What My Work Away Experience Taught Me Before I Even Left Boston
When Castle announced a Work Away program—a benefit that allows us to work remotely from anywhere in the world for up to a month—I jumped at the opportunity. A chance to change my routine, experience somewhere new, and still stay connected to my work? It felt like the perfect balance. What I didn’t expect was that one of the biggest lessons from my Work Away would come before I ever got on the plane.
The Moment the Plan Fell Apart
The plan was simple: depart from Boston, connect through Atlanta, and head to Buenos Aires. Plus, if anything happened in Atlanta, I could at least make a pit stop at our local offices!
Within a span of a few hours the night before departure, everything began to unravel. Trying to get ahead of potential delays due to inclement weather in Boston that could cause a missed connection, I decided to switch to an earlier Boston-to-Atlanta flight. It seemed like a reasonable, proactive move. However, in an instant, my Atlanta-to-Buenos Aires boarding pass disappeared, and with it, no trace of the second leg of my trip.
At that moment, the trip I’d been planning and looking forward to suddenly felt very up in the air.
When Overpacking Saved the Day
When I went to check in, I noticed something off—my baggage perks had changed. What’s important to know is that I am a chronic over-packer. And since the itinerary for this trip included hiking in the Patagonia mountains in 30-degree weather, exploring the urban landscape of Buenos Aires, and tasting Malbec wine in the Mendoza region, there was a lot of variety in my packing list. Enough to warrant two full-size suitcases.
Since I was flying internationally, I knew I had one complimentary checked bag but would have to pay for the second. However, when I got to the baggage portion of the check-in process, I noticed the airline was prompting me to pay for two bags, instead of one.
Naturally, I turned to the airline’s chatbot to get to the bottom of it. I came prepared with screenshots of my initial booking, which confirmed I had one free checked bag. I was then told that sometimes booking terms change, and the airline was sorry for the inconvenience.
Just as I am a chronic over-packer, I am equally a stickler for the rules and held firm that one checked bag should be free. After some back-and-forth, I realized why my first bag was not complimentary – I no longer had an international flight.
My connection to Argentina was gone and was now only booked on a flight to Atlanta.
Assembling my Unexpected Crisis Team
In my day-to-day work, I help clients navigate high-pressure situations. I am used to being the calm voice in the room, the person who steps in with a level head. However, faced with my own travel crisis, I did what many do when things feel overwhelming: I panicked and started calling reinforcements.
Within minutes, I had a small but highly effective crisis team assembled—my parents.
While I tried to piece together what had happened and figure out how to eliminate six pounds from my suitcase, they got to work calling the airline, asking questions, pushing for answers, and escalating the issue when needed. We eventually learned that my flights had been “married,” meaning changing one segment affected the entire itinerary. The airline’s first response was to charge a significant fee to fix it.
My crisis team didn’t stop there. They asked for a senior leader, challenged the policy, and kept advocating. After what felt like an eternity, everything was restored. Same international flight. No extra fees.
The Lessons I Learned Before Takeoff
Once the dust settled, one thing became very clear: I am excellent at managing other people’s crises. I can be much less effective at managing my own. But that is not unusual. When you’re in the middle of a stressful situation, it’s harder to think strategically. Emotions take over, and even straightforward problems can feel overwhelming. That experience gave me a new level of appreciation for what we do every day, and why having the right support system matters.
What I’m Packing for Next Time
The two main takeaways from this adventure that I will carry into every future trip and project are:
- Sometimes, overpacking is the smartest thing you can do. I went into this trip embracing my usual habits: packing options and leaving extra space for the inevitable items I would pick up along my travels. What felt like overkill ended up being the reason I caught a major issue just in time.
- When you’re feeling overwhelmed, call for backup. There’s a reason teams exist, whether in travel or communications. Having others step in during challenging moments brings clarity and often faster solutions. It also reinforced something I see often in my work: the best outcomes usually come from collaboration.
Castle’s Work Away program gave me the opportunity to step outside my day-to-day routine, experience a new environment, and return with fresh ideas. But perhaps most importantly, it reminded me—before I even left my apartment—to be prepared, even when it feels unnecessary, and not to hesitate to ask for help.
So, pack that extra jacket and pair of shoes. It might just save your trip.
