DEAR DIARY: I’ve Moved to a Greek Island With My Two Young Kids and I (Finally) Feel Alive Again 🇬🇷

Dear Diary #001: A slightly unhinged yes, and the right kind of crazy.

👋🏼👋🏼👋🏼 👋🏼👋🏼👋🏼 Hey! I’m Stevie. I’ve been on the internet for over a decade now (officially an internet grandma), building a business and figuring out how to make work fit around life — not the other way around. This newsletter is where I share what I’m learning. It’s for women who don’t just want a “successful” life on paper… but one that actually feels good in their bones.

Think business — online business, remote work, money (FIRE) — mixed with lifestyle — travel, motherhood, millennial chaos (and the behind-the-scenes of making it all work).

I’m a mum of two, running a solo online business that’s served over ~2k students and a podcast with ~2 million downloads, and I’m currently living on a Greek island where my kids are in world school for a few months (and sharing my adventures along the way — they went viral on Instagram here last week).

PS. If you’re getting this, you subscribed at some point. Not your thing anymore? Unsubscribe below — no hard feelings (but you will miss a wild ride).

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DEAR DIARY: I’ve Moved to a Greek Island With My Two Young Kids and I (Finally) Feel Alive Again

Well, feck.

Didn’t think I’d be saying those words any time soon — but here we are.

I’m writing this from a co-working space on a Greek island I hadn’t even heard of six weeks ago… after pulling my kids out of school and moving us here.

Solo.

With two kids under six.

Cool cool cool.

Psssst: if you want the full cliff notes on where we are, what we’re doing, and why the craziest thing I’ve ever done may also be the best, click here.

Right now though, I’m sitting at a big shared table, windows open, the kind of blue outside that doesn’t even look real, after doing a very normal school drop-off in a place that still doesn’t feel entirely real yet.

And I’m just… here.

In Syros.

If you’re not familiar with it, don’t worry — neither was I until six weeks ago.

Most non-Greek people don’t know it. They know Mykonos, Santorini… they come, take the photos, tick the box, choof off.

But that’s never really been how I like to travel.

My favourite way to travel is what I call “pretend living.”

Not the highlights.

The normal stuff.

The same coffee spot every morning.
The same walk to the park.
The grocery store where you stand there for 10 minutes trying to work out what anything is.

The rhythm of a place, not just the sights.

And so when an opportunity came up to actually live somewhere new for three months… in a place I’d never been, but that looked like a neoclassical dream…

I said yes, and then figured out the rest later.

Getting here wasn’t exactly seamless.

There was some very last-minute planning, a fair bit of finance jenga, and multiple moments across trains, planes and ferries where I was like… this is a terrible idea… while also handing out snacks, carrying bags, and trying to keep two small humans vaguely on track.

But also?

It’s been… easier than I thought.

Not easy.

But easier than the version of this that lives in most people’s heads; the one that says:

“I couldn’t do that.”
“I couldn’t afford that.”
“I could never take my kids out of school.”

But the thing I’m realising is, it kind of starts with letting yourself believe it’s even an option in the first place.

From there, it’s mostly logistics.

Messy, imperfect, slightly chaotic logistics… but still just logistics (and finances of course, which I talk more about here too).

I found a school, booked the flights, packed the bags, got on the plane — and now I’m here, ten days in, doing school drop-offs and coffee runs and work blocks in a place that, not that long ago, felt completely out of reach.

And something about that has shifted things for me a bit.

Not in a big dramatic “anything is possible!!!” kind of way — but more in a quieter, steadier way where I’m starting to question what else I’ve filed away under “not for me” that maybe… actually is.

TRUST ME when I say that this wasn’t some perfectly timed, fully thought-through decision.

It was an idea, followed by a slightly unhinged yes, followed by figuring it out as I went.

And now I’m here, and it’s beautiful and hard and a bit chaotic and really, really good — and I think that might be the point.

I don’t have a neat lesson to wrap this up with yet.

But I know this was the right kind of crazy for me, and I have a feeling there’s more of that to come.

I’ll share the rest as I go.

Specifically, I’ll be sharing more of my Greece adventures over the coming months in my weekly Dear Diary entries, and will write and record more in-depth guides and breakdowns too.

Have a question, or something you’d love for me to cover? Let me know in the comments. I’m all ears.. and DYING FOR THIS TO LIGHT A LITTLE SPARK IN YOU, TOO.

WORDS TO LIVE BY.

Source: Simon Alexandero

THINGS I LOVE.

💻 Working Remotely? This second screen is the best remote-work item I’ve packed. It lets me host Zoom calls with a second screen, and not miss a BEAT.

🇬🇧 Visiting London? My Airbnb in Chelsea was a London dream — and the perfect space for a family with young kids.

🧘🏻‍♀️ 75 Soft: This article of mine (about the tiny steps I took to save $20k, write a book and get strong in 75 days) is having it’s moment with 4,000 views in two days. Check it out here.

LET’S BUILD A LIFESTYLE BUSINESS AND HAVE FUN DOING IT