I have had this problem a number of times. First, in the Culinary career, and now in the criminal career. Sofar, on this particular day - being a Monday, my sim who is a getaway driver (4) did not start 'working' and getting progress in their career tab until midnight, no matter what I did. I left the building and entered again. Twice. I tried reset sim, for both my sim and her boss, separately, and that didn't work etiher. I tried exiting, deleting the caches and restarting, then doing all those things over again. All to no avail. No matter what I did, her performance didn't increase until midnight. I'm wonding if it is a programing glitch, where at some point EA changed the time that the career was supposed to start/end?