CHICAGO— My wife’s off on a girls’ trip, and my son happened to have two days off work. That was all the excuse I needed. I booked a flight, packed a bag, and headed north. A couple of days in Chicago with him? That’s time I’ll always take.
Chicago has always been one of my favorite cities—probably number two on my list, right behind New Orleans. Over lunch yesterday, that very topic came up. Turns out my son ranks New Orleans as his favorite city, too. Chicago is his second. I’d have pegged New York higher on his list since he spent a couple of years living in the area, but he says it’s a close third.
This trip, like most of mine, is anchored by restaurants. Reservations were made weeks ago. We’re mixing it up—he’s showing me some new spots he’s discovered, and I’m bringing him to a few I’ve been frequenting for nearly 40 years. We’re covering ground and eating well. But it’s not just about the food.
The conversations have changed over the years. We’ve always had open dialogue—nothing off-limits. When he was younger, the topics ranged from superheroes to which magical power he’d choose if he could have just one. But even before he hit his teenage years, food crept in. Around eight or nine years old, he came to me with a fully fleshed-out restaurant concept set in a treehouse. He walked me through the layout, the menu, and even the steps of service. At first, I thought he was just trying to bond with me. I’ve always eaten, slept, and breathed the restaurant industry, and I assumed he was trying to meet me where I lived. But it wasn’t a phase. He was genuinely into it.
Still, I never pushed it. Wouldn’t dream of it. The restaurant business is too brutal to do half-heartedly. If you’re not in it for the love of food, the thrill of service, the rollercoaster of daily challenges, the deep connection with your guests, and the satisfaction of building something from nothing—don’t bother. It’s not for the faint of heart, and it’s certainly not for those just chasing a payday.
The restaurant industry is unpredictable. It’s creative and chaotic. It’s built on hard work and hospitality. It’s for people who understand that we’re part of people’s lives—on their birthdays, anniversaries, breakups, funerals, and everything in between. We serve meals, but we also serve memories.
And yet, the biggest misconception about our industry is that anyone can do it. Joe grills a good steak in his backyard, his friends rave, and someone says, “Joe, you oughta open a restaurant.” Joe’s tired of his 9-to-5, pulls from his retirement, borrows from family, and opens a steak joint. Six months in, Joe is dragging greasy rubber mats to the back dock at 1:00 in the morning because the dishwasher didn’t show. That glow he pictured from the corner booth? It’s been replaced by exhaustion and an overflowing grease trap. It ain’t the Food Network.
But I loved it. Still do.
When I opened my first concept, I was working 90 hours a week, living in one room above a garage, and paying myself $250 a week. And I would’ve paid someone that much just for the opportunity to do it. For some people, that sounds like misery. For me, it was heaven. The hustle was pure joy. These days, I probably work around 70 hours a week, depending on how you count. But it still doesn’t feel like work.
I don’t hunt. I don’t fish. I don’t golf. I love my family, my business, and travel.
Back when my son was 14 and said he wanted to go into the restaurant business, I nodded and probably said something like, “That’s great.” But inside, I figured it was a whim. At 16, he was still talking about it. So, I laid out a plan: Four years of college majoring in management with a minor in accounting. Two years of culinary school—at the Culinary Institute of America in Hyde Park, because that’s the Harvard of cooking schools. Then, two years working for someone else. And when—and only when—he completes all of that, he can come work with us. But he’ll start at the bottom. His education, his experience, his last name— none of it will matter. He’ll rise through the ranks—or not—based on effort and results.
He’s about six and a half years into that eight-year plan. And he’s killing it.
These days, when we talk shop, he’s the one leading the conversation. It’s not me passing down wisdom. It’s me often learning from him. That’s a beautiful thing.
My son and I have always connected over a lot of things—restaurants, movies, travel. He’s got the same kind of wanderlust I do. But one of the strongest connections we’ve built over the past dozen years has come from the gym.
When he was about 12, I asked if he wanted to come work out with me. He lit up. I told him I went early—5:30 in the morning. Didn’t faze him. For the next two and a half years, he got up three mornings a week before school to work out with my trainer and me. I bragged on him a lot back then. Rightly so. Not many junior high kids are climbing out of bed before the sun comes up to lift weights with their dad.
Then one day he started begging off. I figured he was just tired. But it kept happening. A few weeks later, we were riding in my truck, and I told him how proud I’d been of his commitment—and how I’d hate to see it slip.
He said, “Dad, you don’t work out long enough or hard enough.”
What I didn’t know is he’d started working out on his own. He had outpaced me. Within four years, he was stronger than I’d ever been—and I was pretty strong back then.
If that’s any indication of how his restaurant path will go, I figure he’ll pass me again soon enough.
And when he does, I’ll be the proudest man in the room.
Fatherly pride is real. I’ve got a daughter who’s one of the kindest, most talented people I know. She’s an interior designer and incredibly good at what she does. I couldn’t be prouder of her. And my son is carving his own path—making a name for himself. He’s not just my son anymore. He’s his own man. The goal has always been to hear someone say, “That’s Harrison or Holleman St. John’s dad.” Because all I’ve ever really wanted was to one day be known, not for what I built, but for who I raised.
So yeah, this quick Chicago trip is about food. But really, it’s about family. It’s about shared experiences. It’s about that strange and wonderful transition that happens when your child becomes your equal, your partner, and your friend. It’s about the kind of love that evolves but never fades.
We had our restaurant to-do list. He showed me a few of his new favorites, and I brought him to some of my old standbys. It was all predictable and perfect. We ate too much. Talked too long and walked just enough to pretend we earned dessert. And somewhere in between all the plates and conversations, I realized what this trip really was.
Not about restaurants. Not about cities.
It was about legacy. And the quiet, grateful realization that the next generation may just be ready—and maybe even better prepared—for all this than I ever was.
That’s the thing about kids. Sometimes they turn out to be exactly who you hoped they’d be—and somehow still better than that. There is no meal, no city, no moment more fulfilling than the quiet joy of knowing your children are becoming exactly who they’re meant to be.
Onward.
