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I found at first that you could only do it when a resident came to you with the problem that they hated their job and then you tell them "wait for me to find a new job." Eventually you notice job advertisements popping up in the KittyFeed with the option to apply. So check the feed! Scroll down and look for the big apply button to check if you missed any. If not, wait until a resident comes to you saying they hate their job to kick it off.