The Part You Never See
Journal · The Why
From Adjusting Claims to Planning Journeys
Before I planned trips, I was an insurance adjuster.
For years, my job was to meet people on some of the worst days of their lives… after the accident, the loss, the thing that went wrong. I was good at it, and I cared about it. Helping people through hard moments is real work, and I don’t regret a day of it. But it meant I spent my career walking into rooms where everyone was at their lowest.
Travel was the opposite.
On the side, I’d started planning travels — for friends, for family, for anyone who’d let me. And I noticed that this version of helping people felt completely different. Nobody calls their travel advisor on the worst day of their life. They call because they’re about to do something they’ve been dreaming about for years. I was meeting people at their happiest. After a career spent on the other end of that, I can’t tell you how much that mattered to me.
So for a while I did both. I kept adjusting claims and planned trips on nights and weekends until 2021, when I finally let myself do the joyful thing full-time.
Here’s what both careers taught me, though, and it’s the same lesson: no matter how carefully you plan, something eventually goes sideways. A tour cancels. A transfer falls through. A confirmation that was supposed to come never does. It happens on trips more often than people realize, usually in some small way. The question is never whether something will wobble, it’s who’s going to handle it when it does.
Do you want to spend a day of your hard-earned vacation on hold, trying to fix it in a country where you don’t speak the language? Or do you want someone in your corner who quietly takes care of it behind the scenes while you go enjoy your day?
What That Actually Looks Like
A couple of examples of what that actually looks like.
I had a client traveling through Paris with his daughters. Their tour of the Louvre cancelled on them suddenly and it looked like they’d miss it entirely. I found another tour, but by the time he was able to authorize the payment, that one sold out too. So I found a third, and I paid for it myself on the spot, so there was no chance of losing it again. They saw the Louvre. They never spent a second worrying about how.
Another time I had clients in India who were sure their tour company had forgotten them. And this was not a small tour; this was the one moving them to their next destination the following day. They couldn’t reach anyone. I took their call at 2 a.m. my time and started working the phones until I had answers. (It turned out the company had left a message at the front desk while they were out, but my clients got to go to sleep knowing someone was handling it.)
That’s the job, really. Not booking as anyone can book. Noticing. Thinking of the things you’d never know to think of, and standing by to catch the things no one could have predicted, so the trip simply works and you get to be fully present for it.
The best compliment I get isn’t “that was beautiful.” It’s “I didn’t have to worry about a single thing.”
I think travel is one of the few things people spend real money on and then come home wishing they’d done a little differently. A trip you saved for, waited for, took precious time off for, and a few avoidable missteps quietly take the shine off. After a whole first career spent showing up for people when things went wrong, that’s the part I can’t stand to see. It’s also the part I’m best at preventing.
So that’s why I do this. Because everyone deserves someone in their corner — and I’d so much rather be in yours on the best week of your year than the worst.
If that’s the kind of trip you’re after, that’s exactly the conversation I love to have.
