Maria Montessori’s and John Holt’s work intersect in their focus on letting a learner’s intrinsic motivations be the primary guide for their education, though both educators took different routes to achieve that end. Montessori’s ideas are being adapted by some to meet the growth of the homeschooling movement and the organizer of the Montessori Homeschool Online Conference asked me to talk about some general principles I’ve learned as an homeschooling advocate and father that can benefit parents who are new to living and learning with their children at home. It is a workshop called “Special Tips for Your Homeschool Journey,” where I describe, for beginners, how living and learning in your community can be, and has been for millions of families, a satisfying and bonding experience that nurtures lifelong learning without turning your home into a miniature school.