Next Sales Huddle? Start with This Travel Protection Story

Welcome back to Selling with Sabine. I’m Sabine Taylor, your host. I’ve spent years working in sales enablement, cybersecurity, and telecom, helping large sales organizations train reps to confidently sell complex products using real-world experiences and storytelling. If you’d like to connect or explore sales training support, you can reach me at [e-mail]. 

In this episode, I share a real experience from a recent trip to Italy where a stolen piece of luggage turned a smooth trip into a stressful and time-consuming situation. I talk through what happened, the challenges of managing an incident like this while traveling abroad, and the hours spent navigating reports, receipts, and claims instead of resting or enjoying the trip.

I then connect the experience directly to sales, explaining why stories like this are effective teaching tools especially for reps selling travel insurance or protection products they may never have personally used. This episode is designed for sales leaders looking for practical ways to help their teams better understand the customer experience and communicate the true value of coverage. It also marks my first podcast release of 2026 and my return to the mic.

https://www.linkedin.com/in/sellingwithsabine/

 

Transcript (English):

Happy New Year, everyone. I’m Sabine Taylor with Selling with Sabine, and I’m going to…
kind of…go off the cuff.

There won’t be much production on these podcasts, at least for the next few episodes, because it takes a lot of time. And I’ve learned that this has become a barrier for me when it comes to working on my podcast. But even so, I set a personal goal that on January 1st, 2026, I would produce and release a podcast.

So… I just got back from Rome, Italy, and I’m tired because I landed last night.

It was a great trip. There was a small issue. And what I mean by that is I was traveling with my family, and someone decided to steal my luggage—my mother’s luggage. And honestly, I believe it was the bus driver. And that’s why I’m talking about it.

And in a somewhat strange way, I’m going to connect this to sales. Okay?

We took a really great trip to Italy. I got an amazing deal. I had miles, and each ticket cost literally five dollars and sixty cents. And I thought, there’s not much fun you can have in the U.S. for five dollars and sixty cents. The return trip was about seventeen dollars.

So per person, it was around twenty-five dollars. It was a great deal. We arrived in Milan, Italy, and it was wonderful. I noticed that everyone was very well dressed. The dogs were well dressed.
Grandmothers were well dressed. Everyone looked good. My mom even noticed that all the men had a full head of hair.

We spent about three days in Milan, and then we took a bus from Milan to Rome, or Roma, as they say in Italy. When we arrived at the bus station, we had a somewhat strange interaction with the driver.

He looked at my boarding pass, and I had paid for six pieces of luggage to be stored, but we only checked about four. So I had overpaid, and yet there was still a discussion about whether I needed to pay more.

And I want to say this: as someone who worked in cybersecurity for seven years and telecom for three years in HR, I’m very alert to anything that feels like fraud. While I was speaking with him, another woman who spoke English and Italian suddenly inserted herself into the conversation and began translating for us. And we said, hold on—we never asked you to translate. Thank you, but no thank you.

She had a very distinct look, almost like she didn’t belong. She had so much filler in her lips that she looked a bit unusual. She definitely left a lasting impression. But regardless, the driver said we should put our luggage on the other side of the bus.

And I thought, this is strange, because we’re sitting on the passenger side, and he wants to isolate our luggage on the driver’s side. So I decided to take a picture. That ties directly to my cybersecurity background.

I’ve spent many years studying crime, writing about it, and teaching company partners how to educate their customers. I have a sharp eye for things that don’t follow procedure. So I took a photo of all the luggage.

As someone who has traveled extensively and experienced missing luggage before, I developed the habit of taking photos of my bags and their contents. That helped, because when we arrived in Rome, instead of four bags, we only had three.

Our luggage had been isolated, and the only person with the key was the driver. He was very dismissive, didn’t file a report, and didn’t give us a reference number. To me, those were clear signs of something very calculated—what I would call a fraud scheme.

When you’re American, people involved in fraud and theft tend to pay attention to that. When I worked in cybersecurity, we had threat reports showing how many risks were targeted at Americans. For me, it feels the same when I travel.

Italy doesn’t have many Black people. In the three cities I visited—Milan, Florence, and Rome—I may have seen about six Black people. And the others were working in restaurants or hotels. When I’ve traveled to Asia with my daughter, we clearly don’t look Asian, so we’re seen as tourists and constantly approached to buy things.

I believe the transportation industry, which moves passengers from many countries, pays close attention to who is American and who isn’t. And I believe that’s what happened to us.

We arrived with three bags instead of four, and I had to deal with the emotional impact. That bag contained medical equipment, cameras, and other important items.

The next day, I spent my time writing a report and going to police stations. I went to one, and they told me they closed at one. I went to another, and they told me to go back to the first. All while paying for taxis. It was exhausting.

Finally, at the police station, they were writing the report in Italian and asked me to sign it. I asked for a translation because I didn’t understand what I was signing, but I signed it anyway.

Later, I used ChatGPT to translate it, and the report stated that I explicitly said I did not want to know who was responsible. And I thought, wow.

So how does this relate to sales? I think about people who sell travel insurance or credit card benefits. I wish they promoted this feature more. I spent so much of my vacation navigating police stations, signing documents in another language, returning home, calling the bank, starting a claim, and finding receipts, dates, and merchants. It takes a huge amount of time.

Instead of exercising or working on my goals, I was researching and documenting a theft.

If I were a company selling travel insurance, I would use real stories like this—the exhaustion, the feeling of violation, the loss of trust. I didn’t know this man, so why isolate my luggage?

The sales takeaway here is peace of mind—knowing that if something like this happens, you’re covered. I had a Chase credit card with travel benefits, including coverage for lost or stolen luggage.

I had to restart the audio for the second half because it stopped working. But what I wanted to say is that if I were a sales leader, I would play this podcast for my team. It’s hard to sell a product you’ve never used. Stories help customers understand why they need travel insurance.

I spent hours reviewing receipts, organizing them in Excel by category, date, location, and currency. My credit card showed charges in U.S. dollars, while my receipts were in euros. It was a mess.

This is what customers experience. Sometimes they think, “What are the chances my luggage gets stolen?” And then it happens. The real selling point is saving time. Today, time is money.

This can happen to anyone. And I do believe this was a crime involving an employee. Internal fraud happens all the time. It makes travelers wonder why they were targeted and lose trust.

I was grateful to have insurance. I don’t know if Chase will ever hear this, but during the holidays, I thought—who wants to go through this? And yet, I was thankful.

I wanted to return to the podcast without worrying so much about production. I don’t have the capacity right now to make everything perfect. I’m committed to not being perfect.

If you hear something I said wrong, please forgive me. I’m learning to move forward without perfection, because that need held me back. I hope you like and share this episode.

If you need sales training, you can find me on LinkedIn. I’m Sabine Taylor, also known as the Sales Training Architect. I’ve worked with large teams, including Fortune 150 companies, and I’d be happy to partner with you.

Happy New Year. Don’t get stuck on perfection. Keep moving forward.
That’s my commitment to myself. I hope you give yourself grace too.
Ciao. Bye.