SEND Parenting Podcast

EP 144: When School Doesn't Fit: The Homeschool Solution


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What if the problem isn't your child—it's the system?

If school mornings feel like a battlefield and your child is shrinking under constant pressure, this episode offers hope. Dr. Olivia sits down with Cassie Olguin—homeschooling mother of three (including neurodivergent twins) and Outschool education lead—to explore what learning looks like when you step outside the traditional classroom.

Cassie's Journey: From early motor delays and night terrors to navigating autism, ADHD, OCD, and anxiety, Cassie shares the messy, real path many families walk. You'll discover how labels became tools for changing the environment—not verdicts on her daughter's potential.

What You'll Learn:Charter homeschooling demystified – How oversight works without rigid timetables
Personal pace over grade levels – Why your child doesn't need to "keep up"
Practical strategies that worked – Delaying reading until readiness, reframing maths as everyday numeracy, using interest-led classes
Outschool's magic – Live sessions with expert tutors (think: veterinary science with a practicing vet, maths through Minecraft, virtual history escape rooms)
Redefining success – Why standardised tests don't measure intelligence, creativity, or resilience

The Twin Perspective: Perhaps most moving: Cassie's twins are taking completely different educational paths through adolescence. One thrives with college-level work; the other flourishes at a gentler pace. Different tracks, equal worth.

Key Takeaways for Parents:

  • Start without decision paralysis—you don't need to figure it all out at once
  • Find your support network and share resources
  • Outsource subjects you don't love (yes, really!)
  • Mastery-based learning vs. arbitrary grade levels
  • Small online classes that respect sensory needs and attention spans

If your child is struggling, this conversation offers relief, clarity, and a roadmap forward.

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Terms: Offer expires 12/31/25 at 11:59 pm PDT. Registered Outschool account required. Enter code at checkout for $40 USD off a new membership. $40 off membership only valid for first-time memberships. Limited to the first 500 users. Cannot be combined with another offer. Subject to Outschool's Terms of Service

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📩 Contact Me
If you would like to get in touch, you can email me directly at [email protected]
I would genuinely love to hear from you, especially about the topics you would like covered and the guests you would love to hear from in 2026.


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SEND Parenting PodcastBy Dr. Olivia Kessel


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