Be an Outlier. Interview Series | Meet Cindy & Tom, Nomadic House Sitters
Imagine being able to spend time with someone who’s living the life you want. Someone who’s living a life that most people only dream of. From traveling the world, to working remotely, to being financially independent and retired early (FI/RE)… and beyond. In other words, being an outlier!
In the fourth edition of our Be And Outlier interview series, we’re excited to talk with Cindy and Tom from Blue bag Nomads! As nomadic full time house sitters we share a bit in common, but it’s always fun to see and learn from people who have a different approach. And trust us, after 77+ house sits completed and 29 countries visited, they have plenty of great stories and experiences to share!
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Be An Outlier Interview Series
After several years of sharing our story on Screw The Average (be an outlier.) we thought it was time to ask others about their story living outside of the norm. Considering our way of living isn’t the only or correct way of living, we’re excited to see what life others have chosen to live.
Being a digital nomad couple pursuing financial independence, retire early (FI/RE) while traveling and house sitting full time is a unique way of living. It comes with many adventures, times of pushing our comfort zones, and significant personal growth.
We’re two outliers among many more and this interview series seeks to spend time with others that look at the world a bit differently. We want to hear their stories, learn from their mistakes, and walk away with a few good pieces of advice.
We’re glad to have you join us on this journey!
Each interview is unique in that responses are done by our guests in their own voice/writing. We’ve done minimal editing to stay true to their personal stories.
Meet Cindy & Tom: Nomadic House Sitters
Similar to Cindy and Tom, a large part of our lifestyle is house sitting. It enables us to see the world at a fraction of the cost! Plus, we love that it gives us the comforts of home while we travel, including the companionship of adorable and fun pets. Not to mention, we’ve made friends all over the world!
Now, you’d probably guess that the friends we’ve made along the way have been homeowners. And yes, that’s correct. But, we’ve also met other house sitters along the way; Tom and Cindy being the first full time house sitting couple we had the pleasure of getting to know.
Our paths crossed while we were both house sitting in the San Diego, California area and meeting for a cup of coffee turned into a few hours of easy and fun conversation.
We’re honored to share their experiences, advice, and love for life and we hope you enjoy learning about Tom and Cindy just as much as we have!
London, San Francisco, Paris, New York City, Athens and more?! Trusted Housesitters has allowed us to travel the world on a budget, but more importantly given us an opportunity to make new friends and have cute and cuddly companions along the way. Sign up and start your next great adventure!
Introduction
Tell us about yourself!
We are Tom and Cindy, married for oh so many years. We met, at a Halloween costume party, because of a cat. Who knew cats would be an important part of our current lifestyle as full-time house sitters.
We published magazines for 25 years after having successful careers in Finance (Cindy) and Convention Audio Visuals (Tom).
We were both born in California and lived in San Diego almost all our lives. Then we moved to New York City, and lived in Manhattan right by Times Square, for two years. We sold our house and all our furniture, only keeping our nick-nacks. Now we are full-time nomads.
We’d guess you didn’t dream of a nomadic life as kids. Curious, what did you want to be when you were a child?
A stewardess (flight attendant nowadays), but one little problem: I get motion sickness. Ended up being a financial analyst and then a magazine publisher - a little different then what I had imagined.
What does a typical day look like for you?
We are connected to our computers. Fortunately, the computers come with us. Smile. Mornings are usually all work and then the afternoons depending where we are, we make time to explore and of course take advantage of all the wonderful places to get tea and coffee!
Tom is retired, but stays busy working on his photography and now flying his drone! He has had several images on covers of magazines and was a Google Trusted Photographer when we lived in New York City.
I work part-time remotely as an editor, editing hundreds of articles a month. In my free time I write articles for magazines and blog posts.
We heard you had a bit of a change of plans to your travel recently?
Things sometimes go as planned and sometimes they don’t. There was a huge snowstorm in Lake Tahoe that knocked out the power in a large area, including our homebase. There was no power for 10 days. Imagine having no power - it was cold and very dark! And of course, our lifeblood - there was no internet. So instead of going to our homebase we went to San Diego to stay with family until the power came back. Well San Diego in the winter, we’re not complaining.
Nomadic Lifestyle
We are full-time nomads for over six years. We sold our house before we moved to New York City and haven’t looked back. We love to experience new places. We usually try to stay a month or two at each new city, so we get a feel for where we are in the USA or internationally.
“We often joke that when we no longer need help with a GPS to get around, it is time to move on. ”
Our next destination is an island off the coast of Sweden, with an amazing view of the Baltic Sea for a month.
What led you to change your lifestyle?
With both our sons married and living on their own we decided there was no reason we couldn’t go traveling. We definitely were not ready to settle down and stay in one place. When we owned our own business that meant we could only be away for a week at a time.
We sold our magazine and now we travel full time. My sister’s friends say we are like ‘Where’s Waldo’. They are always asking her where we are now.
A nomadic life must come with challenges, what was something you faced?
Our challenge was, being retired and semi-retired we had the funds to get somewhere but how could we afford hotels or even Airbnb’s for months at a time? That is where housesitting has set us free.
And what about your achievements?
We have completed over 75 housesits in 10 countries. This year we have housesits in two more countries and have visited other countries along the way. So far we have been to 29 countries with more to come this year. We were also selected as Ambassadors for Trusted Housesitters.
I was interviewed on Jet SetTV, Travel Itch Radio, Chicken Soup of the Soul Podcast – with Amy Newheart, and our lifestyle true story was included in the book Chicken Soup for the Soul - Stepping Outside Your Comfort Zone.
What do your friends and family think?
Most are amazed. They can’t believe all the places we have been. We try to get longer housesits so we can really experience living there. We have friends and family that have now joined the housesitting community.
Like they say, hindsight is 20/20. Any regrets?
We probably should not have sold our house, as we watch housing prices skyrocket. But we felt it was a huge risk to keep it since we would be in Europe a lot of the time and not able to deal with any issue that might come up, even if we had a property manager. I do think it was the right decision, but …?
COVID-19
We were housesitting in Manhattan (New York City) when COVID hit. The person we were housesitting for was at a retreat in India. India canceled all flights before he could return. So we didn’t know when he would be back. We were in total limbo of how much longer we would need to stay. Plus Manhattan was one of the worst places to be! After about two weeks the US Government had rescue flights from India and he was able to return.
“We had 13 housesits lined up after Manhattan in Europe - all were canceled of course. Two years later two of those sits have been rescheduled and we are going to get to do them this year!”
After Manhattan, we stayed with one of our sons for a little over a month. At first there were no ‘real’ housesits available, no one could travel. Then we started to see a few and started housesitting again and have been housesitting almost continuously after the initial one month break. We were also lucky to get a six month housesit in 2020/2021 which helped a lot.
We are heading to Europe again for the first time since we were there at the end of 2019, and can’t wait to return. First stop is going to be Copenhagen, then a month in Sweden.
Financial Independence, Retire Early – FI/RE
Tom was able to retire early at 59 and Cindy works part-time. We owned a magazine that we sold which gave us a base to start our full-time traveling lifestyle.
Now that you’ve FI/RE’d do you still do any work?
Tom sells his photos and dabbles with website development. I edit articles part-time and occasionally write articles and blogs for others.
What’s one of the best and one of the worst things about being FI/RE’d?
The best thing is we can be anywhere in the world. Hmm I haven't found anything bad yet, fingers crossed.
If you’re wondering how to travel internationally, or simply vacation nearby and not spend a fortune on airfare or hotels, then we’d like to welcome you to the world of ‘travel hacking’. See what credit cards we carry, and how we take full advantage of the points and miles we’ve earned.
Travel
We travel full-time:
Tom and I have traveled to 29 countries on 4 continents. We would love to add another continent in the future.
We have been to 46 of the 50 states in the USA.
We are going back to Europe for eight months in 2022.
Do you only house sit, or do you travel more conventionally as well?
On occasion we will visit with family, but usually we are on the go. We price shop like crazy and love to stay at fancy hotels (our next hotel stay is at a four-star hotel in the heart of Copenhagen), but usually it is more in the three-star range. We used to stay at Airbnbs but they have gotten expensive and they are not always close to the city center. Overall though we try to get housesits back-to-back, so we rarely have any open nights.
We have housesat in 10 countries and will be adding two more this year, Sweden and Northern Ireland - smile.
There are all types of house sits, from a couple of days to upwards of a year. What does house sitting look like for you?
On average, we stay for about three weeks at any one place and we were in Asheville, North Carolina for seven months. Asheville was our longest stay and it was actually a bit too long. At only two months I started to get the travel bug, but it went by faster than I expected. We were staying at a beautiful home with two very large, loveable Great Pyrenees (dogs).
What did this past year of travel look like?
This past year we didn’t really keep track of travel costs. We were in Reno for six months and then had several month-long sits. We did go to Hawaii for a three-week housesit. Airfare was under $700 total for both of us. Now with COVID restriction lessening, we are going back to Europe in February 2022. We were able to get round-trip tickets for a total under $1,600.
Any tips?
I have signed up for emails from several major and budget airlines. Priceline often has good deals on hotels, especially if you can take advantage of their special deals. But if you see a price too low, buyer beware. If the price is too low for a hotel you may want to check to see if the hotel is being renovated!
What’s your packing style?
Weight is number one for us as we fly a lot.
We have a luggage scale we bring with us, always! You never want to be overweight and every airline is different, so you need to know. We have downsized the size of our ‘checked bag’ which helps keep our overall weight done and within the airline's limits.
We are big fans of the hard-sided luggage with four dual wheels.
Since we switched to the hard-sided luggage we have had nothing break and they seem to last much longer - yeah.
Wondering which type of luggage is for you? Check out Cindy’s article Which is Better for You Soft-sided or Hard-sided Luggage? And for a third take, read our Finding The Travel Backpack We Call Home.
We each pack something a bit unconventional, what you about you and Tom?
Usually I bring a few spices to cook with. When you are in a foreign country they don’t always have the same spices, so I take a couple so when we cook a meal it tastes like home no matter what country we are in.
Don’t miss our Ultimate Gear and Packing Lists! Whether you’re traveling long-term or going on a short vacation, we'll show you how to travel with a single carry-on. We share our packing lists (his and hers!), packing tips, and our favorite gear. Plus, we discuss what we don’t carry and why!
It might be hard to narrow down, but what’s one of your favorite travel stories?
We had two housesits in Oslo, Norway. The first one was for Christmas and New Years. Then we returned in the summer for 10 days. That summer, on the second day we were there, someone knocked on the door - this was in a somewhat remote location, so who was at the door??
“I open the door and my younger sister, who lives in California, is standing there. What? It was amazing. ”
I always share the list of places we are going to be with family. My sister contacted the people directly and asked if it was okay for her to come and they were very happy that she could. It was a total surprise for us. One of the best surprises I have ever had!
What’s the most memorable place you’ve visited and why?
We loved Edinburgh, Scotland during their Fringe Festival. You should look up the festival if you are not familiar with it. We had a month-long sit, so we were there for the whole festival. We went to dozens of events, including the Military Tattoo that is held at Edinburgh Castle. My sister, the one from California, was even able to join us for a week. A very special time.
What about the most unique place?
Marrakech, Morocco, everything went so well we are almost afraid to go back; It was so perfect! It was also our best bargain trip, which you can learn about in our blog.
The history, the markets, and the people were amazing. We stayed in a Riad in the old town (Medina). Riads are old homes that have been converted into small boutique hotels.
This was our first time to Africa, so it was very exciting to be there. We had breakfast served daily on the rooftop patio, with amazing views. A great way to start the day, before exploring the city. Oh - the shopping at the markets was excellent!
Digital Nomads
We’ve been digital nomads for 6 years and counting! Well over 2,200 days. Before that we had home offices for 20 years (way before it became a thing), so transitioning to nomads was relatively easy for us.
Now, I edit articles and on occasion write articles and blogs for magazines and online outlets. As long as I have a decent internet connection I can be and have been able to work anywhere.
How do you find writing work?
I have, luckily, worked for the same company for three years, so I am not looking for work. If I happen to come across someone looking for a blog post that interests me I will write one or on occasion I will submit an article pitch to various magazines. We also have sold images to magazines, books, websites, and one was even for a calendar.
Since you’re moving around a lot, your work environment must change a lot. What does your ‘office’ typically look like?
“Coffee shops to kitchen tables - LOL. ”
Most of my work is done at kitchen tables - just me and my laptop. On occasion the place we are housesitting will have an office I can use. When we had a six month housesit, we did go to a WeWork about once a week. It is always good to get out of the house!
How do you meet people while traveling?
We have found since Tom is a photographer, we often reach out to local photography clubs. They have always been very open and love to have us join in, in their outings. It has been a great way to meet local people and learn photography tricks and tips. Plus their outings often take us to places we would not have found on our own, so they are a win, win, win.
House Sitting
How did you learn about house sitting?
A Google search for alternative lifestyles included a website called TrustedHousesitters.com. Little did I know that it was going to transform our lives to become full-time travelers. We have been housesitting for over six years.
“As of January 2022, we have completed 77 housesits in 10 countries, for 160 animals. This includes dogs, cats, chickens, rabbits, ducks, and this year we have a sit in London that has 2 tortoises and 7 turtles (or called terrapins since it is in England).”
Our housesitting covers 235.3 weeks or 1,647 days of house sitting.
We have housesat in the USA, Canada, England, Scotland, Norway, France, Germany, Italy, Poland, and Luxembourg. We will be adding Sweden and Northern Ireland in 2022, and hoping to add one or two more countries before the year is over. We are currently booked out until August.
House sitting so many different pets must come with a few good stories…?
In Scotland we had a housesit for two adorable dogs. The smaller, younger dog was bought as a birthday present for the other dog on that dog’s first birthday. They are the best of friends.
They had this game they played where the younger dog would take the ball and run while the older dog was chasing him through the house and out in the big yard - it is probably hard to visualize but it was very cute and they were just so funny together. The older dog would bring us the ball and we would give it to the small dog and the chasing would start all over again! They made us laugh a lot.
Do house sits ever not go to plan?
Of our 77 completed housesits only 2 were difficult - I even wrote a blog about all the things that went wrong with a housesit in England - We call it our ‘nightmare housesit’.
Interestingly, both of the housesits that I would put in the ‘gone wrong’ category were because of the owners - one was a lawyer and one was a real life rocket scientist - you would think they would have known better. But we survived and we do enjoy meeting new people and their pets. Many of the owners we are still in contact with and have gone back to visit when we can.
Nothing’s perfect, what do you dislike about house sitting?
Cleaning - we feel the house needs to be as clean or cleaner than when we arrived. Yes it needs to be done, but shoot. Sometimes I wonder about hiring house cleaners, but so far we haven’t. LOL.
Advice
If you could do it all over again, what would you do differently?
I still wonder about selling our house. If nothing else we should have invested that money more wisely.
What’s your best travel advice?
Be patient with others and don’t get mad while traveling, it can completely ruin a vacation.
Something different we do is we buy Tru Earth laundry detergent strips - it comes in small strips, one strip per load. You can buy a pack of 36 loads and it only weighs 2.3 oz. You will not have to think twice about doing your laundry, add some dryer sheets and you are ready for the next several months.
One of the first things we do in a new city, we take a ‘free walking tour.’ It says free, but be prepared to pay a tip at the end, which is still a good deal. The hop-on, hop-off bus tours can also give you a good overview of any new city you are staying in.
We often use Priceline and Google Flights. There are many, many other websites that are great. One thing is if you are not looking you will not know if you are getting a deal or not!
In the UK, traveling by train they have a discount card that will get you great low prices and can be used on the website The Trainline. Again there are many city and travel discount cards that may work for you, and buy tickets for everything in advance.
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…
What’s your best house sitting advice?
Read each listing carefully! Be sure it is a good fit for you, i.e. if the dog needs to be walked an hour, twice a day - are you up for that? I love to take dogs out for walks but not an hour plus everyday. We also highly recommend doing a video chat and staying connected using the app - What’sApp.
What advice would you give to someone starting on a path similar to yours?
How much time do you have? Our lifestyle works best if you are flexible and love cats and dogs.
Be sure you have a retirement plan, no matter your age.
More About Cindy and Tom
Tell us about your blog!
We post stories of our six years of nonstop travel from months in Europe to an 18-month cross-country USA road trip, our adventures are diverse. We share our experiences, photos, locations, and travel tips learned along the way.
“Our goal is to encourage others to get out and travel. ”
Traveling internationally, many people are worried about what will the food be like. Will language be a problem? We have written blogs about both. The one I like best is ‘43 Countries to Visit that Speak English’.
If you want to get away and go international this article includes many tips and a long list of countries to explore that speak English. From experience, Norway is number 22 on the list and when we were there for a month everyone we encountered knew enough English that we never had a problem.
“You will discover things that you thought were really important aren’t as a nomad. It will be an interesting journey; enjoy it along the way.”
Where can people find you?
Facebook: BlueBagNomadsBlog
Twitter: lovetravelingto
Instagram: bluebagnomads
