The engine idles with a low, apologetic rumble. It’s the wrong sound. It’s the sound of a shared shuttle, of compromised space, of a schedule that isn’t yours. Outside the sliding glass doors of the terminal, the heat is a physical presence, pressing on your skin with the damp weight of a thousand tiny decisions you were hoping to escape. You see the logo, the one from the website, plastered on the side of a van designed to hold 17 people. And the feeling that settles in isn’t anger. It’s a quiet, sinking deflation. The realization that the first act of your long-awaited escape is another logistical problem to be managed.
The Lie of ‘All-Inclusive’
This is the lie of ‘all-inclusive.’ The industry sold us a beautiful, simple-sounding promise: one price, zero worries. What they delivered was a checklist. Airport transfer? Check. Meals? Check. Drinks? Check. They bundled the services, but they forgot the soul. They forgot that true luxury, the kind that people who spend their lives managing complexity actually crave, isn’t about having more things available. It’s about having fewer things to consider.
For a long time, I judged this desire. I saw it as a weakness, a lack of adventurous spirit. Why would you want someone to handle everything? The joy is in the discovery, the happy accidents, the navigation of the unknown. And then I tried to open a jar of pickles yesterday. A brand I buy all the time. My flight had been delayed, my brain was frayed, and all I wanted was the simple, acidic crunch of a pickle. But the lid wouldn’t budge. I ran it under hot water. I tapped the edge with a knife. I wrapped it in a towel for grip. Nothing. In that moment of absurd, powerless frustration, I didn’t want options. I didn’t want a challenge. I wanted a pickle. The company had included the pickles, but they hadn’t considered the state of the person trying to access them.
Bundle vs. Solution: The Core Difference
That’s when it clicked. The goal isn’t to be helpless. The goal is to consciously delegate the cognitive load of everything outside the core experience. We aren’t paying to have our vacation bundled; we’re paying to have it solved.
The shuttle van: a service
The black SUV: understanding
One is a service.
The other is a demonstration of understanding.
The Art of All-Considered: João K.-H.
I think about a man I met once, João K.-H. His job title was something like ‘Quality Control Taster,’ which sounds lovely until you understand the terrifying precision it requires. He didn’t taste wine or chocolate. He tasted single-origin, shade-grown coffee beans from 17 specific micro-lots in South America. His palate was insured for a figure that felt like a statistical error. He would follow a 47-step process for each tasting, and his notes weren’t ‘good’ or ‘bad.’ They were about the unstated.
“
“This batch,” he’d say, swirling a tiny cup, “was harvested 7 hours too late. You can taste the anxiety in the bean.”
— João K.-H.
”
He wasn’t just checking a box for ‘coffee flavor.’ He was considering the entire lifecycle of the experience, from the soil to the sip. He was practicing the art of ‘all-considered.’
Anticipating Needs You Haven’t Verbalized
Most of the travel industry operates on a checklist. They ask what you want from a list of their pre-approved services. An ‘all-considered’ approach starts by asking who you are. It anticipates needs you haven’t even verbalized. It knows that after a 7-hour flight with children, the last thing you want to do is negotiate with a driver or install a car seat. It knows the best table at the restaurant isn’t the one with the best view, but the one furthest from the noisy kitchen door. It knows to stock the fridge with not just champagne, but with the specific brand of oat milk your assistant mentioned in passing three months ago.
My Own ‘Inconsiderate’ Experience
I made this mistake myself, spectacularly, a few years ago. We booked a ‘premium’ villa experience on a remote Greek island. It came with a concierge, a boat transfer, the works. On paper, it was perfect. The concierge sent us a 17-page PDF of activities. Included. What they didn’t consider was that the ferry to the mainland-the only way to get to the ‘must-do’ taverna everyone recommended-only ran on Wednesdays and Sundays. We arrived on a Thursday. We were stranded in paradise, a place with 237 pristine beaches but no way to reach them without a level of logistical wrangling that felt suspiciously like my day job. The service was ‘inclusive’ of a list of options, but it was utterly inconsiderate of our actual context.
It’s a subtle distinction that changes everything. It’s the difference between an app that presents you with a hundred buttons and an app that intuits the three things you are most likely to need and puts them front and center. Good design, whether in software or in service, is about the ruthless elimination of friction. It’s about anticipating the path and clearing it before the traveler even knows there’s a path to be cleared. We had to salvage that trip ourselves, spending hours on the phone, trying to charter a private boat at an absurd cost, all because the ‘service’ we’d paid for was just a menu. After that, we started looking for places where the details are the entire point. Not just a villa, but a curated stay. We spent an evening looking at these incredible Los Cabos villa rentals just to see what was possible when someone else was doing the thinking, when the entire philosophy was built around anticipating, not just providing.
Mental Energy: Deposits, Not Withdrawals
This isn’t about being pampered into oblivion. It’s about buying back the most precious resource we have: mental energy. High-achieving people, the ones who build companies and manage teams of 237 employees, aren’t looking for a vacation where they have to make another 77 small decisions every day. Should we eat here or there? Do we need to book that in advance? What time does the pool close? Did anyone remember to get cash for the tip? Each question is a tiny withdrawal from a mental bank account that is already overdrawn.
Withdrawals
77 daily decisions
Deposits
Thoughtful gestures
An ‘all-considered’ journey makes deposits, not withdrawals. It surprises you with thoughtful gestures that eliminate a decision you didn’t even know you’d have to make. It’s the rental car’s navigation system pre-programmed with the address for the villa and the grocery store. It’s the note by the coffee maker explaining that the local bakery delivers fresh pastries at 7 AM if you just text a number. It’s João tasting the anxiety in the coffee bean so you don’t have to.
Empathy-at-Scale: The New Luxury Frontier
The future of luxury service isn’t about gold-plated taps or ever-larger television screens. The material components are table stakes. The next frontier is empathy-at-scale. It’s the operationalization of thoughtfulness. It’s the quiet, confident, and almost invisible anticipation of need.
It creates a space so seamless, so frictionless, that for a few precious days, you can forget you’re a person who manages things and simply be a person who experiences them.
