Every year, back-to-school season creeps up on me. It’s the joy of anticipation of warm weather, the beach, the sun, beautified by the dull gray that is the norm in the Midwest most of the year. This year’s summer also meant facing wildfire smoke, a random parasite affecting the lettuce, and multiple heat waves. It just felt like I’d never really had a moment to breathe and appreciate what this season is at this stage of my life.

The point of this is how every year, July 5th marks my slow slide into the illustrious world of back-to-school. Call it being a masochist. Call it nostalgic, but in my journal entry on July 6th, I’d already called it back-to-school season. The season of life may look different, but in my soul it’s still a bit of a heightened anxiety and yet another transition.

This particular one hits different, though.

Parenting for what feels like the last time.

It’s the last one. The last time I get to feel that specific ache of watching a summer close out, because after this, the back-to-school seasons stop belonging to me in the way I’ve grown accustomed. There’s a version of anticipatory grief in that, wrapped in a small quiet mourning for the end of a stage I didn’t realize I’d miss until it was closing. This is the last summer of ice cream cones and “what are we doing today,” and next year that question gets answered by someone else’s calendar, a roommate’s schedule, a job, a person she’s dating, who knows. Parenting doesn’t end when this stage does. But this particular chapter of it does, and I don’t have anything left to do with it once it’s gone.

There’s excitement tangled up in that grief too. We’re walking into a different kind of relationship now. One where I’m not packing her lunchboxes or managing her day-to-day. One where a trip together is just a trip together. Two people choosing to spend time together in a place instead of one person managing the logistics for the other.

Parenting never warns you how many times you will pivot toward a final destination that is simultaneously thrilling, mortifying, and, dare I say, gratifying. The kiddo’s a senior, and now it’s about choice. Which institution do you desire to make an entry-level splash of adulthood a part of? Even more so, where do you want to live? I think that’s the real question of college shopping. When you enter adulthood, where do you want to be?

The college experience

College is about the experience as much as it’s about the education, and choosing is a big choice. Our journey took us to my favorite big city, Chicago, well, more specifically Hyde Park, to the University of Chicago. Hyde Park is a beautifully green, historical neighborhood filled with neo-Gothic architecture, and in fact, the college itself is a registered botanical garden. This feels like a storybook ending to childhood. A way to beautifully go about searching for that higher knowledge that’s going to challenge you, push you a little bit forward, but give you a beautiful landscape to frolic through when the ground has thawed.

We toured. We soaked in the allure of campus. Then we did what any two people who love pen and paper do in a new city: we went hunting for a good pen. We started at Paper Source Lab on State Street, and by the time we were chasing down Field Notes, we were nowhere near where we started. Which is how I ended up on a bike…

Let it be known, biking across downtown Chicago with a frozen shoulder and a forty-pound backpack is not a great plan.

It sounded fine in theory. We grabbed a Divvy instead of a Lime, so a scooter sat right there, mocking us the whole time, and no, we did not learn that lesson until later. The bike lane through downtown starts lovely, green paint, a nice little divider between you and traffic, all very promising. Then you hit Greektown, and the divider… ends. No warning, no gentle taper. You were protected, now you’re in a pencil-thin lane with a dotted line next to a truck that is FAR too big for this street. My GPS, naturally, chose this exact stretch to lose its mind. Re-routing, re-routing, re-routing, while I white-knuckled the handlebars with one half numb arm and the other gripping my cell phone for dear life.

The saga

I bring this up not just to complain, because honestly it’s funny in hindsight, but because I couldn’t turn the advisor part of my brain off even mid-panic. I noticed exactly where that bike infrastructure worked and where it fell apart, the same way I clock those things in every city I visit. Chicago is trying, genuinely trying, to build a city that moves people around sustainably. Some stretches are done beautifully. Others are an afterthought bolted onto streets that were not built for it. That’s the job, though, even on a family trip. You experience a place and take notes the whole time. Why? Because somewhere down the line, that’s exactly what a client is going to need to hear from you.

We made it, eventually, panting and grateful, and once we’d Ubered to our hotel in Hyde Park and dropped our things, we walked over for Mediterranean sandwiches on housemade sourdough. For a moment I forgave the whole city for the bike lane situation. Hangry and on a bike is a new low I never want to reach again. Then we ducked into Powell’s for used books. Certain seasons of life are for theme parks and character hugs, and others are for watching your kid’s eyes light up over a Socrates printed in 1904 for six dollars. A find now destined to become a gift for one of her favorite teachers during senior year.

In the end

The day ended with a visit to the Obama Presidential Center. I’m not here to make this about politics. Yet, I will say it’s rare and worth noticing when we get to watch someone honored for the sheer scale of what they contributed to the world while they’re still here to see it happen.

Great thinkers don’t always hold political office, and the ones who do are so often reduced to just that role, when what actually made them matter was the thinking itself.

My mom grew up on the South Side of Chicago, so watching this rise in that same part of the city meant something extra for me. There’s an indoor basketball court; a rooftop garden the public can actually us; a wooden, imaginative playground padded soft enough for little feet; wetlands trail; and water features kids were shrieking their way through in the heat. Families were everywhere, picnics spread out on blankets, kids tearing across the playground, everyone just together, enjoying the sunset outside. A sense of community is exactly what you want a kid to feel on a college visit, even if they don’t know that it’s the lesson. Because that’s what college actually is, underneath the syllabus and the dorm tour, it’s about finding your next community. Watching one built with intention, in the same neighborhood my mom once called home, was the closing of the loop.