This achievement is unlocked for helping Justin, a patron at the bar.
To help him through his problems, you must answer a series of conversation choices with him a certain way, both in the Stray Sheep and on the Landings. On the Landings, he is identified as the Sheep with Glasses. This will unlock on day 8 after talking to Justin if you answered all the conversation choices correctly.
See Everyday Hero for a full guide on helping everyone.
Catherine - Read All About It! Trophy