If you have an employer, this is usually a pretty easy sell. Approach your boss about transitioning Aging Product X to a new technology stack because the current one is becoming defunct. Of course this will require some training for you, but it is easier to teach you a new skill set than to hire someone with that skill set and get them to learn about Aging Product X.
If you aren't employed and are contracting/freelance, it is just as easy. Since your skill set is niche, not everyone has it, and you can charge more for that niche. Up your rates enough that you can cut 10 hours a week out to study something new.
Is convincing employers to transition technology stacks really something that is generally considered easy (or even doable)? I'm stuck maintaining 'enterprise' software running on VB6 and ColdFusion 9 and the idea of getting my employers to sanction a migration to something newer is laughable.
Not necessarily, but convincing your boss to be mindful of your medium-term career goals definitely is and at largish companies there should be opportunities for you to spend time working on something else. Career-wise, I'd be more concerned about working for someone that wants you to stagnate than about the specific software you're maintaining. (Not saying that that's necessarily the case, BTW.)
It's a thing. I don't know about convincing employers, but employers do it. I've participated in such projects. hell, I know people who have done such things in government and military contracting contexts. It does happen
so yeah, it happens. Legacy systems are re-written. convincing your employer? yeah, I've never seen that part happen, so I can't say anything, but I certainly have seen the aftermath.
If you aren't employed and are contracting/freelance, it is just as easy. Since your skill set is niche, not everyone has it, and you can charge more for that niche. Up your rates enough that you can cut 10 hours a week out to study something new.