Last Friday, I invited LaDonna Witmer and Heather Afar to join me LIVE to talk about what it’s actually like to build a life in Portugal.
Not the visas.
Not the tax schemes.
Not whether you should live in Lisbon or Porto.
The life.
Hit play on the video above to catch the replay.
Keep scrolling to read the highlights.
Meet Heather Afar
Heather is an American immigrant who traded Florida’s coast for Portugal’s. In March 2024, she and her husband packed up their two dogs, and moved to a village on the Silver Coast while their kids stayed stateside to finish college.
Heather spent years as a high school teacher, then as a content writer and strategist for companies like Slack and Salesforce. She rekindled her teaching roots on TikTok, where she built a following of nearly 200K across two accounts before walking away from the platform entirely in 2025. These days she still writes for big tech clients, but finds joy in building essays and community on Substack.
She writes New Ground, a Substack about immigrating to Portugal at 50—the leaving, the landing, the empty-nesting—all as she tries hard not to be the kind of immigrant who makes locals tired.
You can connect with Heather on Substack at New Ground and if today’s conversation has you curious about her own move, a paid subscription to New Ground includes a 30-minute consultation.
Meet LaDonna Witmer
In previous lives, LaDonna spent her days writing for other people as a newspaper journalist, advertising copywriter, brand voice expert, and editorial director. After moving to Portugal in 2021 with her family (husband, teen, two dogs, one parrot), she now spends her days writing for herself.
On her small quinta just south of Lisbon, LaDonna has been busy learning Portuguese, tending her garden, teaching writing workshops, undoing a lifetime of American programming, and writing a memoir about fundamentalism and fire.
You can find her essays and poems published (or forthcoming) in literary magazines including How I Learned, The Turning Leaf Journal, KHÔRA, Thimble, Identity Theory, SWWIM, Literary Mama, Carmalarky, Zero Readers, and the book Take the Fruit: An Anthology of Religious Trauma. She also writes regularly about her life in her Substack publication The Long Scrawl.
You can connect with LaDonna on Substack at The Long Scrawl, on Instagram, through her website, or on BlueSky.
We talked about a LOT!
Here are some highlights.
What makes you actually decide: I’m going to move to another country?
LaDonna’s answer started in the summer of 2020. Somewhere in the middle of living through a pandemic, watching her mother with Alzheimer’s, and looking at the life she’d built, LaDonna found herself asking a fairly enormous question: If I only have a couple more decades with a good brain, is this how I want to spend them?
The answer was no.
So she and her family made a list. Warm weather. Lower cost of living. Safety. A slower pace of life. And, ideally, a path to EU citizenship before their kid went to university.
Portugal kept coming up. But none of them had ever been. And they couldn’t exactly pop over for a scouting trip because…2020.
Eventually, LaDonna said, they had to decide: “Are we going to talk about it? Or are we going to do it?”
They did it.
Heather’s moment came two years later. And she was actually in Portugal when it happened.
She and her husband were visiting a friend while Hurricane Ian was heading toward their home in Florida. Their house wasn’t prepped. Their dogs were there. Their college-aged kids were there. And from the other side of the Atlantic, Heather found herself thinking: How many more years are we going to do this?
They went home, sold their house, and figured out how to move to Portugal.
So how do you pick where to live in a country you barely know?
Apparently, you buy a house.
And this is where I discovered that I am way more risk-averse than either of my guests.
LaDonna bought an apartment sight unseen before she’d ever set foot in Portugal.
Heather and her husband did a proper scouting trip, complete with spreadsheets, population data, weather research and overnight stays in different towns. None of which felt like home to them.
Eventually, a friend told them: “Portugal is for you. You’re just looking in the wrong place.” And then she told them about her little town on the Silver Coast.
Heather went home, researched it, found a house on Idealista...
…and bought it.
In a town she had never visited.
At which point I believe my only contribution to this conversation was: “You guys are, like, taking ALL of the risks.”
And LaDonna was like: “Once you decide you’re going to do one crazy thing, the other crazy things are not a big deal.”
What turned out to be harder than you thought it would be?
This may have been one of my favorite parts of the conversation.
Because it wasn’t bureaucracy.
It wasn’t learning Portuguese.
It wasn’t even the weather.
(Although Heather did point out that Portugal’s cold and rainy months were not advertised in the brochure.)
The thing that was harder than they both expected was the sheer amount of brainpower is required to be a person somewhere you don’t know how to be a person yet.
Heather described it as a constant hum in the back of your brain. You’re translating. Reading labels. Figuring out how things work. Thinking about every word you say. Trying to understand systems you’ve never encountered before.
And LaDonna talked about the questions you don’t know you’re supposed to ask. Like when her kid started school in Portugal, she asked all the questions an American parent would know to ask. Class size. Programs. Language support. What she didn’t ask about were the things she didn’t know existed. It took her about a year to discover the tutoring centers that Portuguese families routinely use.
Nobody had told her about them. Why would they? Everybody here knows about them.
Except, of course, the person who doesn’t know she’s supposed to ask about it because she has no idea it even exists.
Which accurately describes the life abroad learning curve. You don’t know what you don’t know. And sometimes you don’t even know to ask about something you really should know, but are completely clueless about.
What turned out to be easier than you expected?
LaDonna’s answer: The shoulder drop.
And Heather nodded.
Do you ever forget that you live in Portugal?
No.
Because there’s a Roman road. Or a castle. Or everyone is speaking a language you don’t understand.
And sometimes there’s an ocean between you and somebody you love who needs you.
Has moving to Portugal changed who you are?
This is where the conversation went somewhere I absolutely did not expect.
LaDonna talked about moving abroad as a kind of deconstruction. Once you’re outside the country where you spent most of your life, you can suddenly see things you couldn’t see while you were standing inside it.
You question assumptions. You realize some things you thought were simply how life works are actually just how life worked there.
And then she said: “I am more myself than I’ve ever been.”
At 50-ish, she feels more powerful, not less. More curious. More excited about what comes next.
And she thinks that making this one enormous change of leaving the country she’d lived in for decades was the thing that made those other changes possible too.
Heather had a very specific list of things that have changed. An honest and very female list of things that used to matter, that no longer do.
Houses bought in places people had never lived. 85% of a lifetime’s belongings left behind. At least one Portuguese grocery-store meltdown. One kid who became fluent and 3 grown women who are…working on it. Eleven hundred questions nobody knew they were supposed to ask. And zero conversations about what anybody does for a living.
We all moved to Portugal for different reasons.
And we’ve built very different lives here.
But somewhere in all of that, this same strange thing is happening:
You move abroad thinking you’re changing where you live.
And then the place starts changing how you live.
And then it changes who you think you get to be.
PS. The Expat Diaries spent 3 Fridays in August talking with women who left one life and built another in Europe. Our first stop was France. Then we landed in Spain. And we finished up in Portugal.
Where should we go next?
Is there a place that you’re curious about? Wondering what an ordinary Tuesday is actually like there? Wondering what you’d eat for dinner? Or how you’d fit in? Or whether the things you’re expecting to be hard actually are? And whether what you think is going to be a piece of cake, maybe isn’t?
Hit reply and tell me what country you’re interested in and I’ll see if I can pull together a couple of women who will tell us all about what it’s been like for them to build a life there.
If you’re not just curious about moving abroad — you’re actually thinking about doing it (😳 and yay!) — then you’re probably also thinking, “But what will I do with all of my stuff?”
Because you (probably) aren’t going to take your whole house with you.
Check out my free email series, “We Are Not Taking the Whole House With Us.”
10 days of practical, down-to-earth advice from a home organizer who’s already made the move abroad and knows exactly what it feels like to pack up one life and move into another.
It’s for everyone who’s preparing to move abroad and is wandering around their house quietly freaking out and thinking: “How am I supposed to fit a 5-bedroom house I’ve lived in for 25 years into 4 suitcases and a personal item that fits under the seat?”
Because one of the biggest parts of moving abroad happens long before you ever get on the plane. It has nothing to do with visas or taxes or whether you’ll be able to use your US phone number.
It has everything to do with deciding what comes with you into your next life. And what doesn’t.
