Mr. O’Brien on Mindfulness, Literature, and Guidance

In Episode 13 of Season Two of The Late Start Show, we sit down with Mr. Kevin O’Brien, English teacher, coach, and mindfulness advocate at University School. He takes us from a Cleveland childhood fueled by library stacks and elementary-school talent shows to a life-changing scholarship at Phillips Academy Andover, where mentors and coaches sharpened his love of literature, leadership, and team culture. We trace his journey from multi-sport athlete to Division I lacrosse at Penn (and a position switch that taught him humility), and the winding early-career path through New York film sets, the wake of 9/11, and head-coaching stints that ultimately led him home to US after impactful chapters in Potomac, Western Reserve Academy, Episcopal Academy, and The Hill School.

Mr. O’Brien reflects on building classroom and team trust, why boys thrive when they can be their full selves, and how journaling, breath, and “discernment” turn hot takes into thoughtful choices. We get into attention in the age of AI, the battle for focus in an attention economy, and why he has students write to “figure it out”, because, as he reminds them, “paper is more patient than people.” He unpacks what real preparation looks like at US, the mentors who shaped him, and the quote he keeps close about our finite time, attention, and energy. His “why”? Simple: to be kind, to help students do hard things, and to honor the teachers, coaches, and family who made that possible.

Credits to Theo Walter for Production and Editing, Russ Nobles for the Intro and Outro songs, Mr. Wickboldt for being our advisor, and you for listening to our podcast and keeping up with the latest US news.