It’s a high-stakes month for booking. Holiday pricing dominates almost everywhere through the second half of December, and availability tightens fast for anywhere warm or scenic. The first two weeks are workable in many regions; the back half of the month means peak-season pricing and crowds across most warm-weather destinations.

All the more reason to find a place you enjoy and settle into the slow travel vibe.

In Africa, December is dry season across the north and a real winter-sun alternative to the pricier Caribbean. Morocco stays mild and dry; Marrakech inland, the Atlantic coast at Agadir and Taghazout warmer and good for surf.

Egypt hits its prime month: Cairo, the Nile at Luxor and Aswan, and the warm, cheap, increasingly nomad-friendly Red Sea towns of Dahab and El Gouna are worth checking out. Out in the Atlantic, Cape Verde (Sal, Boa Vista) is warm, dry, and breezy. Picture the Canaries, with fewer crowds.

West Africa is in its dry Harmattan season; Dakar and Accra are warm and dry, and Accra runs especially lively in December as the diaspora comes home. East Africa’s coast — Zanzibar, and Kenya’s Diani and Mombasa — is warm and mostly dry, though the short rains can linger early in the month and prices climb toward New Year.

Southern Africa is in full summer, but December is its peak local-holiday season: Cape Town and the Garden Route are beautiful and at their most expensive and crowded of the year, with load-shedding still a risk for a work day. Lovely, but this is not the value month.

In Asia, December is one of the strongest months across much of the region. Southeast Asia is at its reliable peak — Thailand, Vietnam, Cambodia, Laos, and most of Indonesia are dry, warm, and at high-season prices that climb sharply around Christmas and New Year. Bali, Phuket, and Hoi An effectively double their rates from December 20 through early January; book by October if those are on your list.

Japan’s winter arrives; it’s cold, dry, and clear, with the ski regions in Hokkaido and Nagano entering peak season and Kyoto quieter than autumn.

South Korea is cold but workable for city travel. Taiwan is at its mild winter best. Northern India and Rajasthan are in their peak season — dry, cool, and at their most pleasant for travel. Nepal’s lowland areas (Kathmandu, Pokhara, Chitwan) are workable; the high-altitude trekking season has wound down.

In Latin America, December marks the start of South American summer. Patagonia opens for its prime hiking season; Argentine and Chilean Patagonia are at peak demand and prices through February. Buenos Aires, Uruguay, and southern Brazil are warm and lively, with Brazilian beach destinations climbing toward New Year peak.

Mexico is in its high-season window across the coasts and the Yucatán; Tulum, Sayulita, and Puerto Escondido are all at their year’s most expensive. Costa Rica is in dry season and at high-season prices. Colombia is good and somewhat more affordable than the Mexican coasts.

If you’re looking to party the holidays away, head to Playa del Carmen, Mexico, or Granada, Nicaragua. Nicaragua and Ecuador each have fascinating New Year’s Eve traditions, if you want to burn away your troubles and ride a wave of fireworks into the new year.

In Europe, most of the continent is in winter, but Christmas markets in Germany, Austria, France, and Czechia run through most of December and are a draw for that specific kind of traveler. Southern Spain, Portugal, and Italy retain mild city-stay weather. The Canary Islands and Madeira are at their mild winter best and are good value compared to the Caribbean.

In North America, holiday travel dominates flight pricing from mid-December through early January. The Caribbean is at peak season and peak prices. Hawaii is in its high-season window. The U.S. and Canadian ski regions enter peak season around Christmas.

A booking note: anywhere warm and beachy in the Western Hemisphere is at its most expensive between December 20 and January 5. If you have flexibility, book either side of that window for noticeably better rates and availability.

A note for the moment: I’m not currently recommending US travel to international or Canadian readers. If you’re already in the US and looking to stay close, the Pacific Northwest and New England windows are real. For Canadians and international visitors, British Columbia is your best winter bet unless you really love cold and snow.

This month's Shortlist features sixteen places across four continents, picked for the month that’s hardest to get right — when prices spike and the good rooms vanish. A diving town on the Red Sea. A community house in the Canaries for anyone arriving somewhere alone and not wanting to stay that way. A festive town where the fireworks run most nights. A Patagonian summer base under the Andes. A rural hideaway in the Galician hills for the work-and-walk version of the month.

Each one timed to when it’s genuinely worth being there, with the real prices, the honest catches, and where to book direct.

Members-only beyond this point.

The Shortlist is Midlife Nomads’ members-only calendar of vetted stays — colivings, city stays, nomad trips, cruises, and the occasional artist residency for people in their 40s, 50s, 60s and beyond who are still working, value reliable internet and real comfort, and want community without dorm energy. Each month I publish a small set of places I’d actually send a friend, organized by region and timed to when each destination is at its best.

Read more

Midlife Nomads explores how people are redesigning work, travel, and life in our 40s, 50s & beyond.

Of everything I was bracing for on this trip — the flight, nine people in one group, my youngest’s four high school friends in tow — the thing I was actually anxious about was the time difference.

It turned out to suit one part of my work almost perfectly. This morning I woke up, journaled, had a good breakfast, then wrote up the Owen Sound news from our Tokyo apartment before anyone else was awake. Soon, we’ll we leave for Disney.

The thing I’d worried about most for this trip turned out to be the thing working best.

We landed in Tokyo late Monday, straight through from Toronto, no connection. Trevor and me are here with my oldest and his girlfriend, and my youngest with four of his high school friends. We’re here to see the exchange student he hosted last year. We meet him and his family tomorrow.

We took a city tour yesterday and hit some of the iconic spots: Asakusa and Senso-ji Temple, the Shinto shrine Meiji Jingu, the Imperial Palace and gardens, Shibuya Crossing.

Two experiences were real highlights for me, the first being a goma (護摩) — a fire ceremony for local worshippers at the Fukagawa Fudō-dō temple — no photos allowed so you’ll have to take my word for it. The goma rite is performed to replenish the power of Fudō Myō-ō, so the deity can burn away the obstacles blocking the path to enlightenment. (Yes, please.)

Right after that, our driver took us to my second-favourite, Tsukiji Market. The historic fish market is now packed with incredible street food and fresh seafood.

Somehow, I’ve been keeping up with the only work I didn’t take a few weeks off from — news reporting, and this community. I’d been worried about the time difference. It turns out to suit one part of my work almost perfectly.

The news editing runs on Ontario time. I read what came in overnight while I slept, write it up over coffee, and we head out for the day. I’m back before dinner to do final checks, catch anything that landed after business hours at home, and publish for 6am there. The thirteen-hour gap I’d been dreading became a head start.

And of course, you’re not time-sensitive at all, and I love Midlife Nomads for that.

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The rest of my work doesn’t travel as gracefully. Client technical writing wants my regular hours, and court coverage for the cases I follow would have me up at strange hours of the Tokyo night. None of that is sitting this week, which is the only reason the arrangement holds together as cleanly as it does.

So it’s not that the life travels or it doesn’t. Some of the work travels and some of it doesn’t, and you don’t really know which is which until you’re in the other time zone trying to do it. I’d assumed the whole thing would be a series of compromises. One piece of it turned out better than it is at home (where I work nights to get everything out before our readers wake up).

This is also the seventh continent I’ve set foot on, which I plan to celebrate this week. Antarctica was 2017, on a client trip I still can’t quite believe I got to take, so Asia was the one left on the list. I’m glad my first time here is with all of them. Even the four extra teenagers.

So that’s what’s working for me this week, in a place I expected to feel a lot less accommodating of my schedule.

What’s working well for you right now?

ICYMI on Midlife Nomads

Where I'd Send You This Fall

Nomad Cruise 18* — Barcelona to the Dominican Republic aboard MSC Opera, November 2-16, 2026. Fifteen days with 300 digital nomads and entrepreneurs, including a seven-day Atlantic crossing where most of the conference programming happens — talks, workshops, deep work, coworking — plus stops in Tangier and four Caribbean islands.

Solo-friendly (61% of participants travel alone), median age 30-45. Sailing this one myself; readers get €100 off by using discount code MIDLIFENOMADS

From our November Shortlist. These are my handpicked recommendations for stays of a month or longer for working travelers 40+ with quality accommodations, the option of community, and reliable wifi.

Recommended Reads

Pamela Marshall — When People Choose to Leave (The Frugal Traveler, Trail Mix #22)

Pamela read my piece on the people who leave and wrote back with her own version of the feeling, except hers goes back twenty years. Sometime in the mid-2000s she started reading about how civilizations come apart, and the checklist she found read like a description of the present.

Her essay tracks that dread from a 2016 Facebook post nobody reacted to all the way to the decision, now, to put some distance between herself and the country she was born in.

Keep reading

• Brian Clark's Greetings from Glasgow checks in from a slow loop through France and Scotland while he runs week two of his Sovereign Startup Foundations challenge (which is still open if you want to catch up).

• Chris Lutkin's The Next Atlantic Crossing untangles the rumor that Google is building a data center in the Azores (it's a cable landing station for two new transatlantic cables), and sits with the harder question of who actually benefits when remote workers and foreign capital arrive in a place that's suddenly strategically valuable.

• Carol Seymour's What Starting Over at 76 Has Taught Me is a campervan writer's case that beginning again takes more nerve at 76 than it did at 30 — and that the freedom she's found has more to do with needing less than with proving anything.

That's it for this week. Wherever you are right now, I hope it's turning out to suit you better than you expected.

✌🏻 Miranda

P.S. This week’s newsletter is brought to you by Viator, the place to find trips and things to do wherever you end up next. I earn a small commission when you make your booking through this link.

By every measure, Penelope Fitzgerald should have been a writer by 30.

She came from a famously literary English family. Her father edited Punch. Her uncle translated the Bible. She took a first at Oxford. She was, by every available measure, the daughter who was going to be the writer.

And yet she didn’t publish her first novel until she was 60. Her best one came at 79.

The thirty years in between are the part of the story a lot of people would call “the wasted years” — the marriage to an alcoholic, the teaching job that kept the family fed, the barge on the Thames that sank twice

The years she should have been writing. The decades she “lost.”

That isn’t what they were; not at all.

Right On Time is our weekly series of lessons in courage, clarity, and change for those rewriting their story.

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Penelope married Desmond Fitzgerald, a barrister who came back from the war with what we would now recognize as severe alcoholism. He couldn’t sustain his practice. Money got thin, then thinner.

By her early forties, Penelope was teaching at a tutorial college in Kensington to keep the family afloat. (Her students would later include a young Anna Wintour and the novelist Edward St Aubyn.)

For a stretch of years in the 1960s, the Fitzgerald family lived on a leaky barge moored on the Thames in Battersea, because it was what they could afford. The barge sank, taking with it most of what they owned.

They moved into temporary housing. The barge was salvaged. They moved back. It sank again when she was in her late forties.

This is the part of her life where a different kind of story would call her resilient, but she wouldn’t have used the word.

In the letters and interviews that survive from this period, she’s mostly just describing what’s happening — the children’s schoolwork, what she’s reading, the weather on the river. She is not narrating her own struggle. She is living inside it, persisting, as so many of us do.

Penelope published her first book — a biography of the painter Edward Burne-Jones — at 58. Her first novel came at 60.

Her third novel, Offshore, won the Booker Prize in 1979 when she was 63. It’s set on a leaky barge moored on the Thames… and she could not have written that book at 30.

Her last novel, The Blue Flower, came out when she was 79. Most critics consider it her masterpiece.

Julian Barnes once wrote that it was a matter of rueful pride to Penelope — and should serve as a warning to aspiring novelists — that she didn’t pass into the higher tax bracket until she was 80.

The decades when she wasn’t writing novels weren’t the absence of her writing life; they were the conditions that made the novels possible. She just wasn’t ready to draw on it yet.

This is the part most stories about late starts get wrong. The years before the work began aren’t the waiting room. They aren’t the part you apologize for. They’re the part that made everything after it possible.

Most of us are inside some version of this right now. A stretch of years that feels more like maintenance than meaning. Caretaking. Earning. Holding things together. Showing up to the job, the marriage, the apartment, the responsibilities, and wondering, quietly, what all of it is going to amount to.

The thing is, it already amounts to something. You’ve raised the kids, kept the household standing, built the career, paid the bills, held people together through things they didn’t know you were holding them through.

None of that is nothing. None of it was wasted.

And — this is the part that matters — none of it requires you to stay where you are.

Penelope Fitzgerald didn’t stay on the barge. She drew on it.

The years you’ve lived are yours, and so is what you do with them next.

You don't have to know what that looks like yet. You don't even need a plan.

What you've lived is already worth something, even if you can't see it from where you're standing. None of it has been wasted.

✌🏻 Miranda

Sources:

• Penelope Fitzgerald biography — Britannica

• LA Review of Books, “Late Start, Spectacular Finish: The Life of Penelope Fitzgerald”

• The Spectator, “Why did Penelope Fitzgerald start writing so late?”

• The Common Reader, “How Penelope Fitzgerald became a late blooming novelist”

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You’ve been talking to someone about a possible partnership. The conversations have been good. The thinking is sharpening. Within a few weeks, you’re discussing formal structures, splitting equity, signing agreements.

And then, often within six months, the partnership falls apart. Sometimes spectacularly, with hurt feelings and obligations that take months to untangle. Sometimes quietly, with one party drifting away and the other left holding more of the work than they signed up for.

Either way, the time and money are spent, the relationship is damaged, and the project is now harder to attempt with anyone else.

Most of these failures share a single underlying cause:

The work that should have happened before any structure was designed never happened, or happened too late.

That work isn’t legal work. It doesn’t require a lawyer, an accountant, or an entity registration.

It’s the practical work of figuring out whether the partnership you’re imagining is actually the partnership the other person is imagining, and whether the two of you can actually work together at the pace and pressure a real venture requires.

This piece walks through the early, exploratory steps that help separate partnerships that hold up from partnerships that don’t: the conversation that has to happen before any structure gets designed, the test run that validates what the conversation reveals, and an honest debriefing that informs what you can take forward for legal and accounting support.

This is all available to you before any binding agreement exists. Both cost almost nothing to do well. And both filter out the partnerships that would have failed in the first year of a more formal arrangement — which saves enormous time, money, and relationship damage on the other side.

The Conversation

The hardest part of a good partnership isn’t the structure. It’s the conversation that has to happen before the structure gets designed.

Most projects fail not because the legal arrangement was wrong but because the parties never had an honest conversation about what they were actually agreeing to.

They had a vision conversation, full of enthusiasm and possibility. They had a logistics conversation, working out who would do what.

But they didn’t have the harder conversation about asymmetries, motivations, capacity, and exits. Those unspoken questions surfaced later, under stress, when both parties had already invested too much to walk away cleanly.

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A few questions worth working through with a potential partner before anyone starts drafting anything:

What Is Each of Us Actually Bringing?

Be specific. Not experience or expertise — what concrete capabilities, time, capital, network, brand, or work product is each person contributing?

This is the question most partnership conversations skip, because the answer is usually less symmetric than both parties are comfortable acknowledging up front.

One party is bringing twenty years of established client relationships and a recognizable name in the industry. The other is bringing operational discipline and the willingness to do work the first party doesn’t want to do.

Those contributions are both valuable. They’re not equal in any easily measurable way, and treating them as if they are creates the conditions for resentment later.

The answers usually reveal asymmetries that need to be acknowledged, and revealing them now is much easier than negotiating them under stress when one party feels they’re contributing more than they signed up for.

Read more

Midlife Nomads explores how people are redesigning work, travel, and life in our 40s, 50s & beyond.

This week’s newsletter is part update, part field report including the kitchen-table math many are doing on whether to leave their country, and what recent news suggests about doing it without betting everything at once.

I’m in Canada this week for family visits and a suitcase swap (because what I packed in April for Normandy is not what I need for June in Japan). There is a particular pleasure to packing for a trip you’re excited about. You can feel it in your hands.

But that isn’t what I’ve been thinking about while I sort through what to take.

I’ve been thinking about the people in my inbox. The DMs, the long emails, the replies that start with I’ve never said this out loud to anyone but. People who are not packing for a vacation. People who are seriously, privately evaluating what it would take to leave and start over or rebuild — not for two weeks, but for good.

They are terrified. Most of them have never lived outside the country they were born in. Many of them have partners who aren’t sure. Some have parents who won’t understand, or kids whose schools they’d have to figure out. Jobs they’d have to reshape or replace.

The whole architecture of their belonging would have to come apart, carefully, before any of it could be packed up and hopefully reassembled somewhere new.

And still. They are looking.

I’m not here to tell anyone whether to go. The reasons people are looking to relocate, to move abroad right now are their own, and the people doing the looking already know what they are. They don’t need me to validate them and they don’t need me to argue them out of it.

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What I want to say is smaller than that.

If you are doing that other kind of packing right now — the kind where you’re not sure yet, where you’re researching at the kitchen table at 11pm, where you’ve started reading visa pages and looking at apartment listings in cities you’ve only seen in photos — you are not alone in it. You are not being dramatic. You are not overreacting.

You are paying attention.

I’m going to keep writing about this — the looking, the deciding, the doing — through this summer. If you're somewhere on that path, hit reply or leave a comment.

You're not the only one working through this.

So here's what I've been writing this past week and reading while I sort through the suitcase… people already living what so many in my inbox are weighing, and the news changing the terms underneath them.

ICYMI on Midlife Nomads

Where I'd Send You This Fall

Enchanted Coliving — Nachamps, France

A small, book-lined coliving in the French countryside between La Rochelle and the Atlantic, created by Bianca after years of living in other colivings. Phone-free Sunday brunches. Slow mornings. Rooms named for imagined worlds: Narnia, Rivendell, Arendelle, Neverland.

For the reader who wants a small intentional community, not a coworking conveyor belt. 2.5 hours from Paris by TGV. Highly recommended by friends I trust who’ve stayed at Enchanted.

From our October Shortlist. These are my handpicked recommendations for stays of a month or longer for working travelers 40+ with quality accommodations, the option of community, and reliable wifi.

What’s On My Radar

Bali Bans Sponsored Posts: What This Means for Your Tourist Visa

The headline is about influencers, but the story underneath is bigger than that. Indonesian immigration has been actively enforcing a much stricter definition of "work" since April — including barter arrangements, unpaid promotional shoots, and brand collaborations with no money changing hands.

Sixty-two foreign nationals detained in three weeks. The pattern matters even for readers who aren't going to Bali, because the assumptions a lot of nomad and slow-travel arrangements rest on are getting tested in real time, and Indonesia probably won't be the last country to do this.

Read more in Asia Lifestyle Magazine

The Future of Remote Work — Nomad Magazine

Nina Hoeberichts maps where remote work actually stands in 2026: some companies clawing back flexibility while others build their whole model around it, hybrid hardening into the default, more countries rolling out nomad visas. The section on economic displacement alone is reason to read it.

Keep reading at Nomad Magazine

Also worth your time this week… a few pieces that, read together, suggest the same thing: stay longer, commit less.

• The Rise Of The 'Slomad': Digital Nomads Moving To Chiang Rai In 2026 — Chiang Rai Times

• Not a tourist, not an expat: the rise of the midlife working trip — Buenos Aires Herald

• The new European train routes that could replace your next short-haul flight — Focus on Travel News

• Golden Visa holders to file lawsuit against Portugal over the new Nationality Law — The Portugal News

That’s it for this week. Whatever rooms you find yourself in until we meet again, I hope they're the right ones.

✌🏻 Miranda

P.S. This week’s newsletter is brought to you by Airalo, the eSIM app I’ve used to stay connected in over a dozen countries. I earn a small commission when you sign up through this link; you get to skip the SIM card hunt and get online as soon as you land.

The deal was simple, and most of us took it. We tried, anyway. Work hard for forty years. Stay loyal. Defer the life you actually wanted. Cash in at sixty-five and enjoy yourself.

The deal is broken. It’s been breaking for a while, but the pace has accelerated to the point where the math no longer pretends.

And every year we keep buying into it costs us something we’re never getting back.

What the Lie Promises, and What It Pays

The median American aged 55 to 64 has $185,000 in retirement savings against a “magic number” of $1.46 million that Americans say they’ll actually need. The gap between what people have saved and what the math says they need is too large to close in the working years most people have left.

The median working American has $955 saved for retirement. Not a typo. Nine hundred and fifty-five dollars, against a thirty-year retirement that’s supposed to fund itself.

The full Social Security retirement age has moved to 67 for anyone born in 1960 or later. Economists are floating 69 or 70. In Canada, household debt-to-income ratios are among the highest in the OECD and the federal pension covers a fraction of pre-retirement income for most workers.

The math is bad in different ways on either side of the border, but the answer is the same. The deal is not going to keep its end.

That is the first cost: the years we hand over for a payout that’s already known to be insufficient.

The Cost of Waiting for Retirement to Live

The biggest line item on the bill, and the one no spreadsheet captures, is the life that gets postponed.

We were taught that the good years come later. After the kids. After the mortgage. After the title. After the gold watch.

The phrase “I’ll do that when I retire” is the most expensive sentence in the English language, because it spends decades of the only thing that doesn’t come back.

The trip you keep meaning to take. The work that uses you instead of using you up. The version of yourself you remember being curious about, before you started using your weekends to recover from your weeks. All of it has been moved to a date that the deal is no longer underwriting.

And here’s the part the brochure didn’t mention: the body you’re saving the good years for is not the same body that will be waiting for you at sixty-seven.

Whatever you defer, you defer to a version of yourself with less of what makes the deferral worth it. That is the second cost. It compounds.

The Cost of Staying Loyal to a System That Stopped Being Loyal

The bargain was supposed to be: hand over your productive years, get security in return. The security at the end has been disappearing for decades. What’s new is that the security in the middle is going, too.

Companies announced more than 1.1 million job cuts in the U.S. in 2025, the highest since the 2020 pandemic. Wall Street is publicly planning to cut 200,000 jobs over the next three to five years. Amazon eliminated 14,000 corporate roles citing AI.

Modeling-based estimates put actual AI-driven white-collar displacement at 200,000 to 300,000 positions and rising quarter over quarter. The work you traded your twenties and thirties for is being repriced in real time, and the people doing the repricing are not asking your permission.

The wages that remain are buying less of what people need. In nearly every major North American metro, rents rose faster than wages from 2021 to 2024. New York alone has 2.5 million people living in poverty. Two full-time salaries no longer reliably keep a family out of poverty in cities where, a generation ago, one income bought a house.

That is the third cost. Loyalty to a system that has stopped being loyal back.

Every year you keep paying in, you pay alone.

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The Cost the Body Keeps

Even if the math worked, even if the deal still paid out and the pension still arrived, the version of life it’s selling is a version that ends you faster than the work did.

Retirement, as the culture imagines it, is rest. In practice, it’s sitting. Studies of the retirement transition show daily free-time sitting jumps from about four and a half hours to six. Television time goes up. Light activity goes down.

And the longer you sit, the faster you age biologically — a 2025 analysis found people sitting eight or more hours a day had a 58% higher risk of accelerated aging compared to those sitting under four.

Settling into the comfy chair at the end is not rest. It’s a different chair from the one at work, but the body cannot tell the difference. You can spend forty years in one chair making money for someone else, retire on what’s left, and spend your last decades in another chair watching television. The body keeps the score the whole time.

That is the fourth cost. It’s the one no one mentions because no one is selling the alternative.

What Sovereignty Costs, and What It Doesn’t

The script most of us were handed has been failing in slow motion since the 1980s. What replaces it is not the start-a-side-hustle-grind-your-way-out script the algorithm wants to sell you next. That one ends in burnout, not freedom. It is the same deal in a different costume.

What actually replaces it is harder and more honest: building a life that doesn’t rest its weight on any single point of failure. Income from more than one source. Skills you can put down or pick up. Relationships and communities you’ve invested in before you needed them. A body you used for the forty years instead of waiting until you stopped.

This is not a self-reliance pitch. The point of sovereignty is not to need no one. The point is to not be vulnerable or held hostage to any one thing.

Sovereignty does not cost what the deal cost. It does not ask for your twenties and thirties and forties on the promise of a sixty-fifth-birthday payout that’s not coming. It asks for honesty about what you actually want, what you actually need, and what you are still willing to trade.

The math of that conversation is different, and usually better than people expect when they finally sit down with it.

That is the fifth cost — but it is a cost in a different ledger. The deal asks for your life and gives you a guess. Sovereignty asks for your attention and gives you back the years.

What We Owe Each Other

Building your own sovereignty is necessary, but it’s not sufficient on its own.

The conditions that made the original deal work for the generation that got it were not gifts of nature. Pensions, housing people could afford, wages that supported a family — those things existed because workers fought for them, and because governments, for a while, listened.

They’ve been dismantled by policy choices that benefitted a few over the last forty years. That sucks, but it also means that policy choices can rebuild them.

To get there, we have to admit that individuality is killing us. We’ve been trained to read every structural failure as a personal one — your savings gap, your burnout, your housing or lack thereof, your crumbling retirement plan — while the people hoarding the resources read us correctly, as a mass.

Sovereignty happens inside the collective. Outside it, you’re in a bunker — and bunkers are designed to be picked off one at a time. That’s the whole point. The people hoarding the resources are not afraid of the bunker. They’re afraid of the block.

The sovereignty worth building is not the kind that pulls you out of the collective, but the kind that lets you show up for it, stronger and more often. That’s the only way it works. That means:

• Sharing space instead of duplicating it.

• Joining the union if there is one, and rebuilding it if there isn’t.

• Investing in friendships and communities before you need them.

• Voting in the local elections where housing and labour policy actually get decided.

• Pooling resources with people you trust.

• Buying less from the companies that are eating your wages and building more of what you need with people who live near you.

None of these are “lifestyle” choices. This is the structure that makes individual freedom possible for more than a privileged few. We cannot afford to wait for permission, and there’s no point waiting for the old deal to come back.

You can build your own deal, and you should. At the same time, the conditions for more people to build theirs do not arrive on their own, and the work of making them arrive is the kind of work that gets shared, or it doesn’t get done.

The script that says otherwise has had a long run, and it’s running out of road. What it has cost us is already on the ledger. What it costs from here is still up to us — and it gets paid together, or not at all.

✌🏻 Miranda

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If you’ve been doing the math in private — what your life would actually cost somewhere else, whether you could get residency, what you’d have to give up and what you’d get back — you’re not delusional or hysterical.

And you’re not alone.

A lot of people are sitting at their kitchen tables and on their couches and in their cars right now, working through the same calculation. Most of them haven’t told anyone yet.

Those thoughts of packing up and starting over somewhere carry quite the stigma. We’ve been trained to read these kinds of question as a personal failure. Buck up. Be stronger. This too shall pass.

The instinct, the moment the math stops working, is to assume the problem is you. That you should be more grateful. That a more resilient person would be making it work.

But it doesn’t always pass. The lifetime of relative stability most of us grew up inside of was the exception, not the rule. Wages tracked productivity. Housing was affordable on a normal salary. The country you were born in could reasonably be expected to be the country you’d retire in. None of those things are historically normal.

They were the conditions of a particular moment, and the moment is ending.

In the United States, an estimated 180,000 citizens emigrated in 2025, the largest outbound migration in decades. Applications from Americans seeking European residency jumped 183% between Q1 2024 and Q1 2025.

In Canada, 106,134 people left in 2024. That’s the most in nearly sixty years. 2025 is on track to break it.

In the UK, 257,000 British nationals left in the year ending December 2024, eight years after a Brexit vote that still hasn’t delivered the country anyone thought they were voting for or against. When the Office for National Statistics switched to a more accurate counting method last year, it revised its emigration figure up by 180,000 people. The people leaving were already leaving. The state just hadn’t been counting them.

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Different catalysts. But I’d bet there’s a lot of overlap in their browser histories.

I want to say something carefully here, because it matters.

If you’ve been feeling that something has shifted in the country you live in, that the deal you thought you were making has stopped being on offer, you are not imagining it.

The labor share of US GDP, the slice of the economy that goes to wages instead of to capital, is at 54.1%. That’s the lowest reading since the Bureau of Labor Statistics started keeping the number in 1947. In the year 2000, it was 63%. Three-quarters of that decline happened between 2000 and 2016. The drop has been building for a quarter of a century, and the technology arriving now is going to accelerate it.

In Canada, the share of household income going to housing has reached levels that, for younger households, are functionally unprecedented in the post-war period. Average rent in Toronto and Vancouver runs higher than mortgage payments did a decade ago. The grocery bill is no longer the small line item it used to be. The math of a normal life has been shattered.

In the UK, real wages spent most of the 2010s stagnant or falling, and the post-Brexit recovery the country was promised hasn’t arrived.

The CEOs know. Lawrence Winnerman, writing in Blue Amp Media, pulled the numbers together recently in a way that's worth reading in full. The short version:

In 2026, Jeff Bezos sold $5.7 billion of Amazon stock. Michael Dell sold $2.2 billion. Safra Catz at Oracle sold $2.5 billion. The people running the largest companies in the world sold shares at levels analysts called staggering.

Insiders sell when they think the stock is closer to its top than its bottom. They have access to numbers the rest of us won’t see for months.

American companies authorized $665 billion in share buybacks in the first four months of 2026, the largest figure to start a year in history. A buyback is what a company does with cash when it can’t think of anything more productive to do with it than return it to its existing shareholders. Boards authorize record buybacks when they’ve stopped believing in the growth story they’re supposed to be investing for.

Berkshire Hathaway is sitting on cash equal to 31% of its total assets, an all-time high. That’s Warren Buffett, the most patient investor of the modern era, refusing to spend. He’s telling you what he sees coming by what he’s declining to buy.

These are not the moves of people who think the next few years are going to be good for ordinary households.

You can feel the math shifting under you. You’re correct that it’s shifting.

And this is the part I want to say plainly: choosing to build a life somewhere else doesn’t make you a traitor.

The contract was simple. Work hard, stay loyal, contribute, build, and the country you do it in protects the life you build. For two generations, that contract more or less held. The people who signed it got a middle class. Their children got a shot at one. A lot of you organized your whole lives around it.

It isn’t on offer anymore… not in the form it was offered to your parents. Not in the form you were told it would be offered to you.

Noticing that out loud is not a moral failure.

In November of 1948, a 24-year-old writer named James Baldwin bought a one-way ticket to Paris with forty dollars in his pocket. He’d never been out of the United States. He didn’t speak French. He had no job waiting and no real plan beyond getting on the boat.

He stayed for nine years.

The reason he left, in his own telling, wasn’t that he hated America.

It was that he could see, by 24, that staying was going to cost him the ability to do his actual work.

He was Black. He was gay. He was a writer. The cumulative weight of trying to be all three of those things at the same time in 1948 America had become, in his words, a matter of survival (and not metaphorically).

He wasn’t running from anything in the sense the word usually means. He was going somewhere he could finish the sentence.

He wrote Go Tell It on the Mountain in Paris. He wrote Giovanni’s Room in Paris. He wrote most of Notes of a Native Son in Paris. The work that made him James Baldwin was the work he did after he left the country that was supposed to be his.

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Baldwin wasn’t an isolated case. He was part of a pattern the twentieth century kept producing.

The Lost Generation went to Paris in the 1920s for the same reason in different clothes. Hemingway, Fitzgerald, Stein, the rest of them. They didn’t leave because they hated America. They left because the country had narrowed after the First World War in a way that made staying feel like a slow form of suffocation.

Tens of thousands of Americans came north to Canada during Vietnam. I’ve met a lot of them over the years. People who left the country they were born in because they didn’t believe in the war their government was asking them to fight. Most of them stayed. Some of them became the doctors, the teachers, the librarians, the civic leaders of the small towns that took them in. They built lives that, by any honest measure, mattered to the places they ended up. The places they left mostly went on without them.

Americans moved to Mexico in the 1970s, the artists and the disaffected, the ones who’d watched Watergate and concluded the version of America they’d been promised wasn’t on offer anymore. Brits left Britain after the war, after Thatcher, after Brexit. Canadians have been quietly leaving Canada for the better part of a decade.

Most of them don’t return to their country of origin.

Not because the country they left got worse, though sometimes it did. The life they built somewhere else turned out to be the one they actually wanted, and they hadn’t known it until they were inside of it. The leaving wasn’t a leap. It was the part where they finally got close enough to see what they’d been agreeing to without choosing it.

Baldwin came back to America in 1957 and spent the rest of his life moving between countries. He never lived full-time in the US again. He didn’t describe his nine years in Paris as a detour from his real life; they were the period in which his real life became possible.

That's the pattern. The people who leave stopped trying to fix a situation that wasn't fixable, and started building a life they wanted to be inside of.

The politics are a catalyst. The cost of living is a catalyst. But the people doing this aren’t making the decision in a panic. They’re making it the way most consequential decisions actually get made: gradually, over months, in the searches no one sees.

You’re allowed to be one of them.

Not because leaving is the answer, or the brave thing, or the right thing. Sometimes it isn’t. Sometimes staying and building something inside the country you have is the best answer. People do that too, and some of them are right.

But if the math has stopped working, if the country you live in has stopped being a place where the life you want is possible, naming that out loud is not disloyalty or a moral failure on your part.

It’s just accurate. The contract was the deal you were offered. That deal isn’t on the table anymore.

The people who leave are usually right about one specific thing: the feeling came first. The gut said something had changed before the numbers caught up. The conditioning told them the problem was their own ingratitude or lack of resilience.

They were correct to stop believing it.

Baldwin didn’t have demographic data. The Lost Generation didn’t have economists confirming the long stagnation of post-war Europe. The Americans who came to Canada during Vietnam didn’t have polling that said the war was unpopular.

They had what they could feel. They trusted it before the culture told them it was safe to trust it. Many were called names or vilified for leaving. And yet the historical record, when it eventually caught up, said they had been reading the situation accurately the whole time.

That’s the thing they were right about. Not that leaving was the answer. That the feeling that something had broken was real, and that no one was going to give them permission to act on it before they acted on it.

You’re allowed to look at what is.

✌🏻 Miranda

Sources:

• The Boston Globe, “A record number of Americans are leaving the country and seeking to renounce citizenship”

• Inman, “More Americans are moving abroad and not looking back”

• MovingTo / Stacker, “The ‘Plan B Passport’ boom: How political uncertainty is driving a record surge in Americans seeking European residency”

• Yahoo News Canada, “Canada just broke an emigration record with more people leaving the country than ever before”

• MTL Blog, “A record number of Canadians fled the country in 2025 but Quebec is not following the trend”

• BBC News, “UK net migration 20% lower in 2024 than first thought, ONS says”

• Office for National Statistics, “UK emigration explained: what we know about Brits moving abroad”

• Blue Amp Media, “This Isn’t a Recession. It’s Worse.” — source for labor share data, CEO insider sales, buybacks, and Berkshire cash position

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You've been thinking about a project. Maybe it's a publication, a small business, a consulting practice, a digital product, a local venture, a creative collaboration. You can see the shape of it. You can see why it would work.

What you can't see is how you'd actually build it on your own, because the project needs capabilities you don't have — or shouldn't have to develop from scratch.

So the thought arrives: what if I built this with someone?

And then, almost immediately, the next thought that kills it: but that means forming a company together, and that’s a whole legal thing, and I don’t even know if this person would want to, and what if we have to split everything fifty-fifty when we’re contributing different amounts, and what if it falls apart...

That mental model is doing more damage than most people realize. It’s also wrong, or at least incomplete.

A note before going further: this piece is information, not legal or accounting advice. The structures described below have real legal and tax implications, and those implications vary by jurisdiction and depend on your specific situation. If your project gets serious, talk to a lawyer and an accountant who know your context. What follows is meant to help you understand your options and prepare for those conversations — not to replace them.

The Default Mental Model & Why It’s Incomplete

When most people imagine working with someone on a project, they picture a 50/50 partnership: shared ownership, shared decisions, shared bank account, shared liability. A formal business, jointly held. That structure exists, it’s a real option, and sometimes it’s the right one.

But that’s the most legally and emotionally complex version of working together — and most projects, especially in their early stages, don’t need to land there.

The mental shortcut of partnership = shared company is part of why so many promising midlife projects never get started. The reader looks at a project that would require working with someone, decides the partnership overhead is too much for what the project warrants at this stage, and quietly puts the idea down. The project dies before the structural question has even been examined honestly.

The structural question is worth examining honestly, because the actual landscape of options is much wider than the default model suggests.

Partnerships & Collaborations Exist on a Spectrum

Two people can work together on a project without ever forming a shared entity.

• They can collaborate informally and bill their own clients separately.

• One can subcontract to the other.

• They can split revenue through a contract without sharing ownership of anything.

• They can create a joint venture agreement that defines the project as a shared effort without creating a new company to hold it.

• Or they can form a partnership, an LLC, a corporation — the formal structures most people associate with the word partnership — when the project genuinely warrants the overhead.

Each of those options has different implications for legal exposure, tax treatment, brand ownership, exit terms, and how the work actually gets done day to day.

None of them is universally right.

The structure that fits depends on what the project is, what each party is bringing, what they need from the arrangement, and what stage the project is at.

For most projects in their early stages being undertaken by experienced people, the lighter end of the spectrum is the right place to start. You don’t have to begin with shared ownership of a company.

You can begin with a clear conversation, a written agreement that names what each person is doing and what each person is getting, and a structure that lets the project develop before it requires the legal apparatus of a formal entity.

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Why This Matters for Midlife Professionals

The default mental model is particularly costly for midlife professionals, because it kills projects that would otherwise be viable. The reader looking at a potential project usually has something younger founders don’t: a network of other midlife professionals with built-up expertise, often quietly looking at the same kinds of questions.

The right partner for the project you’ve been thinking about may already be in your contacts.

Underneath the reluctance to have that conversation is a structural concern most partnership advice fails to address: shared liability.

A formal partnership or jointly-owned company means each partner is exposed to the consequences of the other’s decisions, debts, and mistakes. If your partner makes a bad call, you’re on the hook for it. If the business takes on debt, both your names are on it. If something goes legally wrong, both of you are named.

That risk is real, and it scales with what you have to lose. A 25-year-old with no assets has limited exposure to shared liability. A 55-year-old with a house, retirement savings, and twenty more years before they can replace lost capital has a lot more at stake.

The instinct to be cautious about formal partnerships in midlife isn’t timidity. It’s accurate risk assessment.

The point of this article isn’t to argue that formal partnerships aren’t risky. The point is that you don’t have to start at the formal end of the spectrum.

Lighter structures exist that let two people work together without exposing each to the other’s liability — without shared debts, shared legal exposure, or shared ownership of an entity that survives them. Those structures are where most midlife projects should start, and many can stay there indefinitely.

What follows for paid subscribers is a walk through the actual structures, how each one operates, when each fits, what the trade-offs are, and the threshold at which informal arrangements need to become formal.

It includes how to think about IP, brand ownership, exit terms, and dispute resolution, and a worked example using a partnership I’m actually in.

Read more

Midlife Nomads explores how people are redesigning work, travel, and life in our 40s, 50s & beyond.

This week's edition is brought to you by Wise, a preferred partner of Midlife Nomads — the account I’ve actually used over the last 10+ years to move money across borders without getting quietly skimmed on every transfer.

I’ve been in a lot of coliving conversations this week. Some at tables, some over coffee, one that ran long enough that I forgot to eat dinner.

These aren't new conversations for me. Failed projects in Canada. A failed project in Panama. Ten years of versions of this. Some never got a shovel in the ground. Others looked promising right up until they didn't. It would be easy (and perhaps logical) to lose hope.

And yet, the model works. It’s been working for years, in places most people pitching new coliving builds have never actually visited. I just didn't seem to be in the right rooms — with people who were in it for the right reasons, with the will and funding to actually build the thing — until now.

North Americans were trained to accept a particular kind of waste as success. Everyone with their own washing machine, their own lawnmower, their own car in their own driveway. Excellent for capitalism. Not so excellent for the people doing the buying, who at some point stopped being called citizens and started being called consumers, and mostly didn't notice the swap.

Plenty have noticed since. But the people who’d benefit most from sharing some of this often look at coliving with disdain. I could never spend that much time with other people. I need my privacy — as though privacy were something you had to give up to live near other adults.

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It isn’t. The communities that actually work have figured out the privacy question; how to ensure there’s privacy when you need it, and community when you crave that, too. That’s part of what makes them work.

Some have been quietly building this for a long time.

In the U.S., Bryn Gweled Homesteads in Pennsylvania has been doing private homes on commonly owned land since 1940. The model that became the modern cohousing movement traces back to Sættedammen outside Copenhagen, which opened in 1972. Sixty adults and twenty children live there now across twenty-seven privately owned households.

In Canada, there are around twenty-four established cohousing communities with more in progress, most of them in BC and Alberta (not because those provinces are better at sharing, but because their Strata Titles Act actually permits cohousing in a way the rest of the country's condo laws don't).

Prairie Sky in Calgary is an eighteen-unit ownership community of about forty residents, diverse in age, income, and occupation, who share weekly meals and manage the place themselves. In Ottawa, four single women in their sixties pooled resources to build Soul Sisters — six thousand square feet, four private apartments inside what looks from the outside like a single-family home, because that's how they had to design it to meet local zoning.

These aren't rentals or membership clubs. They're ownership models structured legally as condos, co-ops, strata titles, community land trusts. People hold standard deeds. They get standard mortgages. They build standard equity. The only thing that's different is that they also own one forty-third of the lawnmower.

These places are full of people who go to jobs, raise kids, retire, host grandchildren, deal with illness, and bury their dead. The model has been working at this scale, with this kind of seriousness, for decades.

It’s just underrepresented in the rooms where new builds get decided.

Most US municipalities define “family” as related individuals, or cap unrelated adults sharing a home at three or four people. The Supreme Court upheld this in 1974 (Village of Belle Terre v. Boraas) and it’s still on the books, meaning in many places a group of friends sharing a home is literally illegal. Texas just moved to overturn this. Washington tried and got watered down. Boarding houses and SROs were a normal part of American cities until zoning made them essentially illegal.

In the U.S., 75% of residentially-zoned land in many cities is zoned for single-family detached homes only. Coliving can’t exist on most residential land by definition. (Wikipedia is blunt about its history: it emerged partly as a tool to keep minorities out of white neighbourhoods.)

In the UK, the political action against shared living is more targeted. Boroughs like Hackney, Camden, Tower Hamlets, Newham, and Waltham Forest specifically removed the permitted-development right to convert single-family homes (C3) to small shared houses (C4). This forces a full planning application with refusal rates of 30–50% in the most active boroughs.

NIMBY objections to communal living are common in Canada, often citing the unfounded concern that "property values will go down" — even when the housing being objected to is residential by definition.

In most Canadian municipalities, the path of least resistance is still the thing it's always been: a thousand small families, each in their own increasingly unaffordable box, each paying property tax, each filling a school catchment, each buying their own everything.

Coliving doesn't generate the same downstream consumer spending, and doesn't produce homeowner voters who'll show up to council meetings to defend it. So it gets zoned into corners, stalled in committee, or repeatedly refused until the money gives up.

This isn't theoretical. I’ve invested in these projects. Served on the board of one, but eventually pulled my investment back when it became clear the local government would simply never let it happen.

So I've sat in these rooms before, skeptical, watching pitches that were really just real estate plays in softer language. The investor-pitch version always has one slide about "community" so vague it's clear they've never actually lived in one. It's the slide with the stock-photo strangers laughing at a long table. Nobody in the photo is doing dishes. Nobody is figuring out the laundry schedule, or having the awkward conversation about the person who keeps leaving their stuff on the kitchen counter.

In much of the real estate investment world, this concept of “community” has been reduced to glossy photos and a few adjectives. Vibrant. Connected. Intentional. Just put people in a space and they’ll work that stuff out (except they don’t… it actually takes effort).

The conversations I'm in now don’t sound like pitches. They sound like people who understand what they’re getting into comparing notes and making plans that could actually work.

The people in these rooms already know coliving works. They’ve built it, and lived in it. Adults and multi-generational groups can absolutely share a life together — with well-defined private spaces, shared amenities that are actually maintained, and someone whose job it is to hold the community together rather than just hold the keys.

So the questions in the room aren’t whether it’s possible — they’re how, here, with these particular people, on this particular piece of land.

What does the guest policy actually say? How do you handle the season when half the residents are away? Who’s the person who notices when somebody’s gone quiet at dinner three nights in a row? What happens to your space when your mother gets sick and you have to leave for two months?

These are not the questions you ask if you’re trying to assemble a deal. They’re the questions you ask if you’re trying to build something you intend to live in, with people you actually care about.

And I think that’s the thing I’ve been waiting for, across ten years of these conversations. Not better arguments for coliving; I’m convinced.

But better company. People who know it's possible because they're already doing it. People doing it for the right reasons, figuring out the next version with the kind of care you can only bring to something you see as the future for yourself and your family — not just your investment portfolio.

And here’s something I didn’t expect, which would probably surprise the naysayers most of all. In all of these conversations, I haven’t met a single person looking for a free ride. Not a hippie in sight.

Just productive, creative, capable people — most of them well into careers and families of their own — who’ve looked at the current setup and decided they want something more from the next thirty years than a mortgage and a lawn to mow.

I’ve met so many people in recent years who’ve given destination coliving a try and learned the “sacrifice” isn’t near what they’d braced for. You give up a second bathroom. You get back a dinner table where the conversation is worth staying for.

So I'm hopeful this week. Ten years is a long time to wait for the right room. But the right rooms exist. The right people are out there too, looking for coliving that actually works for the people who'll live in it.

You just have to keep showing up until you find them.

✌🏻 Miranda

Our partner: Wise

ICYMI on Midlife Nomads

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What’s On My Radar

Your expertise was probably worth far more to your employer than they paid you for it. Brian Clark unpacks why — and why that gap is so disorienting when you go independent.

The phrase that's stuck with me: the corporate job was never the right container for your expertise. If you've ever wondered why pricing yourself feels so hard, this is it.

Read more at Further

Croatia was one of the first European countries to roll out a digital nomad permit, and for a while it was the success story. Now the question has shifted from can we attract them to can we keep them — and the answer is running into the same wall Spain, Portugal, Bali, and Greece have already hit.

Coastal landlords prefer short-term tourism income to year-round rentals, summer prices have climbed sharply, and locals are increasingly ambivalent about the whole arrangement.

Keep reading at Total Croatia News

Also worth your time this week:

• "Employers Are Hiring Freelancers To Fill Gaps As 2026 Layoffs Hit Pandemic-Era Levels" in Self Employed — a useful snapshot of how the corporate-job container is actually changing right now. Layoffs at pandemic levels, freelance demand at record highs, and tax policy quietly tilting toward independent work. This is the structural argument behind every conversation about going sovereign.

• "Bosses take remote work less seriously when it's geared toward parents, study shows" in Fast Company — the study confirms what a lot of people figured out on their way out the door: flexible policies framed as parent perks get penalized, and the penalty falls hardest on the people who actually use them.

• "The $2,700-a-Week House We're Staying in For Free" by Jo Barnes — house sitting is one of the most useful and underrated strategies for long-term travel, and Jo lays out exactly how she and her husband use it as their main accommodation across multiple continents. The free portion sets up the case; the paid section walks through how to actually get your first sit.

• "More Women Are Starting Businesses Than Ever but Many Are Doing It Alone" in Inc. — honest data on the cost of solopreneurship, and an even more honest argument for building your support system before the business depends on it.

• "I don't think I'll ever be able to retire" — BBC interviews with three Britons in their seventies and eighties still working, for very different reasons. A useful counter to the binary framing of retire or grind, and a reminder that the more interesting work is figuring out what kind of work you'd actually want to be doing at seventy-five.

That’s it for this week. Whatever rooms you find yourself in until we meet again, I hope they're the right ones.

✌🏻 Miranda

Think back to the dream you had at 22. Not the polished one you’d tell people about now, with hindsight smoothing the edges. The real one. The thing you wanted so badly it embarrassed you a little to say out loud.

Maybe it was a city you were going to live in, or a book you were going to write. A life you could picture in such specific detail it felt almost like a memory of something that hadn’t happened yet.

You can probably still see her; the version of you who wanted it. What she was wearing. Where she was standing the first time she said it out loud. The light in her eyes and conviction in her voice when she shared it with others.

And then life happens. The dream gets put in a drawer. Not abandoned, exactly. Just… set down, while you do the work of the next two or three decades.

For too many us, that drawer stays closed.

Diana Nyad opened hers back up at 60.

Right On Time is our weekly series of lessons in courage, clarity, and change for those rewriting their story.

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In 1978, at 28, Nyad tried to swim from Cuba to Florida.

She was already an accomplished marathon swimmer. She had the credentials, the body, the team. She swam for almost 42 hours inside a steel shark cage that battered her with every wave.

But she didn’t make it.

Strong currents pushed her off course. She came out of the water badly injured, hallucinating, miles short of Key West.

She walked away from the swim. Not just that attempt… she walked away from the sport entirely.

For the next thirty years, Diana built another life — a great one, in fact. She became a sports broadcaster. She wrote books. She gave speeches. She didn’t swim seriously again for almost three decades.

And then, somewhere around her sixtieth birthday, the Cuba swim came back.

Not as nostalgia or a bucket list item. It came back as a question she couldn’t put down:

What do I still have in me?

She started training again at 60. She attempted the swim in 2011. Failed. Attempted it again later that year. Failed. Attempted it in 2012. Failed.

Four times in her sixties, Diana got in the water, and four times the ocean sent her back.

On the fifth attempt, on September 2, 2013, at 64, she walked up onto the beach at Key West after roughly 53 hours in the water. The first person to complete the crossing without a shark cage.

Here’s the part of the story that doesn’t usually get told.

The swim she made at 64 was not the swim she tried to make at 28.

At 28, she was trying to prove she could do it.

At 64, she had nothing left to prove and she knew it.

The body that finished the swim wasn’t a younger, fitter version of the one that had failed. It was an older, slower, more damaged body that had learned, over thirty years, what it could and couldn’t ask of itself.

She wasn’t returning to the dream. She was meeting it as someone else.

We tend to think of unfinished dreams as failures of will. We didn’t want it enough. We didn’t try hard enough. We let it slip away.

But sometimes the thing you set down at 28 wasn’t ready for you yet. And you weren’t ready for it, either.

The thirty years aren’t the detour from the swim.

They’re what made the swim possible.

The broadcasting career taught her how to talk to a team. The decades of speaking taught her how to manage her own mind under pressure. The aging — the actual fact of being 64, of having less margin, of knowing the body has fewer chapters left — was not the obstacle. It was the engine.

She wasn’t fighting time. She was working with what time had given her.

Most of us are carrying something we put down a long time ago.

A version of work we wanted to do. A place we wanted to live. A way of using ourselves that didn’t fit the life we ended up building.

The instinct is to assume it’s too late, that the window closed somewhere in our thirties or forties, that whoever we were when we wanted that thing is gone now and the dream went with her.

But maybe she’s not gone. Maybe she just put something down, and the thing is still there, waiting for the version of you who could only have shown up after all of this.

The question isn’t whether you can still do the thing you wanted to do at 28.

The question is what it would look like if the person you are now did it instead.

✌🏻 Miranda

Sources:

• NPR, “On Fifth Try, Diana Nyad Completes Cuba-Florida Swim”

• LA Times, “Diana Nyad, after swim: ‘You’re never too old to chase your dreams’”

• ABC News, “Diana Nyad: ‘We Should Never Ever Give Up’”

• NPR, “From Cuba To Florida: Diana Nyad’s Final Attempt At A Record-Breaking Swim”

• BBC News, “US woman, 64, makes historic swim”

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A few days ago I read an essay by Chris Lutkin called “I Am an Immigrant, Not an Expat.” Chris and his partner moved from the United States to the Azores, and the piece is about why he calls himself an immigrant rather than an expat.

He’s embedding. Learning Portuguese. Steering away from the American crowd. Choosing, deliberately, to live inside someone else’s long story rather than build a smaller version of his old one with better weather.

It’s a thoughtful piece, and I’m grateful he wrote it… it’s been turning over in my head ever since. He’s chosen a shape that fits him and he’s named it honestly.

I want to offer another shape, because I’m doing something different and I think a lot of people are doing some version of it without quite having the language for it yet.

I’m not making the same choice Chris is. But I’m also not making the choice the word “expat” suggests. Before I get into what I’m doing, though, the words themselves deserve some honesty.

“Expat” almost exclusively gets used for people from wealthy Western countries living abroad. The same person moving in the opposite direction — from the Global South into Europe or North America — would not be called an expat. They’d be called an immigrant.

The two words are doing political work that goes well beyond personal identity, sorting people by passport strength, by where the money flows, by whose presence in a country is assumed to be temporary and whose is assumed to be a transfer.

I hold a Canadian passport, and that fact alone makes most of the choices I’m about to describe possible. It would be dishonest to write about this life without naming that.

So I’m wary of both words. “Expat” because of what it tries to launder. “Immigrant” because it doesn’t describe what I’m doing — and because borrowing it would be its own kind of laundering, claiming the harder word for the easier life.

I’m not sure “nomad” quite fits either. There’s a purist version of the word that means you live out of a suitcase, have no fixed address, and treat any kind of home base as a kind of cheating. I’m not that.

I have a home base north of Toronto. I pay Canadian taxes. I vote. I have a doctor, a dentist, long friendships, family. I am not in any way a former Canadian. I haven’t been pushed out by politics or pulled out by tax strategy or quietly checked out of the country that made me.

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But I’m also, right now, not in Canada. I’m writing this from somewhere else, and in three months I’ll be somewhere else again, and after that I’ll be home for a stretch and then probably gone again.

I have a country. I haven’t left it. I just don’t choose to live there twelve months of the year.

There isn’t a clean word for that.

Maybe that’s part of why so many people struggle to imagine lives like this in the first place. We’re handed a very binary story about movement: stay home where it’s safe and familiar, or leave permanently and become someone else entirely.

The news cycle doesn’t help. If your primary relationship to the world is mediated through headlines, it’s easy to start believing everywhere is unstable, dangerous, politically hostile, or one missed train away from collapse.

You stay or you go. You’re home or you’re abroad. You hover (expat) or you commit (immigrant) or you go fully untethered (nomad).

The big move — the one-way flight, the sold house, the new country adopted as your own — is the version of this life that gets sold, written about, made into brave Netflix shows. I gave it all up and moved to Italy. That story is real.

But the strange thing about actually spending time in other places is how quickly abstraction collapses into ordinary human life.

Chris is living his version of it. Some of my readers are, too.

But it’s not the only version.

There’s a whole spectrum between “I never leave the city I grew up in” and “I emigrated permanently.” Most of it doesn’t have a name.

People spend three months a year in Mexico and nine at home. People keep an apartment in Toronto and move through colivings in Europe in the summer. People split the year between two places and call neither one a relocation. People take six months off between contracts and stay in different places, or maybe just one.

People build a life that includes movement without it being the whole story.

None of that is hovering. None of it requires denouncing where you’re from. None of it requires becoming someone else.

You don’t have to close the door on one life to open another.

The change can be smaller than the binary suggests. A month somewhere. A season. A coliving stay. A trial run that doesn’t have to lead to anything.

The point isn’t to land in a new country and become a new person. The point is that you’re allowed to design something that doesn’t fit the existing words for it.

I think that’s what a lot of the people reading this kind of writing are actually after. Not the dramatic, burn-it-all-down version but the one where the life they already built stays mostly intact, and they add more movement to it.

Where they keep the country, the friendships, the doctor, the tax base… and also get the Lisbon winter, or the slow summer in Croatia, or the three weeks every spring somewhere they’ve never been. Where the world becomes less frightening and more human because you’re actually spending time in more of it.

That life doesn’t have a perfect word yet, but that doesn’t mean it doesn’t exist.

Labels are messy things. Maybe the answer isn’t to find the right one. Maybe it’s to stop waiting for the language to catch up to the life you actually want.

✌🏻 Miranda

Most people who try to build a publication on Substack fail at the same point.

They write good pieces. They build a small list. They publish consistently for six months. And then conversion to paid stalls out at one or two percent, the writing starts to feel like a treadmill, and they slow things down.

The diagnosis they reach for is almost always the same: I just need to write better content. I need to find my voice. I need to post more consistently. I need to figure out what makes me different.

Sometimes that’s true. Usually it isn’t.

The actual problem, in most cases I’ve seen, is upstream of the content. The publication is built backwards. What I mean by that is that the writing came first, and the structure that converts readers to paid subscribers was supposed to figure itself out later.

It doesn’t. It can’t. Conversion architecture is a strategic decision, not a content quality outcome.

I’ve built two Substacks that converted well, in two different ways. I've also built publications that didn't work, and I learned just as much from those as from the ones that did.

And before we go any further, it’s important to note that Owen Sound Current isn’t a solo project. It’s a partnership with Maryann Thomas of The Ginger Press, an experienced publisher who handles the strategic direction, insurance, legal, and operational architecture that any serious news publication needs.

I bring the editorial work, the conversion architecture, and the digital expertise. She brings the publisher’s discipline and decades of book and magazine publishing experience. The publication works the way it does because both of us are doing what we’re best at, and neither of us could have built it alone.

That matters for what comes next in this piece, because most of what I’m about to walk you through is strategic and structural — and getting the strategy right was a collaborative process, not something I figured out by myself.

The principles hold regardless of whether you build solo or with a partner, but I’d be misrepresenting the work if I told this story as a one-person project. We’ll be talking more about the power of partnerships and joint ventures in the weeks ahead.

For now, know that those two Substack publications I’ve built could not be more different on the surface. One is for an international audience contemplating a life change. The other is for the people on my street, telling them what’s happening at the city council meeting.

The voice is different. The cadence is different. The economics are different.

And yet the strategic foundation driving their success is the same.

The local news version is the cleaner test of whether the foundation works for subscriptions, because local news is the hardest category to monetize on Substack. Local media has also been in structural collapse for two decades, and even the most well-funded efforts have failed.

Canada has lost hundreds of community papers since the early 2000s. Vast regions have become news deserts where no one is covering city council, no one is reading the meeting agendas, no one is asking what happened to the infrastructure tender.

Major corporate efforts at filling the gap have folded. Well-funded nonprofit ventures have folded. Local news is, by any honest measure, the hardest place in publishing to make economics work right now.

If the principles hold up there, they hold up.

What I want to walk you through here is what those principles actually are. Because the difference between a publication that converts and one that doesn’t usually isn’t visible in the content. It’s visible in the architecture the content sits inside.

And why are we talking about this on Midlife Nomads? Because as we talk about building income streams and recurring income, this is one platform you should be considering. There are Substacks for every interest now, and if you’re building community and authority in a space, the platform takes a lot of the technical and integration legwork out of getting yourself out there.

Subscribe now

Good News: You Probably Don't Have a Content Problem

Most aspiring publication owners think they’re solving a content problem. They’re not. They’re solving a positioning problem disguised as a content problem.

The publications that convert paid subscribers reliably are the ones where four strategic decisions have been made — explicitly, before any pieces are written — and where every piece of content that gets published reinforces those decisions.

The publications that struggle are usually publications where one or more of these decisions has never been made, or has been made implicitly and inconsistently, or has been left to emerge from the writing itself.

The four decisions are:

• Who, exactly, the publication serves — and who it doesn’t.

• What that reader believes when they finish reading you that they didn’t believe before — the shared conviction at the centre of the publication that unites you and your reader.

• Where the value lives at each tier — what the free reader gets, what the paid reader gets, what the role of each is in the funnel.

• How conversion happens, mechanically and regularly — not as an annual launch, but as a built-in part of how every issue is structured.

A publication where these four decisions are clear, consistent, and reinforced by every piece of content will convert. A publication where any of them is fuzzy will struggle, regardless of how well the individual pieces are written.

Conversion is structural. The content is downstream.

If you’re nodding because this matches something you’ve been suspecting, keep going… the rest of this piece walks through what each of those decisions actually looks like in practice, including the specific architecture that makes Owen Sound Current convert paid subscribers in a category many people struggle to monetize.

Read more

Midlife Nomads explores how people are redesigning work, travel, and life in our 40s, 50s & beyond.

Hello, Nomads!

Quick check-in from Chateau Coliving in France, where a precocious young deer and her bunny friend have been distracting me from work. That, plus near-daily conversations with other residents about the best colivings for the "well-seasoned" among us — which is, conveniently, what I want to tell you about today.

There’s a gap in the travel-resource landscape, and you’ve probably felt it.

The digital nomad lists are written for 22-year-olds, by 22-year-olds, who’ll happily share a 12-bed dorm and call it “community.”

Retirement-travel content assumes you’ve stopped working and have nothing to do but tour cathedrals.

And the general travel internet has gotten loud, paid-out, and increasingly unreliable, packed with marketing copy that doesn’t pass the smell test, “best of” listicles that keep surfacing the same five places, and AI-generated guides regurgitating summer 2017’s greatest hits.

When you’re considering a month or more somewhere, rolling the dice on any of it feels reckless.

That gap is what The Shortlist is for.

The Shortlist is our brand new 😄 members-only monthly calendar of vetted stays — colivings, city apartments, artist residencies, nomad trips, the occasional cruise — for people in their 40s, 50s, 60s and beyond who are still working, want reliable internet and real comfort, and occasionally want to drop into a community without the dorm energy.

You’ll see recommendations six months ahead, organized by region, timed to when each destination is actually at its best.

These are places I’ve stayed in, or vetted through friends and communities whose judgment I trust. Some have built-in community; some are deliberately quiet. Some months a region has multiple options; others get one or none. No filler, because filler is what makes most travel resources useless.

The first six months are live now: June through November. A new Shortlist drops on the first of each month. Members can read any of them, anytime, from the collection on the website.

See The Shortlist →

If you’re already a paid member: this is for you. Dive in.

(Remember, you also have full access to our archives including actionable guides and tools in the Members Vault.)

If you’re not yet a full member, and you’ve been considering it, this is the right moment. The Charter Member offer I sent a few weeks back is still open until this Friday or the first 50 spots are gone (whichever comes first). That lets you lock in $59.25/year for as long as you stay subscribed, before the new pricing of $79/year kicks in for everyone else.

Lock in Charter Member pricing →

Either way, I’m glad you’re here.

✌🏻 Miranda

From Midlife Nomads

In case you missed them — a few new pieces from this past week:

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What’s On My Radar

It’s a long read, and not a light one… content warning for assault and a brief mention of past suicide attempts.

Jameela writes about what happened to her body — not her mind, her body — after an attempted kidnapping a few months ago. The diagnosis was Dorsal Vagal Shutdown: pulse slowed, digestion stopped, she felt nothing for weeks and walked around the flat in a duvet trying to quit her career.

But it’s the most useful thing I’ve read this year on what burnout actually does to the nervous system, and on the difference between being checked out and being a bad person.

Keep reading

Reina spent nineteen years at the UN — peacekeeping missions, compounds, hardship duty stations — and walked out a year ago.

Now she lives on the road and works with full-time travelers on the things that quietly start slipping when the routines that used to hold you together don’t fit a life that keeps moving.

Keep reading

Also worth your time this week:

• In Transit — Ibtissam C. - We travel more than ever. So why are we enjoying it less? On why most trips leave us needing a week to recover, and what changes when you start planning for the tired version of yourself who actually shows up.

• Fugitive Margins — Grant David Crawford, PhD - The End of Elsewhere - A long, careful essay on the slow ending of the 300-year Western search for elsewhere — and what its author, who helped take it apart, finds himself missing now that it’s going.

• Sharp Monica — Who Deserves to Travel? A Florence resident on what it’s like to live inside a UNESCO center being consumed by short-term tourists, and what we imagine we’re actually doing when we travel.

• Crow’s Feet — Linda Melone What If I Don’t Want to Travel? A 67-year-old on why the “travel more while you can” pressure isn’t universal, with the actual numbers behind the assumption that everyone retires into a passport.

A quick note on Nomad Cruise 18

I’ve mentioned this trip before, and here’s the update: cabins are going fast. Over half a dozen people at Chateau Coliving this month have already booked, and two readers from this community are in! That makes at least three of us from Midlife Nomads who’ll be onboard, plus the Chateau contingent.

So if you’ve been quietly thinking about it, this is the part where I tell you the cabin you want probably won’t be there in a month.

The basics: Barcelona to the Dominican Republic, November 2–16, with stops in Tangier and four Caribbean islands. Seven days at sea in the middle, which is where the actual conference programming happens — talks, workshops, a lot of long unhurried conversations of the kind you don’t usually get on land. Around 300 nomads and remote workers onboard. Median age is mid-30s to mid-40s, and all ages are welcome.

Deposit is €250 to lock in the current price. Use code MIDLIFENOMADS at checkout for €100 off.

If you’re on the fence and want to ask me something specific before you commit, just hit reply. Otherwise…

Let's Gooooo

This is where you’ll find colivings, city stays, nomad trips, cruises, and the occasional artist residency for people in their 40s, 50s, 60s and beyond who are still working, value reliable internet and real comfort, and occasionally want to drop into a community without dorm energy.

The picks below are starting points, not a closed list. These are organized by region and timed to when each destination is at its best. I look at dozens of options — places I've stayed in or had recommended by friends and communities I trust — and surface the ones I'd actually send a friend to.

The hope is that even the places you don't book teach you something about what's out there: how colivings vary, what residencies cost, what's possible at a price point in a location you perhaps hadn't considered.

The more of these you read, the more your sense of the landscape sharpens.

Not everything on The Shortlist is a coliving. You’ll also find long-stay city apartments, hotels with workable wifi, artist residencies, nomad group trips, and the occasional cruise or conference event.

After several years of moving between all of these options myself, I appreciate there are seasons for both the comfort of community and solo time to recharge your social battery. The picks each month are chosen with that in mind.

Some months, a region has multiple options; others get one or none. Forcing recommendations into every cell of the matrix produces filler, and filler is what makes most travel resources useless.

Read more

There’s a stretch of November, from about the second week through American Thanksgiving, that tends to offer great travel value if you can move before the holiday flight prices spike. Most of the warm-weather hemisphere is in its pre-Christmas window: prices haven’t climbed yet, the weather has settled into something reliable, and the December crowds are still a few weeks away.

Mexico’s coastal cities, the Yucatán, and most of Central America are in their best stretch through about the third week of the month. Warm, mostly dry, and still at pre-holiday pricing. Pacific hurricane risk drops off sharply after mid-October but the season technically runs to the end of November, so it’s worth checking.

Costa Rica is fully into dry season. Colombia’s two rainy seasons are winding down, but the Caribbean coast (Cartagena, Santa Marta) is the most reliable bet this month; Medellín and Bogotá can still surprise you with rain.

Much of Europe is cold and quiet, but that’s part of why November works there. City stays in Spain, Portugal, and Italy can be unusually good value, particularly for slow-stay rentals. Lisbon, Seville, and Valencia hold workable weather through most of the month.

Asia is at one of its strongest stretches of the year. Japan is in peak autumn foliage, with Kyoto and Nikko hitting from mid-to-late month and the Japanese Alps peaking a bit earlier; book well ahead, because this is one of Japan’s biggest domestic travel windows and prices stay high.

South Korea is cooling rapidly but still pleasant through most of November before winter arrives in earnest. Taiwan is at its reliable best — dry, mild, uncrowded.

Southeast Asia is in full dry season across Thailand, Vietnam, Laos, Cambodia, and most of Indonesia. Nepal and northern India are in late trekking season; lower-altitude areas remain workable through the month, and Rajasthan begins its peak.

South America is transitioning into summer. Buenos Aires, Uruguay, and southern Brazil are warming pleasantly before the December heat sets in. Patagonia’s window opens late in the month for the well-prepared, though prime season is December through February.

One scheduling note for anyone whose route touches the US: American Thanksgiving falls in late November and affects flight pricing and availability heavily for the week around it. If you can, book around it.

A note for the moment: I’m not currently recommending US travel to international or Canadian readers. If you’re already in the US and looking to stay close, the Pacific Northwest and New England windows are real. For Canadians and international visitors, Atlantic Canada, the Maritimes, and British Columbia are at their best window of the year — and the Canadian dollar makes them unusually good value right now.

This month's Shortlist features 17 vetted stays across Asia, North America, Latin America, Africa, and Europe — coliving villas, beachfront apartments, an Atlantic crossing, two artist residencies, and a handful of city bases for the regions in their best stretch of the year.

Members-only beyond this point.

The Shortlist is Midlife Nomads’ members-only calendar of vetted stays — colivings, city stays, nomad trips, cruises, and the occasional artist residency for people in their 40s, 50s, 60s and beyond who are still working, value reliable internet and real comfort, and want community without dorm energy. Each month I publish a small set of places I’d actually send a friend, organized by region and timed to when each destination is at its best.

Read more

The travel industry tells you to book summer, but I get pretty excited about October. This is the Northern Hemisphere preparing for winter, and one of the year's best windows for slow travel in Mexico, Central America, and East Africa.

Northern Europe is in full autumn. Expect it to be beautiful but cool, with rain frequencies climbing. Central and Eastern Europe — Berlin, Prague, Krakow, Budapest — settle into full autumn: cool, dry, dramatically cheaper than the western capitals.

Spain, Portugal, Italy, and Greece are warm enough through mid-October for outdoor work and activities, with prices at autumn lows. The British Isles are workable but increasingly wet through the month.

In North America, the Pacific Northwest, New England and Southern Ontario are at peak fall colour, with prices for prime areas (Vermont, the Maritimes, the Columbia River Gorge) climbing accordingly. California shakes off the August fog and settles into warm dry days, with wine country at harvest.

The Southwest at altitude — Santa Fe, Flagstaff, Sedona — finally cools into one of its better windows after a punishing summer. Atlantic Canada holds into early October before the temperature drops sharply.

In Latin America, Mexico's Pacific coast and Yucatán emerge from rainy season by mid-October — dry, warm, and still below high-season pricing, though hurricane season officially runs through November 30 with Atlantic-facing coasts most exposed.

Oaxaca and the central highlands peak around Día de los Muertos, but expect inflated prices and full bookings in Oaxaca City and surrounding villages from October 28 through November 3.

Costa Rica's Pacific coast is drying out as green season ends. Colombia hits its second dry-season window. South America's southern cone moves into spring; Buenos Aires, Santiago, Montevideo, and Valparaíso are all warming pleasantly. Patagonia begins its prime hiking season late in the month.

October is also one of the year's strongest windows for East Africa. Zanzibar and the Kenyan coast are in dry season — sunny, warm Indian Ocean swimming, low rainfall. Tanzania and Kenya's safari parks see excellent wildlife viewing before November's short rains arrive. East African highland cities — Nairobi, Kigali, Addis Ababa — are sunny, mild, and dry.

South Africa moves into spring, with Cape Town warming up and the Garden Route at its pre-summer prime. North African destinations (Morocco, Tunisia, Egypt) settle into one of their two most pleasant stretches — past the summer heat, before winter chill.

In Asia, October delivers some of the year's most reliable travel weather across the continent. Japan moves into peak autumn anticipation — cool, dry, and gorgeous through the month, with foliage starting in Hokkaido and moving south. Prices climb late in the month around the foliage windows in popular areas like Kyoto and Nikko. South Korea is in its prime travel season with clear skies, comfortable temperatures, and excellent hiking weather. Taiwan emerges from typhoon season and becomes reliably good.

Southeast Asia settles into dry season across most of the region by mid-month; northern Thailand, Laos, and central Vietnam are particularly worth the timing. Nepal and northern India hit their trekking peak, with the autumn Annapurna and Everest base camp seasons in full swing — and India broadly emerges from the monsoon, with most of the country travelable again by month's end.

Central Asia (Almaty, Tashkent, Bishkek, Tbilisi) settles into clear skies and harvest season.

A note for the moment: I’m not currently recommending US travel to international or Canadian readers. If you’re already in the US and looking to stay close, the Pacific Northwest and New England windows are real. For Canadians and international visitors, Atlantic Canada, the Maritimes, and British Columbia are at their best window of the year — and the Canadian dollar makes them unusually good value right now.

This month's Shortlist features seventeen picks across five regions, spanning colivings, residencies, private long-stay apartments, surf lodges, an island chapter, and a quiet countryside community. October catches Europe in its last reliable stretch before winter, Latin America is moving into green season, and East Africa is enjoying one of the best months on the continent.

Members-only beyond this point.

The Shortlist is Midlife Nomads’ members-only calendar of vetted stays — colivings, city stays, nomad trips, cruises, and the occasional artist residency for people in their 40s, 50s, 60s and beyond who are still working, value reliable internet and real comfort, and want community without dorm energy. Each month I publish a small set of places I’d actually send a friend, organized by region and timed to when each destination is at its best.

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September is shoulder season's best argument. The places I'd usually hesitate to recommend — too hot in August, too booked, too expensive — settle down by mid-month.

Marrakech becomes workable. Cape Town warms up. The Greek islands are still warm enough to swim and finally quiet enough to stay a month. Most of the travel map is in its best window of the year, and the people who built their trips around July and August have already gone home.

It’s arguably the single best month of the year for European travel, and the one to plan around if you have flexibility. Locals return from the coast, prices drop sharply by mid-September, and the weather is reliable across most of the continent through early October.

Spain, Portugal, and Italy are still warm enough for swimming. Central and Eastern Europe — Krakow, Vienna, Budapest, Prague, Berlin — are at one of the year's best windows; Northern Europe is in its last reliably warm stretch before autumn sets in.

The British Isles are still fairly warm and dry(ish), and less crowded than peak summer.

Africa is also enjoying one of its strongest stretches of the year. Southern Africa is at its dry-season peak. Cape Town is warming into spring, the Garden Route at its pre-summer best, wildlife viewing exceptional across Botswana, Namibia, Zambia, and Zimbabwe as animals concentrate around remaining water sources.

Morocco is past the summer heat and at its most pleasant — Marrakech, Fez, Essaouira, and the Atlas Mountains are all comfortable.

East Africa is reliably dry on the coast (Zanzibar, the Kenyan and Tanzanian beaches), and the Great Migration window in the Mara and Serengeti extends through the month. Egypt and Tunisia move out of summer heat by mid-September. If you’ve been thinking about the continent, this is one of the best months to go.

In Asia, September is a month of significant transitions. Japan’s heat begins to break by mid-month; Tokyo and Kyoto become workable again, and the typhoon risk on the southern islands starts to ease. South Korea’s autumn arrives and brings some of the year’s best travel weather. Taiwan remains in typhoon season (statistically one of the higher-risk months) but with longer windows between storms.

Southeast Asia begins its dry-season transition late in the month — northern Thailand, Laos, and central Vietnam become reliable by month’s end, while southern Thailand and the Gulf coast of Malaysia stay wet. Bali remains dry. Central Asia — Almaty, Tashkent, Bishkek — is at one of its strongest months: warm but not hot, dry, harvest season.

The high-altitude regions of Nepal and northern India enter their prime trekking window as the monsoon retreats. The rest of India remains monsoon-affected, with the southwest monsoon retreating gradually from north to south through the month.

In parts of Latin America, it’s the start of green-season transition. Mexico is still in rainy season; the interior cities at altitude (Oaxaca, Mexico City, San Miguel, Guanajuato) are reliably workable, while the coasts are wetter and Atlantic-facing regions face peak hurricane risk through mid-September.

Costa Rica and southern Central America are in green season with afternoon storms and lower prices. Nicaragua and Panama are similarly workable, with green-season pricing in effect.

The Andes are still in dry season but starting to wind down. Patagonia is in its shoulder period, workable for the well-prepared. South America's southern cone is moving into spring; Buenos Aires, Montevideo, and Santiago are all warming pleasantly into their pre-summer window.

In North America, the Pacific Northwest, New England, the Great Lakes region, and Atlantic Canada are at their reliable best — warm days, cool nights, and the early edge of fall colour in eastern Canada and northern New England late in the month. Coastal California emerges from August fog into its annual best window. The Southwest at altitude (Santa Fe, Flagstaff) becomes workable again. The southeastern US and Gulf are at the statistical peak of Atlantic hurricane season — plan around it.

A note for the moment: I’m not currently recommending US travel to international or Canadian readers. If you’re already in the US and looking to stay close, the Pacific Northwest and New England windows are real. For Canadians and international visitors, Atlantic Canada, the Maritimes, and British Columbia are at their best window of the year — and the Canadian dollar makes them unusually good value right now.

This month's Shortlist features 15 vetted stays across Europe, Africa, North America, Asia, and Latin America — timed to where each region is at its best in September. Coliving villas, beachfront apartments, a transatlantic crossing, an artist residency on an island, and a handful of city bases for the months when the weather finally cooperates. Each one is somewhere I'd actually send a friend.

Members-only beyond this point.

The Shortlist is Midlife Nomads’ members-only calendar of vetted stays — colivings, city stays, nomad trips, cruises, and the occasional artist residency for people in their 40s, 50s, 60s and beyond who are still working, value reliable internet and real comfort, and want community without dorm energy. Each month I publish a small set of places I’d actually send a friend, organized by region and timed to when each destination is at its best.

Read more

Well — where are we headed next? August in the Northern Hemisphere is a month of extremes: too hot, too crowded, too expensive almost everywhere people are telling you to go. Which is why this month's picks lean toward the places everyone else is forgetting about.

Europe is at peak congestion and many locals are away — smaller restaurants, shops, and family-run accommodations close for the month, particularly in Italy, France, and Spain. Heat is a real factor; coastal Spain, southern Italy, and Greece regularly hit 40°C/104°F.

If you must travel in Europe in August, head north — Scandinavia, Scotland, Ireland, the Baltics — where the weather is at its best and the August closures don’t apply.

In Asia, conditions vary widely by region. Japan is hot, humid, and at peak domestic-tourism prices through mid-August around the Obon holiday (around August 13-16); cooler at altitude in Hokkaido and the Japanese Alps. South Korea is similarly hot and in monsoon transition. Taiwan is hot and at peak typhoon season.

Southeast Asia is largely in monsoon, with Bali in its dry-season sweet spot and central Vietnam often workable. The Himalayan regions of India and Nepal are in monsoon; the high-altitude trans-Himalayan areas (Ladakh, Spiti, Mustang) are at their accessible best. Central Asia (Uzbekistan, Kyrgyzstan, Kazakhstan) is hot but in their travel season.

Latin America is where flexibility pays off: it’s still dry season in the Andes (Peru, Bolivia, Ecuador), great in Colombia, and Patagonia begins emerging from winter late in the month. Mexico is hot across most of the country with hurricane season at its peak on both coasts; Yucatán and the Caribbean coast are particularly affected.

A note for the moment: I’m not currently recommending US travel to international or Canadian readers. If you’re already in the US and looking to stay close, the Pacific Northwest and New England windows are real. For Canadians and international visitors, Atlantic Canada, the Maritimes, and British Columbia are at their best window of the year — and the Canadian dollar makes them unusually good value right now.

This month's Shortlist features fifteen picks across four regions including art residencies in Portugal, Finland, and a Shanghai water town, two values-vetted travel groups in Poland and Norway, plus a Buenos Aires winter retreat, a Central Asian apartment for the curious-and-early, an Indian Himalayan cottage for monsoon settling-in, and more.

Members-only beyond this point.

The Shortlist is Midlife Nomads’ members-only calendar of vetted stays — colivings, city stays, nomad trips, cruises, and the occasional artist residency for people in their 40s, 50s, 60s and beyond who are still working, value reliable internet and real comfort, and want community without dorm energy. Each month I publish a small set of places I’d actually send a friend, organized by region and timed to when each destination is at its best.

Read more

We’re hitting peak summer almost everywhere in the Northern Hemisphere, with prices and crowds to match. This month’s Shortlist features thirteen picks across three regions — a mix of community-focused colivings, longer-stay serviced apartments for solo time, a Canadian artist residency, and one music-festival-adjacent recommendation that works precisely because it isn’t where you’d expect.

Europe is at its most expensive and busiest; if you’re going, book early or accept that you’re paying for the timing. Coastal and rural areas in Spain, Italy, France, and Greece are nearly fully booked weeks in advance.

Northern and Eastern Europe (the Baltics, Scotland, Ireland, parts of Poland) are genuinely lovely in July with more reasonable prices and fewer crowds.

In Latin America, it’s deep dry season in the Andes — Peru, Bolivia, and Ecuador are at their reliable best for highland hiking and Sacred Valley travel, with Cusco busy but workable. Patagonia is in full winter; Argentine and Chilean Patagonia are for skiers and hardy travelers only.

Brazil, Colombia, and northern South America are in their dry season and good. Mexico’s Pacific coast remains workable for those handling the heat; the Yucatán and Caribbean coast are hot and humid with hurricane season ramping up. São Paulo in July is an underrated and genuinely strong recommendation for a specific kind of nomad. After the muggy Brazilian summer, July is when the city actually feels comfortable for working and walking.

North America is split between peak summer in the south and prime season in the north. The Pacific Northwest, Atlantic Canada, the Maritimes, Quebec, and British Columbia are at their reliable best — long days, warm-but-not-hot temperatures, and the trail and water seasons in full swing.

The American Southwest and inland California are at dangerous-heat levels in many places, with desert temperatures regularly above 40°C/104°F; coastal California stays cool but with marine-layer fog dominating mornings.

Southeast Asia is mostly in monsoon this month and I've left it off the Shortlist; the rare dry pockets aren't strong enough to anchor a recommendation.

A note for the moment: I’m not currently recommending US travel to international or Canadian readers. If you’re already in the US and looking to stay close, the Pacific Northwest and New England windows are real. For Canadians and international visitors, Atlantic Canada, the Maritimes, and British Columbia are at their best window of the year — and the Canadian dollar makes them unusually good value right now.

Members-only beyond this point.

The Shortlist is Midlife Nomads’ members-only calendar of vetted stays — colivings, city stays, nomad trips, cruises, and the occasional artist residency for people in their 40s, 50s, 60s and beyond who are still working, value reliable internet and real comfort, and want community without dorm energy. Each month I publish a small set of places I’d actually send a friend, organized by region and timed to when each destination is at its best.

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June is the last month before peak European prices and crowds, and the first reliable warm-water month in much of the Mediterranean. It’s a strong booking window if you’re heading to Spain, Italy, France, or Greece — but only if you act before mid-June, because the second half of the month is when prices step up sharply and don’t come down again until September.

Latin America splits along latitude: dry season in the Peruvian highlands and Bolivia, green season starting in Costa Rica, hurricane risk building on Mexico’s Caribbean coast. Southeast Asia is mostly in monsoon, with dry pockets in Bali and northern Vietnam.

Southeast Asia is in full monsoon outside the dry pockets in northern Vietnam and parts of Indonesia. Meanwhile, North America is at the start of its strongest stretch.

The Pacific Northwest, New England, the Great Lakes, and Atlantic Canada are warming up but not yet at peak prices. Coastal California is at its reliable best before summer fog sets in.

A note for the moment: I’m not currently recommending US travel to international or Canadian readers. If you’re already in the US and looking to stay close, the Pacific Northwest and New England windows are real. For Canadians and international visitors, Atlantic Canada, the Maritimes, and British Columbia are at their best window of the year — and the Canadian dollar makes them unusually good value right now.

This month’s Shortlist has twelve picks across five regions including a mix of small-group colivings, a ten-day nomad festival, and one wine-country house in southern France.

Members get full details below, including direct links, current pricing, and what I know about each place.

Members-only beyond this point.

The Shortlist is Midlife Nomads’ members-only calendar of vetted stays — colivings, city stays, nomad trips, cruises, and the occasional artist residency for people in their 40s, 50s, 60s and beyond who are still working, value reliable internet and real comfort, and want community without dorm energy. Each month I publish a small set of places I’d actually send a friend, organized by region and timed to when each destination is at its best.

Read more