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I've spent $11,000 this year on my son's baseball career. I know his batting average, his ERA, every coach's assessment of his potential. Last Sunday on the three-hour drive home from a tournament I asked him what he actually wanted to do with his life. He said "I don't know, Dad" and put his headphones in. $11,000. I don't know what my son wants. I've been a baseball parent for six years. Jake is eleven. Travel team since he was eight. I've driven him to 47 games this season. I've sat in bleachers in four states. I know his stats better than he does. .312 batting average. 94% fielding rate. His coach told me last March he has Division I potential if he keeps developing. Last Sunday on the way home from Columbus I decided to do something I'd never done before. I asked him the questions that actually matter. What are you most proud of that has nothing to do with baseball? What do you actually worry about? What do you want your life to look like when you're thirty? What's something you've never told me? I watched my eleven-year-old son stare out the passenger window. Jake: "I don't know." Jake: "Nothing really." Jake: "I haven't thought about it." Jake: headphones in. This is the kid I have been driving to practice three times a week for six years. I know his throwing mechanics. I know his batting stance. I know his fielding percentage to three decimal places. I don't know what he thinks about. I pulled into the driveway and sat there after he went inside. $11,000 this year. Equipment. Team fees. Tournament hotels. The pitching coach I hired in February. I've invested in every part of his game. I don't know who he is outside of it. That night I asked my wife the same questions about Jake. "What does he actually worry about?" She thought about it for a long time. "Baseball stuff. School stuff." "Specifically." Silence. "I don't know," she said. Six years of being present for everything. Neither of us knew him. The following weekend was the regional tournament. I was in the parking lot talking to another dad — Marcus — when his son Eli came running over. Eli is nine. Two years younger than Jake. He stopped in front of Marcus and said: "Dad, I was thinking — what do you actually regret? Like in your whole life so far. I've been saving that one." Marcus laughed. "Where'd that come from?" Eli held up a small card. Marcus took it from him. He read the question out loud. Then he answered it. For real. He told his nine-year-old son about a decision he'd made at twenty-four that he'd spent twenty years carrying. Eli listened with his elbows on the car hood and his chin in his hands. They talked for fifteen minutes in a parking lot. Jake was on his phone next to me the entire time. I walked over to Marcus afterward. "What are those cards?" "QuestKids. His mum found them. We do a few in the car before every game now. He asks to do them. I never have to suggest it." He paused. "Last week he asked me what I was most afraid of. I didn't know how to answer. I sat there and he waited. Nobody had asked me that since I was his age." I ordered them before the first pitch. Week 1: I didn't make a speech about it. I put the box in the cupholder on the way to practice. Jake looked at it. "What's that?" "Questions. Want to try one on the way?" He picked one. "If you could be really good at something you've never tried, what would it be?" He thought about it. "Architecture," he said. "Like designing buildings." I looked at the road. Six years. "Architecture." He'd never mentioned it once. Week 3: Jake started picking cards before he got in the car. He had one ready when I picked him up from school on Thursday. He asked me first. I was learning too. At 43 years old I was answering questions in a car that I hadn't thought about since I was eleven. Jake asked me what I was most scared of. I told him the truth. That I was scared of waking up at sixty and realising I'd spent my whole life optimising for things that didn't matter. He was quiet for a moment. "Is that why you push the baseball so hard?" I kept my eyes on the road. "Maybe," I said. "I like baseball, Dad," he said. "I just don't want it to be everything." Three weeks in a car. More real conversation than six years of bleachers. Week 6: Jake's school counsellor called me on a Tuesday. "Mr. Henderson, I wanted to reach out about Jake. Something has shifted with him this semester. He's participating in ways I haven't seen before. Last week in our group session I asked the students to describe themselves in three words that had nothing to do with school or activities. Every other student froze. Jake said: 'curious, careful, and still figuring it out.' I wrote it down. Whatever is happening at home — it's showing up here." I sat in my car after that call. Three months ago he answered every real question in one word. Now his counsellor was writing down what he said. Last month: Jake asked if we could do cards at dinner. In front of his mother. Without being asked. He pulled one for her. She answered it. Then she pulled one for me. Then I pulled one for Jake. We sat at the dinner table for an hour and a half. Nobody looked at a phone. My wife looked at me afterward. "Why did it take us this long?" I didn't have an answer. A connected kid isn't one who has the most opportunities. A connected kid is one who knows someone actually wants to hear him. If you're a parent who knows your child's stats but not their dreams... If you've spent thousands on their development and nothing on actually knowing them... If you've been in the car together for hundreds of hours and done nothing but drive... The time was always there. The question wasn't. Before he stops expecting you to ask. Before the headphones go in and stay in. Before you're sitting in a parking lot watching someone else's kid talk to their father for fifteen minutes and wondering what you've been doing for six years. I spent $11,000 last year on my son's baseball career. A $39.90 card deck told me he wants to design buildings. The cards that gave me my son back are called QuestKids. 150 questions that work in the car, at dinner, at bedtime. The ones he's been waiting to answer. The ones you've been driving past for years. Two questions on the way to practice. That's all it takes.