My biggest challenge? Dealing with never being able to teach my two children anything together. People said, "Oh, your kids are only X years apart - you can teach them together!" As it turned out, one child is gifted, the other is challenged. So I had to learn:
1) flexibility
2) to let go of my expectation that I could "hand down" curriculum to the younger child - we sell the older child's curriculum every single year
3) to teach to two children with completely different learning styles
4) to be extremely protective of my time and eventually say "no" to the church - juggling two students and running a household is more than a full-time job
5) to stick to my guns in spite of what "everyone" says about how public schools are best for gifted and will "fix" the challenged
My second-biggest challenge came this year when I realized I am simply not as quick with memorization as I used to be. So I have to be content with "flunking" Latin as I work beside my child who is absorbing the language like a sponge. This child learns best when interacting with me - quizzing me, correcting my papers, discussing concepts with me, etc. This means I have to keep up to a certain degree. I learned if I understand the concepts, I'm OK. It's turning out that our strengths and weaknesses are complimentary, so we pretend we're taking the class together and we're "study buddies."
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