Skip Cherryholmes is a former Grammy-nominated musician who transitioned from a life on the road to becoming a dedicated Lead Dad and advocate for fatherhood. As a pre-teen, he began performing with his family’s band, Cherryholmes, and later led his own successful group, Sideline. After over two decades of touring, Skip chose to step away from the stage to focus on his family life in Raleigh, North Carolina.
The decision to retire from performing in his early 30s was influenced by a moment during the pandemic when Skip realized he was missing out on his children’s lives due to the demands of his music career. This led to a farewell tour in 2023 and a new chapter as a full-time father to his two young children, Aiden and Adeline, with his wife, Stephanie.
Embracing his new role, Skip collaborated with Paul Sullivan, founder of The Company of Dads, to document his journey in the “Lead Dad Diaries,” a year-long series exploring the challenges and rewards of active fatherhood. Throughout the series, Skip shared insights into his family’s experiences, emphasizing the importance of communication and presence in parenting.
In addition to sharing his personal story, Skip contributes to The Company of Dads as a writer and their social media director, using the platform to support and inspire other fathers navigating similar transitions.
Skip Cherryholmes’ journey from acclaimed musician to devoted Lead Dad highlights the evolving role of fathers in today’s society and the profound impact of choosing family over fame.
