The Most Important Question to Ask Your Teen

Three years ago, when my eldest was a junior, I fretted over SAT prep, financial aid, and the best manner to get university coaches to view his baseball video. But I have different concerns with my secondborn.

teen boy on staircase
This is the most important question to ask your teen.

My son is in his junior year of high school

I pop my head into my son’s room to say goodnight and am not surprised to discover him in the same position I find him almost every weeknight: propped up in bed, laptop open, books strewn haphazardly across the floor, 3×5 cards littering the down comforter. Often, he engages in an hour or two of FaceTime with classmates because, apparently, friends don’t let friends cram for Biology alone.

“Are you sure he’s really doing his homework up there?” my husband has inquired more than once. But the fact that the kid is juggling three A.P. classes with sports and making top grades effectively squashes any questions about whether or not he’s putting enough time into his assignments.

Quite frankly, that is the least of my worries.

My son, a few months shy of 17, embodies that obscure, in-between enigma that is, almost by definition, a teenager; by no means is he a child, yet it’s clear he still has many miles to log before turning the corner to adulthood. As his mother, this makes the path I attempt to navigate feel increasingly tenuous.

Halfway through his junior year of high school —as grueling as all the experts warn it will be — my son’s goal is to earn a baseball and/or academic scholarship to a top university.

On this particular night, he folds down his laptop screen and motions me into the room. “I need to talk to you about something,” he says solemnly. “Coach asked me today if I want to pitch this year, and I told him I’d let him know. I wanted to ask you first.”

He looks at me expectantly, and I recognize the plea lingering beyond his eyes. I’ve seen it a thousand times before.

He is waiting for me to tell him what to do.

It would be easy for me to suggest that he continue pitching. For a moment, I consider encouraging him to keep cultivating his special talent, which had become evident when, at age eight, he was hurling the ball across the plate and striking out 11-year-old opponents. The same aptitude that, as he entered high school, everyone insisted was sure to be sought-after by the college scouts, especially when paired with my son’s 6-foot-4-inch-and-still-developing frame.

But the rapid expansion of that physique had resulted in a growth plate fracture to his elbow when he was a freshman, forcing him into a full-arm cast and out of the lineup that spring. While the X-rays had long proven the injury to be completely healed and the doctors had given him the green light to return to the mound, he had done so only sporadically and always with trepidation, convinced he would re-injure his arm and require surgery.

Gone was the exhilaration of the strikeout, replaced by lingering fear. The bone had mended; his psyche had not.

So, considering his apprehension, it would seem equally acceptable for me to urge my son to abandon pitching altogether to focus instead on playing third base, a position he loves.

Yet I suggest neither option. Instead, I call upon the four utterly simple words I have relied on increasingly frequently when talking to my teen.

This is the most important question to ask your teen

What do you think?” I ask.

My son doesn’t recognize the magnitude of the question. He doesn’t appreciate how cavernous those four tiny words are. They stretch far beyond his baseball future, winding past the burden of college decisions and the anxiety over standardized tests — assessments that today feel so frighteningly heavy, so undeniably significant.

My younger boy has always been somewhat of an oxymoron; in certain situations, he is eclipsed by confidence and self-assurance yet immobilized by uncertainty in others.

On the baseball diamond, he’s a natural leader. His deep, booming voice commands teammates where to cover, remind them of the number of outs and signals the spot where the batter last drilled the ball. His confidence and poise are undeniable atop the sanctuary of that smoky orange clay dirt. He is also opinionated, at ease speaking in front of crowds, and has a reputation for conversing with his friends’ parents far beyond the typical teen articulation of “hello” or “thanks for having me over.”

Yet this same man-child requires painstaking directions before attempting to perform the simplest new tasks — popping the hood on the car, attaching a file to email, swiping an ATM card.

“How long should I reheat the pizza?”— he waits for my answer, even though he has successfully executed this activity dozens of times.

I suspect he’s just being lazy with his brain in such instances. Why exert energy thinking through a basic question when somebody else can answer immediately? But other times, especially with more consequential decisions, it is painfully clear that he requires affirmation to escape a self-induced paralysis.

Over the years, I’ve struggled to understand the foundation of his uncertainty to identify why he seems stuck in his head. Is it simple anxiety? Fear of failure? Or perhaps that ever-evolving sense of overachievement, the tendency that worries me most. I feel like a broken record, constantly reminding him that he doesn’t have to be perfect, emphasizing that his effort counts; if he spends hours studying for a test or puts 100 percent into writing a term paper, then the resulting grade is irrelevant, even if it’s not the A he expected.

And then there is the possibility that the bulk of his self-doubt could be attributed to the fact that the very blood pulsating through his veins — carrying oxygen between his heart and his brain and up and down his gangly 6’4” frame — is 100 percent teenager. Is it too much to hope that his need for validation is nothing more than the tangle of hormonal and physical changes churning to mold his sense of independence and identity?

When faced with a decision, I want my son to be able to fire off a mental pro/con list like he maps out DNA before a Biology test, pausing to distinguish the unique characteristics of the chromosomes, the nucleotides, and the alleles. I want him to work through a dilemma the way he analyzes his swing in the batter’s box. He knows, inherently now, when it’s slightly off, and he assesses every angle until he detects the hitch — is he reaching for the pitch, are his knees too tightly locked, is he shifting his weight to his front foot?

I hope he will find a way to channel these skills — the diligence he pours into his studies, the precision that fuels his baseball regime — into other aspects of his life. I want him to try something new and fail. Then try again.

Perhaps becoming proficient at trusting himself isn’t all that different; it just takes practice.

After all, my son knows he can’t review his flashcards once and expects to get a good grade on the test; he must continue self-checking until he can flip each card confident in the knowledge he has mastered. Likewise, he doesn’t take a single round of balls in the batting cage and call it a day; he works on his stance, bat position, and hand placement over and over until every facet ultimately folds into the muscle memory that will translate to successful execution come game time.

So armed with my four little words, I try to help him build up that same muscle memory in his gut — shaping and shifting and stretching his ability to trust it.

What do you think?

I watch him considering the words as he mulls over the pitching dilemma. “Well,” he says finally. “I know I don’t want to pitch in college. I want to be a position player. So maybe I should focus on that?”

He looks up at me, waiting. I gently guide him to delve deeper, to weigh the advantages and disadvantages, and to examine the potential outcomes of either choice. And most importantly, to help him understand that while there may be a thousand little choices to be made in the course of any given day, very rarely will any of them be life-altering. He will almost always have the opportunity to regroup, change his mind, and forge a different path. If my son embraces this lesson, it might release his mind from the binding gridlock.

He continues — partially out of habit, I suspect — to ask me inconsequential questions that I refuse to give in to, such as how long he should reheat a bowl of spaghetti (“What do you think?”), if he should hit off the tee or take out the trash first (“What do you think?”), if he should play in the travel ball tournament or take the weekend off (“What do you think?”). Other queries are more significant — like which colleges he will apply to or if he should join another school club to pad his resume —and merit deeper consideration and reflection. Still, my lead remains the same: What do you think?

Asking my son what he thinks is making him more confident

And while practice hasn’t made perfect, it appears to yield progress.

Tonight, when he asks me to sign off on his schedule for next year. I can’t mask my alarm when he has elected to take five A.P. classes. I can’t help myself from throwing out my unsolicited opinion. (Wait, did I say unsolicited?)

“This is quite an agenda,” I tell my son, choosing my words carefully. “I want you to enjoy your senior year. I don’t want you to be completely stressed out by this workload.”

But it looks good for colleges, he counters. And he’s heard that A.P. Psychology isn’t that difficult anyway. And he needs Physics and Government to graduate, so why not just take A.P. Physics and A.P. Government? He certainly seems to have thought all of this through.

You’ve worked so hard, I think to myself, worried that he will push himself to the breaking point. You don’t have to do all of this.

But he remains steadfast, vowing that he will drop one of the classes if the load gets too much.

So, veiling my trepidation, I sign my name on the form and pass it back to him, my endorsement of his decision magnified in solid black ink.

His decision.

Which is really all I’ve been hoping for.

More Great Reads:

Dear Mom of High School Junior 

About Melissa Tamberg-Heffron

Melissa Tamberg-Heffron is a former newspaper reporter who now predominantly writes technology-related articles and blogs largely about her three children (ages 20, 17 and 5) at Her work has been published on Scary Mommy/Club Mid, Mamalode and Ravishly, as well as in numerous newspapers and magazines.

Read more posts by Melissa

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