A lot of the things people are making now are being driven by young people. Young people have an ignorance about the past, so miss some of the lessons, but they also lack the cynicism which prevents revisiting things that people have determined "don't work" in the past.
I generally see tech as a large ecosystem which is in fact progressively improving, with minor setbacks that often do echo the same setbacks in the past. The error is to pattern match too strongly on these setback patterns as though they contain some kind of timeless wisdom. If there's any industry where past performance isn't indicative of future results, it's technology. (Which is and of itself, is a process of knowledge discovery at its core.) My general approach to thinking about this is I grow older is to guard against the kind of cynicism I see in so many of my peers. Yes, it means I will be wrong on things where the cynic turns out to be right. But given the pull of cynicism, I suspect more likely I will remain cynical in many places I shouldn't be anyway, so I'd rather focus on being right in the places where the cynic is wrong by forcing myself to remain optimistic and give the young the benefit of the doubt.
This also has the added benefit of making the process of working on things more fun in general - not just because it leads to actually making stuff (cynicism demotivates this) and it also leads to being surrounded by peers who are optimistic and interested in continuing to make stuff (being surrounded by cynics is generally miserable, and breeds cynicism.) A few years ago, I found myself in a broad peer group of technologists who were deep into the abyss of cynicism, and made a conscious decision to just sever myself from these networks because this kind of negativity was becoming my dominant mode of thinking about technology. I've done some of my best work since then and much of it has probably come about due to the fact that I dove into it due to the counterfactual level of optimism I had due to this one decision.