Leadership, Technology, and Teaching | Curtis Valentine & Jen Womble

In the newsletter this week: Two Powerful Podcasts, The State of AI in Education, and Voice-to-Text.

🎙️ This Week on the Podcast: Curtis Valentine and Jen Womble

🎙️ Episode 5, Curtis Valentine, Real Men Teach

In this episode of the Learning Can’t Wait podcast, I talk with Curtis Valentine, director of the Reinventing America’s Schools Project, founder of Real Men Teach, and professor at the University of Maryland. Curtis shares how his path has been shaped by mentors, community, and a lifelong commitment to public education.

We talk about how the pandemic pushed him to think deeply about his legacy, and how that led to the creation of Real Men Teach—a movement focused on uplifting and retaining male educators, especially men of color. At its core, it’s about creating spaces where educators feel connected, affirmed, and supported in their growth.

Curtis reminds us that education is about community, not going it alone. He draws on his experiences both in the U.S. and internationally to call for more collaboration, equity, and authenticity in our schools. But what stuck out most is how he encourages teachers to bring their full selves into the classroom, because students benefit most when we lead with passion and purpose. His story is a powerful reminder of what’s possible when we build spaces where everyone, teachers and students, can thrive.

📖 Key Quote: “Be all the things, be all of it... your students are all those things, and they need to see that in you. And you being who you are gives them permission to be who they are, and that's the beauty of it all.”

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🎙️ Episode 6, Jen Womble in Techno Optimism

The JenniferWomble, chair of the Future of Education Technology Conference (FETC), was also in the hot seat this week on Learning Can’t Wait. Jen shares her unique journey from criminology and law to leading one of the biggest edtech conferences in the country. She credits her path, and her passion for blending teaching and technology, to her early influences and a deep belief in the power of public education.

Jen talks about why one-off events aren’t enough and why we need year-round communities that support educators as they tackle big challenges like teacher shortages, shifting student needs, and fast-moving changes in technology.

She also shares how we can improve recruitment and retention by changing the story we tell about teaching. It’s not just a job. It’s a career with long-term impact, and we should be using tools like AI to make the work more sustainable and rewarding. Jen makes a strong case for building AI literacy, investing in meaningful professional development, and creating stronger partnerships between teachers, leaders, and communities. This is what Jennifer is known best for, partnership and community, and it shines on Thursday’s episode.

📖 Key Quote: “Teaching is an amazing profession that touches lives and impacts in so many ways. We've got to turn that story around.”

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📚 What I’m Watching

It turns out that some of the smartest people I admire are making a compelling case for how AI might actually help re-engage students in school. Rebecca Winthrop, co-author of The Disengaged Teen: Helping Kids Learn Better, Feel Better, and Live Better (written with Jenny Anderson), recently joined Ezra Klein on his podcast to talk about the book and how AI fits into the bigger conversation about teen disengagement.

This topic has been on my mind a lot, partly because I’ll have teens in my house before I know it, but also because every generation faces its own version of this crisis. My parents worried when personal computers came into the home and we weren’t outside as much. Their parents probably worried about televisions. And before that, it was radio. Technology has always reshaped the homes we live in and the way we live with our kids.

Both Klein and Winthrop argued AI could actually be a tool to revive and reimagine American schools. Definitely worth a listen if you're thinking about what comes next in education.

As someone who listens to, reads about, and interviews folks on the topic of AI nearly every week at this point, I didn’t think the conversation went as deep into use cases as it could have. But for people who are less exposed to this space—like many of my mom peers—it offers a helpful picture of how personalized learning and support for individual kids could be transformed with AI.

That said, I still hold onto this question that I can’t quite shake: Why do so many of the creators of these tools send their kids to schools that don’t use AI—and won’t let their own kids use it at home? It’s something I’ve touched on before, and it’s a tension I think about often in my own home. Like my recent podcast guest Jen Womble, I consider myself a techno-optimist. And yet, I’m also incredibly cautious when it comes to what that means for my own children.

I do not have answers here, but I appreciated this watch/listen.

If you’re curious, you can watch it here.

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💭 What I’m Thinking About

Voice-to-text has completely changed the way I write.

Three years ago, someone casually mentioned that using a speech-to-text browser extension might make writing easier. I tried it—and I haven’t looked back since.

I now use a simple Google Chrome extension almost every time I write. I even “wrote” this newsletter by speaking out loud and transcribing it, instead of typing. If you know me, you’d probably say it sounds the way I talk, and this is why.

For someone like me—chatty, thinks by talking, probably (definitely) raised their hand too much in class—this approach feels way more natural. Writing has always felt like a bottleneck for my ideas, but when I talk them out, they flow. I can be clearer, faster, and honestly, a little more me.

Lately, I’ve been meaning to test out more advanced tools like Whisper Flow. Everyone says it's next-level. It’s installed on my computer, but I haven’t carved out the time to get fully onboarded yet. For now, the Chrome extension does the job.

If you’ve never tried voice-to-text, please give it a shot. If it works—amazing. Tell me. If it doesn't—I still want to hear why.