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problem writing reflection-type essays (wait till he tries to write his college apps!) because he is an introvert; the teacher suggests that he take a step back and write such things from another perspective, and that would be fine... What words of advice and comfort can I give my son to boost his confidence in writing
NotherBen, as your son seems to be a strategist at heart, investing time in seeking alternate methods to achieve things, the books of Elizabeth Wissner Gross come to mind. Two for parents, one for kids but you may want to read it first
What High Schools Don't Tell You and Other Parents Don't Want You to Know, What Colleges Don't Tell You, and Other Parents Don't Want You to Know, and Write Your College Essay in Less Than a Day. These books help parents and kids see that there are many activities helpful to kids when looking forward to college, and many approaches to essay about them.

In addition to being an author, Elizabeth Wissner Gross is an educational strategist coaching for college admissions.