While making an academic or career transition, as students we often struggle to make decisions about things we have never experienced. PaperHat empowers young adults to craft a fulfilling career path through “life experimenting.” Life experimenting is when we do small activities that help us get a taste of a bigger life experience. They require little time and money, are easy to do and give us actionable insights. With the help of an interactive web application, students learn and practice the process of life experimenting: identify potential career paths and related questions, design life experiments to answer the questions, synthesize what they learn from their experiences to iterate on their career path, step-by-step.