**This achievement is MISSABLE**
In the end of chapter 3 (or the beginning of chapter 4, can be done both places) you will need to talk to Reuben until you exhaust dialog options. This takes approximately 10-15 times interacting with him.
NOTE:
If you have not received this achievement by the end of your playthrough, rewind to the beginning of chapter 4, walk through the door right behind you, and have a very constructive dialog with Reuben.