Quite true! Having been fairly instrumental in a few areas that I'd eventually moved on from, it was always interesting to see some of my trademark accomplishments become The Old Thing We're Trying To Replace (or even just The Big Thing We Have To Maintain); gave me a lot of empathy for prior contributors of code I ended up inheriting.
I tend to assume that the old thing seems dumb because of the constraints when it was written and changing requirements over time; if a tool made by one person in a few weeks seems hopelessly naive to the medium sized team investing a few quarters in replacing it a few years later, that seems to be a rousing success for the original author.