Cassandra Jens & Whitney Whealdon: Author Interview #17, AI Everywhere, Volume 1

AI Everywhere, Vol. 1, Ch.11: The Heart of Learning. Why human relationships matter most and how AI serves parents as an “assistant principal”. By Farida Khalaf.

Welcome back to the She Writes AI interview series, where we talk with the authors behind AI Everywhere, Volume 1, exploring their personal journeys and professional expertise to understand how we can build a future for AI that is truly ethical, responsible, and human-centered.

This is the 17th episode in our series, and today I am joined by Cassandra Jens and Whitney Whealdon. Their Chapter 11: AI and the Heart of Learning for Young Children challenges one of the most pervasive fears in the digital age: that AI will eventually replace the human mentor and turn education into a series of addictive screen-based checklists.

Cassandra and Whitney Whealdon bring a powerful dual perspective to this conversation. Cassandra, a homeschooling parent, shares her hard-won lessons of using AI as a partner to bridge gaps in her children’s daily learning, from generating targeted reading stories to mapping self-initiated play back to educational standards. Whitney, an educational professional, focuses on the structural shift from “one-size-fits-all” standardization toward dynamic, responsive learning that meets the individual needs of every child. Together, they move the conversation away from “gradable outcomes” and into the territory of attunement, showing how AI can actually free up the mental space required for parents and teachers to be more present with the students in front of them.

In this conversation, they explore why we must protect the “messy middle” of the learning process, how to maintain a “relational lens” when selecting tools, and why analog sovereignty, using nature, paper, and physical books, is essential for a balanced “Heart of Learning”. Whether you are a parent navigating homeschooling or an educator rethinking the classroom, their insights offer a roadmap for ensuring that technology serves as a tool for inquiry rather than a replacement for human curiosity

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Below is Cassandra and Whitney Whealdon’s full interview response to Farida Khalaf’s questions on AI and the Heart of Learning for Young Children. from AI Everywhere, Volume 1.

Topic: AI and the Heart of Learning for Young Children. (Chapter 11)

Intended Audience: For parents, educators, and caregivers seeking a disciplined framework to integrate AI into early education without sacrificing human connection, and for anyone wanting to move from standardized "one-size-fits-all" schooling toward a learning culture that values the “messy middle” and the productive struggle of the human process.

Part 1: The Professional Path & The Collective Mission (Cassandra)

The Expert Perspective: Cassandra & Whitney Whealdon, your chapter focuses on “AI and the Heart of Learning.” What was the “spark” that made you realize AI wasn’t just a corporate tool, but a necessary partner for navigating the unique challenges of K-12 homeschooling?

Cassandra: I can’t say that I ever took AI as “just a corporate tool.” To me, it started out as a fascinating way to fill in gaps, whether in my own daily life or in my homeschool. I first used it for cooking. The recipes were great, but what was most helpful was that I could get immediate clarification instead of getting stuck on a missed ingredient or understanding. I think that’s where I began to trust the tool.

I first used it for learning when I was deep into teaching my oldest how to read. The resources I had for practice had fallen flat, and I was left empty-handed: just me, a kid who loved to draw, and reading goals that felt out of reach. The idea came to me that she would love to read stories in order to illustrate them, but nothing like that existed for targeted reading practice. So I made a ChatGPT project to track her reading progress alongside the standards in order to generate little stories she could illustrate. I’d write the stories onto folded blank pages, and she’d read them and draw them. It became a practice we both enjoyed, it created a positive association with reading, and it became a regular practice. As I mention in our chapter, the LLM struggled (and still does to this day) to only include the targeted letters. But, even with this limitation, it was a starting point I could tweak.

I also remember using ChatGPT to map their self-initiated learning back to standards, since it didn’t come from a curriculum timeline but did map to learning goals. So I’d say my spark came from necessity and from dreams, seeking better ways to meet the learner and the moment in front of me.

Whitney Whealdon shared with me that her realization came in conversation with her coworker and mentor, Steve. Early on, Steve shared that AI isn’t just another trend and that it has the power to disrupt similar to the internet in the 90s. He learned from experience that it’s helpful to get in front of that and start figuring it out and not let someone else figure it out for you.

The "Home" Perspective: Your work is situated in the “Learning” section, but it is deeply tied to the “Home” experience. Why is it critical for parents to understand that AI is fundamentally reshaping how we approach our children’s primary education and their early “learning hearts”?

Cassandra: I think it’s critical for parents to understand that AI can be used in a lot of ways, for better or worse, and how it’s used in the workplace will likely look very different 10 years from now than it does today. So as it stands, I don’t think we need to rush into training every six-year-old on how to use AI. What hasn’t changed since this technological disruption is what we know about young learners. They’re already the most optimized learners on the planet! They evolved to learn through play, through curiosity, through relationships with others. We just need to make sure we don’t get in the way of that. We need to feed it. Generative AI can help a teacher or a parent feed curiosity, build relationships, and create more play. But that’s going to look different for every kid, and that’s where parent and teacher attunement comes in.

Attunement as a parent means keeping your finger on the pulse of your child and building a learning culture in your home. The two main fears I hear from most parents are that their kids will be stuck on addictive computer programs posing as education, and that they won’t actually learn because AI can do it for them. Those are real concerns. But we have a powerful tool in our pocket: culture. Create a family culture that values the process of learning: the messy middle, what it feels like to struggle with something, how it’s normal and ok to get things wrong. Share what you’re learning. Value things that come from the heart and mind of a human. Ask your kids how learning feels for them, and make sure the learning environment feels nourishing. And if it doesn’t, ask about alternatives.

AI is adaptive through computer screens, but it’s also adaptive person to person. Parents can use AI to support their kids in filling in gaps, to create relevancy, to help them dive deeper. It’s funny: Generative AI can be used as a tool to avoid mistakes or vulnerability (using AI to do your homework), or it can be a tool to make mistakes and be vulnerable (using ChatGPT to work through something you’re afraid to ask about in class). The power is in the hands of the student. That’s why protecting the heart, the relationship with learning, of the young learner is essential.

Part 2: Navigating the Learning Curve (Whitney)

Solving for Friction: You discuss using AI to help with homeschooling challenges. What is one specific “educational friction” or logistical hurdle that AI has helped you overcome in your daily curriculum that previously felt insurmountable?

Whitney: Traditional education systems are most often built to create standardization. The expectation is that students will learn a set of standard topics and ideas, be assessed on their knowledge of those, and then advance to the next grade, where they will repeat this process. With AI, there are now opportunities for presenting and assessing learning in dynamic ways that are responsive to individuals rather than the traditional “one-size-fits-all” approach.

For example, AI tools can enable teachers to adapt and produce multiple versions of content when the first presentation doesn’t work. The speed of development of content for teaching has vastly improved. Where it may have taken 2 years to produce a curriculum for a whole class of kids, AI tools can create 30 different versions of that based on individual needs or interests in a few minutes.

Of course, teachers are still very much needed to vet those versions to ensure they are still quality. When the work happens in the creation process is shifting, and the work itself is also changing from creation to evaluation and revision. This requires a different investment of skill and time.

Skill Evolution: You explore how these tools affect kids’ skills. In a world where AI can generate text and solve equations, how are you shifting your focus from what children learn to how they think and utilize their unique human agency?

Whitney: This will vary based on the children you’re working with and the learning culture you’ve established. It seems nonsensical and potentially harmful to give a genAI tool to a 4-year-old and expect them to be ready to engage with it productively. For some teenagers, it might still be nonsensical to expect quality. It depends a lot on who the children are and what they need.

Many technologists are speaking to how their work is shifting from being creator to manager; instead of coding a website, they are using AI to do the coding and then evaluating through review or use whether the website is quality. This requires a set of foundational knowledge, skills, and experiences to deeply understand what quality is and responsible use.

We need to consider the same ideas when deciding when to introduce AI tools to kids to engage with directly: Does the child using the AI tool possess the foundational skills that AI is using? Can they look at what the AI tool does and determine whether that’s quality? If not, then it’s probably too early for them to be using AI.

The risk here is that we move too quickly and children end up letting AI do the thinking for them, and they never gain foundational knowledge and skills. This speaks to the larger point in the chapter about learning in relationships with others and engaging with individuals and their needs. Some kids may be ready to engage with AI tools earlier than others. Cassandra shared that her daughter is using AI via apps, and while it can sometimes be a stepping stone to something larger, it does require her child to have a mental reckoning: Do I want to use AI to do this or do I want to learn how to do this without a tool?

While the decision to be made here will vary by individual, it also speaks to a larger value structure. If we’ve established a learning environment that values the process of learning, children are less likely to choose to use an AI tool to do the thinking or creation for them. They will value the productive struggle and frustration that often characterizes the learning process. However, if I establish that I only care about getting a measurable/gradable outcome, then children will be more likely to resort to outsourcing their creation or thinking to AI to “get it done” and move on to something else that feels more important to them.

The Heart of Learning: The title of your chapter emphasizes the “Heart.” How do you define the “Heart of Learning” in an AI-filled world, and how do you prevent the technology from automating away the curiosity and “spark” that young children naturally possess?

Whitney: I believe that human relationships are at the heart of learning. While we can and should learn independently to generate knowledge and create meaning, when we learn with others, we hear alternate ideas and viewpoints, which, in turn, influence us. Going through a learning journey with others is in itself rewarding, even if it doesn’t lead to a defined result or product. Experiences also matter: flipping through real books, writing on paper, touching concrete to feel the heat of the sun, creating a model to see how something works. These things cannot be replaced by hearing a summary of them by an AI chatbot.

This also points to the culture of learning and values that we hope to instill in children. If learning is about outcomes and competition (e.g., producing a bunch of work and getting grades better than someone else), then AI will automate away the curiosity. But, if we develop and value intellectual curiosity and seeking clarity through inquiry, then the process of learning and the development of knowledge and skills that help us find clarity becomes more important. In this case, AI remains a tool to support that mindset rather than a replacement for that mindset.

Part 3: The Interconnected Impact (Whitney)

The Addressing Cognitive Load: Homeschooling can lead to a high "Ecosystem Tax", the hidden labor of building infrastructure that should already exist. How has AI acted as your "assistant principal," freeing you from administrative tasks to focus on the relational side of teaching?

Whitney: If there is an AI tool or AI-based app that organizes work or learning assignments (e.g., spelling lists of words students have mastered and words they need to work on), that can be a huge cognitive offload, a way to give AI tools the responsibility of keeping track of details that I don’t have to mentally maintain. Cassandra agrees. She believes that this kind of offloading support from AI will free up some of her mental space to allow her to focus more on her children and think about what they need.

The Efficiency Trap: Sarah Ennett - Seeking Ikigai warns about the “ikigai-risk” of AI, where the joy of the struggle is lost. How do you ensure your children still experience the “flow state” and the satisfaction of solving a hard problem themselves, rather than just prompting for an answer?

Whitney: As I shared earlier, this is about establishing a learning culture that reflects what you value. In many cases children lost the ability to access a “flow state” in learning even before AI came onto the scene. There are potentially many reasons: increased learning standardization, a focus on outcomes over process, and accountability attached to performance on standards-based assessments. Our education systems are built on learning standards. While that has been beneficial for establishing a strong foundation for learning, it also limits what kids learn. Often what teachers teach typically excludes any learning content that can’t be directly tied back to a specific standard. This is detrimental to my vision for education and learning, where children are intellectually curious and have the tools and self-efficacy to pursue clarity rather than only correct answers.

For example, in reading comprehension, there are no standards for building knowledge, yet knowledge is essential for robust comprehension. Given that, if I stick to only what is in the standards, then I’m missing out on a key aspect. Also, this checklist mentality replaces intellectual curiosity and the rewards that come from finding clarity when there was once confusion. AI can potentially provide new opportunities for remedying some of these systems that have slowly eroded children’s joy in learning.

For example, AI could support assessing content that may not have been able to be assessed through item-response theory models. A thoughtfully-designed AI assessment tool could engage in conversations with students and map their knowledge base to identify where they have depth of knowledge and where they have more superficial knowledge. This is not something that has been assessed previously, so it hasn’t been a focus of instruction. All too often what is assessed is what is taught, so if we are able to assess a wider range of content in more authentic ways, the hope is that teachers will also teach the same.

Relational Learning: Sydnor Hain (they/them) (Chapter 3) argues that relational ethics matter more than rules. How does your approach to AI in education prioritize the parent-child relationship over the “algorithmic efficiency” of a curriculum?

Whitney: I approach AI in learning through a relational lens. While it can make the creation of learning materials more efficient, its real value is in creating more space for parents and teachers to be present with children. When AI tools handle routine tasks or help generate materials, it allows adults to better notice, interpret, and respond to a child’s thinking, which builds trust and respect through care. If an AI tool allows a parent or teacher more time to focus on a student, then it’s worth using. If the tool bypasses that relationship and goes direct to a student, then it’s not.

The power is in the hands of the student. That’s why protecting the heart, the relationship with learning, of the young learner is essential.

Part 4: Governance & The Human Signal (Cassandra)

Governance for Young Minds: When using LLMs with young children, what specific safety boundaries or "governance" practices do you implement to ensure they are using the technology safely without sacrificing their privacy or digital identity?

Cassandra: When I think of safety and LLMs, I think of privacy, and I also think of well-being. From a privacy perspective, if I’m using an LLM for my child’s learning, the only identifying information that I use are their first names. I never send images of them or anything else, and that’s what’s comforting to me. I also think it’s important for kids to understand things like sycophancy, hallucinations and homogenization.

From a learning perspective, it can be harmful to let a kid use AI without them understanding the nature of how it works. It means they might not be challenged, they might rely on inaccurate information, or they might not value more complex or divergent thinking - including their own.

The Analog Defense: In a learning environment that can easily become saturated with screens, what role does "going analog" using physical books, paper, and nature, play in your strategy for a balanced "Heart of Learning"?

Cassandra: When I think of analog vs. screens, two things come to mind: wellbeing and attunement. We need to understand what is healthy and supportive for most humans, with additional attunement to the individual. Humans need physical activity and human interaction; this is something we all share. But whether a kid should be in nature four hours a day or one hour a day will depend on the child. We all have that one friend who would love to have their nose in a book all day, and then there’s the other person that we know who learns through constant movement and tinkering. Some individuals might benefit from digital books and iPads, where another might thrive with paper and physical books. We are all beautifully different in that way.

What we all share, in addition to our needs of movement and connection, is the need to be free from addictive environments. We know that too much screen time is unhealthy and computer programs, even educational ones, can be intentionally engineered to be addictive which impacts the brain and the ability to function in the real world. Whether in the name of education or not, these are not good for our kids’ brains, in addition to being questionably effective.

Part 5: Interactive Closing & Promotion

The Substack Connection: As a member of the SheWritesAI community, what is a specific "Learning" or "Workplace Wellness for Parents" tip you’ve shared on your Substack recently that helps families stay grounded while exploring these new tools?

Cassandra & Whitney: We need to define AI for kids: What is it? How and why was it developed? How does it work?

1. We need to demonstrate for children common uses of AI.

2. We need to help children recognize what AI does well and not, including what to avoid when using AI.

3. We need to introduce children to various tools that are available to them and tools that are restricted and why.

4. We need to teach children how to use AI responsibly. This includes:

   1. Recognizing when content is AI generated

   2. Fact checking and evaluating AI

   3. Understanding the environmental, social, and economic implications of AI use

   4. Understanding privacy and safety concerns when using AI

The Final Message: If a parent or educator takes only one lesson from your chapter to help them avoid educational burnout and stay connected to their child’s learning heart this week, what do you hope it is?

Cassandra & Whitney: See, hear, and respond to the student in front of you and value the process as well as the outcome.

“If an AI tool allows a parent or teacher more time to focus on a student, then it’s worth using. If the tool bypasses that relationship and goes direct to a student, then it’s not.”

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Why This Matters

Cassandra & Whitney Whealdon’s perspective is a vital reminder that the “human signal” in education is relationship and attunement, not just data delivery.

• Valuing the Struggle: They argue that if we focus only on “getting it done” via AI, children lose the ability to access a “flow state” and the satisfaction of solving a hard problem. A disciplined framework protects the “productive struggle” as the place where true learning happens.

• The Assistant Principal Effect: They reframe AI as an “assistant principal” that handles the “ecosystem tax” — the hidden cognitive load of administrative tasks and content generation—freeing parents to focus on the emotional and relational needs of their children.

• Relational Governance: They prioritize relational ethics over algorithmic efficiency. Their rule of thumb is simple: if a tool creates more space for the adult to be present with the child, it is worth using; if it bypasses that relationship, it is not.

• Digital Defense for Young Minds: Their work provides practical safety boundaries, from protecting a child’s digital identity to teaching them to recognize sycophancy and hallucinations so they remain the directors of the technology rather than its passive consumers

Thank you, Cassandra & Whitney Whealdon, for your thoughtful and deeply grounding contribution to this conversation. For readers looking to protect the "human spark" in their homes or classrooms, their chapter in AI Everywhere, Volume 1 offers a beautiful reframing of what it means to learn with heart in an automated world.

Don’t miss their ongoing work and tips on their Substack, where they share practical strategies for families, such as defining AI for kids and helping them recognize when content is AI-generated. Their final lesson is one we should all carry into the week: “See, hear, and respond to the student in front of you and value the process as well as the outcome”. I personally highly recommend their approach as a vital “analog defense” for any parent or educator navigating this new frontier. check their newsletter here Whitney newsletter & Cassandra

And if you’re interested in more conversations like this, consider subscribing to She Writes AI. I’ll continue sharing insights from the voices shaping the future of AI, including contributors from AI Everywhere, Volume 1, where 26 women from across five continents explore how artificial intelligence is changing the world we live in, and how we can change it for the better.

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References

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