The Romantic, Creative Spirit of Lisbon, Portugal—And Why This T-Rex-Hearted City is the (New) New York for Digital Nomads

Is everyone you know talking about Portugal right now—or just me? Because I should warn you: this is the kind of place that causes divorce. 💔 🤣 (Because you definitely ain't coming back.)

Provence is that kind of place.

Florence is that kind of place.

And, oh yes, Lisbon is becoming that kind of place, too.

When we first arrived in Lisbon in the fall, I posted this on Instagram:

“Woke up in Lisbon and I’m SCARILY obsessed. This is already high up on the list of “places we’d live if we had thighs of steel.” 🇵🇹🦵The hills are a trip but I don’t even mind because everyone is friendly and the sun is shining and the vibe here just screams “young, energetic entrepreneurship”—and also “secret speakeasy gin bars through ancient alleyways,” which is obviously also a plus.”

We had no big plans to do Portugal—it was a quick stop in between Spain, France, and the US. But as soon as we got to Lisbon, we realized we HAD to go back.

What is this vibe?! These people?! This food?! This place?!

They had told us the people were friendly, but my goodness: this was other level friendly. Our taxi driver was probably the nicest man I’ve ever met. The host in our bed & breakfast literally walked us outside, around the corner, and halfway up the hill to show us where to go. (They say that all Portuguese are famous for this: you ask for directions, they close their shop, find a babysitter for their kids, put on their best Sunday clothes, and personally escort you. It happened to us twice, so this might actually be true. 🤣) Furthermore, I wanted the woman driving our tuk-tuk—Paula—to be my auntie. Even the lady who gave me my COVID test was a 5-star human being.

Beyond their friendliness, there was this undeniable creative spark I felt in the city, like everyone and everything was coming alive. Where had you been all this time? It felt a little bit like being in a big Santa’s workshop: hand-crafted cocktails of basil and cachaça were being lovingly made in this corner over here; in that one, a young girl is selling trendy orange geometric dresses to the beat of Ariana Grande. The next place I looked, a moody, prohibition-era bar had covered its shelves with figurines, and old army helmets, and fringey lampshades, and big, gilded mirrors. A building on the corner said “Workshops Popup,” where I discovered a chef gives cooking classes in English, a maker designs fashionable raincoats, a producer of olive oil fresh-squeezes the olives within 12 hours of picking. The lobby of a new hotel splashed big, bold letters across the back wall: “Your love makes me strong. Your hate makes me unstoppable.” Every place seemed to be reinventing itself. I even passed a truck delivering wines to local restaurants that said, “Wine, Spirits & Attitude.” And nothing could be more appropriate.

Even more wild? Everyone spoke English like damn-near native speakers. Not that they should have to—American ethnocentrism is for morons—but admittedly it is kind of tricky when you’re trying to buy tampons in French and the person standing on the other side of the counter is tapping their foot impatiently, not offering even a hint of help, despite the fact that they speak English and COULD help you out if they wanted to…but don’t. 🙂

And, god, and it was so clean. Sparkling. The streets felt like they were made of fine china, carefully polished that very morning. Except, of course, where there was artful graffiti—like the grinning mouth on the front of one of the trams that rattled defiantly up the hill. It was just enough to give the city the perfect amount of grit—and, oh yes, attitude. That attitude, juxtaposed against grand, majestic architecture that rivals the likes of Italy and France, made it feel a little bit like Hansel and Gretel go to New York. Storybook, but make it edgy. 💅🏻

The architecture of a place is about so much more than a practical need for housing—and Lisbon knows this. Historically, they could have just plopped plain, sturdy buildings up the sides of their hills, of which there are many, but instead, they lovingly constructed each and every one with style, pride, and presence. You’ve heard of Portuguese tiles, no doubt: I was surprised to discover that this wasn’t just a tourism gimmick, but a true form of craftsmanship. Buildings are covered with ‘em! And we thought it was expensive to do a kitchen backsplash. 🤷‍♀️

I am one of those annoying people who stops to take photographs of every other building, so you can imagine I spent endless hours roaming the city. Architecture makes me fall in love with a place more than almost any other factor: if there’s no good architecture, I don’t want to live there! (A beef I have with Costa Rica, by the way.) This is why I’m obsessed with London, Madrid, Charleston, Santiago—even Alexandria, Virginia. Their buildings were not made to be practical: they were made to say, “Go on, fuck with me—because I will fight for this place that I love.

That’s what I see when I look at a building: a romance story. It is the story of a people and a time; the things they believed; the pride they had. It is a relationship to place; to a sense of belonging. But, most importantly, great architecture gives us our sense of self: it’s a reflection of what we think matters.

It’s a reflection of our priorities, our dreams.

And the people of Lisbon certainly have some. Dreams, that is: and also FISH THAT I ACTUALLY LIKE TO EAT. I know, what is this?! Who am I?! Alas, Portugal does this to people. It lures them into thinking they could be a different kind of person, someday.

A dress maker. A mixologist. An olive oil producer. A divorcée who’s uprooted her entire life to become someone new.

If you’ve been quietly fingering your options (wait, that didn’t sound right?), Lisbon is a digital nomad’s ecstasy.

Beyond all of my poetic waxing and waning, here are a few more reasons why you miiiiiight want to put this place on your list ASAP:

  • The weather! They’ve got sunshine that’s not too hot and humid and sweaty, but “leisurely picnic on the grass” kind of sun, which is clearly the best kind of sun. (No, seriously, the average annual temperature is 62 degrees, with over 3,000 hours of sunshine a year, compared to London’s 1,400.) (That’s okay, London, you’ll always be my baby!)
  • Safety—Lisbon is one of the safest cities in the world, alongside Copenhagen, Stockholm, and Toronto. You can check out The Economist’s Safe Cities Index here—see “Personal Security.”
  • The hella reasonable cost of living. Digital nomads currently there are reporting that the average cost of living is $2,587/month—compared to Boston’s $5,999/mo, New York’s $5,566/mo, or L.A.’s $4,754/mo.
  • The internet’s fast AF. Speedtest shows that the average download speed in Portugal is faster than Canada. In fact, Portugal gets rated #19 in the world, whereas the United Kingdom is #54.
  • It’s super walkable. This is always a top factor on my list. Granted, there are hills here, so it’s not the best choice if accessibility is a concern, but otherwise it’s fairly easy to get around, even if you grab a tram on the way back home.
  • Family friendly and female friendly. Lisbon gets high marks for both. That’s a big deal. I felt way safer in Lisbon than I did in Las Vegas.
  • Very friendly for LGBTQIA+ and rated low for racism. A progressive society—hallelujah! This makes me so happy: I want to be a part of an inclusive, forward-thinking community.
  • Start-up friendly. It’s easy to do business, there are plenty of places to co-work, there’s lots of free wifi-in the city—and, like I mentioned before, it just FEELS like excitement & progress.
  • Foreigners can purchase property. There are no restrictions on foreigners: plus, the government wants to incentivize foreigners to invest, so if you purchase a property worth a certain value, you qualify for residence in Portugal and it gives you a permit to legally travel freely across Europe. That’s like having an E.U. passport. 😲 Whatttttt!
  • It’s close to a lot of things. It’s 6.5 hours to New York, 3 hours to Rome, 2.5 hours to London, 2 hours to Paris.
  • And, it’s friendly to foreigners (AS I MENTIONED.) This is a biggie! It’s no fun to feel like you aren’t welcome. Even though I LOOOOVED living in Santiago, Chile, I remember when I first got there in 2009, staff in a pharmacy once argued over who would help me. (They clearly didn’t know I was fluent in Spanish. 🤣) This past year in Biarritz, France, the owner of a restaurant we frequented gave us THE MEANEST GLARE every time we showed up. And in Bordeaux, forget it: at a wine bar called Vins Urbains, we were practically mocked by a couple sitting nearby. (Even though the owner was suuuuper sweet to us: his attention almost seemed to fuel their spite.) Don’t even get me started on Zurich.

Yes, Lisbon definitely belongs on your travel list this year—though hopefully, it won’t result in divorce. 😉

Fortunately, today’s creator economy means you CAN stay a while—and so can your partner, your spouse, your dog, your kids, and your 80-year-old grandma, too.

It is time for a grand adventure.

It is time to write yourself a new romance.

It’s time to take stock of who you are and what you believe; what things matter; what kind of belonging you want to feel.

You can be the person you wished you were ten years ago, before life got in the way.

You can be the one who uprooted everything to try something new.


P.S. I’ve been developing something I view as critical for the next generation of creators and digital nomads. 👩‍🏫

Something that’s designed to get creators, females, and historically resilient groups to the $250K mark in 24 months or less by focusing on the things most people don’t, while working 4-hour half-days so you can leverage your hours AND have a life…all while doing so from anywhere in the world. 🌍

This is really, really important to me, specifically as a digital nomad who views travel and pleasure as a form of income. What’s the point in working for yourself if you’re stuck to your computer and can never leave the house?

Here’s the kind of income I want for you:

$250K and….take your family for an entire summer in Ireland. 🇮🇪 🍀 🐑 (Or Lisbon!)

$250K and…let’s rent you a design-forward apartment in Florence, surrounded by incredible wine bars, ateliers, & art galleries. 🎨 🍷 🧥

$250K and…let’s send you to Scandinavia in the spring to write, photograph, or draw from the hazy shores of a little red summer house. ✍️ 📸 ⛵️

$250K and…let’s give you the ability to worldschool your kids in a walkable and friendly neighborhood in Portugal, France, or Scotland, surrounded by luscious parks and green space and incredible schools. 👩‍👩‍👧 🏞 ✏️

You can have it all—as a female (YES.) As a professional. As a creator. As a family. As someone who wants to soak up the pleasures of the entire world.

Sound like a breath of fresh air?

It’s invitation-only to begin.

Subscribe to the email list below if you’d like to receive an invite once we’re ready. ✨

XOXO,

Ash

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