However, there are special cases where you are exposed to a new technology which enables new outcomes.
I was fortunate enough to blunder into using the Web in '92 and Java in early '95 and they were tools where the "how" did matter quite a lot...
[NB I haven't touched Java in a dozen years or so]
I mean if you have a problem to solve and you have a choice to use some old tech that you already know, but it is going out fashion, and some new one, then the choice of the newer one improves your employability in the future. For example, I guess in 2000 there was not that much people with 5 years of experience of using Java in production, but those who had it, had to have pretty good chances to easily find decent job.
Of course there is a risk to bet on wrong technology, but at least you keep learning instead of just using ageing tools and becoming more and more disconnected from the current state of the art. It can be as scary as this https://news.ycombinator.com/item?id=11886753, a story of a guy who successfully solved business problems and delivered products with jQuery for a long time and then eventually found that he was out of demand because businesses started looking for people with experience of using React and he didn't have it.
When I've recruited I've always tried to assess the candidate on ability to get things done rather than knowing a specific framework. I'd look at how deep their knowledge goes and see if they can ship stuff - if they've been using jQuery but I need React then I'm not too fussed if they've shipped quality products using jQuery and have taken the time to learn pretty deeply how it works, the keenness to learn and ability to build things should easily translate to React and I'd rather have this person that someone who has skimmed the top of React for a few Hello Worlds.
I would hope and prey that interviewers would take a similar approach, if they are just ticking off keywords from your CV then it's a pain.