re: HS aged son has expressed interest in joining the military

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If he can get into any of the service academies, absolutely go. He will get a great classic education and will have a more rewarding enlistment.

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I had an initially awkward but incredibly informative conversation with an Air Force Academy Graduate in April this year.
He's a young black man originally from a poor Philadelphia neighborhood. He said a local politician came to his high school and sought him out after the ASVAB test. They did the whole dog and pony show of "getting a smart black kid out of the ghetto" and sent him to the UNITED STATES AIR FORCE ACADEMY.
He only did it to make his parents happy. Now, 4 years later and a month from graduation, he's miserable and dreading the next 8 years of his life(5 years active and 3 years reserve).