Member-only story

Dakota Montgomery
3 min readOct 30, 2019

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The Challenges of Homeschooling Someone Else’s Kid

Photo by Chris Liverani on Unsplash

Technically, I’m a tutor, but for one student, I’m his only teacher.

Full disclosure: I am not a teacher. I started tutoring when I was 16. Through the Air Cadet program, I had experience in teaching, and I was academically strong. Combining these things to make some extra cash seemed like a pretty obvious conclusion. Once I started post-secondary, tutoring became a way to supplement my grocery budget. I trained as a commercial pilot and started teaching groundschool at various flight schools around the airport. At one point, teaching was a substantial part of my income.

Life eventually took me down a different path, and I stopped tutoring for two years or so. Divorce and the accompanying crippling debt caused me to post new advertisements and start looking for new students last fall. In February, I started working with a teenage boy who we’ll call Dave. Dave hates school. He has ADD and some learning difficulties but is not unintelligent by any stretch of the imagination.

We started just with math. Dave was sitting around a Grade 5 level and, within six months, he was at a passable Grade 9 level. So this year, we are doing his entire Grade 10 together. The system is working well. Everything moves at his pace, we spend more time on things when he gets stuck, and he can text me a photo of a question and ask for help. Our relationship is…

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Dakota Montgomery
Dakota Montgomery

Written by Dakota Montgomery

Crazy dog mom, mental health advocate, project manager and writer

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