Many people say that they want careers in information security, often latching onto the stories of penetration testers or other security rockstars for the promise of a job with better pay and more cool factor. While looking to this as an escape from their current reality, most people don't realize the work or challenges involved in the realities of these other jobs. This talk will help to arm people with the insight needed to uncover the truth about careers in information security and to perform the self-reflection to determine what it means to find the right fit.