The Bittersweet Life

Whether you're a newly minted expat wondering how to go about filing your US taxes, or a longterm expat who wants to make sure you're doing it right—or maybe it's been years since you filed a return and now you're scared to get help—this episode is for you. Expat tax expert, and founder and CEO of  My Expat Taxes , Nathalie Goldstein joins us to make sense of the often mystifying tax requirements...

Katy continues to have epiphanies as she challenges herself every week in her pottery class. In a continuation of our Trying Something New episode, we talk about what it is that keeps us trying when those new things inevitably continue to be hard work. We also discuss those "fantasy self" items we buy for ourselves when, full of ambition, we decide we are going to start a new hobby before we reall...

Want to hear more? Become part of the Bittersweet Life community by supporting just on   Patreon ! For as little as $5 per month—less than the price of a coffee in some places—you will have access to multiple bonus episodes every single month.  You'll hear conversations that would never take place on the main show, you'll be part of our new chat community, you'll have access to Patreon-only conten...

The Pope has given the green light to canonize the very first saint from the millennial generation, Italian Carlo Acutis. Does it seem strange to have a saint from your own generation? Or one from a generation even younger than yours? Does it take away a little from the "magic" of the saints, who lived 2000 years ago and have improbable and unbelievable legends swirling around them? Or does it add...

Want to hear more? Become part of the Bittersweet Life community by supporting just on   Patreon ! For as little as $5 per month—less than the price of a coffee in some places—you will have access to multiple bonus episodes every single month.  You'll hear conversations that would never take place on the main show, you'll be part of our new chat community, you'll have access to Patreon-only conten...

The difficulty is the point. How often have we been seduced into thinking that something we've never tried must be easy, simply because experts make it look that way? On this episode, we talk about the new things we've recently tried, and how often we underestimated how difficult they would be. As Katy dips her toes into the art of pottery, she learns that failing is a crucial part of the learning...

Want to hear more? Become part of the Bittersweet Life community by supporting just on Patreon ! For as little as $5 per month—less than the price of a coffee in some places—you will have access to multiple bonus episodes every single month.  You'll hear conversations that would never take place on the main show, you'll be part of our new chat community, you'll have access to Patreon-only content...

If you've been dreaming of moving to Italy but thought it was impossible, your chance has finally arrived! Italy has just launched the so-called "Digital Nomad Visa" which enables non-EU-nationals who are self-employed or remote workers who derive their income entirely outside of Italy, the chance to live in Italy on a year-by-year basis. For Italaphiles and wannabe expats around the globe, this m...

In a world that is becoming ever more homogenized, what sets places apart? What are the blaring indicators that communicate we are in a place vastly different from anywhere we've ever been before? After a magical and sometimes maddening week in Bali, Katy lays out the ways the island delighted and surprised her, the aspects that felt wholly different from what she is used to, and discusses with Ti...

What's it like to be a sociopath? This week's guest tells us. On this episode, Katy sits down with author and self-described sociopath Patric Gagne for a LIVE interview with audience at Seattle's Town Hall venue , whose recent book Sociopath has been acclaimed as a "fascinating, revelatory memoir revealing the author's struggle to come to terms with her own sociopathy and shed light on the often m...

What happens when you go back to a city you used to live in after not stepping foot there for twenty years? Tiffany finds out on this episode. After spending some of the most formative years of her life, her univeristy and post-univeristy years, in Boston, she moved to Rome and never went back. Earlier this month, she finally got a chance to visit Boston again, now with a husband and son in tow, a...

Who knew that "going native" was a topic that would resonate so strongly with our listeners? We got so much feedback on this subject—both social media comments as well as voice messages—that we just had to share them with you, and of course, open the discussion back up! So many new ideas came up hearing your thoughts, so we weigh in on them as well. By the way, we love love love hearing from you,...

What happens when an expat "goes native"? How long does it take, and is it inevitable? Is it a conscious choice or does it just happen? Today we chat about this idea, and Tiffany lays out the ways she has gone native—eschewing American culture and habits entirely in favor of Italian ones—as well as the aspects of Italian life that she staunchly resists and rejects, even after two decades in the co...

Would you move across the world to a country without ever having been there? That's what this week's guest did. We sit down with Brie Ripley to talk about her decision to take a 4-year contract with the World Food Program, which meant a relocation to Rome—a city she had never even visited.  She talks about the challenges of adjusting to life abroad as a brand-new expat, struggling to speak the lan...

An exciting discovery out of Rome has recently rocked the archeological community! We have the details on this week's episode. ------------------------------------- ADVERTISE WITH US: Reach expats, future expats, and travelers all over the world. Send us an email to get the conversation started. BECOME A PATRON: Pledge your monthly support of The Bittersweet Life and receive awesome prizes in retu...

Last week we talked—among other things—about what it would be like if the year started in March, as it used to do in ancient Rome. This got us thinking about seasons and how they effect our lives. On this week's episode we talk about what we love about certain seasons, how where you live can vastly affect how you experience the seasons (and therefore which ones you prefer), and the drawbacks of li...

Is early January—the deepest, bleakest, darkest moment of winter—really the best time to make New Year's Resolutions? Isn't early spring a more fortuitous time for new beginnings? (And did you know that March used to be the first month of the year?) We mull this and other season-related questions on this episode (including a check-in to see how Tiffany and Katy are getting on with their resolution...

Today we explore a story of one woman whose family legacy—in particular her close relationship with her mother whom she lost suddenly to cancer—brought about a life pivot that she was never expecting. Kaila Merrill joins us today to tell her moving story, from growing up in tiny island town in northern Vermont to a carefree life on the beaches of Australia where she met her future husband, to her...

What if travel doesn't actually change you? A few weeks ago, we discussed this controversial idea, a conversation inspired by an essay in The New Yorker . (Make sure you listen to that episode first, because we had a lot to say on the topic!) It turns out, our listeners did too, as we got a lot of feedback on the subject. Today, we share some of it and dig even deeper into the topic. -------------...

What makes a song a good road trip song? This is something Katy has been musing over for several years now.   What better person to ask than a musician who has crossed the country on tour numerous times?   This week, Katy sits down with musician and podcaster John Roderick to talk about the allure of the American road trip, as well as what you should listen to while you are doing it.   John talks...

Tell me about that trip that changed your life... and I'll tell you how you're lying to yourself. So claims a recent essay in The New Yorker titled The Case Against Trave l . In it, author Agnes Callard makes some pretty bold and sweeping assertions, including that travel "turns us into the worst version of ourselves while convincing us that we're at our best." Visiting a new place doesn't change...

What makes a life meaningful? Can a meaningful death transform an otherwise meaningless life into a meaningful one? These are just a few of the many ideas touched on in this week's episode, an interview with poet and author Kaveh Akbar. He joins us this week to discuss his new book, Martyr! , released in January 2024 and already a New York Times bestseller. This story follows a " newly sober, orph...

A line from a new book by poet Kaveh Akbar sparks the idea for this episode: in a nutshell, does language have the capacity to truly express what we are trying to convey, or is there always something that can't be put into mere words? Is it true, as Akbar claims, that a photograph can describe what it was , but words can only describe what it was like ? Also, when you speak two languages fluently,...

How do we discover our passions? Is it a given that we will discover them at all? And where do they come from? Are they something we are born with and just need to be discovered within ourselves? Or are they triggered by something we are exposed to externally? Or is it a bit of both? Are there people with incredible innate talent for music or painting, walking around who will never know it because...

Is it Covid or are we just getting older? This week we discuss how the social world seems to have changed drastically in recent years—but is it due to this post-Covid era we're living in, or is it simply because we're getting older? We wonder: Is it acceptable now to simply not respond (indefinitely) to text messages? Even if they are from a close friend? Is it normal to have a sudden social anxie...