July 1, 2026
Travel has a funny way of humbling even the best of planners.
You can map out every smooth connection, pick the perfect hotel, buy the best travel insurance (because your trusted travel advisor told you so) and, still, the travel gremlins will throw you a curveball.
The question is: Will you be ready to pivot when it does?
I’m not talking about the kind of pivot you deploy to deal with inconveniences like delayed flights and lost luggage —travel insurance has your back there. I’m talking about the kind of pivot too big for travel insurance to manage – your high standards. Those non-negotiable personal preferences that can make or break a trip. Preferences that caused me to pivot during my 50th birthday trip.
Twice.
Venice: The Calm Before the Storm
Picture it: Venice.
My 50th birthday.
I spent my days sipping spritzes, nibbling cicchetti, and gliding along the canals without a care in the world—soaking up some much-needed me time before meeting my clients in Athens to board our Virgin Voyages cruise.
And my hotel? Honestly, if you’re headed to Venice, book it.
You’ll thank me later.
The Molino Stucky Hilton sits on its own island, so you’re close enough to the action, but far enough to feel like you’ve unlocked a private retreat. It is a hotel that I’d call Sexy AF (yes, I said it). Chic rooms, water taxi at the ready, spa on site. I was floating—literally and figuratively. It was a whole vibe straight out of a book on effortless style.
But like every good story, the plot twist was waiting for me on the next page.
Athens: The Birthday Buzzkill
The hotel arrangements I’d made for my clients in Athens was the ideal place for us to connect, rest, and get the good vibes going before our cruise. It was in a great location with good amenities. My hotel-luck in Venice was so good, I was ready to continue riding the high of in Athens – a high that immediately crashed when I opened the door to my hotel room.
I was too struck by the bathroom to measure any other aspects of the room against my high standards.
Calling the bathroom small would be generous. It was microscopic. So tiny that the genius maintenance team sawed a notch out of the door so it could be opened without smashing into the sink. That’s not clever – that’s a massive mistake. One that a quick “Measure twice, cut once” approach easily have avoided.
And the shower?
Let’s just say I like my spritzes cold, not my parts while they’re being cleaned. Only one of my cheeks ever would have made it inside that shower. Then it would have been assaulted by the pervasive mold.
I knew that I could not stay here. I would NOT stay here. Not because my high standards were not reached, but because these standards were lower than anything that could be measured. If I could not, then my clients would NOT. My reputation and my brand are too valuable to risk on a place that was giving Haunted Hostel, not Hellenic Holiday.
I was too busy being appalled to document my disappointment with photos. Me. The Queen of the Camera. If I’m too shocked to grab my phone, you know that things have gone from bad to epic disaster.
I pivoted out of there.
Pivot #1: The Midnight Hustle
So there I was, in Athens, at midnight. Exhausted, uncomfortable, and spiraling.
Hotels were either sold out or laughably expensive. I always travel with extra funds for a rainy day, but $10K for 3 nights isn’t a rainy day – it’s a Category 5 Hurricane.
Then it hit me: Airbnb.
By 5:00am, I had found and booked the perfect place in a chic neighborhood with plenty of bedrooms and bathrooms. With a price tag of $2,500, I saved the day before the clients would ever have a manage the matchbox bathrooms. I quickly shared the revised hotel location and told them I was happy to meet at the new digs.
Done, right?
Of course not. Nothing in travel is ever that simple.
Pivot #2: The Taxi Strike
To everyone’s surprise there was a taxi strike the following day.
Anyone who hadn’t booked transport in advance was basically stranded. Thankfully, my client’s transportation was taken care of well in advance and they were happily awaiting my arrival at the Airbnb. I, on the other hand, was with my photographer waiting several hours for a car that didn’t show up until 2:00pm. By then, I was hungry, cranky, and desperately in need of a shower.
But when we finally rolled up to the Airbnb?
Instant relief.
It was perfect—enough rooms, laundry facilities (hallelujah!), and everything we needed within walking distance.
My clients loved it.
I loved it.
And honestly? Sharing the space let me connect with them on a deeper level. It turned out to be one of the best decisions I could’ve made.
The Lesson: Pack Patience (and a Pivot Fund)
Travel is unpredictable.
You’ll face delays, surprise strikes, hotels that look nothing like their photos, and a million little things that test your patience. The key is to be flexible enough to pivot—even if it costs you.
Because, at the end of the day, comfort and safety matter more than anything. And, sometimes, the pivot leads you to something even better than what you planned.
Next time you travel, bring your patience, keep your sense of humor, and maybe—just maybe—tuck away a “pivot fund.”
Trust me, it’s worth it.
Let’s discuss some of the non-negotiables for your travel so we can plan your next luxury birthday extravaganza or cruise. Schedule a free 30-minute consultation with me
