In Episode 50, Billy Donnelly discusses how valuable other people can be in teaching you how not to do something. He talks about the various ways he tries to observe others and, in doing so, gets a better feel for who he doesn't want to be, how he doesn't want to act and how he doesn't want to behave, so he can forge a path forward that is more aligned with what he does want. He talks about how we often try to learn from the success stories of others, but their failures can often unlock just as many lessons for us to take from as far as what not to do. He taps into this learning process with several examples, detailing what he was able to uncover in trying to find improvement and growth for himself. 

In Episode 49, Billy Donnelly discusses the idea of individuals as brands and the mental health toll it can take in eyeing yourself as a company rather than just as a human being. He explores the purpose of a "brand," in relation to a company's goals, and how that often runs in contrast to how we behave and act as people. He talks about the commodification of people and the problems that occur as a result of removing our humanity from everything we say and do in order to better serve the brand. He questions why we now want to be considered products and the idea of being partially owned by anyone who buys into our brand, in addition to offering up the prospective harm that comes from not allowing yourself the time or space to be messy and make mistakes when you've carefully crafted and cultivated a vision of yourself as a flawless entity. 

In Episode 48, Billy Donnelly opens up about his difficulties finding joy and happiness as of late and wonders where exactly his once-present ability to laugh, smile and generally have a good time has disappeared to. In talking through his feelings on the matter, he further dives into struggles of wanting to be liked and accepted as well as his own worries about how others perceive him as he navigates potentially finding a reason for this happening. He discusses imprisoning parts of his own personality in efforts to further exhibit control in those areas and the new issues that then creates moving forward. 

In Episode 47, Billy Donnelly travels back in time 30 years to revisit a period of his life playing Little League baseball and relay a particular story that he believes serves as a source point for a number of future struggles. He examines how issues of self-confidence, self-belief and self-doubt may have been created in one decision made by someone else when he was 12 years old and how it all factors into where he stands now with validation and affirmation from others. 

In Episode 46, Billy Donnelly discusses the negative impact social media has had on his mood and mindset as of late, laying out his history with platforms like Facebook, Twitter and Instagram over the years. However, recently he went ahead and did a thing: creating a TikTok account, and has found an incredible amount of positivity and enjoyment in both using it and creating on it that he hasn't found in other spaces. He details the lessons he has taken away from his entry into the TikTok space and what it means for him personally in regards to his own self-care when it comes to social media. 

In Episode 43, Billy Donnelly welcomes director Nick Bilton to the show to discuss his HBO documentary Fake Famous, which attempts to turn three individuals into "famous" social media influencers. Through their talk, Billy and Nick dive into the idea behind the film's social experiment, lessons learned about why people seek fame through social media, the dangers of relying on social media platforms for personal validation, the presence and importance of bots in establishing one's social media presence, the economic system that allows a rigged social media system to persist, the amount of work that goes into a social media's online persona and facade, the mental health impact that pretending has long-term on influencers, the financial cost of paying to be internet famous, the bet that influencers make in keeping up their charades, the effect that social media has on our overall self-worth and self-esteem, and whether or not social media's chapter in history will be written as one of benefit or destruction. 

In Episode 42, Billy Donnelly talks about some recent reflections that have him stuck in negative thoughts of feeling like a loser. He discusses his feelings that the universe is working against him and that, no matter what, he can't seem to catch a break, and the impact that has on self-esteem over time. He dives into his frustration of seemingly and repeatedly ending up back in the same bad endings, no matter how much he changes things or tries to learn past mistakes, and lays out the scenario of being stuck in a maze that refuses to let you find any degree of progress. He also discusses why he has trouble believing he deserves opportunity or success. He also has an update on his stomach health and stresses the importance of the National Suicide Prevention Lifeline. Plus, this week, there's some homework. 

In Episode 41, Billy Donnelly details another recent bout he had dealing with his validation struggles. This time around, he discusses how an absence of Words of Affirmation and a lack of outside validation feel an awful lot like rejection. He talks about how the structures of social media and their algorithms factor into feelings of irrelevance, in particular when posts/tweets/photos are met with silence and/or no reaction whatsoever. He dives into the crises of self-doubt that begin to creep in during these downswings, as we are denied the doses of dopamine that make us feel worthy, while elaborating on how badly we just want to be seen, heard, understood and supported when it comes to things that are deeply personal to us.