The Friction Is A Feature, Not A Bug: Teaching and Mentoring in the Age of AI

Those who have been following me for a while will know that teaching and mentoring are a Big Deal™️ to me. Before I got into tech I was a teacher, and still consider myself a teacher at heart. Being a teacher and mentor was never separate in my eyes from being a good programmer and engineer; on the contrary, teaching was a tool that helped me become better at my craft at every stage of the journey. But in the last few years, and accelerating in the last few months, the landscape for teaching and learning has been changing at a scary pace. The advent of LLMs and "AI" coding assistants has drastically shifted how we acquire engineering skills in ways that we are definitely not prepared for. All of that has prompted many thoughts and conversations, and I hope to distill some of them in this blog post. In true Talmudic fashion, this post doesn't contain too many answers and will hopefully leave you with more questions than you started with. But asking the questions is how we start these conversations, and these conversations need to be happening if we are to do right by the coming generation of programmers and engineers. Don't Spoon-Feed Me As a student, whether in Yeshiva when I used to spend hours each day poring over dense Talmudic legal debates and esoteric Chassidic philosophy or later while learning Rails and React at the Flatiron bootcamp, I quickly realized an uncomfortable truth about skill acquisition. My best, most profound learning never happened when a lesson went smoothly; it happened when I was painfully stuck, banging my head against a cryptic error message or wrestling with a concept that just wouldn't click (usually at 2 AM, fueled by cold coffee and sheer stubbornness). When you strip away that struggle, you get rid of the growth. And when you get rid of the growth, the learning just doesn't happen. Even if you memorize just enough to pass the test, "easy come easy go." Without that cognitive friction, the knowledge evaporates the moment you close you