Story related, cannot be missed.
This will unlock automatically just by playing through the game. After the Chapter finishes loading, you'll see John looking at a clipboard with a checklist called "The Routine". He does these things everyday:
They're all self-explanatory, but I recommend that you read the middle book titled Domestic Nuclear Shelters - Technical Guidance when you're given the chance. Assuming you've read The Bible during Chapter 2: The Last Goodbye, you'll obtain the missable achievement, Bookworm. Additionally, you need to be sure that you interacted with the Puzzle Picture on the wall near John's mom's bed. When you do, inspect the missing puzzle piece because this will later cause that missing piece to spawn near the end of the game, which will later give you another missable achievement called The Missing Piece. With those two things in mind, when you finish Day 11,111 routine, this achievement will unlock.
**All credit goes to themindisacity for the help!**