When I first reached out to Holliday to join me in a conversation, I was slightly nervous. I really hadn’t known much about her; in our acting class where she served as TA, she saw me take punches from teachers and try to hang on to every shred of control. I would find myself shrinking before her. In every show, I would watch her command a stage. She was stoic. She was well-respected. It was clear she was incredibly talented. However easy it may have appeared, behind-the-scenes, Holly was an intensely hard worker and incredibly dedicated, putting aside a “play hard” lifestyle in college to get what she wanted. She always led with kindness, writing notes to everyone in her cast and crew and remembering everyone’s names, a tradition she has taken with her as she reaches new heights in her artistic career. Holliday’s humility has allowed her to be thoughtful. For someone who has achieved such success so quickly, she is incredibly inquisitive about the world around her and her place in it; her perspective on her life now is wise and mature. She has reached a level she did not think possible so early on - booking The Ferryman on Broadway and now, working with a group of incredibly important women in theater on The Suffragists all before 24 years old. But it is the time she spends wondering not in a group of artists but alone that may be the most special to hear about, for she is tackling every obstacle and celebrating every victory in an artistic way, whether it be through a public visual journal or at a piano. In those years since we were TA and student, much has happened to us both. It took us a while to reconnect and for me to find common ground, but now we have a mutual understanding that this reconnection needed to happen at this time, specifically. I never expect a cosmic connection in an interview, especially with a subject I didn’t know as well as some others, so this interview took me by surprise. Holliday’s ability to ask questions about herself, what she knows and what she does not, led to one of the most open and honest communications about art and love. I am indebted to Holliday for this conversation and for reminding me why I love talking to artists. She is the perfect person to start off the year for The Scout Archives. Whether she is writing songs about the women who have left an impact on her or thinking about the diverging paths of love, the curious way she moves through life is infectious. She is a reminder of how being candid with yourself and with others can only lead to great things. In part one, we delve into conversation about the moment she got the call telling her she had booked a broadway show, about her role in creating safe spaces for female artists, and what the name 'Holliday' means for her.