The Ultimate House Sitting Guide: Part 6 | Stories, Funny Moments, and the Not So Glamorous
There was a time when we thought getting a house sitting job would consist a lot on luck. So, it’s incredible to think that we’ve been house sitting for three years and have completed nearly 60 house sits! But, if you’ve read parts one through six of our Ultimate House Sitting Guide series, then you know that it actually does take effort and work to not only get a house sit but also fulfill the responsibilities and complete the house sitting job.
Now that we’ve shared our tips and tricks for everything house sitting, we thought there’d be no better way to complete this guide than with a few of our favorite house sitting experiences, challenges, and lessons learned/takeaways.
Our goal is to have this series be the ultimate house sitting guide available anywhere. In it we’ll share what house sitting is and our secrets, including how to house sit for beginners, the not so glamorous side of house sitting jobs, and how to score the best house sits among fierce competition!
To fit in so much information we’ve made it a multi-part series, so don’t miss any of it!
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A few friends we’ve made while house sitting! Clockwise from the top left: Niko in Greenwood Lake, NY; Mercedes in Hoboken, NJ; Zara in Atlanta, GA; Laszlo in Atlanta, GA; and Bippy in Chicago, IL.
House Sitting Job Stats
We thought you might be curious, and honestly we were as well, so we ran a few numbers to see what three years of house sitting looks like*.
*Numbers are based on our house sits at the time this article was written, not published (54 house sits!).
Total days spent house sitting: 806 (that’s 2 years and 76 days)
Most animals cared for in one house sitting job: 8 (3 cats and 5 kittens in Paris)
Total cats cared for: 61
Total dogs cared for: 33
Total pets cared for: 94
Number of countries we’ve house sat in: 13
Number of cities we’ve house sat in: 31
Largest pet: Kayla, South African Mastiff at ~150 lbs!
Smallest pet: Fish
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House Sitting Stories and Experiences
We started house sitting in 2016, thinking it would be a small part of our travel adventure abroad. However, after our first house sit, we realized how much we enjoyed it and house sitting quickly became an integral part of our lifestyle as digital nomads pursuing financial independence, retire early (FI/RE) and long-term travel!
We have house sitting memories that could last for many evenings of story telling, so we’re going to spare you the countless hours of narrated slides and share our favorites!
Along with funny, happy, and heart warming stories, we’ve of course had our challenging moments too.
Before we get started, we want to preface our stories and experiences with one very important point…
This helps turn difficult moments into constructive situations, or as one would say, lemons into lemonade. And when we’re successful at focusing on the wonderful and positive things, the negative are much less impactful to our overall experiences, happiness, and quality of life!
A few friends we’ve made while house sitting! Clockwise from the top left: Tinkerbelle and Tigerlily in Greenwood Lake, NY; Bailey in Toronto, Ontario, Canada; Caira in Kingston, Ontario, Canada; Barry in Greenpoint, NYC; Mishti in Kingston, Ontario, Canada; and Luna in Upper West Side, NYC.
Funny House Sitting Stories
Bailey Hittin’ the Switches
Pets do the cutest things!
In Greeley, Colorado, US, we had the privilege of house sitting a dog named Bailey (and a cat named Cupid). Bailey loved to speak, especially at food time. She would get so excited that she would bark, howl, and bounce up and down. At first we compared her bouncing to a pogo stick, but then we thought it was much more like a low rider car hittin’ the switches!
Tip: If you find this humorous, we highly recommend checking out the sub Reddit r/tippytaps!
Leave it to Shannon
One of the questions we ask homeowners when we’re doing a tour of their home is if there are any quirks we should know about. Like a toilet that runs and needs the handle jiggled, a window that sticks when opening or closing, or a door handle that has a trick to locking or unlocking it.
This question is one that we started asking after a few lessons learned sessions because somehow if there was anything odd about a door, Shannon would inevitably find herself unable to lock it (or unlock it). It’s now a running joke!
What Was That?
We often arrive a day early to a house sit because it allows us plenty of time to meet the pets and get a walk-through of the home.
One time at the beginning of a house sitting job, while the homeowners were asleep in their room and we were asleep in the guest bedroom, Sergio got up to use the restroom. Shannon scooted over to make sure he had plenty of room to get back into bed, so much so, that all of a sudden Shannon fell straight to the floor, flat on her back!
Thankfully, Shannon was okay. And, we can only imagine what the homeowners must have thought, hearing a rather large thump in the room across from them. They didn’t bring it up the next morning, but we’ve always wondered if they were tempted to!
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No Dull Moments
We’ve cared for sibling Siamese cats in Brooklyn Heights, New York City, Toretto and Hobbs. They were incredibly curious, loved to play, and always seemed to be up to some sort of antics.
Whether is was having them chase the laser pointer or treats, we always enjoyed play time with them. But it was one impromptu play session in particular that had us laughing uncontrollably…
Being the minimalist packers that we are, we were weighing our umbrella to check its weight against an ultra light umbrella we ran across. The stainless steel scale caught the light just right and reflected a bright spot on the ceiling. The always keen Toretto and Hobbs immediately caught sight of it and were at once determined to hunt it and kill it.
In the process they climbed over each other, jumped, and stretched out like meerkats trying to reach the ceiling!
So Many Different Pet Personalities!
Of all the dogs we’ve taken care of house sitting, we’ve cared for very few of the same breeds more than once. This has exposed us to so many different breed types with varying traits and personalities. Not to mention, even within the same breed, a pet’s personality can be so incredibly unique!
We’ve cared for dogs that are incredibly calm and reserved, like Bruno the Greyhound during our sightseeing time in Budapest, Hungary. Or the slightly more energized Charlie the Greyhound we cared for in New York City.
We’ve cared for the most spastic, energetic, and ‘crazy’ dogs, like the runt of his litter, Cooper the Jack Russell Terrier who never stopped moving during our sightseeing time in New York City.
We’ve cared for cats that didn’t mind one bit if you picked them up, pet them, or cuddled with them whenever you wanted. Like Garfunkle (whom we affectionately nicknamed G-Funk) who was so patient with us that he let us clean his face and put water and black pepper on it after he was mauled in a cat fight during our sightseeing time in Oslo, Norway.
We’ve cared for dogs that lived, and we’re actually bred, to chase and corral things. Like Kayla, the ~150lb South African Mastiff who’s mission in life was to hunt anything that moved. Poor neighborhood bunnies.
We’ve cared for several rescues that didn’t do well with children or other dogs. Patience, love, and awareness were key with these guys. Like Mono in Vienna, Austria who had a very tough life before being rescued, who was constantly on guard and only gave his trust if you earned it.
On the left are Cooper the Jack Russel and Charlie the Greyhound and on the right is Kayla the South African Mastiff.
Awww Moments
Cupid!
Cupid the cat in Greeley, Colorado was the most dog like cat we’ve ever met! He played like a dog and cuddled like a puppy. One afternoon we were playing a video game and Cupid cuddled up on Sergio’s leg and fell fast asleep. Those two were inseparable!
Last Minute House Sitting Changes
We’ve had a few times where we’d agreed to house sit a set number of pets but by the time the house sitting job started, we ended up caring for a different number of pets.
Twice we had kittens added to the mix. In Paris, France a street cat was adopted who ended up being pregnant. She had five kittens a few weeks before we arrived! And, in Athens, Greece a street kitten was added to the family.
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Unfortunately, it’s not always good news of a pet being added.
Twice now, we’ve had homeowners send us incredibly sad messages before we arrive to house sit letting us know that one of their pets has died. This is always hard for us, but even more so for the homeowner and the other pets who’ve lost their companion.
Other times the situation simply changes.
In Oslo we were caring for a dog and a cat. The dog, was going to be with us about a week, but then be picked up by the homeowner to go to Greece with her. We’d only have the cat to care for and since he was self sufficient, we were told it would be fine to leave him (with plenty of food and water of course!) and explore Norway for two or three days at a time.
Quite sadly, the homeowner’s parent became ill and her travel plans were immediately changed to visit her instead. This meant that Lucy, her dog would have to stay with us the entire house sit.
We didn’t get to see the beautiful landscapes of Norway, however we’re glad that the homeowner was with her parent during the last days of their life.
Clockwise from the top left: Two of the five kittens in Paris, France, Shannon with mama cat and kittens eating their first solid food, Sergio walking Lucy in Oslo, Norway, and Lilo the adopted street kitten in Athens, Greece.
House Sitting Locations that Would Make Almost Anyone Envious
The Views
Have you ever walked down a street and thought, ‘wow, I bet the view from that apartment building is phenomenal!? Well, we’ve been fortunate to have a couple house sits in apartments like that in New York City.
In Long Island City and just across the river from Manhattan, we stayed in an apartment that had access to a clubhouse and roof deck. The view was incredible!
We didn’t think we’d top that view, but then we ended up in Brooklyn Heights. Directly from the living room and bedroom was a view of the Manhattan skyline that blew us away each and every time we looked out the windows!
As if that wasn’t enough, we were fortunate enough to make our way back to another house sitting job in Long Island City, that had panoramic floor to ceiling windows and an outdoor balcony with equally wonderful views, landing sea planes and all!
Just a few of the amazing New York City views we’ve had while house sitting!
City Center
Hotels are incredibly expensive in the center of any metropolitan area, but they offer the most convenient access to all of the city’s top attractions.
We’ve house sat in London, Paris, Amsterdam, Prague… etc. But in Europe no location even came close to our house sitting job in city center Athens. We were blocks from the Presidential Palace and 400 meters from the Panathenaic Stadium! Had we stayed at a hotel nearby, we’d have had to fork out over $1,500 USD for the week of our house sit.
We house sat in city center Athens, 400 meters from the Panathenaic Stadium (top) and blocks from the Presidential Palace (bottom).
Challenging Experiences While House Sitting
Animals Get Sick
In Chicago we cared for the sweetest ‘grumpy old man’ cat named Seth who had heart problems and sadly had a ‘heart incident’ just a couple of days into our sit. We were in constant contact with the owner, kept a close watch on him, and gave him extra love and affection.
It was very scary for us and we consider him and ourselves fortunate. We’ve heard stories of pets becoming ill and dying under the care of a house sitter.
In the end we bonded a bit more strongly with Seth than most other pets we’ve cared for.
House sitting Seth in Chicago, IL!
What Happened to the WiFi Connection?
We learned right out of the gate how reliant we are on a good, stable, and fast internet connection. Being digital nomads, we need it to make a living.
So, it took one house sit with a very poor and intermittent connection for us to add internet speeds and connection quality to our must have list. From then on we wouldn’t apply to house sits that listed their WiFi as ‘basic’.
Then, it took just one house sit with a very slow connection that had listed their home as having ‘high speed internet’ for us to add a question to our homeowner/house sitter interview that asked for specific download and upload speeds and latency.
High speed seems to be pretty subjective. However in the US, the FTC considers anything under 25Mbps not technically ‘broadband’ or ‘high speed’ internet.
Tip: If you ask your host for internet speeds, include a link to a speed test website (i.e. fast.com or speedof.me) for their convenience.
What is ‘Clean’, Really?
We all have our own way of doing things and or own interpretations of words like tidy and clean.
For some, walking into a home and being surprised by the condition or level of cleanliness can be too much. For us, it’s part of the adventure and comes along with the house sitting territory.
From time to time we may have to do a bit of cleaning when we arrive, for our own sanity and comfort levels. But really, we make an effort to super clean every home we stay in as a ‘thank you’ to the homeowner, so it’s typically not that big of a deal.
In the end, the positive far outweigh the negative here!
Tip: When applying for a house sitting job pay close attention to the pictures in the listing for a better sense of cleanliness and clutter. And if you’re still not quite sure what to expect, ask the homeowner for more pictures or a video call with a virtual walk through.
Our tool box is full of resources! From travel hacking to house sitting, digital nomad jobs to privacy and security, financially independent retire early (FI/RE) to entertainment, plus travel hacking (credit cards, miles, points, and rewards), and much much more…
Who Needs Privacy?
We once arrived at a house sit to find that there were no window coverings, meaning no blinds or curtains. We thought, okay this isn’t too unusual since it’s just the living room and kitchen.
… Then we walked into the bedroom to find there weren’t any coverings on the windows there either. It was only made worse because the windows were nearly floor to ceiling on two sides of the room and faced a common area with neighbors, leaving us completely exposed.
We quickly adjusted to getting dressed in the bathroom where thankfully there were no windows!
A few friends we’ve made while house sitting! Clockwise from the top left: Devi in Nashville, TN; Pepper in Vancouver, WA; Phineous in Harlem, NYC; a baby opossum we found under a trash can!; Matilda in Brooklyn, NYC; and Scout in Jersey City, NJ.
Proceed with Caution
It took just one time of a child approaching the dog we were walking and promptly getting snarled and snipped at for us to rethink our assumptions that all dogs love kids (and other people and dogs for that matter).
We now ask homeowners how dogs behave in different situations, like with children, other pets, or when someone comes to the door. We also try to avoid situations that could lead to surprises. Like keeping a short leash or crossing the street to avoid other dogs.
Things Break!
This is one of the most frustrating things that simply can’t be avoided.
We’ve broken dishware, cooking utensils, a thermometer, a shower head, a perfume bottle, etc. Sometimes it’s our doing, sometimes it’s simply due to normal wear and tare, and sometimes things just go bad on our watch.
We had a house sitting job outside of Manchester in a newly renovated and beautiful home. Everything was working perfectly and the homeowners turned the house and their two adorable dogs over and into our care.
The first evening we thought it odd that the water wasn’t really heating up in the kitchen sink, but we were off to bed and didn’t think much more of it. The next morning though, it was the first thing on our minds because a cold shower isn’t anything anyone looks forward to.
We spoke a bit with the homeowners, but ultimately the next step was going to be calling a repair person. However, Sergio took the matter into his own hands and looked up how-to videos on YouTube, and soon enough we had the water heater repressurized and working like a charm!
A few friends we’ve made while house sitting! Clockwise from the top left: Buddy in Hell’s Kitchen, NYC; Jasper in Chicago, IL; Daikon in Long Island City, NYC; Bruce in Manhattan Valley, NYC; Seth in Chicago, IL; and Stinky in Rockaway Beach, NYC.
The Not So Ideal House Sitting Fine Print
Each house sitting website is unique and has its benefits and drawbacks. We can’t speak on every single site and can only share our experience. So, with that being said…
Balance of Power
In our humble opinion and experience, house sitting platforms tend to favor the homeowner. Logically this makes sense. There are fewer homeowners listing house sitting opportunities than there are sitters applying for opportunities. So, a platform needs to do a bit more to attract homeowners to sign up.
In our experience, this imbalance of power is subtle but plays out in a couple of ways that we’re aware of and cautious of as we navigate house sitting full time.
First, we’ve always been a bit curious why we as house sitters have the options to go through advanced levels of security checks but homeowners don’t. It’s reasonable to think that both homeowners and house sitters have security concerns.
Second, we’ve always appreciated services that employ a blind review system (for example Airbnb). Meaning, a person can’t see the review left about them until they’ve also left a review or the review window has closed. Generally speaking this takes out the element of ‘fear of retaliation’ and both sides are able to leave helpful, truthful, and factual reviews. Unfortunately, the platforms we’ve been members of don’t have blind reviews.
Only a ‘Broker’ or ‘Platform’
Finally, and probably most importantly is that every house sitting website we’ve looked at or been a member of takes a stance of merely being the ‘broker’. In other words, they only provide the platform that connects homeowners and house sitters. They’re not liable or responsible for anything that happens once the connection is made.
The website may mediate a disagreement, however they probably won’t guarantee, reimburse, or take disciplinary action. For us, this means:
We only book travel when both sides are fully committed.
We often wait to book travel until a few weeks or a month out from the house sitting job.
We do our own due diligence.
Peruse the listing, including pictures.
Pay attention to previous reviews.
Video chat.
Ask questions about the home, pets, and all responsibilities.
Assume nothing.
Our communications and reviews are very factual. We attempt to steer clear of emotion and opinion.
We take pictures during and after a house sit if there are any uncertainties.
We communicate often and sometimes ask questions that could seem obvious, just to be sure we understand correctly.
We understand and accept that there will always be risk.
Ultimately, everything in life comes with upsides and downsides. We continue house sitting because the upsides WAY outweigh the downsides. We’ve had a few sticky situations, but nothing catastrophic. The day-to-day of house sitting is good and the positives are amazing. We absolutely love house sitting!
A few friends we’ve made while house sitting! Clockwise from the top left: Maisie in Philadelphia, PA; Bunny in Alexandria, VA; the Twins (Toretto and Hobbs) in Brooklyn Heights, NYC; Fiona in Jacksonville, FL; and Huntley in Long Island City, NYC.
People are Overwhelmingly Kind and Generous
Naturally, everyone is different, but we’ve honestly never walked into a home and not felt welcomed by a homeowner.
Every time homeowners go out of their way to provide fresh bedding and clear instructions. Most times they clean up, clear some space for us, and even offer us a meal.
Homeowners have always understood that we travel and house sit full time and have never denied us sending packages to their home in advance. We’ve had people leave us tickets to museums and botanical gardens, library cards to check out books, and keys to city bikes.
We’ve made more friends than we can count house sitting. We absolutely love getting messages and pictures of pets we’ve cared for after we leave. We’re often asked to come back and house sit again, and sometimes even extended an open welcome for whenever we’re in town or if we need to use their address.
We couldn’t help but laugh when one homeowner told us that whenever we were back in her city to let her know, she was sure she could find somewhere to go on vacation so that we could sit for her!
A few friends we’ve made while house sitting! Clockwise from the top left: Hidey Spot in San Francisco, CA; Ronya in Munich, Germany; Kitty Face in San Francisco, CA; Gatsby in Prague, Czech Republic; and Percy in Leeds, UK.
Final Thoughts
After three years of house sitting, two of which have been full time, we can honestly say we’re enjoying our current house sit just as much as we did our first!
House sitting may not be for everyone, it can be hard work and definitely not a worry-free vacation. But for us, having a pet at our side while we explore new parts of the world, makes house sitting perfect!