I quit my afternoon coffee. Not because I wanted to — because I found something better.

You know that wall you hit every day around 2–3 PM? I used to just accept it as the cost of doing anything. Another coffee, a quick spike, then the crash — and somehow I'd still feel dehydrated by dinner.

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The plane was a boat until it was a plane.

That's the part I remember most. The Grumman Mallard would roll down the ramp at Watson Island, nose dipping, tail bobbing, and then it was floating in Biscayne Bay. The engines would roar, spray would fly past the window, ocean water beading and streaking sideways across the glass, and the whole hull would strain against the water until it broke free and lifted. Sixty miles to Bimini, flown low, a thousand feet or so above the water.

The airline was called Chalk's. I didn't know it then, but I was riding a piece of history. Chalk's started flying between Miami and Bimini in 1919. For most of a century it was the world's oldest scheduled airline. Errol Flynn flew it. Howard Hughes flew it. Hemingway flew it constantly in the forties, because Bimini had the best deep-water fishing on earth and Chalk’s was how you got there.

The seaplane in the opening credits of Miami Vice? Chalk's.

I was just a kid. Many summers were spent on a boat, and Bimini was where we went. I remember the dogs on the island. The homemade Bimini bread. Snorkeling for starfish in water so clear you could see them from the dock. I remember fishing for sergeant majors off the dock with a bamboo cane pole. No reel, no tackle, just bread you wet in your mouth and rolled into a ball onto the hook. I remember yellowfin tuna for dinner, caught that day, and how it tasted like nothing I've had since. Then the seaplane home to Florida, boat until it was a plane.

Chalk's is gone now. A crash in 2005, the airline finished by 2007. Nearly ninety years of flying, ended.

And Bimini… Bimini has a cruise ship port now. A Norwegian Cruise Line ship docked where the flats used to be. Resort development. Time shares and matching wristbands. Discovered, developed, packaged and sold.

I've been thinking about this because of a report that crossed my desk recently. Bain & Company, writing about the luxury travel market, describing the hot new thing wealthy consumers want: "immersive wayfaring." Slow travel. Undiscovered places. Local tradition. Authenticity. That word doing a lot of heavy lifting these days. Travel to non-traditional destinations is up 20 percent. The industry is building packages around the feeling of finding somewhere before everyone else does.

I know that feeling. I had it at eight years old, with a cane pole and a bread ball on the hook.

What I understand now: my parents weren't giving me trips. They were giving me a way of moving through the world. Nobody handed them an itinerary for Bimini. There was no package. They had a boat and they went, and the island was just the island, dogs and bread and water and fish. The experience wasn't “curated.”

Fifty countries later, I live in Medellín. And I can trace a straight line from that dock in Bimini to this desk in Colombia. I didn't end up here by accident. I've spent my adult life doing the thing my family taught me, finding the places before they become destinations. Not because undiscovered is morally superior. Because I learned young what a place feels like before the world prices it, and once you know that feeling, the packaged version never quite works on you again.

Most of what gets written about family travel is about the trips. Where to go, what to book, how to keep the kids entertained. All of it misses the actual transaction. Your kids aren't collecting destinations. They're absorbing how you move: whether you follow the crowd or the chart, whether you need the itinerary or trust the day, whether a place is something you consume or somewhere you simply are.

The Bimini I knew is gone. Chalk's is gone. I can't give any of it to anyone.

But the way of arriving somewhere, boat until it's a plane, no package, no plan, bread bait and open water… that transferred. That's the only part that was ever going to.

Design what you hand down. The rest gets a cruise port eventually.

🇺🇸 U.S. (Outbound) - In April 2026, the State Department cut the fee to renounce U.S. citizenship from $2,350 to $450, an 81% reduction. The administrative fee was always the smallest cost of leaving, but the psychological barrier just got a lot lower. Globalexpatadvisors

🇿🇦 South Africa - Overhauling immigration with a new points-based system prioritizing economic contribution, allowing spouses of skilled workers to work and replacing passive income requirements for retirement visas with active investment mandates. Worth watching for anyone who has Cape Town on their list.

🇮🇹 Italy - American retirees are now fueling a surge in Golden Visa applications, with the program up nearly 63% since 2018, driven by the zero-day stay requirement and flexible path to EU residency. Now the fourth most popular destination for U.S. retirees.

🇵🇹 Portugal - A small sign the AIMA backlog is moving: the agency and the University of Lisbon signed an agreement to pilot a 30-day processing window for student residence permits. The broader backlog for everyone else remains unchanged.

🇱🇻 Latvia - The president sent the golden visa closure bill back for a second reading, but investors are treating January 1, 2027 as a hard deadline regardless. Last call for one of the few remaining lower-cost EU residency options.

🇸🇦 Saudi Arabia - The Premium Residency program is growing fast as an alternative to European golden visas, with multiple investment, talent, and property routes offering long-term legal certainty. A country that wasn't on most expat radars three years ago.

🇵🇭 Philippines - The digital nomad visa signed via executive order in 2025 still has no live application system as of mid-2026, with implementing rules not yet in force. Promising on paper, not yet real in practice.

Check your target country’s official immigration page for exact income thresholds and application windows. They move quickly.

I have a beautiful Penguin edition of this book, illustrated by Maira Kalman.

I've been reading The Elements of Style since college. Every time I think it’s going out of style, I reread it and it feels more relevant than ever.

Strunk first wrote it in 1919 for his students at Cornell. White, his former student, revised it in 1959. It has not required updating since, which tells you something about the nature of the rules inside it. Other than the beautiful illustrations in this edition by Maira Kalman.

What made me pick it up again this time was AI.

I've been thinking a lot about AI writing lately, for obvious reasons, and something kept nagging at me. The prose that comes out of these systems is fluent. It's structured. It's often technically correct. And yet it reads like something assembled rather than written. It has the shape of writing without the substance of it. I kept trying to put my finger on exactly why, and one afternoon I picked up Strunk and White and inside of twenty minutes I had my answer.

AI writing would fail this class. Badly. And here's the indictment, rule by rule.

Here are a few of the things that stuck out immediately. I am doing a deeper dive on this soon on my Youtube channel.

The now-infamous em dash.

Rule 9: Use a dash only when a more common mark of punctuation seems inadequate.

AI uses the em dash the way a nervous speaker uses filler words. I want to call it the “um” dash. It is also, not coincidentally, one of the easiest ways to spot AI writing at a glance. Before you read a word, the dashes announce themselves, like a ChatGPT copyright.

Use the active voice.

Rule 14: The active voice is usually more direct and vigorous than the passive. "I will always remember my first visit to Houston" versus "My first visit to Houston will always be remembered by me."

AI defaults to passive construction:. "It has been noted that..." "Mistakes were made." "The report was written by..." "This approach is often used by..." No one doing anything to anything. Strunk and White would circle every one of them.

Omit needless words.

Rule 17: "Vigorous writing is concise. A sentence should contain no unnecessary words, a paragraph no unnecessary sentences, for the same reason that a drawing should have no unnecessary lines and a machine no unnecessary parts."

AI is incapable of following this rule. It pads everything, like a student who forgot to do his essay starts looping together larger and larger “o”s to take up space.

It constantly says “Honestly” when I have learned not to trust anyone who says that a lot.

V. 6. Do not overwrite.

AI reaches for impressive language when plain language would do more work. It "utilizes" instead of uses. It asks you to "delve into" things. It finds things "fascinating" and "crucial" and "groundbreaking." Everything is a "tapestry." Every problem is "multifaceted." Every solution "leverages" something.

Strunk and White's version of this rule is simple: do not explain too much, do not use a long word where a short one will do.

V. 9. Do not affect a breezy manner.

AI is enthusiastic about everything. "Absolutely!" "Great question!" "It's worth noting that this fascinating topic has captivated thinkers for centuries!"

Strunk and White despised this in human writers. They would have found it even more unbearable in a machine.

V. 2. Write in a way that comes naturally.

This is from Element’s final chapter, "An Approach to Style," which is the most personal and least rule-bound section of the book, and what elevates this book to a classic. The argument is essentially that style cannot be taught, only cultivated. It emerges from the irreducible individuality of a writer (or artist or musician or simply a personality (emphasis on the “person” who has something to say and has figured out their own way of saying it. "The beginner should approach style warily," he writes, "realizing that it is himself he is approaching, no other."

AI has no self to approach. It has an averaged voice. It sounds like everyone and no one.

Strunk and White's entire project was pointing writers toward their own voice. AI has perfected the voice of everyone else's.

Strunk and White published the first edition of this book in 1919. Over a century ago. And the failures they were trying to correct in their students then are precisely the failures that define the most sophisticated writing technology ever built.

We fed it everything. Apparently nobody thought to add this one.

Read it and then read something generated by an AI, and you will see the same red marks on every page that Strunk was putting on his students' papers in 1919.

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See you next week. Don’t Escape. Design.