When going on the job market for the first time, it is easy to feel like you are drowning in a sea of questions: When should I apply? Should I print my application on fancy paper? What is a standard “benefits” package? This article is based on our own experiences of applying for postdoctoral and academic positions, combined with our more recent experiences of serving on hiring committees. Certainly every story is different, but this article will attempt to answer the most common questions that we faced. Several other resources listed at the end can provide more perspectives.