At the beginning of the first book, One For the Money, Stephanie has been laid off from her job as a lingerie buyer, she is being forced to sell off her appliances one by one in order to pay her rent, and her car is repossessed. This last straw prompts her to turn to her cousin Vinnie, owner of Vincent Plum Bail Bonds, for a job. She originally hopes to find a file clerk job at the Bail Bonds office but the position was taken, and the only position available is as an apprehension agent or bounty hunter. Vinnie refuses to hire her, but she manages to convince him to give her a shot by threatening to blackmail him. Stephanie's financial situation is still rather perilous, partially due to her poor financial skills, and she often finds herself seeking alternative ways to earn money in order to pay her bills.
When the series begins, Stephanie Plum is single and living with her hamster, Rex, in an apartment building with predominantly elderly neighbors. She revisits her parents who live several miles away in the Burg for meals, "family time," and pineapple upside-down cake. While Stephanie finds her family stressful, they often give her tips or connections which assist in her job.