I had this exact experience. Growing up I had nothing but good memories of reading Dilbert over my breakfast cereal, and then laughing as I got into the workforce and realized how accurate the satire was. And then seeing what "he" was actually like just completely threw me for a loop.
I had an opposite experience. I found his comics not-funny when I was a kid, but then as a grown-up who had worked in a corporate environment, I found many of them funny.
I had 100% the same experience. I thought they were stupid when I was young, after working in an office for a year or two I thought they were peak humor.
At some point he had a mailinglist called Dogbert's New Ruling Class (DNRC) which would soon come to rule the world. In it he wrote lots of really weird, unhinged, occasionally funny stuff. At the time I thought it was all one massive joke, layers of irony and trolling. But more recently I've been wondering if he was actually serious.
