As artificial intelligence becomes increasingly embedded in education and the workplace, the challenge is no longer whether students should use AI, but how they can use it without outsourcing the critical thinking that learning is meant to develop. On this episode of Just Thinking..., host Kevin Dougherty speaks with Jordan Wolff, CEO and Co-Founder of Typed By Hand, about finding the balance between human intelligence and artificial intelligence. Drawing from more than a decade in education, including experiences as an English teacher, high school principal, international educator, and edtech leader, Wolff argues that schools can embrace AI while still protecting student authenticity, creativity, and independent thought. Their conversation extends well beyond technology. Wolff reflects on teaching and leading schools in South Korea, China, and the United States, and how those experiences shaped his belief in multiculturalism, curiosity, and learning from people with different perspectives. Dougherty shares his own experiences leading diverse schools, emphasizing the importance of helping students recognize what they have in common and approaching others with a desire to understand before being understood. The discussion also explores opportunity and professional reinvention. Wolff describes his transition from the classroom into edtech and roles with organizations including Houghton Mifflin Harcourt, Lexia Learning, Instructure, and LinkedIn. His career, he says, has largely been shaped by a willingness to say yes to unfamiliar opportunities and recognize how transferable educators' skills can be outside the classroom. That philosophy ultimately connects to the mission behind Typed By Hand. Rather than treating AI as something schools need to eliminate or attempting to detect AI-generated work after the fact, Wolff advocates for transparency at the point of creation. The goal is to give educators visibility into what comes from the student and where AI played a role, while allowing students to develop the AI literacy they will need in the workforce. His own LinkedIn writing follows the same principle, openly identifying when AI assisted with editing or imagery while distinguishing it from his original writing. For Dougherty and Wolff, the future of education lies somewhere between rejecting AI and surrendering human thinking to it. AI can be an effective collaborator, but students still need opportunities to struggle with ideas, create, problem-solve, and think for themselves. And as the conversation closes, Wolff brings the focus back to educators themselves, calling for greater patience, grace, and appreciation for teachers carrying an increasingly complex workload.
