We love to ask the question: Is it the journey or the destination that matters more? It’s a philosophical favorite, the kind of thing you’ll find printed on throw pillows, dropped into late-night conversations over cheap wine — or, in my case, floating across an Instagram meme. The journey, we’re told, is where growth happens — where we find ourselves, earn our scars, and learn to see beauty in struggle. The destination, on the other hand, is where we arrive. The goal. The reason we start walking in the first place.

I’ve thought about that question a lot more than I ever expected to — especially since 2015, when I left a job in Miami and came back to Madison with no plan and no prospects. Driving for Uber was never the dream. But necessity has a way of rewriting your story. What started as a stopgap became something else entirely — something unexpectedly human and strangely intimate. More than 4,500 trips and three cars later, I still find myself surprised by what people are willing to share from the back seat.

Driving, you hear that question in new ways. Some nights it feels laughable — like when you’re five minutes into a ride to Kwik Trip with someone silently eating Hot Cheetos. Other nights, it hangs in the air like a hymn.

Every ride asks its own question. But it’s not always about where we’re going — or how we get there.

One night, I picked up two gay men outside the Olive Garden at East Towne. They were headed first to a friend’s place to grab a pool cue, then to a bar on Atwood they liked — just a little spot they’d found by accident, three minutes down the street from their favorite Italian restaurant. It was a longer ride than usual. Long enough to stretch out into something that felt like more than a transaction.

They slid into the backseat laughing. “Hope we don’t smell like garlic,” one of them said. “We just demolished the Tour of Italy.”

They were in their mid-20s, I was guessing. Thin like I’ve never been in my whole life.

They told me they’d met on TikTok. One posted something funny, the other left a comment, and the conversation kept going. A few DMs turned into video calls. Then visits. Then one of them packed up his life in Wyoming and moved to Wisconsin to start something real.

Now they both work at a suburban hotel — one managing the front desk, the other managing housekeeping. They’ve got a joke they’ve clearly told before:

“I get our guests when they’re angels,” said the front desk manager.

“And I get them when they’ve turned into devils,” his partner added.

The line landed with perfect timing. They laughed together — not just at the words, but at the fact that they’d built a life full enough to recycle them. I laughed too. But it was their rhythm that got to me. There was an ease between them. Not just the practiced flow of a couple, but something deeper. When one adjusted the other’s collar without saying anything, it wasn’t a correction. It was affection. Familiarity. A tiny act that said, you matter to me, without needing the words.

And it wasn’t just that they were together. It was how they talked about it. They liked working together. “We don’t get sick of each other,” one said. “We just… work better in the same room.” There was no performance in it. No overreach. Just the lived-in ease of two people who had chosen each other, and kept choosing each other.

As we drove, the conversation wandered. When they mentioned the restaurant on Atwood, I smiled — my husband Mark and I had been there too. We’d gone for an anniversary dinner once. For us, getting to the east side feels like a journey worthy of preparation: snacks, books on tape, maybe a hotel room and a ceremonial patchouli bath to mark the crossing. It’s not far — just far enough to feel like a miniature pilgrimage.

The waiter surprised us with a complimentary champagne toast — sweet, memorable, and not-so-complimentary when it showed up on the bill.

We raised our overpriced glasses and toasted to another year of figuring it out — love, life, Madison traffic. Even the east side felt a little kinder that night.

“They got you good,” one of the guys said when I told them the story.

“There’s no such thing as a free toast,” his partner added.

And I laughed again. But this time, it hit differently. Because I realized I was watching them live a version of something I’d also built. Something hard-won and oddly mundane. Partnership. Timing. Joy in the middle of a Tuesday.

When we pulled up to the bar, they were still laughing. One of them slung his pool cue bag over his shoulder like a baseball bat. They looked like characters from a film you’d want to keep watching, even if the plot never really started. Just two people who made the ordinary look lovely.

And as I watched them walk into the bar, it hit me — again.

The journey matters. The destination matters. Some say the journey is about learning life’s lessons, and the destination is about experiencing its bounty. I like that. The growth and the gratitude. The work and the wonder. But sometimes, those things fade into the background. Sometimes they’re just the scaffolding.

Because after thousands of rides, after all those mapped routes and changed plans, I think I finally understand:

It’s not the journey or the destination.

It’s the company you keep.