I’ve been asked this more times than I can count. Repeatedly, by people who mean well, usually right after I’ve mentioned where I’m going next.

It’s the same shape of question as how could she — a verdict with a question mark stapled on.

The assumption underneath it is that movement is a phase. It’s something you do until you’re finished doing it, at which point you stop, and stopping is the proof you’ve arrived.

I don’t blame the people asking. Settling down used to describe something concrete and worth wanting… like a house that appreciates in value instead of sucking your bank account dry. Or an employer that would keep you until 65 and then pay you for the rest of it.

That was a real deal, and for a stretch of the last century it was mostly honoured. The people asking me this question grew up watching it work.

But it’s stopped working. Not gradually, and not because anybody in particular failed at it. The pension dried up, the house and all of its utilities and insurance got expensive, the loyalty stopped running both ways.

Plenty of people did every part of their end and got a fraction of what they were promised.

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But the language and the expectations have somehow survived all of that. So we still use settle down as though it means safe, when what it increasingly means is stationary.

Here’s the part that surprises people who ask me this: I did settle down. I’ve never stopped being settled.

I grew up in a village of eight hundred people in rural Canada and I now live twenty-five minutes away from it. There’s a house, and my people are in it. There are people around I’ve known for four decades, some of whom I’d trust with my life, most of whom I cannot buy groceries without running into. That is a settled life by any measure anyone would have used in 1975.

I just don’t sit in it every week of the year.

That’s the whole difference, and it’s the thing the question can’t accommodate, because settling down was never really about where you sleep. It was about being finished. Done choosing. Past the part of life where you’re allowed to want something you don’t already have.

And it isn’t by accident of the English language that it shares a root with settle for. Both come from the same place: to come to rest, to accept a position, to stop.

The better question, I think, isn't when you're going to settle down. It's what you still want that you think “settled” means you're not allowed to have — and who decided it.

Try this, it takes about ten minutes.

Write down three things you’d change about how you live if nobody would say anything about it.

Think of the real things you’d actually do, that are truly available to you, that you haven’t done.

Now, for each one, answer this: who exactly told you it wasn’t allowed?

Don’t worry if you can’t name a specific person. It could be a composite… a tone of voice, a look somebody gave you in 2011, a general sense of what people like you are supposed to do. That composite has been making decisions on your behalf for years, and it has no name, no face, and no stake in how your life actually goes.

For the ones where you can name someone: are they living a life you’d want? Would you take their advice on anything else?

I’m not suggesting your objections are fake. Some of them are load-bearing. Money is real, aging parents are real, a partner’s job and where the kids go to school are real.

But those are constraints to work with, and constraints have workarounds. What people usually find on that list is something else: an inherited rule about what’s dignified at a certain age, which has never protected anyone from anything.

The next time someone asks when I’m going to settle down, I think the honest answer is that I already did, and it just so happened that I settled into a more flexible life rather than a stopping point.

I doubt I’ll actually say it out loud. I’ll just tell them where I’m going next.

✌🏻 Miranda

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If your next useful step is to work through your specific remote work or travel/relocation situation with someone who's done it, there are two ways we can work together. (If you're a brand looking to partner, skip further down the page.)

Consulting Sessions

$200 USD per session

Includes a 45-minute call about whatever you’re working on: where to go next, what to test first, how to build income that travels with you, why your remote business isn’t producing results, etc. Bring the specifics.

I’ll take what we discussed, look into your options, and send written recommendations within a week.

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What I Don’t Do

I’m not a lawyer, an accountant, or an immigration advisor. We can talk about how visa timelines and tax residency shape a plan, but for anything binding you need someone licensed in the relevant country, and I’ll say so.

I don’t do encouragement calls or cheerleading. If you want someone to tell you it’ll all work out, I’m the wrong person. If you want someone to tell you what’s likely to break and what to do about it, book the session.

Making a Move Membership

$300/year USD

If you’re at the start of something rather than working through a single question, the Making a Move subscription includes two consulting sessions plus everything else we publish: The Shortlist, The Vault, the whole searchable archive.

Two sessions alone are $400, so you get those discounted and the subscription year comes with it. You’ll receive another allocation of sessions when your subscription renews, and can book more anytime you need it.

You’ll receive the code for booking your first session in your upgrade confirmation email.

Already a full subscriber? Upgrading is prorated, so what you've already paid comes off the price. Two sessions alone are $400.

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Who I Am

I’m Miranda Miller, founder of Midlife Nomads. I've spent over 20 years working remotely, and most of the last 10 travelling solo through North, Central, and South America, and across Europe. My partner joins me when he can and keeps our home base in Ontario. My business is incorporated in Estonia.

I’m the mother of two grown children; a working journalist, technical writer, and editor; a member of the Canadian Association of Journalists, and co-founder of a top-100 News publication on Substack.

I’ve also made most of the mistakes I write about, some of them expensive.

For Brands: Partner With Midlife Nomads

Midlife Nomads reaches people in their 40s, 50s, and 60s who are actively planning long stays abroad, booking accommodation months out, and building income that isn’t tied to one employer. They’re buying insurance, eSIMs, coworking, banking, and stays. Most nomad audiences skew 25–35 and price-sensitive. This one doesn’t.

Placements available

• Newsletter sponsorship — a placement in the Wednesday dispatch, written in my voice rather than supplied as ad copy.

• Sponsored content — a full post on a topic we agree on, researched and written by me, clearly labelled.

• Property or operator profile — for colivings, retreats, and group travel operators. Requires a stay.

Rates and media kit available upon request.

How I work

Every commercial relationship is labelled, and hosted stays are labelled differently than ones I paid for, because they belong in a different credibility category. I follow Canadian Association of Journalists guidelines on disclosure.

I don’t take placements for things I haven’t used, and I don’t write copy to order. What you get instead is a recommendation readers can trust, which is the only reason a list this size is worth buying.

Affiliate partnerships: I run a small number, all for tools I use. I’m not adding to them at the moment.

Please get in touch with hello@midlifenomads.com to inquire about Midlife Nomads brand partnership opportunities.

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

Good morning from Montreal!

Just a check-in today, as it’s the first leg of an impromptu trip to Eastern Canada, and have Montreal bagels on my mind.

You may (or may not) have seen me post the other day that I haven’t quite figured out yet how my slow travel life translates to relaxing time at home.

It feels frenetic back in Ontario, with so much catching up and maintenance to do. The pressure is mostly internal, as hard as I try to fend off the rushed pace of life there amidst my own noise about what I “should” be getting done. 🙄

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So… I bought a last minute train ticket to Nova Scotia to get some head space and rest before the next appointments that need me in real life.

Meanwhile, I had these three intriguing group travel deals hit my desk this week. If the sticking point is going alone, these all handle it differently, from a three-week coworking/coliving cohort at the beach, to a restful women-only retreat in a French castle, to a week of networking and nomad programming at sea.

These are all either groups I’ve traveled with or am traveling with this year, and each makes an excellent group travel option for a solo traveler in its own way.

1. Costa Rica with Noma Collective

Noma is headed to Playa Grande in Costa Rica less than a month from now with a cohort of 10-20 people (mixed gender). I’ve traveled Estonia with Noma, and the Czech Republic and Cape Town with Hacker Paradise — the group they acquired — before that.

They’ve knocked $500 off the 3-week trip price, and you can take another $150 off with my code: MIDLIFENOMADS150

That means rooms start at $940 USD + fees and taxes for dorms, $1540 for singles, and $2340 for Kings (based on what’s available right now as I’m typing). Check it out, and email sara@noma-collective.com if you have any booking issues.

Take me there

2. Chateau Coliving with Digital Nomad Girls - One Last Hurrah Retreat

Chateau Coliving is closing its doors for good 😭 But before that happens, Katia is hosting Jenny Lachs and the Digital Nomad Girls for one last hurrah! It’s happening in early September and budget rooms are already sold out (limited Castle Rooms are still available).

This one is a retreat, not a coworking, so don’t bring a calendar packed full of meetings. If you’re craving down time with a great community of supportive women in one of my favourite places on the planet, this one’s for you.

Check it out here

3. Transatlantic Crossing Barcelona to La Romana with Nomad Cruise and Midlife Nomads - Update on Rates & Cabins

Nomad Cruise 18 is 80% sold out, and rates increase on whatever’s left on August 1.

Join me along with a few other members of the Midlife Nomads community — and a sizeable contingent from Chateau Coliving! — as we sail from Spain to Dominican Republic, with stops in Morocco, Antigua and Barbuda, St. Maarten, and St. Kitts & Nevis en route.

The Atlantic crossing portion gives us 7 days of nomad life and business programming, so this is the right choice for those seeking a getaway with learning and networking baked in.

Book through the link below or use discount code midlifenomads for €100 off your cabin. Will I see you there?

Get onboard

These three offers came to me. The Shortlist is what happens when I go looking: colivings, retreats, and group trips, organized by region and by when it makes sense to be there.

Upgrade here to access it — Full subscribers get a vetted list in their inbox every month, and you can access the next six months of recommendations anytime on the website.

In the meantime, here’s what you may have missed this week on the blog:

That's it for now. Until next time, may your wifi be stable and your trains run on time.

✌🏻 Miranda

Past issues:

Multiple streams of income are great, and doing what you love is the dream. But getting paid in full, on time, from a customer who could be three time zones away — that's the part that decides whether your business holds up.

Most advice on this starts and ends with one instruction: get a signed agreement, even for the small jobs. That’s correct. A one-page agreement naming the scope, the fee, and what happens if things change is worth having on every job, whether it’s $400 or $40,000.

But a contract is only as strong as your ability to enforce it.

When your client is in one country and you’re in another, enforcement is largely theoretical. Nobody is flying across a border to file in small claims court over an unpaid invoice, and a client inclined to stall knows it.

And it isn't only a border problem. Chasing a $2,000 invoice through even a local court could cost more than the invoice is worth, and a client inclined to stall knows that, too.

What protects you is the order in which the money moves, making sure that at no point have you delivered most of the work while the client is still holding most of the money.

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By the end of this guide, you’ll know:

• how to structure a job so the money keeps pace with the work

• how to set payment terms, late fees, and end dates that work in your favour

• what a kill fee is, and why every agreement needs one

• how to get paid weeks sooner even when a client’s own accounts payable system runs slow

• which payment methods cost you the least, and how to get paid across borders without losing a cut

• why you should never leave much money sitting on a platform you don’t control

Most of what follows is framed around invoicing a client, because that's where the timing risk is sharpest. If you sell products, courses, or memberships instead, the logic doesn't change; you're just swapping "milestone" for "get paid before you hand over access."

None of this requires becoming the difficult one, or treating every client like a problem waiting to happen. It's the opposite. When the terms are clear and the structure is sound, you stop bracing, trust the process you’ve built, and you can just do the work.

Head to The Vault for more members-only guides on the business side of building a life that isn't tied to one place.

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When someone’s life looks enviable from the outside, we tend to call it luck. Right place, right time. As if they happened to be standing there when the door opened.

In reality, the door opens for those who knock.

Readers, I’d like you to meet my friend, Jen. She’s a gardener living in a 12th-century abbey in the south of France. I met her at Chateau Coliving last year and had the good fortune to spend three months as one of her housemates.

Hers is the kind of life that, if you just met her today, seems like a fairy tale; as though she were plucked out of an ordinary life and plunked down in this fabulous place.

That’s not how it went. Jen had to make a series of really difficult decisions, then keep moving through all of the uncertainty, stress, and self-doubt that comes with uprooting your life. What grew out of that is pretty remarkable.

The timing looks like fate, but I hope you recognize the intention and deliberate positioning she did that got her where she is now.

That’s the part worth paying attention to, because it’s available to the rest of us, too. You can’t arrange to be “lucky.” But you can decide your life is going to look very different from now on and start taking steps in that direction — even if you don’t quite know where it’s all headed.

Here’s how it went for Jen, in her own words.

How would you describe your current lifestyle in one sentence?

I’m a Chateau gardener living in the south of France.

How long have you been living this way, and are you doing it solo, with a partner, with kids?

I officially moved to Normandy, France in September 2025, then to Camon in the south of France in May 2026. I am completely on my own.

What did you do before?

I’ve been gardening since my teens, working for my dad’s landscaping company. It has been a lifelong passion.

But in my 20s, I was an art dealer in New Orleans, in my 30s a research analyst in Miami and NYC, and at 40 I got married and moved to the Netherlands. I taught English and International Business Communication there for 16 years.

After COVID hit, I experienced a series of personal setbacks. Going through menopause and work stress were compounded by my father’s death. I was 4,000 miles away as he lay dying in isolation, and said goodbye to him over FaceTime.

We flew home for his funeral, and when we flew back to Amsterdam, my husband and I both got COVID; he had a massive heart attack five days later. Without an emotional support system in place, I spiraled into a very deep depression.

After some soul searching, I decided to go back into gardening professionally. I’d had a fantastic garden at my house in the historic center of Utrecht. It was on the Utrecht city garden tour. That work gave me my life back.

There was a lot going on in your life when you started seriously considering this kind of change?

My 16-year marriage collapsed. I had always felt like a fish out of water in the Netherlands. The Dutch tend to value bluntness over empathy, and I could never quite get on board with that.

My ex said a few things that made me realize I had to make some seriously big choices. He told me I didn’t enrich his life. It was the most painful thing anyone had ever said to me.

I’d created a beautiful home filled with art, books, cats, and a garden I adored, but it wasn’t enough to sustain a relationship where both people had different priorities.

So I decided to put out feelers in France for chateaux that might be looking for a resident gardener. I decided to leave my relationship on a Friday in late March 2025. That following Monday, I got a call from Château de L’Isle Marie in Normandy, asking me to garden and come check out their chateau coliving program starting that April.

It truly was a life raft thrown in my direction.

What do you do for work now?

I stayed at Katia Dimova’s Chateau Coliving in Normandy for a year, working the grounds, 200 acres of nature preserve, reshaping and restoring the garden spaces, cutting back ivy, brambles, and weeds.

The community Katia built there, with Jeanne and Kevin the community managers, changed my life. I was meeting new people every month: digital nomads, writers there for the Writer’s Haven, and I now have friends spread across the world.

There were family dinners, excursions, mastermind workshops, and games like “Murder in the Castle” (my favorite). Katia made room for both — space to isolate in my apartment when I needed it, or join in when I didn’t.

When she told me the Chateau was being sold, I started reaching out to others in France and found one in the south. I moved to Camon at the end of May 2026, and now live and work in a 12th-century abbey chateau.

Getting to work in these magnificent gardens each day has me completely blissed out.

How did you fund this transition, and what does life cost now compared to before?

Savings, plus the proceeds from selling my house in Utrecht. Since I live at the chateau, they pay me a salary plus room and board, so my overhead is very low now.

The move itself hasn’t been easy. The French bureaucracy, especially health insurance and taxes, has been a slow, painful process.

Walk me through the most boring practical thing you had to figure out.

I brought only a few suitcases and my gardening tools; everything else went into storage in Utrecht. It felt like I was detonating my life for the great unknown.

Working 200 acres of nature preserve in Normandy gave me the space to process that. I cried and screamed at a lot of trees. I got the space to sit with what had happened and figure out what I actually wanted.

It was extremely painful, but being part of the coliving community was like living inside a healing cocoon. The friends I made there I’ll cherish for the rest of my life.

What’s something about your life now that would have sounded ridiculous five years ago?

I literally live in a French castle and maintain its gardens. I’m surrounded by history and beauty every day.

What did you give up that you actually miss? And what don’t you miss at all?

I miss the home and garden I created, my two cats, and the amazing Dutch city I lived in, with its lovely neighbors.

I don’t miss the marriage as it was slowly erasing me. I’d started to feel like a secondary character in someone else’s film. Now I’m the star of it.

What’s something you packed that turned out ridiculous — or something you didn’t pack that you’d never travel without now?

I packed every herb and spice from my Utrecht kitchen, which France obviously also has. I don’t know why, but having them still gives me comfort.

What I didn’t pack, and quickly learned I needed: linen dresses. Essential in the south of France.

What would you say to the version of yourself still working out whether this life was possible?

I think, deep down, I already knew I could live this way. But the terror of leaving a home and garden I’d created and adored, and my cats, nearly destroyed me emotionally.

I’m slowly coming into my own, and making peace with the mistakes of the past.

Keep up with the Chateau Gardener

You can follow Jen’s adventures — and simply enjoy her take on art, garden design, and historic properties — on Instagram, where she’s (rightly) known as @chateau_gardener.

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Midlife Nomads is where people in their 40s, 50s, and 60s figure out how to build freer, more flexible lives — one decision at a time. Subscribe to follow along, and reply anytime with your interview and story ideas.

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

Happy Thursday from Canada, readers, where I’m trying my best to stay out of the wildfire smoke and working on my pickling game.

These ones were truly awful 😂

I figured if a little garlic and dill are good, three times as much would be far better! Lies.

Add in the onion, red peppers, and peppercorns, and these poor little cucumber coins turned into a flavour-packed punch in the face.

Quick-pickling — where you use vinegar to preserve foods two to three weeks in the fridge vs. making them shelf-stable — is one way I’m trying to improve my solo shopping and eating habits on longer trips.

Having my own kitchen is a must when I’m slow traveling. I wouldn’t want to eat out every meal even if I could afford it, and am trying to get more protein and calcium in. But I’m so used to shopping and cooking for a family of four that waste can be a real problem.

So how do you get more variety without throwing out a fridge shelf of wilted veggies every week?

Well, I’ve started bulk cooking and freezing at the start of a month-long stay. That came in super handy when I got sick at a coliving a while back and had homemade meals to just pull out of the freezer. And the prices on club packs, a whole chicken vs parts, etc. tend to be better.

I’m hoping that a good pickling recipe helps, too. Even if you mess them up, as I did, they’re still good on hamburgers. And if all else fails, you can always use pickled-somethings to garnish a drink.

So far, I’ve figured out the right ratio for the brine:

• 1 cup vinegar (I like 1/2 cup white, 1/2 cup apple cider vinegar)

• 1 cup water

• 1 tbsp sea salt

• 1 tbsp sweetener (sugar, honey, agave nectar, what have you)

Heat to boiling and let it simmer a few minutes so everything is all happily blended together, then let it cool to room temperature before pouring on your veggies (helps keep them crisp).

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And maybe just don’t pack in as many aromatics as I did. You can always add more, but you can’t take the wallop of those extra 3 cloves of garlic away.

I have a good, long housesit coming up in Nicaragua so will have plenty more time to experiment with my recipe and see what else I can pickle. I’ll pack a couple jars with socks to take in my suitcase.

And I’m curious… do you any tips, or a favourite kitchen tool or technique that travels well with you? Share in the comments.

One more fun thing before we get to what’s been happening at Midlife Nomads and my recommended reads.

I got the most intriguing email about a pop-up coliving happening on the Swedish island of Gotland in late Aug/early Sept, and if I wasn’t already committed to a housesit, I’d be scooping up one of these rooms. I don’t know the operators, but the island and property look magical so it’s worth checking out.

The coliving is only 10 days, but with Gotland located between the Swedish mainland, Latvia and Lithuania, you’re well-positioned to head anywhere in the Baltics from there. Estonia and Finland are amazing in late summer/early autumn.

Related:

Full members, you’ll find a Tallinn recommendation I’ve stayed at in the August Shortlist, and a cute spot in the French Pyrenees for later in September when Europe is (hopefully) cooling down again.

Now let’s see what you may have missed this past week. As promised in my last newsletter, I got some thoughts down after reading that article promoting “Hush Trips” last week.

So we’ll start there:

Recommended Reads

These are a few of the more fun, interesting or thoughtful things that have crossed my desk this past week…

I’m also a big fan of the naps, and appreciate Monica Hebert’s reminder not to let anyone make us feel guilty about it — especially our own inner critic. Read it here.

• Aligned & Awake: The New Kid At Forty-Six, The P.L.A.Y. Papers - Tanya Fraser’s been on a journey of travel and rediscovery since her divorce, and I had the good fortune to meet her at a coliving earlier this year. Her piece is a good reminder that if you’re feeling awkward and out of place trying to meet new people as a solo traveler, you’re not alone.

• Proof Point of An Immigration, Chris Lutkin - I love the Azores, and adore this reflection on a full year spent there. Interestingly, Chris mentioned he finds art and creative projects a good way to make real connections while traveling, which Tanya (above) noted from her most recent adventures in London, too.

• How I Stopped Comparing My New Country to My Old One: and why that matters... from Expat on a Budget - This is a thoughtful read from Kimberly Anne on the tendency to keep score and compare one place to the next. The process of packing up your whole life and physically migrating to another country brings with it some weighty expectations, and the feelings that can bring with it are worth exploring.

That's it for now. Until next time, may your air quality remain high and your bags always make it to the next stop on time.

✌🏻 Miranda

Someone posted a thread last week about how to work remotely from abroad without your employer or clients finding out. Change your Zoom background. Route everything through a VPN so your IP reads as home. Don’t post the location. Keep your calendar vague. And keep your selfies to yourself!

There’s a name for it now. Two, actually.

Quiet vacationing is the umbrella version, where you appear to work while you’re somewhere you haven’t told anyone about. It could be anything from a sneaky afternoon at the nail salon to a laptop open at a ski lodge four hours from home.

Hush trips are the pointier end of the same instinct: keeping your regular hours and your full workload, but logging in from a hotel, an Airbnb, a friend’s place two states over, or a rental in Bali while everyone at work assumes you’re at your kitchen table.

The whole thing runs on one bet: as long as the work gets done, where you did it is nobody’s business.

That thread I mentioned got a lot of excited responses, which truly sucks, because it’s terrible advice. And not for the reason most people push back on it.

The usual objection is you might get caught and fired. True, and worth taking seriously; a corporate laptop with device management often reports its real location to IT regardless of your VPN, so your gear can give you away on its own.

But that framing treats the whole thing as a game of not-getting-caught, where the only failure state is exposure. That’s not the shape of the actual risk.

The actual problem is that hiding doesn't touch the things that can actually go wrong. Most of them aren't triggered by someone finding out. They're triggered by the crossing itself, by the contract you already signed, by the tax residency clock that started running whether or not anyone at head office knows your IP address.

Here's the part that surprises people. You can be a fully authorized remote worker, doing everything above board with your employer's blessing, and still walk into a serious problem the first time you cross a border with a work laptop.

In the US — and this is not hypothetical — border officers can search your electronic devices without a warrant and, in many circumstances, without even a specific suspicion that you’ve done anything.

At borders, you're in a strange legal space where the protections you’d have three feet inside either country don’t fully apply. Depending on the officer and the circumstances, that can mean scrolling your phone, and in a more advanced search, copying the contents of your drive or asking you to log into your accounts.

Now think about what’s on that laptop if you do client work. Proprietary files. A signed agreement that may say, in language you skimmed two years ago, that you will not expose the client’s data to unauthorized access or move it across jurisdictions. Attorney-client material, if you’re in law. Patient information, if you’re in health.

You didn’t leak it. You didn’t do anything careless. You handed it to a border officer because you had no standing to refuse, and now you may be in breach of a contract you fully intended to honour.

For most people reading this, the border scenario is a low-probability event. Most crossings are uneventful; most officers wave you through. I’m not telling you to be afraid of the airport.

I’m telling you that the risk lives somewhere other than where the “hide it” advice is looking. The thread about Zoom backgrounds is answering the question how do I not get caught.

The question that actually matters is what am I exposed to, and to whom did I already promise otherwise.

Those are different questions. The first one has a sneaky, satisfying variety of answers that show up in those threads bragging about working from anywhere. The second question has a real one, so let’s get into it.

The rest of this — the four exposures that actually matter, how to read your own contract for the clause that matters, what to do at a border with a work device, and how to have the conversation with an employer or client instead of hiding from it — is below, for full subscribers.

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In 1955, at the age of 67, Emma Gatewood told her children she was going for a walk.

She didn’t mention that the walk went from Georgia to Maine.

She left with a change of clothes, an army blanket, a raincoat and a shower curtain, all of it in a homemade bag slung over one shoulder. She had on her trusty Keds, and less than two hundred dollars in her pocket.

Gatewood had raised eleven children. She had survived roughly thirty years of a husband who used violence to keep her where he wanted her, and had finally divorced him in 1941. By all accounts, she had earned a quiet chair by a window and nothing more surprising than that.

And yet a magazine article got her up and out the door.

It was a 1949 National Geographic feature about the Appalachian Trail, and it described a wide, well-marked path with clean shelters spaced a comfortable day apart.

Emma worked out that no woman had walked the trail alone, and decided she’d like to see it for herself.

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

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The article oversold the condition of the trail by a long shot.

Emma found it overgrown to her neck in stretches. Unmarked for miles. Washed out. The shelters she came across were burned or collapsed, or too filthy to sleep in.

She got lost constantly. A rattlesnake struck at her. She walked through two hurricanes and lost thirty pounds.

Her verdict, delivered flat to a reporter later: she’d thought it would be a nice lark. It wasn’t.

She didn’t turn around, though.

Emma walked about fourteen miles a day, sunrise to sunset, out-pacing hikers half her age. And when reporters asked why she’d gone in the first place, she gave the least quotable answer available: Because she wanted to.

She wanted to see what was on the other side of the next hill, and then what was beyond that. It turned out to be a lot more interesting than a manicured, well-marked path.

That’s the whole engine. She didn’t have a solid plan or a five-year projection. She was curious, and that was enough for the trip to survive being lied to about the terrain.

We’re handed a lot of stories about how good decision-making runs the other way. Gather the information. Confirm it’s good. Move only once the picture is complete.

But there was no version of that walk that began with good information. Nobody had it. The men who wrote the article didn’t have it. The only way to find out what the trail was actually all about was to be standing on it.

The info we have ahead of time is always a little bit wrong.

The apartment is smaller than the photos. The town is louder at night. The place that looked full of people in the pictures has three people in it, and one of them is on a call in a language you don’t speak, and it rains 23 hours a day.

You find that out by going and doing. There has never been any other method that truly works.

Gatewood reached the summit of Katahdin on the 25th of September, 146 days out. She had one lens left in her glasses and it kept fogging over. She was wearing men’s gloves she’d picked up somewhere along the way.

The reporters were all waiting at the bottom of the mountain. So there was nobody at the top when she signed the trail register, sang a verse of “America the Beautiful,” and said, to no one in particular: “I did it. I said I’d do it and I’ve done it.”

Then she walked back down.

She never said it healed her. She never said what it meant to her. Afterward, Emma told reporters the trail was badly maintained, and that walking is about as nice a thing as anybody can do, and cheap besides.

That is as close to a moral to the story as she ever came.

Emma walked the trail again in 1957. And again at 76, in sections, becoming the first person to walk the whole thing three times. The Oregon Trail at 71, on foot, alone. Into her eighties, out clearing trail in Gallia County, ten hours a day.

The reward for finding out what was over the hill was another hill. She just kept walking over to have a fresh look.

✌🏻 Miranda

Sources:

• Atlas Obscura, “The First Woman to Thru-Hike the Appalachian Trail Alone Did It as a ‘Lark’” — excerpted from Philip D’Anieri, The Appalachian Trail: A Biography

• The Allegheny Front, “Grandma Gatewood’s Epic Appalachian Trail Hike” — interview with biographer Ben Montgomery

• A Mighty Girl, “The 67-Year-Old Who Became the First Woman to Solo Hike the Entire Appalachian Trail”

• Free Range American, “First Woman to Solo Hike Appalachian Trail Was an All-American Badass”

• Appalachian History, “Emma Gatewood, 67, Walks Appalachian Trail Solo”

• Ben Montgomery, Grandma Gatewood’s Walk: The Inspiring Story of the Woman Who Saved the Appalachian Trail

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

Happy July, readers!

I realized today it’s been a minute. I’m home in Canada catching up on all the things… too many appointments, qt with my boys, and even a press trip up a mountain, and a book launch on a boat! What a trip.

Oddly, my partner is down in Nicaragua so I have the home base to myself. Well, myself and Lido. It’s actually his house; he just lets us stay here sometimes.

Typically when Trevor is traveling, it’s on his vacation time — and I’m with him. But like I said, appointments.

There was the annual bleeding disorders check-up, and one dentist appointment that led to a referral to another. The pharmacist appointment to make sure the blood pressure meds aren’t interfering with the migraine meds, and the autoimmune gremlin is still doing okay without the medication that messed with the blood pressure. The appointment to get the 3-month needle that keeps me in menopause at 45 yo (thank the goddesses). The neurosurgeon appointment coming up in a few weeks to have a look at Fred the Friendly Aneurysm.

It feels like a lot all crammed into a few weeks, I suppose.

And it surprises me sometimes, at these appointments, when we go over my file that there are these things going on, because I actually feel great about 95% of the time.

It sneaks up on you, doesn’t it? I’m doing everything I can to stay well, but you can’t fight your gene pool.

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These not-insignificant reminders of my vulnerability and mortality are a strange kind of validation, though. I don’t know how I would have made it through the last 20 years without fully remote work and the ability to shape a career around all the other things that needed — and deserved — attention first.

That’s what I mean when I say a more sovereign, independent life isn’t reserved for the already-wealthy, or some special class of people. My work-from-anywhere life started as a young mother with few options in small town Canada. It’s only grown more necessary as my parents aged (and so am I…).

Maybe yours starts after a layoff, divorce, or health crisis. Maybe it starts out of boredom, or that nagging feeling your life just doesn’t quite fit right anymore.

Or maybe it starts right now.

Nobody could have told me, twenty years ago, that it would turn out like this. Girls like me, with an upbringing like mine, didn’t dare dream past restaurant or factory work. Designing a career around a life (and enjoying it, no less) wasn’t on the menu. You took the job that was there.

It didn’t happen in a leap. It was one small realization, then a decision, then another, and most of them didn’t feel like much at the time.

And now Lido’s asleep on the floor by my feet. Trevor’s texting me photos of the palm trees and getting my desk there set up. I’ve got a neurosurgeon in a few weeks and a fistful of appointments behind me, and I’m sitting here writing to you, working around all of it.

Twenty years ago I couldn’t have pictured any of it.

You don’t have to know exactly where you’re going, either. Not when you’re just getting started, and it’s never too late to move in another direction.

ICYMI on Midlife Nomads

A new shortlist has dropped, too.

It might feel too early to look ahead to January, but there are some decent deals to be had by booking your month-long stays ahead:

Let's go

Recommended Reads

These are a few of the more interesting things that have crossed my desk this past week…

Brian Clark at Further just launched his Leading Expert Launchpad, a four-module course on building a business around your expertise instead of chasing clients one at a time. The free intro video lays out the full framework if you want to see how he thinks before deciding whether the premium course is for you.

The Premium membership bundles all of this — the business-building courses, the frameworks, the investment and home-base guidance — plus all his previous courses, and it's honestly one of the highest-value subscriptions I pay for; I get more out of it than almost anything else in my inbox.

Check it out at Further

• The Quiet Transition: What Men Get Wrong About Menopause (And How to Fix It), Nomads 50 Plus - The 50+ nomadic version of the Manosphere is supportive of our peri- and menopause struggles, and I’m here for it.

• Taiwan Just Launched a 2-Year Digital Nomad Visa—Here’s Who Qualifies, Condé Nast Traveler - Taiwan remains high on my wish list

• Climate crisis reshapes travel as weather risks grow in 2026, Asia News Network - 74% of travelers now consider extreme weather an important factor when planning trips (I know I do… how about you?)

Then I stumbled across this one in HuffPost: What Is A ‘Hush Trip’? This approach to travel carries many benefits, but the risks are difficult to ignore.

This is such a bad idea, for a lot of reasons. The answer to “Gee, I wish I could work remote but my boss won’t let me” is never, “What they don’t know won’t hurt them.” You can expect a piece from me soon on why this is a really, really dumb idea and a roll of the dice.

That's it for now. Until next time, may your air conditioning stay strong and your wifi stable.

✌🏻 Miranda

The most common household in Canada isn’t a couple. It isn’t parents with kids. It’s one person, on their own.

One-person households have been the single most common household type in the country since 2016, and by the 2021 census they made up close to 30 percent of all homes. Some 4.4 million Canadians now live alone, up from 1.7 million in 1981. It’s often assumed to be a story about aging, and partly it is. But it’s happening in the middle of life too — the share of people aged 35 to 44 living alone doubled between 1981 and 2021.

Some see this as “achievement.” Somewhere along the way, living alone stopped being what was left over and became something to strive for — the private apartment as proof you’ve made it and don’t need anyone. We’ve gotten individualist enough that a lot of people don’t seem to register how much they still run on the rest of the community.

Others see it as the inevitable. If you’re not partnered, you’re solo. Coupled up or on your own. Two boxes, and everyone gets sorted into one of them.

There’s a whole category most skip right past, sometimes not even realizing it’s an option, but often due to outdated ideas about what it means.

Intentional community. Coliving. Cohousing. Arrangements where you keep your own space (your own door, your own bed, your own quiet) inside a structure you don’t have to manage on your own. I’m talking shared kitchens and common rooms, group meals when you want them and solitude when you don’t. People who clock it when they haven’t seen you in a day and knock to make sure you’re okay.

It sits between the two boxes, and most people never seriously price it out. Coliving reads as something for students, or for the very young, or a person who couldn’t make it on their own. It’s the commune your aunt joined in 1974. Not for a competent adult in her fifties who simply doesn’t want to eat every dinner across an empty table.

The census only has boxes for who you’re related to and who you’re married to. It has no box for the people you share a hallway and a life with by choice. That arrangement barely shows up in the data, which is part of why it barely shows up as an option in anyone’s head.

We measure the two things we already believe are the choices, and the measurement just confirms the belief.

Four and a half million people got sorted into “alone.” I’d bet a real share of them never wanted the empty apartment. They wanted out of the couple, or never found one, and “alone” was simply the only other box on the form.

There is another box, and it’s not what you might have been led to believe it is.

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I’ve been thinking lately about how hard it is to build a habit and make it stick. There are so many small things I keep meaning to do and somehow never get to.

Too often, they’re the fun things. The joyful things. The entertaining things… sometimes the purely silly things that make me happy anyway.

Part of the problem, for me, is that I tend to pack every open hour with work. There’s always something billable, something I’d feel guilty for skipping. We’ve built a whole culture around that guilt… around that mistaken belief that a moment that isn’t productive is a moment wasted.

So the thing I’d actually get up and do for its own sake keeps losing to the thing I’m “supposed” to be doing, as hard as I try to fight it.

Which is how Carmen Herrera came to mind. You’ve probably never heard of her. For most of her life, almost nobody had.

Carmen made paintings almost no one saw.

She trained as an architect in Havana, moved to Paris after the war, and settled for good in New York in the 1950s, making abstract work the whole time, in sharp lines, two colours, a lot of white and green.

“There is nothing I love more than to make a straight line,” she said, and she meant it literally. Her cleanest series, the white-and-green Blanco y Verde paintings, came out of the 1960s, when New York wanted the drama of Abstract Expressionism and had no use for her restraint.

She was drawing the geometry minimalism would get famous for, before it had the name. Almost none of it sold.

On top of that, a New York gallerist told her that her work was better than the men’s he showed, and that he wouldn’t give her a show anyway, because she was a woman. (Ughhhhh.)

She had every reason to stop. But she kept painting.

Museums passed on her. Barnett Newman was a friend; he got the recognition and the money and the place in the story.

Carmen kept painting.

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She sold her first painting in 2004, at the age of 89. After that, it moved fast: the MoMA acquisition, then the Whitney retrospective at 101. She had an entire life’s collection behind her.

It’s tempting to read this as a patience story. She held on, and the reward finally came. Wait long enough and you’ll be seen.

That’s not how she described it, though.

Asked how she’d worked all those years with no reward, Carmen said she did it because she had to. It wasn’t a bet on being found later, but her work was the thing itself.

She said obscurity had given her something she’d have hated to lose: no one to satisfy but herself. The work was the point.

The payoff was never the point, which is the only reason the missing payoff, and watching everyone else collect the accolades, didn't hollow it out.

There’s a harder truth folded into that. Most people who make unseen work for decades don’t get the Whitney at 101. Herrera is the exception. The recognition was never something she could count on, and it isn’t something you can, either.

Which is exactly why it can’t be the reason you do the work.

Carmen couldn’t have known where any of it was going. She painted anyway.

You don’t need to know where yours goes, either. You need to identify (or maybe rediscover) the thing you'd get up and make every day whether anyone notices or not — then you figure out how it fits the life you're building.

✌🏻 Miranda

Sources:

• Britannica

• The Washington Post

• The Art Story

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Don’t we love January? The holiday pricing bubble finally breaks. Places that were overbooked and overpriced in late December are suddenly workable again. Flights soften, the good rooms open back up, and the long-stay discounts that vanished over Christmas quietly come back.

So if January's the month you want to spend somewhere warmer than you spent Christmas, now's the time to start lining it up. The crowds will have gone back to work, and the second half of winter is the calmest, best-value stretch of the year for staying put somewhere for a month or two instead of rushing through it.

A few of the places below reward booking early, the Southern Hemisphere summer spots especially. Others you can leave till closer to the date and still land well.

First check out the regions, and then we’ll get into my Shortlist recommendations — the specific places I’d send a friend.

Africa

Deep dry season and one of the best winter-sun runs going. Morocco is at its coolest… Marrakech gives you mild dry days but genuinely cold mornings and nights, and a riad with no real heating is the catch nobody mentions.

If warmth is the whole point, the Atlantic coast at Agadir and Taghazout stays warmer and surfs well. Egypt is in its glory: Cairo, Luxor and Aswan are cool, dry and made for being outside all day. The Red Sea towns of Dahab and El Gouna stay sunny but breezier and cooler than autumn — fine for sun, less so for long swims.

Southern Africa is in full summer and gorgeous, but it’s also the priciest, most crowded stretch of the year, with South African school holidays running into mid-January. There’s the wind, too — Cape Town’s summer southeaster, the “Cape Doctor,” can blow for days. Glorious if you’re out moving around, but maddening if you wanted still beach mornings or a calm work terrace.

Out in the Atlantic, Cape Verde (Sal, Boa Vista) is warm, dry and windy. West Africa is in its Harmattan season, so Dakar and Accra are warm and dry but hazy with desert dust, which is worth picturing before you book.

East Africa’s coast is in its sweet spot between the rains — Zanzibar, Diani and Mombasa are hot, mostly dry, and the prices ease once New Year clears out.

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Asia

One of the strongest months on the whole calendar. Southeast Asia is at its dependable dry-season peak — Thailand, Cambodia, Laos and southern Vietnam are dry, warm and sunny, pricey through the first week and then easing.

If you're islanding in Thailand, go west: January is prime on the Andaman side (Phuket, Krabi, Koh Lanta) while the Gulf islands (Samui, Phangan, Tao) are still shaking off the last of the wet.

The one to rethink is Indonesia — Bali, Java and Lombok are deep in their wet season, and January is often the wettest month of all. Skip Bali if you came for reliable sun. Go anyway if you'll take it green, cheap and empty and don't mind planning around the afternoon rain.

Japan is in proper winter; cold, clear, Hokkaido and Nagano deep in ski season, Kyoto blissfully quiet. South Korea is cold but works fine for a city stay, and Taiwan is mild, drier in the south than the damp north.

Northern India and Rajasthan are at their pleasant peak — cool dry days, cold nights — with the real catch being thick morning fog and heavy pollution around Delhi that loves to delay flights and trains. Sri Lanka’s south and west coasts are prime for surf and work, and the Philippines is dry and good.

North to Central America & Caribbean

Flight pricing comes back down to earth after the first week. The Caribbean is at peak season and peak prices, Hawaii is in its high-season window (and whale season, if that’s a draw), and the ski regions across the US and Canada are at their busiest.

Mexico holds its high season across the coasts and the Yucatán, easing a little off the late-December spike but still not cheap. The reason to go in winter is the water: January sits inside the Caribbean coast's clear-water window. The sargassum that fouls Playa, Tulum and the Riviera Maya beaches in summer is at its lowest from late autumn into late winter, which is why the photo above of Playa del Carmen, last January, looks the way it does, all clean sand and turquoise.

One honest catch: the bloom has been creeping earlier the last couple of years, so even January isn't the guarantee it used to be, and a clear beach can turn the other way within a day.

If postcard water is the whole point of the trip, lean toward the naturally sheltered spots — the western side of Cozumel and Playa Norte on Isla Mujeres stay clear when the open coast doesn't — and keep a cenote day in your pocket either way.

Belize is in dry-season Caribbean warmth, and it’s an easy one if you want English-speaking and uncomplicated — Caye Caulker and Ambergris for the water, Placencia for the quieter version (where I traveled with NOMA last year).

If you’re heading here, it’s worth knowing is the “northers”: winter cold fronts that swing down a few times a season and bring two or three days of wind, grey skies and choppy, stirred-up sea before it clears. They pass, but they’re real, and they’re most common exactly now. Belize also runs pricier than its neighbours, so it’s comfort over value.

El Salvador has gone from a place people warned you about to one of Central America’s fastest-rising surf-and-work spots, and January lands squarely in its dry season (November to April), so it’s warm, sunny and prime for the Pacific breaks. El Tunco is the social hub, El Zonte the mellower “Bitcoin Beach,” both with growing café and coworking scenes.

The security turnaround is real on paper… the U.S. State Department moved El Salvador from its highest Level 4 warning down to Level 2, the same tier as France. Two honest notes, though. That turnaround came via an ongoing “state of exception” and heavy military policing, which is visible on the ground and worth going in aware of. And prices in El Tunco and El Zonte have climbed as nomads have arrived, even while the interior stays cheap, so it’s no longer the bargain it was two years ago.

Turks & Caicos is the postcard version of the January Caribbean. It’s dry, sunny and reliably warm, well clear of hurricane season this time of year, and Grace Bay on Provo earns every “world’s best beach” ranking it gets — long, pale, calm, the water almost unreasonably clear.

Two cautions here. It's one of the most expensive places in the Caribbean, full stop, and winter is its peak-price high season, so this is largely splurge territory rather than value. You’ll find some budget-friendly tips here, though:

And it's small and resort-shaped: lovely for a beach week or two, but thin on local texture and long-stay nomad infrastructure compared with somewhere like Colombia or Mexico.

Sitting further north than the southern Caribbean, it runs a touch cooler and breezier in January, so you'll want a layer for the evenings.

Nicaragua is in its dry-season prime, which is why I spend part of the winter here. Granada, San Juan del Sur, León and Ometepe are hot, dry and sunny all month, and Granada carries its festive streak well into January after the December fireworks wind down. It’s also one of the better-value spots on this whole list.

The catch here is the wind: December through February is the windy season on the Pacific side, so expect strong, steady gusts most days — a gift if you kitesurf, a low-grade annoyance if you wanted still beach mornings. The Caribbean side and the Corn Islands run wetter, so stay west for the reliable sun.

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.

South America

It’s high summer down south. Patagonia is at the height of hiking season and at peak demand and prices clear through February — and it's the one to book now. Refugios fill, trails cap out, and the best bases go months ahead, so a July reader eyeing January Patagonia has the timing exactly right.

Buenos Aires is hot, and January is when locals empty out to the coast — that makes the city quieter and cheaper for a base, though some shops and restaurants shut for the holidays.

Uruguay and southern Brazil’s beaches are at their summer-holiday peak. Colombia is lovely and noticeably better value than the Mexican coasts, with Medellín pleasant all month long (but then, isn’t it always?).

One to sit out: the Andes — Peru, Ecuador and Bolivia are in their wet season, so this isn’t your Machu Picchu or high-altitude trekking window.

Galápagos is one of the rare January wins in Ecuador, even though the mainland highlands are washed out, so don't let my "skip the Andes" note scare you off the islands. January opens the warm-wet season: warmer water in the high 70s, calm seas, good snorkelling visibility, and the islands gone green and busy with nesting iguanas, sea turtles and boobies. Brief afternoon showers are the trade-off, and they rarely cost you a day.

Two things to be aware of, both about planning. Early January is peak-season pricing, and the good cabins and lodges go six to twelve months out, so this is the single most book-early item on the list. And if the waved albatross is on your wishlist, pick another month… it leaves Española then and isn't back until April.

Europe

Most of the continent is cold and deep in low season, which is exactly why the southern edge is such a steal. Southern Spain, Portugal and Italy hold mild city-stay weather at the year’s quietest, cheapest rates. Seville, Málaga, Lisbon, the Algarve, Sicily and Puglia all give you walkable, atmospheric bases for a fraction of the summer price. It’s cool, not warm: think jacket-and-café weather and short days, not beach weather. If you’re picturing sun loungers, you want the Canaries instead.

The Canary Islands and Madeira are at their mild winter best and stay the strongest-value warm option against the Caribbean. One catch: book the south-facing side. The green northern coasts of Tenerife and Madeira are green for a reason, and can sit under cloud and rain while the south stays sunny.

A few others worth a look. Malta is mild, walkable and very cheap in January, with the bonus that everyone speaks English if you want an easy first long-stay in Europe. Cyprus runs a touch warmer than the central Med and is one of the quietest, best-value winter bases going, though the island effectively splits between coast and the snow-dusted Troödos mountains, so know which one you’re booking.

Northern Italy, Austria and Switzerland are firmly in ski season if that’s the trip — beautiful, but the opposite of a value month. And the catch for all of mainland southern Europe: January days are short and shops and restaurants in smaller towns thin out or close for the off-season, so cities hold up better than sleepy coastal villages this time of year.

A note on the rest of the continent: Paris, Rome, Vienna and the like are cold and grey, but they’re also at their least crowded and cheapest, which is its own kind of argument if you’d rather have the museums to yourself than sit on a beach.

So Where Are We Headed?

You’ll find 18 recommended stays across 5 continents this month, including a Sri Lankan coliving between the surf towns and Galle. A quiet Recoleta studio while the porteños empty out to the coast. A palm-garden villa on Madeira with an outdoor fireplace for the dark evenings. A Malta house for an easy first long-stay where everyone speaks English. A laid-back Nicaraguan surf town where the power stays on.

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

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.

Members-only beyond this point.

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Most advice about achievement is about how to get the thing. Almost none of it is about the flatness that can follow getting it.

You reach the title, the number, the recognition you spent years building toward. And within a few months, sometimes weeks, it has gone from the thing you wanted to the floor you stand on. Just the new normal. Not the feeling you were promised.

A while back I wrote about Viola Davis, who spent decades reaching for recognition and has been open about how hollow it felt once it arrived. I ended on a question: is this destination still for this version of me?

That was the question. This is the harder part: when the thing you reached for lands flat, how do you read what the flatness is telling you?

Because it can mean two opposite things. Either you achieved the wrong thing, something that was never actually yours to want. Or you achieved the right thing, and the feeling did what feelings do, which is fade. Read it wrong and you either tear down a good life chasing a high that was never going to last, or you keep grinding inside a life that isn’t yours, telling yourself the emptiness is something everyone feels.

So before you touch anything, the first job is telling the two apart.

Why the Glow Was Always Going to Fade

Start with the part that isn’t personal, because it takes a lot of weight off.

The most cited finding in this area comes from a 1978 study by Brickman and colleagues, who compared lottery winners to a control group and found that within about eighteen month,s the winners were no happier than people who hadn’t won at all.

The same study looked at people who had been paralyzed in accidents and found something just as telling: after the initial impact, both groups drifted back toward their earlier baseline.

Psychologists call it hedonic adaptation, the treadmill. Big events move you, then your reference point resets and you’re back where you started, looking for the next thing.

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Right now, a woman named Kelsey Pfendler is alone in the middle of the Pacific Ocean, rowing a 24-foot boat toward Hawaii.

I’ve been following her journey for weeks and I can’t look away.

Kelsey is the 31-year-old Grand Canyon river guide who set off from California on May 21 — no motor, no crew — and has since taken off in our social feeds.

She sleeps about four hours a night. She puts cream on the salt sores every couple of hours so they don’t open. If she makes it, she’ll be the first American woman to do this solo, and maybe the youngest and fastest woman on record.

On Saturday, she was 457 miles out and had just rowed 73 miles in a single day, the fastest of her whole trip.

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Kelsey rowed the same route in 2024 as the skipper of a four-woman crew. She spent years getting ready to come back with a faster boat, weather routers, a safety team onshore. She did her homework. She seems incredibly well-prepared; I’ve enjoyed her video boat tours as she walks us through all her supplies and back-up plans.

Can you ever really feel completely ready for something like that? Out in the wild, on your own… it’s not like she could change her mind and call a cab to come home.

At some point the planning is done, the conditions still aren’t perfect, and the only way to make it the right time is by going ahead.

And so she pushed off anyway, right into headwinds that shoved her backward for a week. Her hands blistered by the second day. She kept going anyway.

Kelsey drew a finish line about 46 days out, and she’s rowing toward it. She’ll land, take a shower, go home.

And on a day she was clearly winning, she said she’d spent the day in two different trains of thought. “I’m so excited that everything’s going so well, and I’m doing the thing I came out here to do.” That was the first one.

The second: “There’s also part of me that spent the day just kind of grieving the loss of this row a little.”

She has maybe nine days left, and she’s already grieving it.

“I’ve been mourning the person I got to be out here in the middle of nowhere, alone for the last 37 days.”

She found someone out there she’s going to miss, and she’s mourning her before the row is even over.

That’s the part most of us could actually borrow. You don’t have to row an ocean. You can pick a thing: a few months in a country you’ve only visited, a season trying the work you keep circling.

Put a start date and an end date on it. Try a different life on for size, with a clear way back.

The way back is what makes it doable. It doesn’t mean you’re coming back the same.

Kelsey will be home soon, and that version of her will start to fade, the way it does once you’re back inside a normal week.

But she got to meet her. And that only happened because one morning in May, she stopped waiting for better conditions and pushed off.

There’s a version of you out there, too… not a better one, but the one you don’t see inside the safety and comfort of your routines. She doesn’t show up because you finally feel ready. She shows up on the far side of a start date you actually keep.

✌🏻 Miranda

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The standard advice for feeling off in midlife is some version of rest. Take a break, use up your vacation days. Protect your weekends.

That’s great advice for the half of people who need it. For the other half, rest does nothing, because being tired was never the problem.

A few months ago, I shared Linda Moran’s essay about spending thirty years living s…

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By 70, Leonard Cohen was supposed to be finished. Not in a bad way, but in the way you’re supposed to be allowed to be finished after a long life of doing whatever thing it was you were doing.

He’d written the songs, made the records, toured the world and come home. Then spent most of the 90s on a mountain outside Los Angeles, ordained as a Buddhist monk, up before dawn to sit in the cold and cook for the others.

He came back down, settled into a place in LA, and was, by his own account, about ready to retire. The savings were handled. Roughly five million dollars, built over a career, waiting for exactly this stretch of life.

But then it just… wasn’t there.

A message reached his daughter: tell your father to look at his accounts. When she said he was about to retire anyway, the man who’d flagged it told her he wouldn’t be able to.

He was right. The five million had been reduced to about a hundred and fifty thousand.

Cohen’s manager of seventeen years had been emptying the accounts for the better part of a decade.

There's a version of this story that calls the theft a blessing in disguise — the thing that forced him back out and handed him a late masterpiece. That version is popular, but I don't think that’s the greatest read on this story.

Nobody hands you a gift by robbing you at 70.

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What I think is really remarkable is how plainly Cohen took it. Asked about it later, he said he’d been devastated but not shattered. He wasn’t performing the catastrophe. He filed the lawsuits, won a judgment for nine and a half million he’d mostly never collect, and then did the only practical thing left.

He went back to work.

In May 2008, at 73, after fifteen years off the stage, Cohen walked out for a run of small preview shows in Canada. By his manager’s account, he’d been reluctant. He rehearsed three months first, then went back out for the money.

Eventually though, he stayed out for something the money doesn’t explain and just kept going.

387 shows over five years, three hours a night, long after the debt was covered. Whatever he was finding out there, the savings were never going to provide it. Call it purpose, or just the proof that he wasn't done.

You Want It Darker came out weeks before he died at 82.

He’d spent the back half of his life stepping out of that whole world. The mountain, the monk’s robes, fifteen years off the stage. He thought that was the ending. The robbery is what told him it wasn’t; something completely out of his control.

And he found out, at 73, with the worst timing imaginable, that the story he’d followed for his own life wasn’t really his.

Most of us are running some version of the same assumption.

That by now, we mostly know how this goes. We’re going to do what we have to do to get through this next set, and do the work to protect it. One day, we’ll be able to kick back and enjoy being past all that noise.

It's worth asking where that picture even came from. The deal — give your strongest decades to the work, and the security will be waiting at the end of them — was built on conditions a lot of us no longer have: pensions that paid out, employers that lasted.

Take those away and "retirement" stops being a finish line you're walking toward. It starts to look like a story you inherited from people whose world worked nothing like yours.

The thing that takes the plan out from under you, whether that's the money or the job or the role you thought you'd hold to the end, tends to take all of our assumptions with it. And it leaves you holding the question the assumption was built to keep you from asking: whether you're actually finished, or only assumed you were.

Somewhere along the way, we were handed this idea of a point where it’s all supposed to wind down.

Where the working is supposed to be over and the purpose along with it, where the rest of it is supposed to be rest.

Cohen reached that point and found nothing there waiting to switch off.

You don’t get to choose when the floor goes. And you don’t actually know where your own purpose runs out. You only know where someone else drew the line, and you can spend your whole life marching toward it only to discover it was never really there.

So stop taking someone else's word for where it is.

✌🏻 Miranda

Sources:

• Billboard, “How an Embezzling Manager Caused Leonard Cohen’s Late-Career Comeback”

• The Canadian Encyclopedia, “Leonard Cohen Goes Broke”

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

The first time I spent Christmas abroad was in 2017. My father had passed away that spring, my husband and I had been defrauded in our business, and my sons were ready to begin new holiday traditions with a younger sibling at their dad’s house.

Somewhat battered and broken, I got my husband’s blessing to take off for the holidays (he’s a chef and his role back then meant working through the holidays, anyway).

I booked a room in a hostel in Las Palmas, Gran Canaria, for a few nights and intended to figure the rest out when I got there. It wasn’t much of a plan… I just knew that staying home rotting in bed wasn’t going to do it.

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For the next three weeks, I toured the island and enjoyed the company of other travelers, many of whom also felt like misfits in some way for not going “home” for the holidays.

I didn’t make any lifelong friends… in fact, I’ve never seen anyone I met on that trip again. And yet it was an incredible and freeing experience, letting go of all of those weighty expectations of the traditional Canadian Christmas.

Since then, I’ve spent several weeks to a month or more over the holidays in Portugal, Mexico, South Africa, Nicaragua and more. This is mostly solo travel… sometimes Trevor joins me for a week, and often a friend traveling in the same area will pop in.

I celebrate the occasion with mine and Trevor’s families before taking off, then enjoy the season as stress- and guilt-free as possible.

Maybe this will be the year you make a new kind of holiday for yourself, too.

That’s what I had in mind while putting together our members-only Midlife Nomads Shortlist for December. These are my handpicked recommended stays of a month or more for working travelers 40+, with quality accommodations, many with built-in community, and most with reliable wifi (I’ve indicated where it’s not).

One of those is Anceu Coliving in rural Spain, which comes highly recommended by a friend in the coliving sphere whose judgment I trust.

If it’s your first time away and the holidays have traditionally meant a lot to you, perhaps a coliving with a vibrant community like Anceu is in order. Or maybe you’re ready for a creative retreat all on your own. Full subscribers will find options like that, too, with vetted stays for December spanning four continents. Check it out:

See the December Shortlist

ICYMI on Midlife Nomads

Recommended Reads

An Italian who's spent years watching Americans move to Europe ranks ten places where they actually thrive, tagged by who each suits — retiree, remote worker, founder, family — and scored on six things the photos never show, like the US tax treaty and whether there's still a community in February.

He's blunt that the dream cities (Lisbon, Paris, Berlin) tend to disappoint, while the unglamorous second cities are where people stay. While I don’t agree with every conclusion, he’s pretty bang-on and there’s a ton of helpful info here.

Read More

• The Protein Pendulum How We Got It So Wrong, and Do We Finally Have It Right? - by Samantha Clark for Further.net

• Gen X Rewrites the Rules: The Age of Adaptation - Bryan Kelly for age/proof design

• 21 Years of Full-Time Travel: The Things I Still Love Most (Video) - Mary Bartnikowski

• My mother died at 64. So I asked for the party I almost talked myself out of. - Marni Battista

That's it for this week. Until next time, may your wifi stay strong and your flights arrive on time.

✌🏻 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.

Japan doesn’t need help attracting remote workers. It has the trains that run to the second, the food, the safety, the connectivity, and a depth of culture that makes an ordinary Tuesday feel like it belongs to a place rather than to a hotel chain.

But Japan’s Digital Nomad Visa is not a relocation route. It’s not a soft landing into permanent residency, and it’s not built for someone testing a side hustle.

It’s a six-month stay. That’s the whole proposition, and it’s worth understanding that before anything else.

For a midlife reader, that’s not a flaw. Most people in their 40s, 50s, and 60s who are drawn to Japan aren’t looking to emigrate. They want longer than the 90-day tourist window allows, on legal footing that lets them keep working. That’s exactly what this visa is for, and almost nothing more.

Here’s what you actually need to know.

First: Who This Visa Is (and Isn’t) For

Japan launched its Digital Nomad Visa on April 1, 2024. Its official status is Designated Activities (Digital Nomad, Spouse or Child of Digital Nomad) — a sub-category of Japan’s catch-all “Designated Activities” residence status, not a standard work visa.

It is designed for people who:

• Are employed by a company registered outside Japan, or

• Work as a freelancer or business owner serving clients outside Japan

You may not work for a Japanese employer or invoice Japanese clients on this visa. The income supporting your stay has to come from abroad. If your work starts pointing at the local market, you’re in the wrong category.

There's also a nationality filter. Only citizens of countries and regions that have both a tax treaty and a visa-exemption arrangement with Japan can apply — roughly 49 to 50 countries and regions as of 2026, including the US, Canada, the UK, the EU, Australia, New Zealand, Singapore, South Korea, Taiwan, and Hong Kong.

The list moves, so check the current Ministry of Foreign Affairs version before you plan anything.

Here’s what we cover in this guide:

• Who the visa is actually for — and who it quietly screens out

• The 10-million-yen income bar, and what counts as proof

• Health insurance: why it’s mandatory and, on this visa, your only coverage

• The six-month limit, the cooling-off period, and why there’s no path to residency

• Taxes and the 183-day line that keeps your foreign income untaxed

• How to apply: documents, fees, timeline, and where to file

• Bringing a partner or children

• Living costs, housing, banking, and connectivity, city by city

• The downsides nobody posts about

• Whether Japan actually fits a midlife nomad

Income Requirements (2026 Reality)

This is where Japan separates itself from most digital nomad visas, and where a lot of midlife applicants will stop reading.

You must show an annual income of at least 10 million yen — roughly US$65,000–70,000, depending on the exchange rate. It’s assessed on your most recent annual gross income.

To put that in context: it’s about double Portugal’s threshold, and well above the global median for these visas, which sits closer to US$2,000–3,000 a month. Japan’s bar is one of the highest going.

If you’re employed, the proof is straightforward: contract, payslips, tax returns. If you’re self-employed with a variable consulting business — which describes a lot of our readers — this is the part that takes planning. A good year and a thin year average out in your head, but the consulate wants documentation, not a narrative.

Clean records, recent tax filings, and invoices that add up to the number are what get you through.

If you’re reading this thinking, okay, but what would I actually do for income? Start with Midlife Nomads’ ‘Turn Your Experience Into Income Ideas’ workbook.

Healthcare: What Midlife Applicants Really Want to Know

For most people over 40, this stops being a footnote and becomes part of the decision.

Private health insurance isn’t optional here — it’s a condition of the visa. You must show coverage of at least 10 million yen (roughly US$67,000) for death, injury, and illness during your stay. If your spouse or children are coming, they each need the same.

There’s a catch specific to this visa, and it matters more at midlife than the brochures admit: a Digital Nomad Visa holder does not receive a residence card, which means no access to Japan’s national health insurance system. Your private policy isn’t a box to tick for the application. For six months, it’s your only coverage.

If you’re over 50, this is where to slow down. Pre-existing conditions affect premiums and eligibility, and nomad-oriented policies vary widely on what they actually pay out. Read the exclusions, not the headline number.

SafetyWing is the policy we use for this kind of stay — built for nomads, monthly billing, and it satisfies the coverage requirement. As always, confirm the specific terms cover what you need before you rely on it. (Affiliate partner — we may earn a commission.)

Duration, Renewal, and the Six-Month Reality

Here’s the structure, plainly:

• The visa allows a stay of up to six months.

• It is not renewable.

• After it expires, you must spend six months outside Japan before you can apply again.

• It is not a path to permanent residency or citizenship. Time on this visa doesn’t count toward either.

• No residence card is issued, which is what cuts you out of national health insurance and, as we’ll get to, local banking.

So this is a long visit with legal clarity, not the first step of a move. For the reader who wants a real season in Japan — long enough to have a neighbourhood, a routine, a regular train line — that’s plenty.

For anyone imagining Japan as a base they return to and build on, the math doesn’t work the way Italy’s does.

In case you missed it…

Tax Reality: The 183-Day Line

Japan’s tax treatment is the quiet advantage of this visa, as long as you understand where the line sits.

If you stay 183 days or fewer in a calendar year, earn your income from abroad, and are paid by a foreign employer or foreign clients, you’re generally treated as a non-resident. Japan does not tax foreign-sourced income in that case. Since the visa caps you at six months, it’s built to keep you on the right side of that line.

The visa itself doesn’t trigger tax residency. Your days do. The 183-day threshold is an important benchmark, but Japanese tax residency and taxation depend on several factors including your circumstances, treaty provisions, and the source of your income. Professional tax advice is recommended.

One caveat that gets glossed over: the 183-day count isn’t the only test. If the centre of your life — your family, your home base — sits in Japan, you can be deemed a resident even under six months. For most solo nomads this won’t apply. For a couple relocating together “just for a while,” it’s worth a conversation with a tax professional.

Japan has double taxation treaties with more than 60 countries, including the US, the UK, Canada, and Australia, so the same income shouldn’t be taxed twice. But treaties apply differently depending on your home country, and documentation has to be clean.

Recommended reading:

Step-by-Step: How to Apply

1. Confirm Your Nationality Is Eligible

Check the current Immigration Services Agency / Ministry of Foreign Affairs list. Eligibility depends on your passport having both visa-exempt entry and a tax treaty with Japan.

2. Gather Your Documents

Typical requirements:

• Completed application form with a recent passport photo

• Passport valid for the full stay (ideally six-plus months)

• A statement of your planned activities and stay duration

• Income proof showing 10 million yen — contracts, tax returns, and/or client invoices

• Certificate of private health insurance (10 million yen coverage), including any family members

• A criminal background check (sometimes requested)

A Certificate of Eligibility (COE) is optional but can streamline the process.

3. Apply at a Japanese Embassy or Consulate

You apply from outside Japan, at the embassy or consulate in your home country.

• Visa fee: ¥3,000 single-entry / ¥6,000 multiple-entry

• Processing: roughly two weeks to one month

4. Enter Japan

You must enter within three months of the visa being issued, and your six months runs from there.

Family Considerations

Your spouse and dependent children can join you under the Spouse or Child of Digital Nomad status. Each files their own application and needs their own qualifying health insurance.

A few realities worth naming. Each family member needs their own qualifying insurance, though you don't have to show any extra income for them. Accompanying spouses and children aren't allowed to work in Japan at all, not even part-time — so a partner who wants to keep working remotely would need their own Digital Nomad Visa, which means clearing the 10-million-yen bar in their own right. And a six-month window is short for enrolling children in school.

For a family, this visa tends to suit a sabbatical-shaped season — a shared stretch of months in Japan — more than a family relocation.

Midlife Realities: What Actually Matters

Infrastructure and Working Online

This is Japan’s home turf. Fibre internet is fast and widespread, coworking spaces are easy to find in any major city, and the day-to-day machinery of remote work — cafés, transit, delivery, payments — is reliable in a way that removes friction rather than adding it.

For getting around, download the Suica app or pick up a visitor’s card for tap-and-go transit.

Connectivity From Day One

Without a residence card, getting a traditional local phone plan is awkward. The simplest fix is an eSIM you activate before you land. Airalo has Japan data plans that work the moment you arrive, which spares you the SIM-counter routine at the airport. (Affiliate partner — we may earn a commission.)

Banking: Plan Around It

Here’s a practical wall. Because no residence card is issued, you generally cannot open a local Japanese bank account on this visa; the traditional banks want that card.

In practice, most nomads run their money through international tools. A Wise account lets you hold and spend yen, pay for accommodation, and move money at the real exchange rate without a local bank — which is how we handle currency in places that won’t issue us an account. (Affiliate partner; we may earn a commission.)

Cost of Living (2026)

Japan isn’t Southeast Asia on price, but it’s often cheaper than major Western cities once you factor in transport and safety. A comfortable single lifestyle with a typical mid-range budget, all-in, runs roughly:

• Tokyo: ¥200,000–280,000/month (about US$1,700–2,100)

• Osaka: ¥170,000–200,000/month (about US$1,200–1,400)

• Fukuoka: ¥150,000–180,000/month (about US$1,050–1,200)

The big variable is housing, and short-stay housing has its own rules.

Walkability and Pace

Japanese cities are built for people on foot. Tokyo, Osaka, Kyoto, and Fukuoka all reward a car-free life, and the rail network makes day trips effortless. The pace in a residential neighbourhood is calmer than the Shibuya-crossing version of Japan suggests — which is often the part midlife visitors end up valuing most.

The Downsides No One Mentions on Instagram

The income bar is steep. At 10 million yen, this is one of the most selective digital nomad visas in the world. A lot of capable, self-sufficient midlife freelancers simply won’t clear it on paper, even when they live comfortably.

Six months, then out. No renewal, no rollover, a six-month cooling-off period, and nothing that counts toward residency. If you fall for the place, the visa won’t help you stay.

No residence card means friction. No national health insurance, no easy local bank account, no local phone plan without workarounds. None of it is fatal, but all of it is paperwork you don’t have at home.

Same-sex marriages aren't recognized for dependent status, so an LGBTQ+ spouse can't currently come as a dependent.

Short-stay housing is its own project. Traditional Japanese leases often demand key money, a deposit, a guarantor, and a 12-month commitment — none of which fits a six-month stay. The realistic routes are serviced apartments, monthly furnished rentals, or share houses, which skip the guarantor and come furnished but run 30–50% more than a standard lease. Monthly furnished rates run roughly ¥120,000–180,000 in Tokyo, ¥80,000–110,000 in Osaka, and ¥60,000–80,000 in Fukuoka. Booking confirmation from one of these also gives you an address for your application.

The seasons are real. Summers are hot and humid, June brings the rainy season, and late summer into autumn is typhoon season. None of it should stop you; all of it may shape which months you pick.

Is Japan Right for Midlife Nomads?

Japan isn’t trying to be the cheapest option or a tax shelter. What it offers is a six-month stretch inside one of the most functional countries in the world, with world-class infrastructure, genuine safety, food and culture with real depth, and the freedom to keep earning while you’re there.

What it doesn’t offer is permanence. There’s no residency pathway, no renewal, and a high enough income bar that this visa quietly selects for a particular reader.

If you want to move to Japan for good, this isn’t your route. But if what you actually want is a real season there — long enough to stop being a tourist, short enough that you weren’t trying to leave home for good — that’s precisely the shape of this visa.

And for a lot of us, a longer stay we can do honestly and legally is an excellent option.

Disclaimer

Visa regulations, income thresholds, and tax interpretations change frequently. The information in this article is accurate at the time of publication, but we strongly encourage you to verify all requirements directly with official Japanese government immigration authorities or licensed visa professionals before making travel or relocation plans.

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Sources:

• Ministry of Foreign Affairs of Japan

• Immigration Services Agency of Japan — Status of Residence “Designated Activities” (Digital Nomad)

• Japan National Tourism Organization (JNTO)

• RSM Shiodome — Application Guide, Eligible Countries, Latest Requirements (2026)

• Wise — Japan digital nomad visa guide (family, foreign-employer rule)

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FAQs: Japan’s Digital Nomad Visa

What is Japan’s Digital Nomad Visa?

It’s a six-month residence status — officially Designated Activities (Digital Nomad, Spouse or Child of Digital Nomad) — launched in April 2024. It lets eligible foreign nationals live in Japan while working remotely for employers or clients based outside the country.

How much income do you need for Japan’s Digital Nomad Visa in 2026?

At least 10 million yen per year, roughly US$65,000–70,000 depending on the exchange rate, assessed on your most recent annual gross income.

Do freelancers and self-employed people qualify?

Yes, provided the income comes from clients or a business based outside Japan and you can document it — contracts, invoices, tax returns, and bank statements showing the required level.

Can my spouse work in Japan on this visa?

No. Accompanying spouses and children hold a dependent status that doesn't permit any work, including part-time. If your partner wants to keep working remotely while you're both there, they'd need to apply for their own Digital Nomad Visa — which means independently clearing the 10-million-yen income requirement.

Can I work for Japanese companies on this visa?

No. The visa is strictly for remote work for foreign employers or clients. Local Japanese employment or invoicing Japanese clients requires a different visa.

Do I become a tax resident in Japan?

Generally not, if you stay 183 days or fewer in a calendar year and your income is foreign-sourced — you’re treated as a non-resident and foreign income isn’t taxed. The visa caps you at six months to keep you on that side of the line, but days can accumulate across multiple visits in the same year, and your home base can affect the determination. Confirm with a tax professional.

Is the visa renewable, and can it lead to residency?

No on both counts. It’s six months, non-renewable, with a six-month wait before reapplying, and it doesn’t count toward permanent residency or citizenship.

Do I need private health insurance?

Yes — coverage of at least 10 million yen for death, injury, and illness, for you and any accompanying family. Because no residence card is issued, you can’t use Japan’s national health insurance, so this private policy is your only coverage for the stay.

Can my spouse and children join me?

Yes, under the Spouse or Child of Digital Nomad status. Each applies separately and needs their own qualifying insurance, though no extra income needs to be shown for them.

Can I open a Japanese bank account?

Usually not on this visa, since no residence card is issued. Most nomads manage money through international tools like Wise instead.

How long does the application take?

Roughly two weeks to a month after submitting at a Japanese embassy or consulate in your home country. You must then enter Japan within three months of issuance.

Karuizawa came to us as a recommendation. Our former exchange student’s mother mentioned it — a mountain town a couple of hours from Tokyo where Japanese families go on holiday, not somewhere on the foreign-tourist circuit.

That was enough for us. Trevor and I both wanted out of the city and up into the mountains, and I wanted a reason to ride the Shinkansen, so yesterday we went, with no plan past the train.

There are nine of us here, ten days in Japan. On the first full day we took a guided tour of Tokyo… the kind you take to get your bearings and pick up a few things to come back to on your own. We had several group activity days, and meetups with our student and his family (the primary reason we’re here).

Then we left three of the ten days completely open. No group plan, no shared itinerary. Each person creates their own adventure.

Yesterday was one of those days.

Trevor and I knew two places we wanted to see in Karuizawa: Harunire Terrace, a boardwalk of shops and restaurants near the ski resort, and Kyu-Karuizawa Ginza Street. Past that, it was our phones and Maps and whatever turned up along the way.

A taxi from the station to Harunire Terrace was easy to find; just queue outside the station.

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Once there, the restaurants run on electronic check-in. You register, they message you when your table's ready. Ours was about an hour out.

Trevor went walking in the forest. I took a cafe table on a small outdoor patio and settled in to write my day’s journal entry.

Then the gasps started. Startled laughter from the tables around me.

Snow monkeys were coming out of the forest from every direction, into the clearing right in front of us.

Two of them shoved and wrestled like they had something to settle. A mother lumbered across the lawn with a baby riding on her back. One bounded across the patio and up a tree a few meters from where I sat.

I messaged Trevor to come back so he wouldn’t miss out. No worries there… he was already surrounded. Dozens of them were streaming past him through the trees on their way to the same clearing.

He caught a glimpse of the same mom and baby monkey in the forest, up in the foliage.

We couldn’t have planned something like that.

About The Karuizawa Snow Monkeys

The ones that wandered out of the forest are Japanese macaques — “snow monkeys,” the northernmost-living primates on earth besides us. The troop at Harunire Terrace is local and wild, going about its business whether or not anyone’s watching.

If you’ve seen the famous photos of monkeys soaking in a steaming hot spring, those are a different group: the habituated troop at Jigokudani Monkey Park, in the same national park but up in northern Nagano, about 80 km away. It’s under two hours by car, though public transit sends you the long way around through Nagano.

Those snow monkeys started gathering at that pool decades ago, after people began feeding them there, and the snow-and-onsen scenes are a winter thing, roughly late December to early April.

The Karuizawa monkeys don’t do the hot-spring soak, to my knowledge. They just turn up spontaneously and entertain.

It’s the part I keep turning over. The monkeys weren’t on any list. They turned up in the one hour we had nothing scheduled, on one of the days we’d deliberately left blank, on a trip we took because someone we knew said the locals like it there.

The guided tour on day one was the opposite kind of day, all structure and orientation, and it did its job.

But the day I’ll remember is the one with the gap in it. We left a little room, and something amazing came to fill it.

Now, that’s not always the case. Sometimes an empty hour is just an empty hour, and I appreciate that, too.

It’s a hard thing to leave empty space in your life on purpose. We plan our trips now with more information than anyone has ever had: every place ranked, every hour bookable before we land. The pull is to plan all of it, to fill every hour, every moment, so we don’t miss a thing.

But a full day has no room left in it for the thing you didn’t know you wanted.

Think about the last time something genuinely, delightfully surprised you. Then think about the last time you had your heart set on something and it didn’t go the way you’d pictured.

I know I’d rather be surprised than disappointed. How about you?

Are you leaving room for surprise, whether that’s in your work, your travels or life in general?

✌🏻 Miranda

Taking the Shinkansen: a Few Notes

The Shinkansen is Japan’s high-speed rail network, and it’s the reason a day trip like this one is even possible. The lines fan out from Tokyo in different directions — west toward Kyoto and Osaka, north and northwest toward the mountains. Karuizawa sits about an hour up the Hokuriku line, close enough to leave Tokyo after breakfast and be back for dinner.

A few things worth knowing before you go:

We didn’t book ahead, and to get two seats together we ended up upgrading to Gran Class, the top tier, at the Tokyo Station ticket desk. For me this trip was about the Shinkansen itself, so I didn’t mind the splurge. If you’re traveling on a budget, reserve early or be prepared to take whatever seats you can get. The fastest trains, like the Kagayaki, skip Karuizawa, so you’ll want the Asama or Hakutaka.

Don’t count on buying food onboard. Cart service has been pulled from most lines and now survives only on a few, in certain classes. Stock up at the station instead: ekiben (station bento), sandwiches, and whatever the platform vending machines are offering.

Japanese trains are quiet. Keep your voice low and your phone on silent.

And take your garbage with you. You’re expected to carry it off and bin it yourself.

Accurate as of June 2026 — onboard service and schedules change, so check the line you’re riding before you go.

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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.

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