** This blog is a playful homage to Mad Libs, with each of my fellow travellers contributing words that I have woven into the story.

I had barely unpacked from my last trip when this opportunity was presented to me—travel to Pittsburgh, which is situated on Indigenous Seneca territory, for an AI conference. I’ve always jumped at the chance to travel—there’s something energizing about the promise of new places, the thrill of small adventures and the chance to step outside my comfort zone. Sometimes, people you can’t say no to ask you to do things that stretch you in unexpected ways—dress in matching outfits on a random Tuesday, create a dance as a team-building activity…for two, or even buy them a gift card—and this trip was one of those times.

The location, the activities, the group—everything was unfamiliar. As the departure date crept closer, so did the nerves: a mix of uncertainty about the destination, intimidation at the thought of being surrounded by brilliant minds talking about things I didn’t understand, and a lingering doubt about whether I was truly ready for what lay ahead. This wasn’t just a journey across the border to the US—it was a leap into the unknown. Okay, maybe a touch dramatic…but let’s chalk that up to sleep deprivation.

The first night was a bit of a blur. Steeler fans filled the streets, gearing up for the game. I’d been warned that the city might not be safe to walk alone after dark, and that caution stuck with me. I had to remind myself not to let others’ fears take root in my mind. Until there was reason to panic, I would take things in stride. Despite the crowds, the city didn’t feel chaotic. After dinner and a short walk, I chose quiet— retreating to my hotel room and calling it an early night.

But sleep didn’t come easy. My room was beside the hotel gym, apparently the most popular spot in the building. The door slammed almost hourly, jolting me awake each time. By morning, I felt like I’d barely slept. I knew I needed a bit of self-care, in fact I was desperate for it—nothing fancy, just a slow morning, a long, just-the-right temperature shower, and a few quiet moments to breathe before heading to my first training session.

With time to spare, I ventured out in search of groceries and a decent coffee—because let’s be honest, hotel coffee is no match for my Lady Gaggia at home. What surprised me most wasn’t the lack of good coffee shops, but the eerie quiet of the streets. For a city that had been buzzing with football fans the night before, the stillness felt almost dystopian—like someone had hit pause the night before but forgotten to hit play. Downtown still seemed to be sleeping.

The day of learning had arrived, and from the moment it began, I felt in over my head. The content was dense, layered, and often just beyond my grasp—which, strangely, I didn’t mind. That kind of discomfort, the kind that comes from not knowing but wanting to understand, is stimulating, and encouraging, things I’ve come to appreciate. It pushes me, reminds me that growth often begins with confusion.

After six solid hours of training, I was ready for a break. Group trips often come with their own set of challenges—especially when you are a newcomer and everyone else already knows each other. Coordinating dinner plans for a large group can also be tricky, but not this time. I was grateful to be included, and pleasantly surprised by the easy camaraderie around the table. Conversation flowed, laughter came easily, and the awkwardness I’d braced for never really showed up—I don’t think.

Earlier that day I’d switched rooms in hopes of a quieter night, and that small change made a big difference. My new room offered a stunning view across the rivers. As I looked out at the end of the day, I was reminded of the short list I’d made: an incline to ride, a sandwich to try, and a museum to visit. After a delicious Mexican dinner—where the stories were as thick as the food was rich—I returned to my room feeling more settled, and inspired than I had since arriving. Sleep came easier, and for the first time on this trip, I felt like I might be finding my rhythm.

The next morning began with a peaceful walk by the water—a quiet moment to continue a new habit I’ve been trying to build: starting the day with movement and reflection. The air was crisp, the path mostly empty. Joggers and a cyclist passed by as I wandered along the river. I spotted the incline I’d read about and seen from my hotel room, and a plan to visit began to take shape. I’m not a great relaxer, so I was already working out the breaks in my schedule and how much time I’d need to get there and back.

The learning sessions resumed, and while my brain felt tired, things were starting to click. The interdisciplinary approach—blending perspectives from different fields—added depth to the presentations. New words, new frameworks, and slowly, connections were beginning to form. It was still a stretch—but a satisfying one.

Later, I wandered over to the Andy Warhol museum—one of the items on my list—only to find it closed. Disappointing, but not enough to derail the day. I took the opportunity to explore more, snapping photos with statues and public art installations. With so few people around, I felt completely at ease stopping to take photos with statues and sculptures—something I usually rely on my travel buddies for. I even took a few candid shots of passersby, wandered toward a clock tower, marveled at the architecture, and eventually made my way back to the afternoon sessions. I was less nervous this time. With a head full of all that I had learned the day before, the conversations were beginning to make sense. My notes were taking shape.

As the sessions ended, I decided it was the perfect time to check off another item on my list. If I moved quickly, I could reach the top of the Duquesne incline just in time to catch the sunset. It was stunning—soft light spilling over the city, casting long shadows and painting everything in gentle hues. I lingered just long enough to soak it in and snap a few photos before heading back to meet the group for dinner.

That night, over another shared meal, I learned about a second incline—one I hadn’t come across in my research. With one day left, there was no time for hesitation. I was going and I could see my enthusiasm must have been contagious because others wanted to join. We made a plan to visit it the next morning, our final day in the city. I felt surprisingly empowered, ready to squeeze every last moment out of the experience.

We met at 6 a.m., bleary-eyed but determined to catch the second landmark before leaving the city. Our taxi driver took us to the same incline I’d visited the day before and I began to wonder if there really was only one—had I been naive to believe my colleague, after all? Despite living in the city for 21 years, he was surprised when we pointed out the lighted track we’d expected to visit. In a bigger city, our late arrival might have meant battling morning rush hour crowds, but not here. We got our tickets and boarded the train heading up the hill, feeling a little more enlightened about the city’s mysteries and history.

Our plan was simple: ride up, take in the view and head back down. But the view was beautiful, the area peaceful and the weather perfect— so we kept going. The night before, we’d noticed Google giving us wildly different walking times, which sparked some curiosity. The gap was so wide, I began to wonder if one of us moved at F1 speed while the other preferred a horse-and-buggy pace. Still, we carried on, walking to the other incline with the hopes of catching the sunrise before returning to the conference.

It was breathtaking. The city slowly waking beneath a soft orange sky, the incline glowing in the early light, the neon pink on the buildings across the water—it felt like the perfect bookend to a trip that had started with hesitation but was evolving into something rich with learning, connection, and discovery.

We made our way back to the hotel, hearts full and feet tired, ready to pack and prepare for our final day. There was still a bit more to learn, a few more conversations to have, and then it would be time to head home—hopefully a little more confident, a little more connected, and certainly more curious than when we arrived.

As the trip came to a close, I found myself reflecting on the unexpected lessons learned, tucked between sessions and sightseeing. I learned that sessions with windows are almost always better, and that sometimes the real magic isn’t in the session descriptions—it’s all about location, location, location. I discovered that K-Pop Demon Hunters is a thing, that asking questions when buying gift cards is essential, and that when your scent is described as “thick and rich“, it isn’t always a compliment. I now know that Pittsburgh was once Fort Pitt (they dropped the fort and added the ‘burgh), that the museum is great and that when you spot one incline, there’s probably another waiting to be explored. More than anything, I left feeling enlightened, empowered, and proud—not just of what I learned, but of how I showed up, stretched myself, embraced the evolving adventure and connected with colleagues in meaningful ways.