Rolling with Flat Tires (and Frozen Treats): The Reality of Transportation Logistics

Some programs are about pretty centerpieces and perfect PowerPoints. Others? They’re about surviving 16-hour shuttle shifts, rerouting in real time, and knowing exactly when to deploy 50 ice cream bars as a peace offering.

Last week, we welcomed 6,700 students and advisors to a national leadership conference spanning three hotels and a fleet of 15 to 25 shuttles, running from before sunrise to well after sunset for four straight days. It was organized chaos — especially when a bus got rear-ended on a hot Florida road by a semi (no one harmed thankfully) and we had to dispatch a backup vehicle before the police even arrived on scene. Kids were cranky, a few adults were ruder than necessary, and tempers ran hot… but cold treats and cool heads helped bring everyone back around.

Just as the last shuttle pulled away, I pivoted to a new program — a luxury celebration for employees hitting service milestones, hosted at The Boca Raton. My portion? Coordinating 290 arrivals across 105 transfers. And just when we thought the heavy lifting was over… we started departures.

296 guests. 96 separate transfers. 3 different airports. First departure at 4:00 AM.

You read that right. Over the course of a single day, our team moved nearly 300 people to three different airports, each on different flight schedules, with ever-changing departure times. Some guests wanted to leave earlier. Others missed their assigned slot and asked us to “just grab a quick car.” And somehow, we made it work.

That’s the thing about transportation-heavy programs: they’re not glamorous, but they’re absolutely critical. You need to trust your dispatch teams, your drivers, your airport staff, your luggage handlers — and yes, the bellmen. Every piece matters. And when the plan inevitably changes (because it will), you need a team who can adapt on the fly without losing their cool.

At the end of the day, the best planning in the world can’t stop a traffic jam, a delayed flight, or a guest who oversleeps. But what it can do is make sure you’re ready when it happens — with backup vehicles, flexible schedules, clear signage, strong communication, and a freezer full of goodwill in the form of frozen treats.

Because sometimes the secret to success is simple: double check everything, then check it again — and always keep the ice cream cold.

Cheers,

Bethany