The Bittersweet Life

Life is full of major transitions. When Katy moved to Rome in 2013, then back to Seattle less than a year later, the transition was hard to say the least. In this episode from our archives, Katy sits down with psychiatrist and former expat John Wynn to explore why change is so hard. He also shares his insight on how to handle transitions in a healthy and productive way.

***The Bittersweet Life podcast has been on the air for an impressive 10+ years! In order to help newer listeners discover some of our earlier episodes, every Friday we are now airing an episode from our vast archives! Enjoy!***

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COME TO ROME WITH US: Our third annual Bittersweet Life Roman Adventure is all sold out for 2025! If you'd like to join us in 2026, and be part of an intimate group of listeners on a magical and unforgettable journey to Rome, discovering the city with us as your guides, find out more here.

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 return for your generosity! Visit our Patreon site to find out more.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

SUBSCRIBE: Subscribe to the podcast to make sure you never miss an episode. Click here to find us on a variety of podcast apps.

WRITE A REVIEW: Leave us a rating and a written review on iTunes so more listeners can find us.

JOIN THE CONVERSATION: If you have a question or a topic you want us to address, send us an email here. You can also connect to us through Twitter, Facebook, and Instagram. Tag #thebittersweetlife with your expat story for a chance to be featured!

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!

Katy recently attended her high school reunion. In this bonus episode—available only to our Patreon supporters—she breaks down all the unexpected drama from the night.

This just a sneak peak at one of our hundreds of bonus episodes. 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 two 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 in addition to bonus episodes, and you'll be invited to join us for regular live meet-ups.

But most importantly, you'll be doing your part to help keep this show alive—an independent podcast with no corporate support. (You'll also help keep it virtually ad-free!)

Check our our Patreon page for all the details, and consider joining us at the $5 level or above. We are eternally grateful!

-------------------------------------

COME TO ROME WITH US: Our third annual Bittersweet Life Roman Adventure is all sold out for 2025! If you'd like to join us in 2026, and be part of an intimate group of listeners on a magical and unforgettable journey to Rome, discovering the city with us as your guides, find out more here.

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 return for your generosity! Visit our Patreon site to find out more.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

SUBSCRIBE: Subscribe to the podcast to make sure you never miss an episode. Click here to find us on a variety of podcast apps.

WRITE A REVIEW: Leave us a rating and a written review on iTunes so more listeners can find us.

JOIN THE CONVERSATION: If you have a question or a topic you want us to address, send us an email here. You can also connect to us through Twitter, Facebook, and Instagram. Tag #thebittersweetlife with your expat story for a chance to be featured!

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!

We've all heard it. We've all said it. But what does "when in Rome" really mean?

Katy reveals the somewhat surprising origin of this ubiquitous catch-phrase, which has become the title of more Rome-based rom-coms and expat memoirs than we could count.

Tiffany and Katy have different opinions of the meaning of this cliché expression, and we end up down a rabbit hole discussing the correct way to use it. (And if Tiffany lives by it, since she does, in fact, live in Rome.)

She also reveals some of the other most common sayings about the Eternal City.

By the way, this episode kicks off Season 13 of The Bittersweet Life! (We can't believe it either!)

-------------------------------------

COME TO ROME WITH US: For the third year in a row, we are hosting an intimate group of listeners for a magical and unforgettable week in Rome, this October 2025! Discover the city with us as your guides, seeing a side to Rome tourists almost never see. Find out more here.

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 return for your generosity! Visit our Patreon site to find out more.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

SUBSCRIBE: Subscribe to the podcast to make sure you never miss an episode. Click here to find us on a variety of podcast apps.

WRITE A REVIEW: Leave us a rating and a written review on iTunes so more listeners can find us.

JOIN THE CONVERSATION: If you have a question or a topic you want us to address, send us an email here. You can also connect to us through Twitter, Facebook, and Instagram. Tag #thebittersweetlife with your expat story for a chance to be featured!

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!

Twenty years ago, on August 29th 2005, Hurricane Katrina hit New Orleans. The Category 5 storm and its aftermath devastated the city, and the consequences still last today. Listen in as Katy takes you on a journey of remembrance to mark the occasion. You'll hear some of the New Orleans voices she has never forgotten in the intervening decades.

-------------------------------------

COME TO ROME WITH US: For the third year in a row, we are hosting an intimate group of listeners for a magical and unforgettable week in Rome, this October 2025! Discover the city with us as your guides, seeing a side to Rome tourists almost never see. Find out more here.

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 return for your generosity! Visit our Patreon site to find out more.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

SUBSCRIBE: Subscribe to the podcast to make sure you never miss an episode. Click here to find us on a variety of podcast apps.

WRITE A REVIEW: Leave us a rating and a written review on iTunes so more listeners can find us.

JOIN THE CONVERSATION: If you have a question or a topic you want us to address, send us an email here. You can also connect to us through Twitter, Facebook, and Instagram. Tag #thebittersweetlife with your expat story for a chance to be featured!

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!

When Tiffany's husband Claudio takes a photo with the karate instructor of his youth, Tiffany realizes that by being an expat, it can sometimes feel like her life has no continuity. She can't revisit old teachers and places. She never unexpectedly stumbles upon people and objects from her childhood, and maintaining relationships longterm takes extra effort. Is this just one of the side effects of moving abroad indefinitely?

How important is a sense of continuity when it comes to life? Hosts Katy Sewall and Tiffany Parks explore the idea on this episode from our archives.

***The Bittersweet Life podcast has been on the air for an impressive 10+ years! In order to help newer listeners discover some of our earlier episodes, every Friday we are now airing an episode from our vast archives! In addition, this August, we are taking a well-deserved rest, and in lieu of new episodes, we are airing episodes from our vast archives every Monday! Season 13 (!!!) starts with all-new episodes Monday September 8th. See you then!

***Katy's sister Dana has recently been diagnosed with stage 4 agressive brain cancer. To help with the staggering medical costs—her specialist is outside her insurance network—as well of the costs of temporarily relocating to San Francsico for her treatments, please consider donating to her GoFundMe. Anything you can contribute will be extremely helpful. Thank you.***

-------------------------------------

COME TO ROME WITH US: For the third year in a row, we are hosting an intimate group of listeners for a magical and unforgettable week in Rome, this October 2025! Discover the city with us as your guides, seeing a side to Rome tourists almost never see. Find out more here.

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 return for your generosity! Visit our Patreon site to find out more.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

SUBSCRIBE: Subscribe to the podcast to make sure you never miss an episode. Click here to find us on a variety of podcast apps.

WRITE A REVIEW: Leave us a rating and a written review on iTunes so more listeners can find us.

JOIN THE CONVERSATION: If you have a question or a topic you want us to address, send us an email here. You can also connect to us through Twitter, Facebook, and Instagram. Tag #thebittersweetlife with your expat story for a chance to be featured!

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!

Have you ever received a sign to do something? Did you listen to it? Do signs even exist?

What about bad and good omens? Are they real or a product of our imagination?

Katy and Tiffany share their experiences and those of our listeners on this episode from our archives.

The Bittersweet Life podcast has been on the air for an impressive 10+ years! This August, we are taking a well-deserved rest, and in lieu of new episodes, we are airing episodes from our vast archives every Monday! Season 13 (!!!) starts with all-new episodes Monday September 8th. See you then!

***Katy's sister Dana has recently been diagnosed with stage 4 agressive brain cancer. To help with the staggering medical costs—her specialist is outside her insurance network—as well of the costs of temporarily relocating to San Francsico for her treatments, please consider donating to her GoFundMe. Anything you can contribute will be extremely helpful. Thank you.***

-------------------------------------

COME TO ROME WITH US: For the third year in a row, we are hosting an intimate group of listeners for a magical and unforgettable week in Rome, this October 2025! Discover the city with us as your guides, seeing a side to Rome tourists almost never see. Find out more here.

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 return for your generosity! Visit our Patreon site to find out more.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

SUBSCRIBE: Subscribe to the podcast to make sure you never miss an episode. Click here to find us on a variety of podcast apps.

WRITE A REVIEW: Leave us a rating and a written review on iTunes so more listeners can find us.

JOIN THE CONVERSATION: If you have a question or a topic you want us to address, send us an email here. You can also connect to us through Twitter, Facebook, and Instagram. Tag #thebittersweetlife with your expat story for a chance to be featured!

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!

On last week's archive episode, we talked about fantasy, and the benefits and pitfalls of focusing on and working toward your personal fantasies.

But somehow, no matter how hard we try, reality always seems to intrude upon fantasy. Is that always a bad thing? Our thoughts might surprise you. Listen in to this week's episode from our archives where we discuss hard reality.

The Bittersweet Life podcast has been on the air for an impressive 11+ years! This August, we are taking a well-deserved rest, and in lieu of new episodes, we are airing episodes from our vast archives every monday! Season 13 (!!!) starts with all-new episodes Monday September 8th. See you then!

***Katy's sister Dana has recently been diagnosed with stage 4 agressive brain cancer. To help with the staggering medical costs—her specialist is outside her insurance network—as well of the costs of temporarily relocating to San Francsico for her treatments, please consider donating to her GoFundMe. Anything you can contribute will be extremely helpful. Thank you.***

-------------------------------------

COME TO ROME WITH US: For the third year in a row, we are hosting an intimate group of listeners for a magical and unforgettable week in Rome, this October 2025! Discover the city with us as your guides, seeing a side to Rome tourists almost never see. Find out more here.

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 return for your generosity! Visit our Patreon site to find out more.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

SUBSCRIBE: Subscribe to the podcast to make sure you never miss an episode. Click here to find us on a variety of podcast apps.

WRITE A REVIEW: Leave us a rating and a written review on iTunes so more listeners can find us.

JOIN THE CONVERSATION: If you have a question or a topic you want us to address, send us an email here. You can also connect to us through Twitter, Facebook, and Instagram. Tag #thebittersweetlife with your expat story for a chance to be featured!

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!

How much of life is us trying to fulfill the fantasies of our youth? And is there anything inherently wrong with weaving fantasies and attempting to fulfill them? Is reality overrated?

We explore this idea on this episode from our archives.

The Bittersweet Life podcast has been on the air for an impressive 10+ years! This August, we are taking a well-deserved rest, and in lieu of new episodes, we are airing episodes from our vast archives every monday! Season 13 (!!!) starts with all-new episodes Monday September 8th. See you then!

***Katy's sister Dana has recently been diagnosed with stage 4 agressive brain cancer. To help with the staggering medical costs—her specialist is outside her insurance network—as well of the costs of temporarily relocating to San Francsico for her treatments, please consider donating to her GoFundMe. Anything you can contribute will be extremely helpful. Thank you.***

-------------------------------------

COME TO ROME WITH US: For the third year in a row, we are hosting an intimate group of listeners for a magical and unforgettable week in Rome, this October 2025! Discover the city with us as your guides, seeing a side to Rome tourists almost never see. Find out more here.

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 return for your generosity! Visit our Patreon site to find out more.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

SUBSCRIBE: Subscribe to the podcast to make sure you never miss an episode. Click here to find us on a variety of podcast apps.

WRITE A REVIEW: Leave us a rating and a written review on iTunes so more listeners can find us.

JOIN THE CONVERSATION: If you have a question or a topic you want us to address, send us an email here. You can also connect to us through Twitter, Facebook, and Instagram. Tag #thebittersweetlife with your expat story for a chance to be featured!

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!

It began with a simple question: what's the most impractical thing you have ever traveled with?

Little did we know it would turn into one of our favorite (and perhaps silliest episodes) as Tiffany reminisces about her earliest trips abroad in the 1990s, when bringing two hat boxes and three full-sized suitcases on a solo trip to Europe was actually doable.

***The Bittersweet Life podcast has been on the air for an impressive 10+ years! In order to help newer listeners discover some of our earlier episodes, every Friday we are now airing an episode from our vast archives! Enjoy!***

***Katy's sister Dana has recently been diagnosed with stage 4 agressive brain cancer. To help with the staggering medical costs—her specialist is outside her insurance network—as well of the costs of temporarily relocating to San Francsico for her treatments, please consider donating to her GoFundMe. Anything you can contribute will be extremely helpful. Thank you.***

-------------------------------------

COME TO ROME WITH US: For the third year in a row, we are hosting an intimate group of listeners for a magical and unforgettable week in Rome, this October 2025! Discover the city with us as your guides, seeing a side to Rome tourists almost never see. Find out more here.

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 return for your generosity! Visit our Patreon site to find out more.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

SUBSCRIBE: Subscribe to the podcast to make sure you never miss an episode. Click here to find us on a variety of podcast apps.

WRITE A REVIEW: Leave us a rating and a written review on iTunes so more listeners can find us.

JOIN THE CONVERSATION: If you have a question or a topic you want us to address, send us an email here. You can also connect to us through Twitter, Facebook, and Instagram. Tag #thebittersweetlife with your expat story for a chance to be featured!

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!

Why does (seemingly) every single person in Italy go on vacation during the month of August?

If you've ever visited Italy in the month of August, you'll know that big cities and small towns alike empty out, particularly during the two middle weeks of August, and it can be a challenge to find a decent restaurant or shop open, or more locals than you can shake a stick at.

Why is that? Would you believe it's a tradition that dates back two thousand years?

Don't miss this week's mini-episode, which also happens to be our last new episode until September, because that's right, we too are taking the month of August off. Have a wonderful rest of your summer and will see you in Season 13!

***Katy's sister Dana has recently been diagnosed with stage 4 agressive brain cancer. To help with the staggering medical costs—her specialist is outside her insurance network—as well of the costs of temporarily relocating to San Francsico for her treatments, please consider donating to her GoFundMe. Anything you can contribute will be extremely helpful. Thank you.***

-------------------------------------

COME TO ROME WITH US: For the third year in a row, we are hosting an intimate group of listeners for a magical and unforgettable week in Rome, this October 2025! Discover the city with us as your guides, seeing a side to Rome tourists almost never see. Find out more here.

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 return for your generosity! Visit our Patreon site to find out more.

TIP YOUR PODCASTER: Say thanks with a one-time donation to the podcast hosts you know and love. Click here to send financial support via PayPal. (You can also find a Donate button on the desktop version of our website.) The show needs your support to continue.

START PODCASTING: If you are planning to start your own podcast, consider Libsyn for your hosting service! Use this affliliate link to get two months free, or use our promo code SWEET when you sign up.

SUBSCRIBE: Subscribe to the podcast to make sure you never miss an episode. Click here to find us on a variety of podcast apps.

WRITE A REVIEW: Leave us a rating and a written review on iTunes so more listeners can find us.

JOIN THE CONVERSATION: If you have a question or a topic you want us to address, send us an email here. You can also connect to us through Twitter, Facebook, and Instagram. Tag #thebittersweetlife with your expat story for a chance to be featured!

NEW TO THE SHOW? Don't be afraid to start with Episode 1: OUTSET

BOOK: Want to read Tiffany's book, Midnight in the Piazza? Learn more here or order on Amazon.

TOUR ROME: If you're traveling to Rome, don't miss the chance to tour the city with Tiffany as your guide!