Listening to parents and school officials, every generation is decried as being more difficult than the last, but in the case of iGens, is there some truth to this fear? Concerns about lack of adulting skills, preoccupation with social media, and higher rates of anxiety and depression are common refrains used to describe this generation of young adults and adolescents. My youngest son, Jacob, and I sit down to discuss addiction, focusing specifically on gaming, social media, and marijuana and the impacts that these elements have had on his teen years. As a college junior, Jacob continues to struggle how to balance his responsibilities and instant gratification that gaming and social media provides. We talk about how parents and educators can help teens navigate the various pitfalls that smart phones and easy access to nicotine and other substances can threaten to derail teens’ health and well-being. As mother and son, we talk candidly, sometimes disagreeing regarding the best ways parents can help their children.