I worked at a company that was mired in tech debt. At least 4 different UI frameworks were in use, one of which was totally not supported. Multiple versions of the app were left accessible, with links from the new to the old, because the new version was not feature complete. "Feature flags" were expressed in at least 3 different ways. It was a nightmare to figure out if something was on or off, and why. The back end was based on a non supported language version, with several old, deprecated third-party packages as a result. The company appeared organized, superficially, but at the lower levels of implementation it was a total dumpster fire.

They were constantly "pivoting", but leaving the old junk around.