I’m in the middle of writing an article for one of my retainer clients, but I’m already thinking about lunch.

I’ll probably get a schiacciata from the café nearby. Schiacciata is a Tuscan flatbread filled with cured meat, pecorino, and whatever else convinces me that it counts as a light meal.

From the outside, my move to Italy may have looked sudden.

And TBH, I didn’t even realize it would become permanent when I first arrived. I really truly believed I was eventually going back to Los Angeles.

At the time, I was trying to get my Italian citizenship through descent. I couldn’t manage to get an appointment at the Italian Consulate in LA (thank you, glitchy website), so applying directly in Italy became my best path.

That meant moving abroad for an unknown amount of time.

And I could only do that because my work could move with me.

I’m an Italian citizen today because I’d spent years building a freelance business before I fully understood what that business might make possible.

The move itself was one big decision, but the runway leading up to all that took years to build.

The Short Version of How I Got Here

Before freelancing, I worked in a tiny three-person office in Encino, California, doing PR and marketing for interior designers.

It involved promoting our clients’ creative work, and tbh, there were a lot of things I really liked about the job.

Still, spending hours in LA traffic up and down the 405 just to sit alone in a windowless room began to feel a little tedious.

My first freelance client came through someone I already knew from an earlier job. She needed help promoting her client’s IRL show on Facebook. I charged that client $1,500/month while still working my 9-to-5.

I didn’t have a huge plan.

I wasn’t thinking about six figures, running an agency, or moving to Italy at that point.

I was mostly thinking: Wait, someone will pay me to post on Facebook? Okay, where do I sign up.

That client introduced me to the people who became my next client. One project turned into ongoing work, and then that ongoing work slowly turned into something I started calling a business.

Within about two years, I had three stable clients and occasional projects on the side.

By 2020, I had five monthly retainers and earned six figures in gross business revenue for the first time.

My highest month was around $14,000.

That number sounds impressive, and it was an important milestone. It also wasn’t what I personally took home after taxes, software, contractors, coaching, and the other expenses required to run and grow the business.

I made all that $$$ from this desk.

But then I also learned that earning more money doesn’t automatically make your life ✨ feel freer ✨

At one point, I was juggling 8 to 10 clients and projects, working from morning until late at night, drinking wine to make it feel more “fun” and eating most of my meals at my desk.

It was like…. hmm, wait a sec. There’s no boss hovering over me, no one tracking my timesheet… why am I doing this to myself???

I was burned out and couldn’t really enjoy much of it (especially during lockdown, especially in a pandemic).

So, things needed to change. I tried to stop believing that success meant adding more clients, more revenue, and more responsibility forever.

I wanted a business that was profitable, stable, and portable, one that could support my life WITHOUT constantly stressing me out….

What This Business Gave Me

The biggest thing freelancing gave me wasn’t a six-figure year.

It gave me ✨options✨

I could book longer trips without counting PTO. I could work across time zones. I could take a doctor’s appointment on a Tuesday afternoon without asking anyone’s permission 💃

Eventually, it gave me the option to move to Italy.

That doesn’t mean freelancing feels free all the time. I still answer to clients, manage deadlines, and carry the responsibility of making sure the business keeps working.

Still, the tradeoff has been worth it.

I wasn’t trying to stop working. I wanted my work to stop deciding where I lived, how long I could travel, and what the shape of my life had to look like.

That’s what I mean when I talk about freedom.

You might have a different definition of what freedom is. But for me, it meant having more say over how I spent my time.

What I’m Going to Show You

You don’t need to build a giant agency, become an influencer, or quit your job next week to start freelancing.

You need a skill someone will pay for, a way to find your first client, and a plan for turning here-and-there projects into income you can actually rely on.

👩‍💻 In the rest of this guide, I’m breaking down:

• How to choose a freelance service people already pay for

• Where to look for your first client

• How to turn one project into ongoing monthly work

• What makes clients stay, renew and refer you

• How to create more predictable income before leaving your job

• When to raise your rates instead of adding more work

• How to make your business portable enough to take abroad

• What I’d do differently if I were starting again today

My path took years, and yours won’t look exactly like mine.

The point isn’t to recreate my career step by step.

It’s to help you build a version of freelance freedom that actually fits your life.

🔍 Step 1: Choose a Skill Someone Already Pays For

You don’t need to invent a brand-new business idea.

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I felt nervous in a way I hadn’t expected. I met him almost two months ago. After two months of waiting, this was our first date because I’d been in the U.S. for the holidays.

I was worried those months of anticipation were collapsing into an awkward evening where we both realized we’d built a stranger into something more in our minds.

I walked into the piazza. He wasn’t there yet. Then I looked up, and I saw him. White fleece coat, beanie, all the pieces of someone who spends his days outdoors.

He walked over, and we greeted each other with a kiss on both cheeks — I knew which side to start on (the right side), the Italian way. My nerves were probably pretty noticeable.

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The Italian Consulate in Los Angeles needed to confirm that my ancestors had never naturalized as United States citizens.

I’d spent months trying to surrender to the process. I hadn’t been pushy. I hadn’t visited the office demanding updates.

I had tried to close my eyes and just trust that everything would happen when it was supposed to happen.

But once I knew exactly what was holding things up, my inner control freak woke up.

“Could we speed this up?"

Because as lovely as my summer in Sardinia had become, my life was still suspended between two versions of itself.

I couldn’t make any real future life plans until I knew whether I was officially Italian.

And underneath the waiting was a fear I couldn’t completely shake.

What if something went wrong?

What if there was a problem with my application and this didn’t happen for me?

What if all the time, money, and energy I had spent changing my entire life had been for nothing?

It wasn’t certain until it was certain.

And while I waited, something else became increasingly clear.

I didn’t want to go back to Los Angeles.

The Plan I Was Supposed to Follow

When I moved to Italy, the plan was to stay for about four months, receive my citizenship, and then return to LA.

My partner at the time and I had talked about eventually moving to Spain together.

At least, that was the idea.

But when I learned I would be in Sardinia through at least August (or even longer!), the plan began to fall apart. Our relationship ended that spring, for reasons that deserve more space than I can give here, and I had to decide what I wanted to do next.

I flew back to Los Angeles, packed up what I could of my life there, and brought my dog, Casper, to stay temporarily with my mom across the country.

Then I got back on a plane and returned to Italy alone.

That was the moment the decision actually became real.

I wasn’t only waiting in Sardinia for paperwork anymore. I was choosing Italy, even though I still didn’t know with absolute certainty whether my citizenship would be approved.

When I boarded my flight in January, I thought I was temporarily leaving Los Angeles.

Instead, I was quietly closing one chapter of my life and choosing a future I couldn’t fully see yet.

🇮🇹 Just below the paywall…

• Why I knew I couldn’t return to Los Angeles

• The trip back to the United States that made the decision permanent

• The fears that shaped my choice to stay in Europe

• What actually happened inside the comune

• The exact words they said when I became Italian

• And what this citizenship means to me now

Read more

Instead, it took my whole life apart first — and I’m going to tell you exactly what that cost me, in euros and in tears. (Mostly euros. But also tears.)

The plan was simple: fly over, hand in my application, get recognized, move home to LA. Four months, tops. I was very hopeful.

Things, of course, did not go according to plan. Which I didn’t see coming, of course.

Why Sardinia

I chose Sardinia because I found a language school there, and the woman who ran it would rent me an apartment. She was also offering a citizenship assistance service.

I decided to hire her to help make the process of going to the Stato Civile office easier.

She knew which paperwork needed to be signed, and she spoke Italian fluently. That would cost €1000.

I was like… well, that sounds like the easiest way to do it.

This all sounded pretty good. I figured I could move there, study Italian, and make friends through the school (side note: I found out later that online classes, even while living in Italy, are way more convenient).

I also figured there wouldn’t be many other people applying for citizenship through descent in Sardinia, and I was kind of right and kind of wrong.

Rather than go to a place like Florence first, with tons of people and an overloaded Comune office, I went someplace smaller.

There were not many Americans, it turned out, but plenty of others.

January: What Have I Done?

I arrived in January 2025. I didn’t realize I’d landed in a tourist town during its off-season.

That meant everything was closed. All of the historic center was empty.

No restaurants open, no stores, no shops. It was cold and rainy, I had no central heating, and I was freezing in my apartment, alone, paying €1000/mo plus utilities. (I found out later that that was an absurd price for the off-season, but I’ll get to that later).

I was far from home, in a place with a different language…. which I actually loved, because I was excited to learn Italian, but even still, it still added so much isolation.

And then the LA fires started back home, literally the day after I arrived. I was so stressed about my friends and partner at the time, and unable to help at all. Just watching it happen from 9 hours away, wearing every sweater I brought with me, indoors.

I remember sitting in my apartment one night thinking:

I didn’t have an answer. I just had the incessant rain, a lot of wind, a space heater, and a folder full of apostilled documents.

The Door Slams (Behind Me)

I submitted my application at the beginning of February.

If you read Part 1, you know what happened next: at the end of March — about a month later — the law changed. People with great-grandparents, like me, were no longer eligible.

There was no advance notice. No one saw it coming. Currently, you now need an Italian parent or grandparent to apply through descent.

The timing felt like destiny. If I had waited — if I’d spent one more season “getting organized” — none of this would have happened. That’s the part of this story I need you to hold onto: the door was open, and then it wasn’t.

But in February, I didn’t know I was lucky yet. I just knew I was cold, alone, and legally stuck in a town where the only thing open was the pharmacy.

And Then: A Sailboat

Here’s where I tell you how this ends up.

Six months after that night with the space heater, I was on a friend-of-a-friend’s sailboat, on the bluest water I have ever seen in my life, in absolutely no rush at all.

I was having aperitivo most evenings. I started running along the lungomare. I had a roommate, a friend group, and sometimes took weekend trips around the island.

My citizenship application was still sitting in a government office, and I genuinely was like, “Well, it takes as long as it’s gonna take.” 🤷‍♀️

What changed wasn’t the paperwork. The paperwork didn’t move for months.

What changed was three decisions I made in February, plus one expensive mistake I’d already made that I want to save you from, and a strategy for dealing with the comune that I’m convinced is the reason this whole thing didn’t break me.

🇮🇹 Just below the paywall…

• A breakdown of every euro this chapter cost (including the rent mistake)

• The three February decisions that turned it around

• How I handled the comune without becoming the annoying American

• What I’d do differently about the town, the timing, and the €1,000 helper — and the fear I’ve never posted anywhere.

Read more

In 2018, I visited the town in Sicily where my great-grandparents were from, and I found their handwritten birth certificates. Standing in that office, holding those papers, I didn’t really know what it would mean for me. It turns out it would change everything in my life.

A few years later, I found out I could apply for citizenship through descent. It’s a law called jure sanguinis, which basically means I could become Italian by proving I was already Italian.

And here’s the wild part. I submitted my application just one month before the law changed. If I had waited, it never would have happened.

Here’s how it started.

Trying to Get an Appointment Was Like Playing the Slot Machine at a Casino

Once I made the decision to apply, my first thought was: I’ll apply in the United States. It sounds easy enough, right?

Make an appointment at the consulate, order all my documents, done.

It wasn’t that simple.

To get an appointment at the Italian Consulate in Los Angeles, I had to go online to a super glitchy website, make sure I had the fastest internet speed I possibly could, keep multiple browsers open plus my email for a verification code and then just pray and hope.

New appointments opened up at 3:00 p.m. Pacific time, which is midnight in Rome, and they vanish instantly.

I got really serious about it. I bought an Ethernet cord for faster internet. I tried to plan which coworking spaces across Los Angeles had the fastest internet speed.

I joined multiple Facebook groups to research the best strategies. I logged in at 3:00 p.m. sharp, day after day.

And even with all of that effort, I still could not get an appointment.

At some point, I realized this was just not going to happen in the U.S.

And because I’m a freelance business owner who works remotely…. a new thought crept in: why not just move to Italy? I could live there for a little while, establish residency, and apply for citizenship through descent while living there.

And spoiler alert…. that’s exactly what I did. But the appointment wasn’t even the beginning of things.

Behind the paywall:

• the two years of document hunting nobody warns you about

• exactly what I ordered and from where

• the one rule that made my case qualify

• the $650 mistake I made so you don't have to

• and what I'd do differently if I started today.

Read more

Ciao bella,

I’m Jen. In 2018, I stood in a tiny anagrafe office in Sicily holding my great-grandparents’ handwritten birth certificates. It took me seven years to understand what I was actually holding: an exit plan.

It took two years of collecting documents and then a move from Los Angeles to a Sardinian tourist town in the off-season, where everything was closed and I knew no one. I cried alone in a cold apartment wondering if I’d blown up my life for a piece of paper.

For most of my year in Sardinia, I lived steps from the beach in an apartment with no wifi. A remote worker of 12+ years, running my entire freelance business off a phone hotspot, in a town where I’d moved specifically to sit out one of the slowest bureaucratic processes in Europe. If that sounds like bad planning, it was. It was also, somehow, one of the best years of my life.

And then, after nine months of waiting, two strangers handed me papers off a printer and said, “Oggi sei italiana.”

This January, I moved to Florence. After a year of hotspots and working from shaky wifi in cafés, I got wifi (thank you, Vodafone). The router blinking in the corner felt like its own little win.

So that’s where this newsletter comes from, and what it’s named for: I write to you from under the tuscan wifi. And I’m finally connected, in every sense.

Here’s what I’m doing with this space. I’ve worked remotely my whole career (I’ve worked in an office exactly two times), and for most of that time, “work from anywhere” was a thing I said more than a thing I did.

Then I actually did travel and work. And that led to moving abroad and working, too.

I discovered that the internet is full of people telling you how dreamy it is and almost nobody telling you what it costs. Not just in euros, though there were thousands of those, but in certainty, in identity.

In eight months of your life spent on hold, waiting for a government office to get back to you that never gave you a tracking number to check when your life would resume.

So that’s the writing you’ll get from me: the real mechanics and the real feelings, kinda blended all together. How I did the citizenship-by-descent process without a lawyer, and also the anxiety spiral of not knowing if it would work.

What it takes to run a freelance business from a country where the bureaucracy has bureaucracy. Why I left Los Angeles after fifteen years and can’t imagine going back, and why I’d still never tell you to do what I did, because the version of this that works is the one you build yourself.

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I got so lucky in ways I didn’t earn. I know that. The door of opportunity I walked through closed behind me, and I’m not interested in pretending my path is a template.

What I can offer is honesty about the whole thing. The marathon of paperwork, the loneliness, the time I spent the night on a sailboat, the rebirth, the taxes and partita IVA… from someone still in the middle of all the chaos.

If you want that, I’d love to have you here.

Tell me what brought you. I read every reply, on an internet connection I no longer take for granted.

Jen

A few years ago, I took a whirlwind trip through the Netherlands, Belgium, and Spain with a friend. We crammed in as much as we could—waking up before sunrise for a tour of the Anne Frank House, rushing through Keukenhof’s tulip fields, dashing between Ghent and Bruges, then hopping a flight to Seville for flamenco dancing and a food…

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