Between the DJ and the Driver

On Road Trips, College Visits, and Becoming

A few weeks ago, Henry and I took a road trip to Philadelphia. The intention I set for the trip was to give him a broad-based sampling of college campuses, much like I advise my client families to do when they begin thinking about their college lists. His sister attends UVM, a public university he’s visited many times, so Henry already has a clear sense of what that kind of campus looks and feels like. For this trip, we chose something different: a suburban Catholic university, a small liberal arts college, an Ivy, and a city school with a co-op program.

We live an hour from Boston and could easily have stayed close to home, but Henry loves Philadelphia, and I figured it would be good to spend uninterrupted time with him. He was the DJ. I was the driver. We set off on a Sunday morning with plans to arrive before dinner.

Henry is an artist and a foodie, so museums and a trip to Reading Terminal Market were high on my list. We got into town too late for either on Sunday, and a packed schedule of campus tours meant we had to let the museums go this time. But Philly isn’t far, just a little over five hours, and we’ll be back.

The drive down was its own kind of adventure. Henry’s musical tastes are wonderfully diverse: Drake, Daniel Caesar, and the Eagles alongside Smashing Pumpkins, Jack Johnson, Steely Dan, Marvin Gaye, and Mount Joy. We had time to sit in comfortable silence, time to catch up on the details of his life.

Our Airbnb was near Drexel, so we walked the campus that first evening in search of dinner. I made a point of taking my counselor hat off so we could have this experience as mother and son. It was fun imagining different possibilities for him in a city we loved but didn’t know well. He immediately understood what a city campus without gates feels like, and he didn’t mind it at all.

Over the two days we had together, we didn’t rush. We wandered. We bickered about parking and timing, the way you do when you travel with your kid. We paid attention to things admissions websites can’t show you: the vibe and rhythm of students on campus, the surrounding neighborhoods, the social spaces, the bulletin boards. As we walked, I knew Henry was quietly asking himself: Could I belong here? Could I be happy here?

We did make it to Reading Terminal Market. Walking through it was a full sensory explosion. We stopped at Beck’s for Cajun food and split a gumbo and cheese fries. We brought bread pudding back to the Airbnb. We stopped at Pearl’s for oysters on the half shell, and picked up donuts at Beiler’s because, honestly, you just have to.

What surprised me most was how much we talked. We talked about school and crew, about his leg injury and how quickly he’d recovered, thanks to his commitment to physical therapy. We went deeper than the surface stuff we get caught up in as we rush through our days: his friends, his summer goals, the AP work he was doing. As we traveled, I was quietly celebrating how much he’s grown. He’s my baby, after all.

“This feels too small,” he said at one small liberal arts college, realizing the student body was smaller than his high school. We crossed it off the list. “This one’s incredible... but what are the actual chances?” he said as we left Penn. So we had the conversation he knew, given who his mother is, was coming eventually. We talked about single-digit acceptance rate schools and how they can function more like lotteries, where getting in feels random and lucky rather than strategized and earned.

And then I went on a professional rant, because I couldn’t help it. I talked about how waitlists have become less about the student and more about institutional yield management: a holding pattern to protect rankings and balance financial aid budgets. I talked about how it kills me to watch students with nearly perfect profiles spend months suspended in that in-between space, not denied but not accepted either. We talked about how demoralizing the business of admissions can feel, even for students who’ve done everything right.

We talked about how much harder it’s all gotten since I went to college, and what it might feel like to be “good enough” everywhere and still not have a home. And then we talked about money, because we had to. In our situation, real numbers matter. Merit aid and need-based aid would be major factors in any decision we made. We talked about need-blind admissions and what “meeting full need” actually looks like in practice.

Henry listened and asked good questions. He’s a smart, practical kid. He started thinking about his list not just academically and creatively, but financially. That was probably the most powerful part of the trip: watching him begin to understand the intersection of his aspirations and the many layers of reality we’d need to navigate together.

I also recognized something in myself. I’ve held the role of guide in this process for so many other families. But that week, I was just his mom, watching and listening and hoping he finds a place expansive enough for who he’s becoming. I was the parent I usually counsel.

Somewhere between his DJing and my driving, between the deep conversations and the easy silences and the singalongs, I found myself reliving his childhood and celebrating the man he’s becoming. He’s thoughtful, analytical, and honest. Confident in ways that feel like a gift I didn’t know I was waiting to receive.

I’m looking forward to more road trips like this one for my boy and me. I really am.