Over the past 4 weeks, my conversations with corporate leaders, startup founders, parents, former students, and students still in school, have kept circling back to this question with the same conclusion: School is not schooling. But why? What’s happened? And what is the point, if this is the case? 

The feedback loop is broken. Advancements in AI offer so much potential, yet it just made these gaps a lot bigger. Why?  

We’re layering powerful, fast-moving, often opaque technology onto an education system already struggling to keep pace with the world around it. AI is already swimming through school, the workplace, and our homes with almost no coherent guidance. Leaving leaders, educators, parents, and students to most often figure it out, avoid, or ban it… with very mixed results. 

When we get it wrong, our students bear the consequences. Limited skills to fill job market demand shifts. That isn’t a strategy. It’s an experiment without shared guardrails.

Schooling is not the same as learning. School is just one way we organize learning. AND this isn't a place to panic about AI; let’s start the conversation and start moving the needle. We can do better than watch the experiment unfold without helping to shape it.

Think Outside the Black Box is about the future of learning in an AI-native world: what school is for, what puts learning at risk, and how we keep people at the center of it.

AI is reshaping how we learn, work, and make decisions. But the systems meant to prepare us for that future are struggling to keep up. The question isn’t simply how to bring more technology into education. It’s how to shape a future where people remain thoughtful, capable, and in control.

That’s the conversation this newsletter is here to have.

Each issue explores the question through four dimensions:

Together, these ideas form a larger argument: here's what learning is for, recognize what threatens it, build the capacity to respond, and keep human agency as the goal.

Whether you teach, lead, build, hire, fund, or parent, you have a stake in what learning becomes. This is a space to examine the possibilities, challenge assumptions, and consider, together, what we should shape next.

This is big but we have to start somewhere. The newsletter is the conversation. With conversation, we can move toward action.

I'm an operator, not a novelist. An educator, on a mission. Some issues will read more like field notes than essays. It’s about moving the conversation to action.

If this work resonates with you, sparks an idea, challenges an assumption, or offers a new perspective, you can leave a tip to help turn the conversation into a true Ed(ucation) Venture! https://ko-fi.com/JVsEdVenture 

I'm glad you're here!

Think outside the black box.
Lean. Learn. Lead.
- Jessica (JV)

Hi, I’m Jessica Votava, a Learning Systems Architect. For the past 14 years, I’ve worked across public education, international schools, tech startups, and corporate learning on three continents, alongside customers, colleagues, students, and parents.

Transformation has been the through line in my career, from my early days as a STEM teacher to helping a medical-device company prepare for a training transformation. Working across sectors has given me a view of how differently organizations use technology and data and where education and work still need to connect.

A few years ago, I explored pursuing a PhD to study that gap. But we don’t have to wait for permission to start asking what learning should become. The time is now.