Rarely, but yes. Some people simply can't grasp that if you say "Yes, I've done this for 5 years and I've done that for 5 years" that you will indeed be able to

Rarely, but yes. Some people simply can't grasp that if you say "Yes, I've done this for 5 years and I've done that for 5 years" that you will indeed be able to fulfill both roles, even if you're maybe not able to give answers that are 100% correct in the details and up to absolute latest standard, but can easily get back into it. (Not fundamentals, just actually "yes, I worked with X, but 3 major versions ago") This is generally not a problem and many people are actually happy to get someone who has not just seen 15 years of one thing. The T-shaped thing is a bit of a meme, but I do believe you shouldn't be a complete generalist and not be quite good at some things, so I guess the depth of your one or few specializations is up for debate. But in summary I don't regret it. I don't want to call it "easily bored" but I can really not imagine myself as still doing the exact same thing as 2001, when I started working, even with the technologies that were around at the time. Sure, even there things change (looking at you, Java and PHP) but still. The only thing I don't recommend is hopping from language to language every 2-3 years, that's simply not enough time to go deep enough.