In Episode 60, Billy Donnelly explores the idea of Has-Beens and Never-Wases and tries to process his reality as one of the latter. He talks about the sadness he feels in constantly trying to measure up and have his moment, only for it to feel like he is constantly making his situation worse. He discusses his understanding of the Has-Been's plight, as they are being forced to leave behind a life they don't want to leave, but he dives further into the frustration of never having your shot at the title, of never being able to attempt proving yourself in the moment. As he seeks answers and a better understanding, he may just walk away with more questions that he entered with. 

In Episode 59, Billy Donnelly tells a recent story of trying to help his son make YouTube videos and the difficulties, resistance and frustrations he encountered along the way. He details some of the lessons and takeaways he was able to grab from the experience, as he tries to come to terms with his inability to assist others who just don't want the help and the whys that surround it.

In Episode 58, coming out of Memorial Day Weekend, Billy Donnelly ponders questions about our legacies and how we want to be remembered. He discusses how these ideas start to become a bit more important to us as we get older and the things that are important to others after we're gone in how they write our posthumous stories and carry on our memories. 

In Episode 57, after struggling with focus throughout the week, Billy Donnelly decides to talk about parenting, and namely the difficulties that arise in trying to do the best job you possibly can for the benefit of your kids. He discusses some recent interactions with his kids that had him feeling a bit down, and the trade-offs that come with that in aiming to raise decent human beings. He talks about the toughness in striking to find the right balance in providing proper guidance for them as they grow and develop while also not creating any unnecessary trauma for them growing up. However, he still acknowledges that no one is perfect doing it and that we all make mistakes as we go, but doing our best is all we can really seek to do if we take this responsibility seriously (as we should).

In Episode 56, Billy Donnelly talks about the recent rise in his anxiety levels, as brought on by the CDC's new Covid guidelines and people's rush to get back to "normal." He discusses his concerns over the new honor system approach to mask-wearing, in addition to increased capacity and social distancing everywhere, while discussing his worry for how it affects people who cannot be vaccinated yet, particularly children. He then veers into different territory altogether, prompted by some recent Facebook memories, in which he confronts feelings about a pair of acquaintances that faded from his life in very different ways but for similar reasons. He looks at what happened, how they made him feel and whether or not he feels compelled to do anything about it in an effort to resolve them. 

In Episode 55, Billy Donnelly tries to answer the question of whether or not he is holding himself back (and by extension, this podcast) due to his fear of failure. He looks at the way he throws himself into chasing success (and the reasons why), in addition to the imbalance often created by this approach. He brings up a past situation that did not turn out well and the lessons he learned from it, while also trying to re-frame what success actually means, particularly in reference to our creative endeavors. Ultimately, he figures that his answer ultimately comes down to what he hopes to get out of what he is putting in, as he sets realistic expectations.

In Episode 54, Billy Donnelly examines the fine line that seems to exist for him between success and failure, and how it has often acted as an obstacle in moving ahead on a number of ideas, projects, etc. He discusses his history of failure and how that has fostered such an extreme dichotomy between the two sides, and he ponders why exactly he hasn't been able to get over the hump of bouncing back from failure in his life when he's been able to move past other hurt he's experiences. He also lays out where the line between the two rests and how its position has become problematic and at times crippling. He also looks at why some failures are taken personally while others aren't as big of a deal, and he tries to figure out why he's so quick to blame himself for the failings of others. 

In Episode 53, Billy Donnelly explores questions of worthiness after finding some difficulty in receiving compliments from others. He tries to figure out why we find these interactions awkward and often downplay the praise that surfaces within them. He discusses ideas of hero worship and putting people on pedestals, while also talking the conflict that exists between his need for validation and affirmation and his discomfort with compliments that reflect upon him personally. He discusses various areas of praise and why some seem easier to stomach than others, in addition to examining our own comfort in expressing negativity more than positivity. He also raises the issue of how one's intent may factor into how they feel receiving compliments, while also looking at what it is we're looking to communicate in extending compliments ourselves. 

In Episode 52, which marks the 1-year anniversary of Getting Old Quickly's launch, Billy Donnelly looks at the various lessons, discoveries and takeaways he has managed to find in the first year of doing the show. 

In Episode 51, Billy Donnelly explores the dangerous game of comparing yourself to others and the toll it can take on your mental health. He discusses why we do it and what contributes to that type of mindset. But he also takes it one step further by raising a different level of comparison that he's struggled with lately, and that is of comparing against his potential and the best version of himself. That avenue opens up all sorts of examinations about past choices, past failures, past regrets, etc. In the end, he tries to find the best way to limit the comparing thoughts, so they don't control the way we think about our lives in the present by putting more focus on where we'd like to be.