went away, I thought I could get a job using something more modern. However, the only job I was able to land was a new development project in Ada2005 (actually it was a port from SPARC to x64 and a partial rewrite of the same legacy application I had been maintaining for 3 years).

It took me forever to find a company that would "take a chance" on me - which is when I started working with Java.

That whole experience taught me that I always need to have side projects going so I have actual work samples to show potential employers.

Ha, I was somewhat in the same position, my first job out of college was working for a NASA contractor using Ada. I programmed on the side using C for fun and was able to find a startup to take a chance on me after a few years.

And even then, experience tells me one needs to have some luck that the HR people are even willing to listen about those side projects.

Good that it worked out for you.

Yes, this is especially true at larger companies. In my case, a small company picked me up.