I had asked if him if he planned on staying in high school forever. So, his look made sense but he managed to say, "No."
"What will you do next?"
"Go to college", he answered.
"I don't know if that's a good idea." I told him, pointing out his three Cs and report card comments that ranged from "doesn't turn in all his work" to "disrespectful in class."
"That's a very large investment you are asking your parents to make."
"They want me to go to college." he said.
"Of course, they do. But, they don't have to send you. College is a gift. It might make more sense for them to save the money for their retirement. You could get a job instead."
Now Kyle was looking at me like I was crazy. "What kind of job could I get without a college degree?"
"Probably a minimum wage job. You could also learn a trade or join the military."
"I don't want to do any of that. I want to make a lot of money."
"Ok, Kyle. Tell me the lifestyle you want to have when you are 40."
Kyle went on to describe the big house, two fancy cars, and boat he wanted. I then walked him through the probable monthly costs related to each. I added on utilities, groceries, insurance, social life, vacation, children's activities (he wanted 3 kids), college savings, responsible retirement savings, and taxes and came up with a salary equivalent of somewhere in the $200-250,000 minimum range needed for the lifestyle he was describing. (I should note that Kyle wanted to live in Westport, Darien, or Greenwich. So, those living in different parts of the country or different parts of Connecticut might not have such high salary requirements).
"How do people make that much money?" he asked.
I described all sorts of ways that people make money and pointed out that not everyone needed higher education to do so. But, most people who earned such income developed high level work skills and college was at least one way that people developed those skills.
Kyle was no longer looking at me with confusion. "I get it" was all he verbalized.