Olive and Pine | Homes in Italy

Bonus Edition: Stepping Into The Dream

šŸ” The parts few people talk about...and why many people don't take the step šŸ‡®šŸ‡¹

Angie Smith's avatar
Angie Smith
Apr 08, 2026
āˆ™ Paid

Ciao, ragazzi! šŸ‘‹ Happy Wednesday!

I hope this finds you having the most amazing week. I just got back from the beach and let me tell you, it has filled my cup! The sun and sea are so energizing and just make me so happy. Not to mention, a seafood lunch beachside makes everything better. Agree? 😊

This is one of the highlights of my work now- finding amazing places to host retreats here in Italy.

Such a fabulous day in the Maremma region. Blue skies, amazing views, yummy food and the sound of waves. Nothing better!

After soaking up some sun and spending a little time reflecting on what I really want to share more of with you, I felt pulled to write something a bit different for this week’s Bonus Edition.

Instead of properties or hidden gems in Italy, I want to talk about something I hope is just as valuable (and honestly, something many of you have been asking for): the real logistics behind moving to Italy—and what it actually took to make this dream a reality.

Over the past few weeks, so many new followers and subscribers have joined this community, and I’m so glad you’re here. Today’s edition is a bit more personal—similar to last week—because behind every beautiful photo of Italy is a story that’s a little more complex, a little more challenging… and a whole lot more real.

I also want to say this feels like a vulnerable one for me to share. But I’m trusting that it will reach the person who needs to read it right now. šŸ’›


Taking a Step Back to Move Forward

One of the biggest misconceptions about moving abroad is that it’s all forward motion—exciting, glamorous, adventurous. And it can be at times.

But for me? It started with taking a step back. Like a BIG step.

And I mean that in a very real, tangible way.

Several people have made the comment to me ā€œit must have been nice to have the money to do thisā€ or ā€œItaly is great if you don’t have to workā€ and although I do acknowledge I had the privilege to do this, those comments couldn’t be further from the truth for me. You see, to make this move possible, I spent two years living half the year with my sister and brother-in-law in Texas. I lived in one of their guest bedrooms that my sister lovingly set up for me (she’s one of my biggest cheerleaders). She even created a work space for me to work while I was there. I didn’t have my own place during that time because I sold my home in order to buy my home in Tuscany. A home I loved. I also had to borrow my sister’s car when I was there, because I also sold my vehicle. I simplified my life in ways I never had before.

I also sold almost everything I owned. That was hard. It was more difficult than I had imagined.

Furniture. Clothes. My car. Pieces of a life I had spent years building. And that I was proud of. What many do not know about my personal life is that I grew up in low rental housing. My mom cleaned houses and mowed yards for a living. My dad died in a house fire right before I turned 2 years old. And my childhood years were hard. I also became a single mother in my early twenties.

This was me with my mom on the left- visiting my dad's grave. The weight in her eyes looking at me in that photo makes me sad. The photo on the right was where I spent most of my growing up years - in low rental housing.

I didn’t come from money—far from it. But as a young adult, I made the decision to change that. I worked hard to create a different life for myself, and even later, when I was making great money, I chose to live below my means, save for a rainy day, and be generous with what I had beyond that.

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