Four People, Two Dogs, and a Two-Bedroom House
For someone who is a so-called travel expert, never have I spent a trip this cramped.
For six weeks this summer, my husband, myself, my two kids and two golden retrievers (watch me write two again) lived in a two-bedroom house in Montauk. It was loud, chaotic, and somehow the best decision I made all year. After a year of insane travel and its own chaos, a quiet summer together was perfect. Our family rules were simple: no flights, no out-of-town meetings, and no babysitters. Just sprinklers, sand, and a truly alarming number of overpriced breakfast pastries. My normal life is filled with airports and hotels and rooms full of people I'll see again in three weeks somewhere else. This year needed some slowing down, and I'm so glad I did it.
By the second week we had a routine: Wednesday nights were family night at Surf Lodge, which meant watching Elizabeth dance next to a group of Gen Z girls like she'd been personally invited. Jack took surf lessons all summer and came back tanner and more confident than I have ever been at anything. And Paul finally met most of my work friends in person instead of hearing about them!! And I think he enjoyed it more than he'll admit. And how can I forget that he made what he called “great timing” driving back to Alabama from New York – a fact that I know for certain thanks to the two radar-detected speeding tickets that showed up in the mail about a week after he got home.
Here's the cheesy part but I'm going to say it anyway: taking a month off meant much more than I expected. I got real, uninterrupted time with my kids and with Paul, and there's a particular kind of joy in being a stranger in a place for a while. Small things like going to the same market for groceries every few days, catching whatever live music was playing that night, and having zero idea what was happening back home and being fine with it. I spend every day immersed in work that sells trips designed around discovery and once-in-a-lifetime moments. Ironically, it turned out what my own family needed was the small, repeatable ones this summer.
Why I'm writing this
Quick hello, since this is post one. I spend most of my week saying measured, on-brand things about the travel industry. First as an advisor and now on the agency side. Back in my advisor days I actually wrote a blog and loved it, so this isn't entirely unexpected. I recently realized my LinkedIn posts were getting suspiciously long, so in an effort to not become an accidental LinkedIn thought leader, I started this instead. Expect industry takes, maybe even a few outfit notes, and definitely a rundown of whatever's happening off the record.
The best industry events don't have an agenda
Inside the travel industry, most events are built the same way: a panel, a deck, a sponsor slide, and then the actual conversation happens at the bar afterward, when nobody's performing.
Earlier this summer, we tried the opposite. We hosted our first “After-Hours” dinner at Roscioli NYC, alongside Corinthia Rome and Queen of Clubs Lifestyle. No pitch decks and no presentations. Tastemakers, advisors, and editors in one room, cacio e pepe, and a conversation that felt exactly like the ones you have at dinner where the wine goes down a bit too easy and the company is too comfortable. Investing in this style event was a risk. We had advisors from multiple agencies, not just our own, and we sincerely put effort into creating an evening focused on cultural convening for our industry. Overall, I think it was a win and I think this was the first of many “After Hours” for us.
Here's the thing most people don't fully understand about this industry: luxury travel is a relationship business, and most of what we do to “engage” people works against that. Webinars, e-blasts, digital tactics. You can't slide-deck your way into trust. You get the right people in a room, feed them well, and leave enough time for someone to say the honest thing.
Same lesson I learned in Montauk, honestly. The best stuff this year didn't have an agenda and wasn't about the big, once-in-a-lifetime moments. It was the Wednesday live music, the market visits, the dinner with no agenda. The small things I'd do again next week if I could. That's the whole strategy.
What I'm loving
Kallmeyer Ellis Skate Short — the one piece that made it from July straight through fall. I've worn these on repeat since summer and no end in sight.
Dr. Stolberg Rest + Digest Tea — I travel over 30% of the time for work and have a shockingly sad number of “travel hacks,” but this is worth it.
TWP Jillian Single-Breasted Blazer, Midnight Blue — in constant rotation, day and night, and yes, it looks great with the Kallmeyer shorts.
UNDO Hairware 4" Claw Clip, Bordeaux — an impulse buy in a hotel lobby that turned into an almost-daily habit, don't you love that?
These sunglasses — shockingly cheap, a little outrageous looking, and everyone assumes they cost triple what they did!
