Same problem for me with my new Mac mini 2018 (Macmini8,1) bought on Black Friday 2019 connected to a MSI MAG321CURV (4K Curved display).
Filevault is turned on.
Ran Mojav, then upgraded to Catalina 10.15.1 then upgraded to 10.15.2
Same behavior for 3 OS:
Connected to HDMI: I must blindly type my password, then after a few sync/no-sync signal, I get the image.
Connected to USB-C (this screen has an USB-c (DisplayPort) input. No image. (do I need to turn off Mac to change connection?)
I didn't test to disable Filevault yet as it says it may takes time.
I have 300GB on disk.... How much time could it take? (I don't want a fief so see my personal documents such a photos and more. How can a crypt software alter a Intel Graphic 630 output? wired it is)...