A student recently asked me if it was acceptable that his AI chat session had veered off course. What began as a simple prompt became an increasingly specific set of questions, spiraling into what he called a “rabbit hole.” He seemed sheepish about it, as if learning tangentially were some kind of mistake. I couldn’t have been more pleased. This, I told him, is precisely the point.
Traditional education rewards linearity. Set objectives, follow the syllabus, color inside the lines. The textbook is stable, the learning goals are preordained, and deviation is called distraction. But learning has never been that obedient. It is recursive, exploratory, and often accidental. Some of the most profound understanding comes not from the direct answer to a posed question, but from an unexpected detour sparked by curiosity. With AI, students now have the power to chase those detours without waiting for office hours, a green light from the instructor, or even a good reason beyond “I wonder…” This changes quite a bit.
When students are asked to submit chat logs with AI tutors, what they’re really doing is offering a snapshot of their cognitive pathways. And more importantly, they’re showing us that they are learning how to learn. If the conversation ends where it began, I feel a twinge of disappointment. The best ones meander. They start with the assigned question, but then dig deeper, clarify a half-understood term, pivot to a related concept, challenge a definition, ask for an analogy, and sometimes loop back to the original point with far more nuance. These logs are not just records of content acquisition; they are evidence of intellectual agency. We can assess that.
In fact, we should assess that. The quality of learning is not solely determined by measurable learning outcomes, but by the process students undertake to arrive there. Are they passive recipients, asking AI to do the work for them? Or are they directing the tool with intent, steering the dialogue, probing deeper? The latter signals a kind of meta-cognition (thinking about own thinking) that is, ironically, hard to teach but easy to observe when it happens naturally.
This brings us to the brittle notion of the textbook. The textbook is a frozen artifact in an age of fluid information. It pretends to be definitive but is invariably outdated, flattened by consensus, and stripped of the lively contradictions that make real knowledge worth pursuing. If I worked for one of the big textbook publishers, I’d be worried. Not because students won’t read anymore, but because they might start asking better questions than the book is designed to answer. The premise of the textbook, that there is a “right” sequence of information to deliver to all learners, has been unraveling for years. AI may be the final tug.
Self-directed learning with AI does something more subversive than democratize access to knowledge. It shifts the locus of control. The student is no longer merely interpreting curated material but actively interrogating it, shaping the path, discovering relevance in real time. This undermines the gatekeeping role that institutions have long held. It’s not that professors are obsolete; they are needed more than ever as guides, critics, and curators. But the assumption that learning must be centrally planned is fading.
Of course, not all rabbit holes lead somewhere valuable. Some are tangents masquerading as insights. Some become compulsive avoidance of harder work. But that’s part of the deal. We don’t disparage writing because early drafts are messy. We understand that missteps are intrinsic to mastery. The same generosity should be extended to exploratory learning. The mess is the point.
And so, if a student gets lost in the weeds of AI dialogue, my response is not to steer them back to the path, but to ask what they found there. Did the journey refine their thinking? Did it unsettle an assumption? Did it spark a new question? If yes, then they’ve learned more than what was in the assignment. They’ve learned to follow the thread of their own curiosity, and that might be the most enduring lesson of all.
In a way, AI exposes the futility of pretending that education is a straight line. It’s more like a conversation with the world, and like any good conversation, it’s full of detours. We should celebrate the rabbit holes, not as distractions, but as destinations.
