When Skookum Digital Works investigated the massive project of re-architecting a large social media site, a common theme arose: their client wanted to experiment, but its LAMP stack was getting in the way. Too big, too heavy, too rigid. Manipulating one variable caused cascading effects, and broke something else. SDW proposed an uncommon, but increasingly popular, solution: a document-oriented database. Dozens of tightly-coupled relational entities could be decoupled into documents. Business logic could grow more flexible and less error-prone. This is the story of moving a large user-driven website from a LAMP stack to a node-mongodb stack: what went right, what went wrong, and everything in-between.