Ep. 2 - Brandon Jacobs: Relationships, Identity, and his ADHD Superpowers

What happens when we hand off the tasks that quietly shape who we are?In this episode of The Line, Sean and Matthew sit down with Brandon Jacobs, leadership certification program manager at the National Association of Episcopal Schools and former independent school recruiter. Brandon makes the case that education has always rested on three Rs — reading, writing, and arithmetic — but has consistently missed the fourth: relationships. For Brandon, AI's greatest value is that it clears space for that relational work. It handles the spreadsheets, the survey synthesis, the interview note collation, so he can show up fully present for the people he serves.Brandon also shares what AI means for him as someone diagnosed with ADHD later in life. Rather than framing ADHD as a limitation, he describes it as a superpower — and AI as the tool that lets him lean into his strengths by neutralizing the tasks that used to drag him down. He talks about the zero-inbox policy his brain demands, the presentation prep that used to stall him, and how AI gets him "out the door" so he can bring his full self to the work that matters.But Brandon's not naive about the tradeoffs. His line comes into sharp focus when he talks about asking school leaders to write their educational philosophy statements — and receiving something clearly AI-generated. "I asked for your humanity," he says, "and you gave me a robot." For Brandon, the line is about honoring the time and attention that genuine relationship demands. He introduces the phrase "human first, human last" — a framework where AI lives in the middle, but the human bookends are non-negotiable.In the debrief, Sean and Matthew unpack the role of time as something more than a resource to be optimized. Drawing on Heidegger's observation that "all distances in time and space are shrinking," they explore how the slow, messy process of writing a teaching philosophy or reading a novel over a month is itself identity-forming. When AI collapses that time, there are real gains — but also real losses that rarely make the headlines. The episode closes with a question worth sitting with: if the tasks we hand off to AI are part of how we become who we are, what happens when we stop doing them?Follow along with our thinking:⁠The PEXE Lab⁠⁠The PEXE Lab on Substack⁠⁠Sean's Substack⁠⁠Matthew's Substack⁠