Where We've Been

This summer/fall season marks the first time in the last five years that Dora and I will be not petsitting. By this coming fall, it’ll have been a full year with no petsits. Whereas over the last five years we’ve spent up to 42% of the year petsitting in between travel and visiting family over six months, generally summer and fall. And the other six months or so spending the winter and spring in southern Portugal. Of course, 2020 was an anomaly with the pandemic; although we did manage over a month of sits that year despite being stuck in Portugal for 14 months straight.

The reasons we've spent large chunks of the year petsitting are many. First is that we both love animals and our perpetual travel lifestyle does not allow for having a pet of our own. Second, after bouts of adventuring, like our two months in Patagonia, we crave being in a real home to relax a bit, rather than some sterile rental. Becoming proxy pet carers for weeks or months at a time gives us the furry cuddles and homey environment we crave. Third is being able to drop-in like a local and really live somewhere. The fourth reason is to maximize nomad-lifestyle economics.

Year Total PetSitting Days # of PetSits % of Year on PetSits
2018 91 days 7 25%
2019 150 days 11 41%
2020 40 days 3 11%
2021 141 days 6 39%
2022 152 days 4 42%

Arbitrage Advocates. Throughout our perpetual travel, we'd already been practicing, without knowing it, what's called geographic arbitrage in the [digital] nomad/location independent/FIRE [Financially Independent Retire Early] communities. It's the practice of taking advantage of lower costs of living or traveling in other places in the world or elsewhere within a country. I had to look up what arbitrage means: typically used in economics and finance, it's the practice of taking advantage of a difference in prices in two or more markets; striking a combination of matching deals to capitalize on the difference.

And with petsitting, we've taken geographic arbitrage even further by eliminating hefty costs such as mortgage or rent and all the associated bills like utilities, insurance, taxes, and maintenance; letting our hosts bear the costs in exchange for caring for their pets and home. We even began only applying for pet sits with the use of the owner's car included, when the location necessitated having a car. Leaving only costs for groceries and going out to see local attractions. And sometimes we even had hosts who pre-shopped groceries based on our dietary preferences and stocked the fridge and cupboards for us.

Rattlesnake Ranch. Over the years we’ve done pet sits in twelve countries on three continents. We’ve sat for the usual cats and dogs. In addition to some stranger animals such as goats, geese, chickens, chinchillas, a burro, and even a llama. Not to mention the unplanned encounters with a tarantula (twice!) and a rattlesnake—while barefoot—on a remote ranch high up on a mount outside of Escondido, California. That sit was so much fun, despite the close call with the rattlesnake. Watching Dora trying to herd the goats from their pen to the pasture each day, a short distance away, was hilarious as they could jump the fence and escape. And escape they did. We also took some amazing day trips into San Diego, La Jolla, and Oceanside for quintessential Southern California experiences.

Jungle Time. Then there was the sit for two dogs we never touched or pet; not once! They were filthy jungle dogs who roamed the Costa Rican jungle for hours on end and simply had not been socialized to human touch. Also on that short, but memorable sit, we woke up with howler monkeys each morning, a scorpion in the bathroom (that I had to, unfortunately, kill for our peace of mind), a giant frog that leaped out of the toilet three mornings in a row and the piece de resistance—six bats that slept on the rafters in the bedroom and flew out each night to hunt and came back in the morning flying through the house. And yes, we had to clean up the guano on the floor every day. There are lots more tails tales to tell so subscribe and watch this tag called PetSitting for more petsitting tips, tricks, and stories.

Our Jungle dog sit in Nosara, Costa Rica in a custom-built indoor/outdoor home. We never even pet the 'jungle' dogs who roamed the jungle for hours and came back for food and water and to rest and sleep.

Professional PetSitters, We Are. We've had some truly amazing pet sits, fallen in love with many pets, met some wonderful people we're proud to call friends to this day, and stayed in gorgeous homes with even more gorgeous views. We’ve also had some horrific sits with both pets and owners that were nightmares; and some challenging locations.

For the bad sits, which were somewhat early on in our petsitting career, we take responsibility for not vetting [pun intended] the sits properly because we didn't know what we were doing. Since then we’ve developed and honed a rigorous set of protocols for selecting and vetting sits that have reduced the bad sits to almost nil. As well as on-sit and post-sit checklists, protocols, and systems that ensure the pets, the house, and the hosts get the highest level of professional service, and endless cuddles for the furry family, that we've become known for.

We've reached the point now with our all 5-star reviews and solid reputation on the platform we use the most, called TrustedHouseSitters, that we only apply for sits that are lux; in their house location, size, and ‘wow’ factor, along with the types and breeds of animals we most prefer. Feel free to schedule a session with us where we'll share our secrets and answer any questions you may have about becoming a pet sitter—and avoiding the pitfalls we learned the hard way.

We worked hard to get these 5-star reviews and we're very proud of them.

Our PetSitting Career So Far

I compiled our petsitting history for this post to get a better picture of where we've been, how many sits we've done, and how long we sat. And thought it might be interesting to include the full list below.

Location MM/YR Animals Sit Length Type
Gorjões, Portugal Apr 2018 Dog (1) 23 days House
Berlin, Germany May 2018 Dog (1) 4 days Apartment
Berlin, Germany May-Jun 2018 Dog (1) 13 days Apartment
Escondido, USA Aug 2018 Dogs (3), Goats (12), Llama (1) 9 days Ranch
Oakland, USA Sep-Oct 2018 Dog (1) 7 days House
Nosara, Costa Rica Nov 2018 Dogs (3) 4 days Jungle House
Playa Coyote, Costa Rica Dec 2018-Jan 2019 Dogs (2) 6 weeks + 5 days House & Apartment
Buenos Aires, Argentina May 2019 Cats (2) 22 days Apartment
Magoito, Portugal Jun 2019 Dog (1) 16 days House
Newtonmore, Scotland Jun-Jul 2019 Dog (1), Cat (1), Geese, Chickens 11 days Farmhouse
Penicuik, Scotland Jul 2019 Cat (1) 7 days House
Wokingham, UK Jul 2019 Dogs (2) 6 days Condo
Hindås, Sweden Jul-Aug 2019 Dogs (2), Cat (1), Chinchillas 17 days House
El Hierro, Canary Islands, Spain Sep-Oct 2019 Dogs (3) 17 days House
Portland, OR, USA Nov 2019 Cat (1) 20 days Apartment
San Diego, USA Dec 2019 Dog (1) 7 days House
San Francisco, USA Dec 2019 Dog (1) 11 days Apartment
San Francisco, USA Dec 2019-Jan 2020 Dog (1) 8 days House
Tavira, Portugal Jan-Feb 2020 Dogs (2) 17 days House
Amieira, Portugal Mar 2020 Dogs (3), Cats (2), Goats (2), Burro (1), Chickens 14 days Farm
Magneto, Portugal Aug 2020 Dogs (2) 5 days House
Quelfes, Portugal Mar 2021 Dogs (2), Cats (2) 14 days House
Lyon, France Jul-Aug 2021 Dog (1), Cat (1) 6 weeks House
Begnins, Switzerland Sep 2021 Cats (2) 9 days Apartment
Gex, France Oct 2021 Dog (1) 20 days House
Paço de Arcos, Portugal Nov 2021 Dog (1) 4 days Apartment
Boliqueime, Portugal Dec 2021-Jan 2022 Dogs (2), Cats (2) 16 days House
Chicago, USA Jun-Aug 2022 Dog (1) 2 months + 1 week Condo
Oakville, Canada Sep 2022 Dogs (2) 15 days House
Saint-Pierre-Quiberon, France Sep-Oct 2022 No Pets 23 days House
Samois-sur-Seine, France Oct-Nov 2022 Dogs (2) 1 month + 2 weeks House

Dora & Steven - Professional Pet and Home Sitters
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Holy Shift!

Nomads No More. Back in 2018 when we started sitting, we were perpetual travelers in full nomadic mode; and the petsits were incorporated into our ongoing travel. When the pandemic hit in 2020—three weeks after our wedding—we became semi-nomadic by circumstance and began spending the winters in southern Portugal. The exception is the year-plus from March 2020 to April 2021, where we stayed in Portugal during the core of the pandemic. In fact, we’ve acquired quite a bit of stuff since then and I can no longer lay claim to only owning whatever I can fit into my carry-on luggage. The nomad era, which began in the fall of 2015; two and a half years before I met Dora, of being a perpetual traveler with two bags to my name was and is over—for now.

My two bags on the left. I have been traveling with them as a nomad since 2015. A 22" Osprey roller that converts to a backpack if needed. And The North Face Router backpack. And Dora's two bags on the right that she has traveled with since we joined forces in 2018. A similar Osprey 22" roller with a Vaude backpack.

Big Blanket. When the pandemic was imminent—forcing us to leave a petsit two days early, and we frantically searched for and found a place to shelter before lockdowns engulfed the world—we bought a fluffy, plush blanket. The bulky blanket took up my entire carry-on bag and I knew our lifestyle, as we knew it, was over. Granted, an atypical effect of the pandemic, but like countless others; the pandemic changed the trajectory of our lives. The plush blanket was a slippery slope from which we've since accumulated a lot of stuff. So much so that when we've been leaving our winter roost in southern Portugal for our petsitting and travel season, we need a small storage unit.

Shewach Shift. It wasn't just the pandemic that changed things for us. A concurrent shift has been underway for me personally. You've heard of a gap year right? Typically associated with college students, well, my midlife gap decade +2 is drawing to a close. I'm extremely fortunate and grateful to have had these last twelve years of not working. I've lived a lifetime in my gap decade+ and cherish all of the amazing adventures. However, with such as long gap, I'm no longer viable for a regular job, nor do I want one.

So last summer, while on a nine-week dog sit in Chicago, I got my website up again and decided to call it the Shewach Shift. Because everything we want in life or that happens to us in life requires a shift. Obstructing shifts, whether small or big, whether proactive or reactive, will make you suffer. I've suffered for sure. And I'm ready, no...superpsyched to be of service and help other people initiate and get through their shifts.

This website [which is in progress] and my new consulting & training offerings, under Pick My Brain in the header, reflect my own shifts while interweaving my unique life experiences, competencies, knowledge, and education. As a multi-passionate creator, consultant and coach, this site is an incubator of sorts. A place where I can publish a variety of content and see what resonates.

The upcoming move to Italy will give me the stability I need to build a foundation for writing, consulting and coaching. It's time for me to integrate my life knowledge and help people Get Shift Done! The tumult and mental fatigue of the cyclical re-locating is untenable and incongruent at this time. But our goal to find La Dolce Vita gives me the novelty and excitement I need no matter where I am—and hopefully strikes a conducive balance of stability and creativity.

A New Tail Tale This Summer

This year is different. In mid-June, we’re going to Firenze (Florence) for 2.5 months for an exploratory stay in order to get ourselves on the ground so we can set up a long-term base in Italy. Use of the term base is intentional; as we'll keep an apartment there year round but begin to travel and petsit again likely for smaller chunks of time, such as one to three months—most likely during the time of year when our base has the worst weather. Which could be winter or summer depending on where we end up.

The first and only time I was in Florence was back in 2006. Part of a three-month trip to Europe and Turkey of which almost two months were spent in Italy, mostly nearby in Tuscany around Arezzo "working" on a small farm. In reviewing pics from that trip I was amazed to see the date stamp is the exact day we will be arriving next month. Seventeen years to the day. Although I've been back to Italy three times since that first trip in 2006; all within the last five years.

Packing. Between now and early June we’re packing up our winter rental in the Algarve and putting most everything in storage. Since we don't exactly know where we want to live long-term, we're taking a lot of luggage with us and shipping two to three moving boxes ahead of our arrival. The rest of our stuff in storage will be moved across southern Europe, hopefully by the beginning of the fall, after we visit the cities we're interested in, pick one and then secure an apartment lease contract.

Meh Timing. The timing isn’t ideal due to the busy tourist season, higher prices, and the expected sweltering summer heat. And August in Italy, like some other European countries, is when the whole country, nearly en masse, takes their holiday—right in the thick of looking for a long-term rental. It is what it is. The fact is we need to be there to find a place to live. And trying to do it from a distance is too difficult and risky.

One plus is that by summer's end, we should have a much better chance of finding and locking in a long-term lease. There’s some similarity to Portugal in some of the Italian cities we'll be looking at; in that the summer tourist season segments the year-round rental market with inflated prices. Although we’re knowingly getting a bit gouged over the summer, we really need to be in-country to find the right city and apartment.

Where O' Where. Besides Firenze being a beautiful and historical city full of world-class culture and art, we chose it because of its central location and excellent transport connections. We can easily visit other places where we’re interested in setting up our base; all in the northern half of the country. That’s obviously still a huge area but we have our eyes on nearby Bologna, the Tuscany coast in and around Pisa, Livorno, Ravenna, Ferrara, Lucca, Perugia, Torino, and Trieste in the northeastern corner of the country bordering Croatia and Slovenia. Or maybe we’ll fall in love with Firenze and stay there—it has a great international scene which we're craving but unfortunately has hot and humid summers.

Why Italy? And Why Now?

Try again. We wanted to do this move last summer. We didn't because we were too overwhelmed with the place-finding fatigue associated with our lifestyle. After being away traveling for six months doing pet sits we long for stability. We look forward to settling for five or six months in southern Portugal. But before we know it, we're halfway through our stable time and we have to make all new plans again for where we'll go after. New pet-sitting applications, flights, lots of logistics, and packing up our stuff. The cycle is exhausting and stressful. And adversely affects our fitness, work, dietary, and relationship routines and schedules.

How things have changed from when I was a nomad. I often traveled with a JIT approach. Just-in-time (JIT) comes from a manufacturing production model in which items are created to meet demand, not created in surplus or in advance of need. I sometimes decided the day of where to go next; both within a country and between countries. I did the latter a lot while traveling the Balkan region deciding day by day as I spontaneously worked my way from Slovenia to Croatia to Bosnia & Herzegovina to Montenegro and to Albania before heading to Greece.

Why Italy? Dora and I independently had dreams of living there well before we met. Dora studied the Italian language and culture in undergrad. She's currently working remotely for an Italian translation company. As I previously mentioned, my first time was there in 2006 spending over two months there; and I instantly felt the connection. Our individual seeds to live there someday were planted long ago. Our shared living in Italy dream was yet another major reason we fell in love. The fact that Dora speaks fluent Italian makes this journey feasible for me; without her, I'm quite sure I'd not make it there. As does my EU residency in Portugal, affording visa-free movement and domicile within EU-Schengen countries. I also recently submitted my Portuguese nationality application, a two-year minimum process, bolstering our long-term arbitrage-oriented lifestyle.

Getting High. I like to get high. We wanted to be closer to, but not in, the Dolomites as we plan to spend a lot of time hiking there. They're some of the most beautiful mountains in the world and I've been drawn to explore them for the last two decades. However, we were sad to learn of the extremely poor air quality in the famous and gorgeous cities in the foothills of the Dolomites such as Como, Bergamo, and Verona. They and other cities lay in the massive Po River Valley basin that traverses below the mountains, an area of heavy industry and agriculture, where polluted air gets trapped against the mountains. Interestingly, we'll be leaving behind the best air quality in all of Europe here in the Algarve of southern Portugal. We relish, and will miss, the fresh, ocean breeze often filled with the sweet scents of orange blossoms, jasmine, and ocean dune grasses.

In between two pet sits in 2021, one in Lyon and the next in Switzerland, we took a 10-day scouting trip to northern Italy. We visited and ruled out living in Aosta, Trento, and Balzano. And we had a chance to get our first taste of the Dolomites. They're spectacular and we plan to spend a lot of time hiking there from wherever we setup our base in Italy.

Grazie. And yes, I will learn, or try to learn, Italian. It's the only language I'm interested in learning as listening to it is literally music to my ears. Without speaking, I can easily pass as an Italian. Same in Portugal or Spain. But as soon as I open my mouth, even just a simple salutation in Portuguese, my shitty accent is a dead giveaway. The person I'm speaking to immediately switches to English. It's incredibly frustrating. Likely the same will happen in Italy, although I have a better handle on pronunciation because of its similarity to Spanish for which I'm functional in speaking. And Dora tells me, nearly every time I get behind the wheel, that I'm a natural Italian driver with my lead-foot tendencies and assertiveness. Same for my intenso nature that integrates well with how Italians often act, hand gestures and all.

Overly Active Arbitrage. Another reason that I’ll briefly share is that Portugal, at least here in the Algarve where we’ve been living plus Lisboa and Porto, have become quite unaffordable due to the government effectively putting the country up ‘for sale’ via a variety of long-term visas schemes. Causing rents, in an already small rental market due to Portugal's fascist history and old inheritance laws that curtail rental properties, to skyrocket and become unaffordable to many citizens who still earn some of the lowest wages in Europe. Same for home prices. Absolutely exorbitant. Entire cities and regions are becoming gentrified effectively pushing the Portuguese out.

It's easy to blame the foreigners, often seeking geographic arbitrage and a new life elsewhere, but the origin of the problem is the government, whose shortsightedness in trying to bolster the economy, chose unfettered capitalism over the welfare of its own citizens. This is why Portugal routinely makes the top lists of places to retire and move to. Thankfully some of the visa programs have been restricted in the wake of citizen outcry and the government is now seeing, and acting upon, the adverse effects their giant welcome mat created.

So. Much. Inventory. We have found a much larger inventory of available apartments, condos and homes to rent in the cities in Italy we're interested in. Plus they're larger; as we want two bedrooms minimum. And appear to be of higher quality construction; while Portuguese construction, in our experience, lacks adequate insulation and soundproofing. So Italy wins out with more choice, bigger footprints, and higher quality; for less money or equal to that found in Portugal. Granted, we thought of staying in Portugal by moving to a smaller town farther away from the bigger cities where prices are still fair and normal, but we're interested in a robust international scene; so rural areas are not appealing to us. And, come on...it's freakin' Italy: the food, the slow life, the history, the coffee. That said........

La burocrazia. A huge difference from Portugal, however, is the famed Italian bureaucracy. I recently read somewhere there are more laws in Italy than other countries in the EU, by a multitude; low thousands versus low hundreds. A neverending, obfuscating runaround of city, commune, regional and federal laws that contradict one another mixed with often slow and antiquated systems. And we're finding this out already from afar as we uncover the fairly complicated laws surrounding renting an apartment and the documents needed.

First is the fiscal number, the codice fiscale, necessary for basically anything and everything in Italy. It has to be on any rental contract longer than one month; even a ‘transitory’ style contract such as ours (1-18 months). Get this, after moving in and registering, the police will randomly show up to verify you actually live there. Feels like Big Brother. While I'm not up to speed on the reasons behind the infamous La burocrazia, part of this stems from trying to reduce the widespread corruption in Italy. Or the mandatory €100/year per household television tax added to one's electric bill, even if you only watch streaming services as we do. The fee goes to the state-run RAI, a broadcasting company of Italy, owned by the Ministry of Economy and Finance.

Italy's Dark Past. Not to mention that Dora always reminds me that the Holocaust was inspired by Mussolini. And therefore to never forget Italy’s history, both before and during the Holocaust. So this is all becoming more apparent as we plan the move. Causing a strange feeling of worry amidst the excitement—that there may be two very different versions of Italy. The romanticized one and the real one. And we will only know if they blend more naturally, or if it’s too much for us until we test it out. What I'm hoping is that dealing with the bureaucracy is an initial and then intermittent downside, while most of the time is living the sweet life.

La Dolce Vita

So there it is. Our plans, our reasoning, our struggles, and a bit of our story—in search of the sweet life in Italy. A time for new adventures while also claiming the stability we need for this phase of our lives.

We'll have a guest room waiting for you.
And an Aperol Spritz.
Or perhaps a Negroni.  A presto!

Care to Share? What's Shifting For You?

We have found that people are interested in our lifestyle and often find it inspiring. And we're happy to share. To that end, I want to know what's shifting for you? Or what do you want to shift that feels stuck? Perhaps I can help. Get in touch for a Shewach Shift Session.

Steven Shewach | Cal.com
**Longevity & Vitality • Men’s Mojo & Health • Slowiness™ • Adventure Travel • Lax Lifestyle Expert • PetSitting Professional • Apple…

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