We moved east largely to be near our son Bobby when we finally, begrudgingly admitted boarding school was the best thing for him. I was determined to be a positive, supportive presence for him in ways I hadn’t experienced as a child.

I was what my parents called “too sensitive.” One disapproving, i.e., “not adoring” look made me feel like a failure for weeks. Since adoration was dished out sparingly in my house, this was clearly all my parents’ fault. I spent a lot of time moping in my room, saying, “Yeah, well, when I have kids, I’m gonna tell them they’re great.” And I did.

FYI, don’t let your children tear your heart out – I mean go to boarding school – unless you’re willing to let them make their own decisions, even wrong ones, like I did. I was a scholarship boy myself years ago. I routinely broke curfew, drank, and smoked to be accepted by the rich kids who really belonged there. I even stole to finance a visit to the rich girlfriend who was only dating me to hurt her parents.

Bobby’s mistakes seemed quaint by comparison: he lived on pizza and coffee, slept through classes because he stayed up all night with his friends, and skipped athletics because exercise was for the weak. But by the end of his junior year he was a strong candidate for some great schools. We visited some on a whirlwind college tour last summer. He was animated and engaged, poised and well spoken, seemingly on track for a seamless transition to the next level. I was feeling pretty good, parenting wise, until he lapsed into a sullen silence in the car on the way home.

Quick tip: when your teenage son lapses into a sullen silence, let him. I learned this the hard way.

“You’re pretty quiet. What do you need from me right now?”

“How should I know? I’m just a kid. I have no idea what I need. You’re the parent. Why don’t you, you know – parent.”

I know. I get a little misty myself just remembering it.

He watched upstate New York go by. I shut up. Half a county later, he said, “I was thinking about how one of your shortcomings as parents …”

“One of” our shortcomings? There was a list?

“… Is you never gave me any kind of work ethic. You never made me stick to anything.”

Really? Because I remembered the childhood where if I got back the time we spent fighting about homework, I could live another couple of years. But this was about his perception, not mine.

“So now I’m in this place where I can’t just coast, and all these other kids are doing way better than me because their parents taught them how to work. I spend most of my time feeling like a failure. I think of all the stuff I could have done by now and it’s like – I haven’t done any of it. And what sucks the most is, if I ever am going to do anything, I have to overcome an entire lifetime of conditioning.”

I made a joke to defuse the tension. Mine.

“On the up side,” I said, “it’s only been a short life.”

He looked like he might actually punch me. When he finally spoke, he had to stop every couple of words.

“Dad. So. Not helpful. So not the thing to say right now. You. Not what I need to hear.”

“But it’s crazy. You’ve done lots of stuff. What about the two math classes you taught yourself last summer so you could take AP calculus?”

He rolled his eyes.

“Dad, math is easy.”

For him, maybe. Monkeys with typewriters would finish “Hamlet” before I could do it.

“OK. How about that summer school teacher? Remember? He offered to write a college recommendation after he read your political science paper?”

“Yeah, but that was fun.”

“So basically, no matter what anybody else thinks, nothing you do is any good just because you did it. What can I even say to that? It’s not accurate, and it’s not healthy. It’s like, crazy?”

He looked at me like he was trying to decide if I was playing with his head.

“Dad. It’s all you ever do.”

So after years of doing the opposite of what was done to me, I reproduced myself anyway. I could just see him moping in his room: “Yeah, well, when I have kids, they’re not getting any praise out of me unless they do something great.”

That was then. A year later, the sullen boy who thought he was a failure is headed for the University of Chicago. He’s grateful for his sweaty summer job. He also works out, plays ultimate Frisbee and occasionally refers to himself as “a giant slice of awesome” – with irony.

I guess I didn’t do too much permanent damage.

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Portland resident Mike Langworthy, an attorney, former stand-up comic and longtime television writer, is fascinated by all things Maine. You can reach him at mikelangworthy@me.com.