I know the conventional wisdom is that even if you have perfect everything, you're just as likely as not to get rejected by Harvard. But, I mean....some people get in. At what point do you decide it makes sense to give it a try? My son's a junior this year, and we have a pretty good idea of what his safety and matches look like, but I'm not sure how much of a...well, REACH his reaches should be (obviously the final decision is his, but I'm hoping to steer him in a realistic but ambitious sort of direction). I didn't have a lot of guidance (or any) on this when I was applying to college and later to grad school, so I went the route of....avoiding rejection at all costs. applying to exactly one school that I knew I would get into for undergrad. And then for grad school I thought I was applying to long shots, but I got in everywhere I applied and wondered if I should have aimed higher.
Anyway, so....suppose a kid has a very strong transcript and test scores, within range for Ivy admission, and decent but unremarkable extra-curriculars--do you encourage them to give Harvard or Yale or wherever a shot (assuming they're interested) in the hopes that something in particular about them might be what the school is looking for or that some random admissions person happens to really love their essay?