A Trip With a Purpose
My Chicago Trip Recap. Last week (mid September) I traveled to my companies Chicago office in Schaumburg, Illinois. I was sent there for a clear reason: to learn as much as possible about processes and lines of business outside my usual scope in Northern Border Operations.
This trip connects directly to where I want to take my career. As I continue to grow within the company, I want to take on leadership responsibility across more areas, not just the ones I already know well. Understanding how other teams solve problems is a critical step toward that goal. So this week in Schaumburg mattered as much for my own development as it did for the Chicago team.
Learning AirSea, ISF, and Traffic
While in Schaumburg, I spent focused time with the AirSea and ISF processing teams. AirSea processing covers ocean and air cargo entries, which work differently from the truck and highway entries I manage on the Northern Border every day. ISF, or Importer Security Filing, processing introduced me to compliance requirements that apply well before cargo even reaches US shores.
A light introduction to traffic coordination work rounded out this part of the trip. The exposure was brief, but it showed how much overlap exists between different support functions inside customs brokerage. Seeing these connections reinforced why cross-training matters so much for someone with leadership ambitions in this field.
Faces Behind the Names
Some of the most valuable time in Chicago had nothing to do with a manual or a system screen. Several team members I interact with regularly over email and phone became familiar faces instead of just voices on a call. Putting names to faces changed those working relationships almost instantly.
We collaborated on shared challenges and, just as importantly, got to know each other outside of work topics. As a result, I left Chicago with stronger connections across the company, not just new technical knowledge. That kind of trust is hard to build remotely, and it will make future collaboration much smoother.
A Taste of Chicago
No trip to Chicago is complete without eating your way through it, and I did my best to represent. Lou Malnati’s delivered on the deep dish pizza hype completely. Portillo’s followed with a classic Chicago hot dog and an Italian beef sandwich, both must-haves according to nearly everyone I talked to.
Fat Rosie’s brought a solid Mexican food option into the mix. Meanwhile, Weber Grill offered something I had never experienced before: an entire meal, from appetizers to entrees, cooked on Weber grills inside the restaurant. That detail alone made it a memorable stop. Between these four spots and a few others, Chicago earned its reputation as a food city during this trip.
Navy Pier and the Obama Presidential Center
Outside of work hours, I made time to see two Chicago landmarks. Navy Pier offered a great view of the skyline and the lake, along with plenty of energy from the crowds enjoying the evening.
The Obama Presidential Center came next on the list, though tickets were not available for a tour during my visit. Still, seeing the site in person, and understanding its significance to the city and the country, made the stop worthwhile. A return trip is already on the list for the next time business brings me to Chicago.
Bills Country, Even in Chicago
One highlight had nothing to do with customs or Chicago at all. While traveling, I caught the Buffalo Bills beat the Detroit Lions, and watching the home team win always hits a little different when you are away from home. It is a small thing, but it added a nice personal touch to an already productive week.
Bringing It Home
This trip reinforced something I already believed: growth happens fastest when you step outside your usual lane. AirSea processing, ISF requirements, and traffic coordination are not areas I work in daily, but understanding them makes me a stronger leader across the business, not just within Northern Border Operations.
Beyond the technical knowledge, the relationships I built in Chicago matter just as much. Leadership is built on trust, and trust is built face to face. As I continue working toward a Director-level role in US customs solutions, weeks like this one remind me why continuous learning and genuine connection both belong at the center of that journey.
