In Episode 100, Billy Donnelly brings you up to speed on his whereabouts the last couple of weeks. He discusses his desire to do the things that he's comfortable doing these days, and tells stories about his recent trip to Orlando for wrestling and back up to Washington D.C. In addition, he talks about having to fight past some limits and restrictions he was putting up for himself, and how he found himself having a good time on the other side as a result. He also reveals his new start with medication and how he had to overcome some stigmatization feelings of his own over time in order to get to this better place. Plus, he reflects upon crossing the 100-episode mark with the podcast. 

In Episode 99, Billy Donnelly takes a look at how the expectations others place upon us can negatively impact the ways we see ourselves as we constantly try to level up those relationships. He discusses the need for reasonable expectations in how we operate but also in how we see others, in order to minimize our disappointment when outsized ideals are not met. He once again talks about being one's own worst critic, and how always chasing the expectations of ourselves and others can led to never-ending feelings of failure and not being good enough. He also offers up the need to find satisfaction in where we're at and who we are rather than who we're supposed to be, or should be, or could be. 

In Episode 98, Billy Donnelly reflects upon a lost weekend of trying to connect with his 12-year-old preteen son and having it go awry pretty quickly. He explains the difficulties, frustrations and hurt feelings he faces with just trying to communicate and bond, only to wind up dissociating in order to protect his own mental wellbeing. 

In Episode 97, Billy Donnelly actually wonders if he is doing the best he can, or if that's an convenient excuse to try letting himself off the hook for not meeting his own expectations. That's the dilemma explored on this show, as he looks at the lack of grace and forgiveness he grants himself, holding onto all his shortcomings and mistakes as punishment for not hitting the marks he believes he should be hitting. He once again discusses his incredible fear of failure and how he perceives letting himself off the hook as an acceptance of failure. As a result, he dives into how being his most brutal and harshest critic continues contributing to this problem. 

In Episode 96, Billy Donnelly stresses the importance of open and honest communication - communicating your wants and needs, communicating your feelings, communicating your thoughts, etc. He takes a look at the various reasons why we are often too afraid and/or reluctant to talk with others, whether it's avoiding feelings of discomfort or worrying about being judged, while also examining how detrimental it can be to then craft a reality in your own mind that is based entirely around assumption. He discusses his own path to being more communicative over the years, and also explains how that factors into working through some issues in his own life that have resurfaced as of late. 

In Episode 95, Billy Donnelly explains how he doesn't have much to talk about this week as he privately deals with a number of issues in his life while feeling numb to just about all of it. 

In Episode 94, Billy Donnelly talks about his struggles with ulcerative colitis. He discusses how he became diagnosed with this chronic condition and the frustrations he's felt since then, including feeling embarrassed to talk about it and feeling like a burden to those around when in a period of flare-up. However, he talks about the revelations that came to light when he recently discussed prep for an upcoming colonoscopy and the openness of others it seemed to prompt in regards to the process and procedure. He found it interesting that this thing we all are recommended to have done is something no one really talks about, and he's not exactly sure why. But in talking about his issues as of late, he found that others were more willing to talk about some things they've been dealing with recently. From those conversations, he felt more supported in coping with his affliction, while also finding others who he felt saw and understood what he was going through. 

In Episode 93, Billy Donnelly talks about the recent announcement of the When We Were Young music festival. He discusses the initial wave of excitement surrounding the show and all the bands tapped to play, and then he dives into how that optimism quickly turned to cynicism and doubt about how and when the other shoe would drop on it. He ponders how and why we have become so pessimistic in all areas of our lives, and how that leads to us constantly saying "No" in an effort to protect ourselves from any bit of disappointment. He talks about the importance of finding ways to get to "Yes" and of doing things and hoping for the best, as a way to just live our lives and avoid an existence filled with "What-ifs" and regrets. He stresses the need to not throw up excuses and obstacles and impediments for ourselves out of fear, but instead to lean into doing the things we want to do and seeing what happens, even if that means things don't work out. He states emphatically that we need to be willing to take calculated risks from time to time.

In Episode 92, Billy Donnelly recounts his recent birthday - turning 42 - and what the age number actually means to him. However, he does talk about the wealth of Happy Birthday wishes and sentiments that came his way as a result and discusses how they carry so much more meaning and impact than we'd readily admit. He discusses what it feels like to be seen on this special day and why we should try to do more of this to brighten the days of others than less. Overall, he dives into why it just feels good to be recognized by others on your birthday.

In Episode 91, Billy Donnelly talks about the birthday surprise he received this year for his 42nd, in the form of an out-of-town visitor. He discusses how the feelings that accompanied this surprise ran counter to how he felt last year (which can be heard in full on Episode 39: Turning 41) when his birthdays felt overlooked and under-celebrated. He also dives into the importance of both showing and telling those that matter to us and that we care about how we feel about them, and that it doesn't have to be either/or... it really needs to be a marriage of both.