Dilbert also failed to keep up with the times. Despite publishing strips about AI or remote work or etc, you can still tell that he has spent so long away from that world that he no longer has any novel insight into it. All of the jokes come secondhand from anecdotes that he hears or reads about.
You had cubicles? Luxury! Im my day, we put our spare-parts laptop on an old door for a desk and sat on a rickety metal chair on a concrete floor in an unheated warehouse. And we loved it!
You had laptops and spare parts?! At my first job we had to build ourselves a desk out of 1's from the bit bucket to put the card puncher on, and a sort of beanbag chair from the 0's. And the old-timers said we were lucky--the old system did not even have ones, which made less satisfying desks. When we got upgraded card punchers that could do ASCII instead of just typing the raw instructions in hex, that was a happy day, let me tell you.
Oh you had a chair! In my day we had a desk scavenged from sticks and rocks. Our chair was a piece of pipe with a 2x4 on the end. You had to balance carefully lets you impaled yourself.
Every now and then a topical quip pops out. Someone tacked a strip about cloud on my more or less cubical—that was my thing at the time and quite good. But yeah mostly 90s or so.
And Adams failed to keep with himself with his fawning over who could be described as the pointy-headed-boss in chief.
Seriously, making your whole career deriding stupid, clueless, cruel top managers and then lionizing Trump... I guess there isn't a single mirror in his house.