When you attempt to open up the jobs window with 5 or more Dupes, the game locks up for a few seconds. As the number of Dupes increases beyond that, this lock up time goes up exponentially. At 10 Dupes I was able to take a bathroom break and go get a snack, and still arrived about thirty seconds before the game began responding again. Ultimately, the game does not crash, but it is very time consuming to access the key feature of the Occupational Update.
Create a colony, and bring the number of Dupes up as normal, towards 10. Keep Dupes assigned to, and working on, jobs. Give multiple Dupes the same job (for example, 2 general engineers and an electrical engineer). My colony had job redundancies. Give Dupes experience in more than one job track, such as starting off in Farming until they master that tree, then switching to being a Engineer, and make your Artist a Farmer instead. Test with both partial and complete job mastery. If you still cannot encounter the issue, bring in two more Dupes, and kill off your most experienced ones. In my case, I lost a Tenured Scientist and a Courier. I did not require any deaths to replicate the issue myself, but I cannot be sure that dead Dupes did not contribute to the problem as if still alive.