In a society where having a job is, for that vast majority not in the non-gilded classes, the only mechanism by which a person can secure their core needs.. losing a job is indeed a pitiable situation for most.
If we've built a society that when it "pivots" leaves swathes of people smeared out as residual waste, I'd argue we should feel bad.
We've certainly reached a point of technological advancement where many of these consequences at the individual level are avoidable. If they're still happening, it's because we've chosen this outcome - perhaps passively. But the clear implication of would be that we're collectively failing ourselves, as a species that tends to put some degree of pride in our intelligence.
And we should feel bad about that failure. It's OK to feel bad about that failure. We tend not to improve things we don't feel bad about.