Research has highlighted commuters' demand for productive work while driving their cars despite risking accidents. Rising levels of vehicle automation may make it a legal and safe possibility though, which is why this project explores working in a highly automated vehicle (SAE Level 3-4) and its challenges by adopting a user interface for text transcription - as representative working activity - to the requirements of Take-Overs (control transitions from automated to manual driving). In turn, the adopted interface - directly on the windshield ("Heads-Up") - is hypothesized to offer more safety and higher productivity than a more conventional "Heads-Down" alternative, and subsequently prototyped and evaluated in a driving simulator study (N=20). Although post-test interviews promoted that "heads-up typing" would need a significant training phase, because of participants not being used to it, quantitative analysis reports significantly better take-over performance with Heads-Up than with Heads-Down feedback. Still, disadvantages were reflected by significantly worse typing performance leading to the result that Heads-Up feedback may not be the perfect solution to balance both productivity and safety.