Constant Evolution | Nic Starr & Tony Hemingway
In the newsletter this week: Two profound episodes, absenteeism, and instant feedback.
🎙️ This Week on the Podcast: Nic Starr & Tony Hemingway
🎙️ Episode 11, Nic Starr, AI Bingo
The latest episode of the "Learning Can't Wait" podcast offers leaders a compelling look at how adaptability, risk-taking, and a commitment to lifelong learning can drive meaningful career evolution in education. Nic Starr, now an education customer success manager at Adobe, candidly shares her journey from classroom teaching and administration to EdTech leadership. Starr’s story highlights the power of following one’s instincts, embracing uncertainty, and leveraging mentorship to navigate complex career pivots—qualities essential for leaders facing rapid change in today’s educational landscape.
What sets this conversation apart is Starr’s innovative approach to mastering new technology. She describes her "AI Bingo" card—a year-long, gamified challenge to explore and implement a variety of AI tools and workflows. This initiative not only demystifies AI for educators but also models how leaders can foster a culture of experimentation and continuous improvement. Starr’s blend of analog and digital strategies, from note-taking to building chatbots and launching podcasts, demonstrates how embracing both tradition and innovation can empower teams to thrive amid technological disruption.
Leaders will find actionable insights in Starr’s reflections on the future of AI in education, the importance of ethical and equitable technology adoption. Her message is clear—embracing change with curiosity and resilience not only transforms individual careers but also has the power to uplift entire organizations. This episode is a must-listen for leaders seeking inspiration on how to navigate and lead through the evolving intersection of education and technology.
📖 Key Quote: “Expect the unexpected in the most optimistic way.”
🎙️ Episode 12, Tony Hemingway, Make Something Out of Yourself
Dr. Tony Hemingway’s journey from a struggling 11th-grade English student to superintendent of Fairfield One is a testament to the transformative power of mentorship and resilience, making this next episode of the "Learning Can't Wait" podcast essential listening for leaders seeking inspiration and actionable strategies. Hemingway shares how pivotal figures—like his summer school teacher, Charlene Proctor, who rebuilt his confidence, and a superintendent mentor who guided his early leadership—shaped his mission to ensure every student experiences encouragement and support, regardless of their background. His story underscores the profound impact that a single educator’s belief can have on a student’s trajectory, and how that experience now fuels his commitment to building robust leadership pipelines and fostering inclusive school communities.
Listeners will be drawn to Hemingway’s innovative approaches, such as the “SOAR Sofa” initiative, where students are celebrated for embodying core values and engaging in meaningful conversations with district leadership. This unique program not only recognizes academic and personal achievements but also strengthens the connection between students and administrators, creating a culture where every voice matters. Hemingway also details how he cultivates a sense of shared purpose among staff through collaborative vision-building retreats and ongoing professional development, ensuring that teachers and future leaders feel valued and prepared for advancement within the district.
For leaders navigating today’s educational uncertainties, Hemingway’s perspective is both practical and uplifting. He discusses the importance of fiscal responsibility, aligning initiatives with student needs, and maintaining a steady focus on legal and ethical best practices amid shifting policies. Hemingway’s advice to new teachers—stay committed, seek mentorship, and never lose sight of best practices—resonates as a call to action for educators at every level.
📖 Key Quote: “I failed that class because my high school English teacher told me that I wasn't college material and that I would never amount to anything..”
📚 What I’m Reading
There’s no more urgent issue in education today than student attendance.
I’ve dedicated two recent episodes of the Learning Can’t Wait podcast to this exact topic, see here and here, speaking with national and local experts to understand what efforts are making a difference.
This week, The 74 Million published an insightful piece on this very issue. It highlighted the essential shift happening in schools across the country: improving attendance isn’t just about enforcing rules—it’s about building supportive, trusting environments, as Hudson Superintendent Juliette Pennyman shares.
That resonated deeply. When I was still teaching, our administrative team would regularly meet and even make home visits to students who were chronically absent. Those visits were eye-opening. We learned so much, not just about the students, but about the barriers their families were facing. It was care, curiosity, and empathy that opened the door, not compliance.
There’s a strong case to be made for re-humanizing how we approach attendance.
And yet, last week, I attended an AI Symposium hosted by Urban Assembly, Amplify, and Elevate Innovation and unlocked a great use case for technology in this dilemma. In a room full of NYC public school leaders, we explored real-world examples of how AI is being implemented in schools. Principal David Liu shared how his team used Playlab AI to predict and proactively prevent student absences. By combining attendance data with weather forecasts, they could predict, with high accuracy, which students were likely to miss school, and then intervene in advance.
It got me thinking: what else could we feed into that model?
Upcoming assessments
Professional sports schedules
Holidays or long weekends
Assignment due/return dates
Extracurricular schedules
Imagine pairing smart data with human intervention—technology that flags the risk, and educators who step in with care and support. That, to me, is the ideal role for AI in education to handle such an important issue: insight at scale, action with empathy.
If you’re curious, you can read it here.
💭 What I’m Thinking About
A lot of kids [my own included] love video games because of the instant feedback loop: take an action, earn points. Repeat. The games are designed to be incredibly reinforcing.
This week, I watched my boys respond to a new gift in exactly the same way they do with video games. What was it?
An old-fashioned basketball hoop.
Shoot. Score. Shoot. Miss. Try again. They’ve been playing nonstop for hours every day. I cannot get them to come inside for dinner. “Just one more shot, Mom.”
I realized the simple act of shooting and scoring creates the same feedback loop as video games—except it’s happening outside, with their bodies, in real life. James Naismith was onto something in 1891.
Earlier this week, my boys were down the street playing basketball with other kids from school when an older woman stopped her car and said, “Wow, kids still play outside? I haven’t seen that in forever.” That gave me pause.
The challenge in our ever-evolving technology-fueled world is finding a form of play that gives them that same dopamine hit.
We’ll start with basketball over here.