About

I’m Oliver Holloway, an experienced educator and homeschool coach with a background in progressive, student-centered education. I’ve taught learners of all ages—from infants in Montessori classrooms to college students—and I use that diverse experience to empower homeschooling parents like you. My passion is helping you create meaningful, effective learning experiences for your children.

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I hold a BA and MEd from Goddard College, and I’m currently completing a doctoral program in Education Leadership at Fielding Graduate University. My work is also informed by coaching, contemplative practice, and decades of experience with progressive education.​

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Homeschooling parents juggle many roles—teacher, parent, curriculum planner—often without the support system that traditional schools have. I understand how overwhelming that can be. That’s why I offer evidence-based guidance and practical strategies to help you succeed as your child’s educator.

 

What Sets Me Apart

• Broad Teaching Experience: I’ve worked with learners from early childhood through college, giving me insight into every stage of development.

• Progressive Education Roots: Raised in student-centered schools and now pursuing a doctorate focused on innovative, learner-driven models.

• Homeschooling Advocate: I understand the unique challenges of homeschooling and support child-centered, alternative approaches.

• Personalized, Judgment-Free Coaching: Every strategy is tailored to your family’s needs—evidence-based, flexible, and respectful.

 

My goal is to help you feel confident and empowered as your child’s educator. I look forward to learning about your family’s story and being a supportive partner on your homeschooling journey—listening to your needs, sharing proven strategies, and cheering you on. Let’s connect and make your homeschooling experience the best it can be!

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Curious if we’d be a good fit? I’d love to connect.