Jeremy Green and Erik Dietrich discuss the unforeseen pain points of becoming a freelancer and share solutions that they have used in their lives and businesses to address these pain points. They considered pipeline management, not having enough work, having too much work and having ill-fitting work. How companies treat vendors and dealing with rejection are discussed. The loneliness of a freelancers life and how to combat it are considered. The hidden cost of working on your own and owning a business are addressed, including health insurance and taxes. The positives and negatives of time and money management are compared. They warn against bad clients and give warning signs against them.