[Interview #022] From normal life in Florida to full-time world travelers in about 8 months: How to harness the power of working remotely and start traveling the world

This interview is part of our interview series, where we curate stories of regular people that decided to design a life they love. (click here to learn more). 

Amy and Ian Anderson

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1. Can you introduce yourself?

We are Ian (40) & Amy Anderson (36), a married couple from Tampa, Florida USA. We’ve been together since 2001 and have been married since 2009.  We are both web designers and for the past twelve years we have been running our own location-independent web design / consulting company and best of all do it together.

We were both born and raised in New Bedford, Massachusetts. Making the leap to self-employed web designers  who could work remotely, made us realize that we had the freedom to relocate from cold and snowy Massachusetts to warm and sunny Florida. That was back in 2011. Since then we’ve started to think a lot bigger and fast forward to August 2020 which is when we kicked off our international travel adventures; all while earning a living from what we were already doing. Four countries into it (Aruba, Croatia, Italy and currently Montenegro) we’re living a life that up until recently we thought only super rich people could live.

Life design journey

2 – What does a typical day in your life look like for you today? How does it differ from your life before?

Because we didn’t go from having traditional “9-5” jobs to international digital nomads in a straight shot; we really have two different “before” lists, compared to the life that we’re currently living.

Life “Before” #1: Traditional Jobs
Location: New Bedford, Massachusetts USA | Number of cars: 2

Ian: Before getting into the web industry, I was a security guard for a grocery store chain called Stop & Shop. For eight hours a day, I would sit alone in a dark room with the only light coming from the glow of a few dozen monitors. Each monitor showed the live feed of a controllable camera mounted strategically around the store. Some notable highlights from my security guard career were getting into physical altercations, a woman overdosing on Christmas Eve, having a knife pulled on me and one time a giant man stuffed a cut of beef into his sweatpants (and the store policy was to put the “crotch meat” back on the shelf… super gross)!  After a few years of dealing with these types of situations, I had a complete lack of enthusiasm about the job and would often sleep in the security office.  

Amy: The last traditional job that I had was working as a junior accountant for a local credit union.  Back then (which was 2009) my life consisted of waking up around 6:30am Monday – Friday, to drive to work and be at my desk for 8am.  My responsibilities were pretty much what you would expect in this line of work; handling accounts payable, payroll, investigating fraudulent charges on customer accounts, etc).  I was actually really good at this job, and the truth is, I didn’t actually hate the work…I hated everything else that came along with it.  This job gave me no control over when I had to show up or could go home, forced me to drive in bad weather and dictated when I could and couldn’t take time off…all for a measly $14.50 per hour…but on the upside I never had deal with “crotch meat.”

Life “Before” #2: Self Employed + Home Ownership
Location: Tampa, Florida USA | Number of cars: 1

Ian: After quitting that grocery store job (very surprised I didn’t get fired!) around 2004 I took my hobby of creating websites and decided it was time to get paid for doing it. That idea worked pretty well and for the next six years (or so) I created websites from our apartment for my clients. 

Around that time, Amy became fed up with her credit union job and asked me to teach her the basics of web design. After she got the hang of it, she and I started working together creating websites.  After a few years of working together from our apartment in New Bedford, Massachusetts, we had enough of the cold weather and since we could work remotely we made the decision to move to Florida.

During a typical workday, we would wake up between 8-11 am (we never set an alarm, which is nice), have some breakfast, stay in our pajamas, and head to our home office (about 10 feet from our bed). Waiting for us – in our email inbox – is new web design work from our marketing partners around the USA. We’ll work through those emails until about 4-7 pm.

Amy: After I quit my day job, I began working remotely as a web designer with Ian.  This changed my lifestyle in the sense that I no longer needed to wake up to an alarm, could take a vacation whenever I wanted, and no longer had a commute.  Once I started working from home, we didn’t see a need to have two cars, so we decided to sell one of our cars  (which between the car payment and insurance saved us around $280 per month).

Over the years as our business became more successful and our income increased, we decided to buy a house in Tampa, Florida.  When we bought our house it increased our monthly expenses; combine that with the down payment and closing costs, we had put a big dent in our savings account.  So until we got used to our new expenses, we spent the first couple of years handling much of the home-related tasks ourselves.  Which meant that the majority of our time was spent between running a web design company and maintaining our house.  And while we both really like our house…we weren’t always happy about how time-consuming it could be.

Current Life: Self Employed + Home Ownership + Traveling Internationally
Location: Earth | Number of cars: 0

Our lifestyle today is quite a bit different than the credit union and grocery store days.  We’re still remotely running our web design company with one major difference; we’re now doing it while traveling internationally.  We rented out our home in Tampa (more on that later) and have been staying in AirBNB’s since August 2020.  Our line of work still sometimes requires long hours but renting out our house has freed up a lot of our time.  Staying in AirBNB’s has made it so we spend minimal time taking care of mundane house-related tasks.  Most of the Airbnb’s we’ve stayed at include some sort of cleaning service, so really the only house-related tasks we need to take care of are things like washing dishes and laundry.  We don’t have to worry about maintenance or anything else house-related, which in the past took up a lot of our time. 

Check the two infographics below for a visual recap of the shift in priorities of Ian and Amy.

3 – What inflection point led you to decide to change your life trajectory?

There are several realizations that changed our trajectory and got us to the point where we are today (which is traveling internationally, while working remotely).

Realization 1:  Amy decided to learn web design (Ian was already doing this)

Back when I (Amy) still had my traditional job, one of the biggest appeals of working remotely was not having to drive to work in bad weather. As silly as that may seem, back when I worked at the credit union, we were open pretty much no matter what. There could be two feet of snow on the ground and we were expected to show up. So I often would need to get up super early and freeze my ass off to shovel out my car (just to be on time for a job that I hated).

Yet Ian only had to roll out of bed, brush his teeth and grab a laptop and he was good to go. For me that was the initial inflection point of needing a change. 

Realization 2:  We relocated from Massachusetts to Florida

About a year and a half or so after Amy had quit her job, we had another major realization.  We were both creating websites (as a location-independent web design company) and we realized that we didn’t have work from Massachusetts.

Back in January 2011, we still lived in Massachusetts, which is known to have insanely cold and often snowy winters. At the time, we didn’t have a driveway or a garage and had to park in the street.  Anytime there was a significant amount of snow, it made parking an absolute nightmare because the snowplows would create these big snowbanks along most of the street. 

One day in January (after a snowstorm) we had just got back home from the grocery store and finally managed to find a spot to park. However, when Ian went to open the driver’s side door to get out of the car, he couldn’t open it because the snowbank was too high. The end result was that he was forced to crawl out of the passenger’s side door and almost fell into the street in the process.

At that moment, something inside him snapped. 

His words were something along the line of “I can’t believe I just had to crawl out of the car like it’s some kind of f’ing clown car.”. It was then that we realized because we work remotely, we can work from anywhere. I’m not sure why neither of us came to that realization sooner… but approximately four weeks after that incident, we had packed up our lives and made the move to Florida.

Realization 3: International travel would decrease our expenses

A more recent mental shift (that occurred at the beginning of 2020) was when we created a spreadsheet that listed our current living expenses in one column and then in the column next to it, listed what our estimated expenses would be if we were to travel internationally (staying in AirBNBs).  

As you read this, think of your current monthly expenses but without an electric bill, a water bill, no internet bill or car payment (you get the idea) combine that with the added bonus of cheaper housing, cheaper food AND you get to experience all those places around the world you’ve looked at online and thought to yourself “I would love to see that one day.”  

By making that spreadsheet and looking at the numbers side by side, it became very obvious to us that we could travel around the world while saving money (further down we get into the specifics on how much we’re saving ).

4 – What were some of the limiting beliefs that hold you back initially?  

Ian: It’s going to sound silly but the biggest limiting belief I had was thinking that jumping from country to country every few months, eating exotic foods, being in the Caribbean sitting under a palm tree one month and then standing in front of the Colosseum in Rome the next month, seemed like something only super-rich people do. I never thought of myself as super-rich (maybe that was part of the problem) but that kind of lifestyle wasn’t even something I considered a possibility.

It turns out that I was wrong. It costs less to live this “super-rich” lifestyle than it does to live in our house in Tampa, Florida… and it’s a lot more exciting. I guess we never really needed to be richer, we could have started this years ago when we were making less money. 

Amy: Back (in 2009) when I realized that I wasn’t cut out to be an employee, I began to plan my “escape.”. With the help of  Ian, I learned how to create WordPress websites. I then took my new skill to market and actually started to earn money from it on a regular basis (often more than my weekly paycheck). Over the course of a couple of months, this income became steady enough to the point that I could finally quit.

But when the day that I had been dreaming about for so long finally came, I froze and didn’t quit. 

Despite being at the point where my job was stressing me out of my mind and often left me coming home in tears, I still clung to it out of the fear of losing the “security” of a steady paycheck.  Until I was finally able to work up the courage to quit, I continued to work there (and put myself through anxiety hell) for a couple of months longer…all because I was afraid of losing a crappy but steady income. 

5 – What did you do to prepare the transition to this new destination and how did you do it?

Since our business was already location-independent, it was our house in Tampa that was the biggest challenge. We could have easily sold our house (and pocketed some money) but turning it into a rental property would not only generate money for us every month (while someone else covers the mortgage… more on this below) it gives us a place to go back to when we want to stop this adventure.

On January 7, 2020, we took the first step and contacted the realtor we used to buy our house (he specializes in property management too). We started talking numbers and told our property manager that we were looking to have a renter in the house sometime in May. So he gave us a list of actionable items to get the house ready to list by mid-April. 

The list consisted of things like freshening up paint here and there, installing a new mailbox, and planting some flowers to enhance the curb appeal. Plus sorting through our personal belongings, making a list of what we were going to put in storage, donate or just throw out. It was all exhausting but the thing that kept us going through the hard times was knowing that at the end of our “to do” list was going to be a never-ending international adventure that very few people ever get to experience.

We worked diligently on our list and the next thing we knew the end of February was approaching but there was this thing called COVID-19 that suddenly seemed to be gaining a lot of attention. Before we knew it, we were being told to prepare for a two-week quarantine and at that point, our attention shifted to getting the supplies that we needed to hunker down. 

And just like that, our travel plans were sidelined because of the pandemic.  

That two-week quarantine turned into several months…but finally, around June there seemed to be light at the end of the tunnel.  Some countries were starting to reopen their borders to US Citizens. So we picked back up our travel plans and by the last week of July, a renter had signed a one-year lease.  Before we knew it, we were getting PCR tests and heading off to Aruba. 

6 – Once on the journey, what were some of the biggest wins you realized? What were the challenges you had to face along the way? 

One big win that we experienced early on (way back when we started our web design company) was getting to work with each other every day. Even though we are self-employed, we are still working.  And like any line of work, there are challenging days…like the type of days that make you want to start pulling hair out of your head. But at the end of the day, getting to work together makes even the most challenging workdays, a million times better.

Now that we’re traveling internationally, one of the major benefits is getting to explore new countries and learn new things such as, ATVs are street legal in Aruba, Zeerovers in Aruba has the most amazing shrimp, when you walk down the streets in Rome you often feel like you’re in a game of human “Frogger” and that Ela’s Ice Cream (located in Diocletian’s Palace, in Split Croatia) is the place to go if you are looking to experience amazing ice cream.

But by far the most rewarding thing has been the experiences we have been able to have together. Here are a few of our favorites so far:

• While sitting at a blackjack table in Aruba, after hearing about our travel adventures, a businessman (who owns several restaurant franchises) told us that we were his heroes. Turns out he does quite well, but as a franchise owner he is very much involved in the day-to-day operations of his business which requires him to be at a specific location, and therefore he doesn’t get to travel as much as he’d like.
• Walking inside the Colosseum (aka a World Wonder) and reflecting on all of the histories that took place there
• Standing in Saint Peter’s Square at the Vatican.
• Sleeping inside the walls of an ancient palace (Diocletian’s Palace) in Croatia.

These are definitely some things that we are going to remember for the rest of our lives. Obviously, because of COVID, there are many restrictions so we’re not able to have the “full experience” but we’re still managing to have a lot of fun. The downside is that because we have to be mindful of social distancing, we aren’t able to really interact with the locals as much as we’d like.

7 – How long did/will it take to reach the destination? Any advice to make the journey as enjoyable as possible?

We’re still very much on the road to our “destination.”.  Even though we’ve created a pretty successful web design company that gives us the freedom to run it while traveling internationally; we’re still not living our dream lifestyle. 

While we’re extremely grateful for the lifestyle it gives us (and it’s true that we don’t have to wake up to an alarm clock or show up to an office) the reality is that we still have a lot of project deadlines to meet, our clients often have very short notice (and at times) demanding requests…so we still very much work a Monday – Friday schedule (which often requires putting in some work hours on the weekend in order to keep up with everything).

Don’t get us wrong, the lifestyle and income that our web design company gives us is one million times better than our old day jobs and we’re by no means complaining.  We’re simply saying that there’s room for improvement.  For us that means creating more passive revenue streams (or recurring income) which will eliminate the project deadlines and demanding requests that we still get on a regular basis.

8 – What did the people around you (friends/family/colleagues…) think of your plan to take on this new life? 

Amy: Back when I was thinking about quitting my job at the credit union, everyone thought that I was crazy.  The people who come to mind the most are my two Moms (my Mom and my Mother-in-law).  Both thought that I was giving up the “good life” of job security and tried to talk me out of it. I know that they both had my best interest at heart and thought that they were protecting me but at the same time, they didn’t realize that this job was holding me back from reaching my potential. 

I remember my Mom saying that I should try to negotiate for higher pay. Negotiating for higher pay was 100% doable. I was a dependable employee and excellent at my job, so much so that when I finally got the courage to quit, the head of the credit union said that he wasn’t going to let me go and that I could “name my price” to stay. 

It was a pretty surreal moment… despite being terrified of giving up a steady paycheck (especially with the offer to be able to earn more money) it was right then and there that I realized that I couldn’t be bought. Even though I had the option of earning more money, I knew it still meant that I would not have control over when I had to show up or could go home, it would require me to drive in bad weather and of course, would still dictate when I could and couldn’t take time off…so I would continue to not have any control over my lifestyle.  That made me realize that a higher paycheck came along with too high of a price tag. 

Ian: Fast forward to 2020 when we told people we were going to be traveling around the world, they thought we were crazy, lucky, or some combination of both. Nobody tried to talk us out of doing this and everyone we told was very encouraging and excited for us.

Because our lives were already set up to be location-independent, it wasn’t that much of a shock when we told them what we were going to do. We already lived thousands of miles away from our family (and all our clients) so whether we are at our home in Tampa, Florida or in Rome, Italy or Budva, Montenegro… Facetime and Zoom calls are pretty much the same (except for time zone differences, which really aren’t that bad).

Cost of living

9 – How much yearly expense did you have before and after this change in lifestyle?

Note from Mr. NN: these expenses are for Ian and Amy traveling together to Budva, Montenegro for 84 days living comfortably.  These expenses might or not might not be more expensive if you travel solo (depending on your travel lifestyle)

Category	Description	Cost per couple and per day
Accommodation	Anything you pay toward keeping a roof over your head (ie. rent, internet, water, utilities…)	$41.00
Groceries	Anything related to the groceries you get to cook at home (including alcohol, food, toiletries, etc…)	$20
Dining out / Take-out	Anything related to what you spend when dining outside of your home.	$6.6 Dining out is currently closed in Montenegro, so this is just for takeout/delivery
Activities / Entertainment	Anything you pay related to ‘fun money’ (ie. park fees, outdoor activity, AirBnB experience…)	$0 because of COVID, everything is closed
Health Care	Any cost related to treatment you are receiving on a given location.	$0
International Health / Travel Insurance	This is health travel insurance that you purchase to get you covered outside of your home country	$26.66  This is for a Cigna International plan that covers preventive / wellness, emergency, dental, and vision care worldwide.
Local Transportation	Anything related to transportation within the boundary of the location you are staying at.	$0.60 We only paid for a driver to take us from the airport to our Airbnb once. This number represents that cost divided by the number of days we are in Montenegro.
International Transportation	Anything related to transportation to go from one location to another.	$6.82 This number represents the cost of the flight from Rome to Podgorica divided by the number of days we are in Montenegro.
Visa	Any cost related to a visa to stay in a given country.	2 Euro  This is not actually for a Visa, but rather is a mandatory per person, per day tourist tax.
Living expenses	Anything else that you are spending money on to live in a specific location that can’t fit anywhere else (ie. Haircut, Netflix, cell phone…)	$8 This represents our expenses for Netflix, cell phones, and our storage unit back in Tampa for our personal belongings
	Monthly total (for a couple)	$3,380.40
	Yearly total (for a couple)	$40,564.80

10 – What strategies have you used to reduce your expenses? And what strategies have you used to fund your lifestyle?

1) Reducing Our Expenses

A major upside of international traveling is that it has actually allowed us to reduce quite a few of our monthly expenses.  The biggest way that we were able to do that was by turning our house into an asset; which meant renting it out. Here are some specifics on the numbers:

Our monthly house payment (mortgage, homeowners insurance, and property tax) for a 2,000 square foot, 4 bedrooms, 2 bathroom house with a pool, totals a little over $1,700 per month. However, we were able to rent out our house (furnished) for $2,500 per month. So right there, we’re getting $800 more per month more than our monthly payment.  

However, there are some monthly expenses that come out of the $800. 

We still pay for the maintenance for the lawn, pool, central air system, and pest control (no matter how clean you keep your house…Florida still tends to get buggy). The monthly expense for all of these items is roughly $250 per month. 

After that, there is the fee that we pay our property manager.  While we could have rented out the property ourselves, we felt much more comfortable hiring a professional company to make sure everything was done properly, especially since we were going to be out of the country.  This service costs us 10% of the total monthly rent collected, which comes out to $250 per month.

So here’s a quick recap:

• Monthly rental income: $2,500
• Monthly mortgage, insurance, tax payment: $1,700
• Monthly lawn, pool, central air and pest care: $250
• Property management fee: $250

After applying the rental income ($2,500) to all our house-related expenses ($2,200), it puts $300 extra dollars in our pocket every month – plus we still own the home – all while someone else is paying down our mortgage.

And the benefits don’t stop there, not only is renting out our house giving us some extra money each month, it’s giving us additional savings as well.  Our tenant pays for all of the monthly utilities (electric, water, and internet). So here’s what that means for us in savings:

• Electric: The monthly amount of our electricity bill varies a bit.  In Florida, for a good six months out of the year, we’re running the A/C constantly, but then in the winter, we don’t need to use it as much. We also have a pool that requires the filter to run for eight hours per day.  So if you averaged out a year of our electric bills it would be roughly $160 – $175 per month.
• Water: This on average is about $65 per month.
• Internet: $60 per month.

Since our tenant pays these utilities, it saves us (approximately) $300 per month.

Knowing that we were going to be traveling long term we also sold our car (a Ford Mustang convertible). By selling the car, we were able to put $6,000 cash in our pocket and eliminate our $250 per month car payment. Since we no longer had a car, we no longer needed car insurance, which saved us an additional $120 per month.  This also meant we no longer had to pay a yearly registration fee for our car and could cancel our Triple “A” (AAA) plan which came out to an additional $12.50 per month in savings.

While eliminating or reducing all of our normal monthly expenses was great, our current lifestyle has a brand new expense and it’s not something we can eliminate, but we can reduce it.

2) Negotiating AirBnb stays

Instead of skimping on lattes (saving $3.50 here and there) and not going out to do anything (that’s not fun) look at where you are spending the most money every month and find ways to decrease your largest expense. Whether you are already a digital nomad – or you’re just thinking about it – it’s always helpful to keep your expenses as low as possible. Where you stay is going to be your largest expense and we can help you lower that. Saving $2,000 a month on your AirBNB can buy you a lot of lattes and fun adventures! When we first started traveling we learned that paying the full retail price for an Airbnb is a very expensive decision. We didn’t negotiate back then, we drastically overpaid and we hated every minute of our first Airbnb in Aruba. Since that disaster, I’ve been very successful at negotiating huge savings on all the AirBNBs we stay at. In just four months I negotiated over $50,000 in savings!  

You can see the AirBNBs we’ve stayed at:

• Aruba: https://www.airbnb.com/rooms/17263689 
• Croatia: https://www.airbnb.com/rooms/1156431 
• Italy: https://www.airbnb.com/rooms/16977120 
• Montenegro: https://www.airbnb.com/rooms/30954606 

I’m particularly proud of negotiating our stay in Rome, Italy where I saved $7,163 (-61%) off the regular price for an 83-night stay. The screenshot below represents the fifteen Airbnb hosts that I negotiated with before I traveled to Rome (I did the negotiating from Croatia). You can see the initial price (the price AirBNB lists (regardless of any discounts automatically applied by AirBNB) BEFORE I negotiate with the host), the final (negotiated) price, and the dollar amount that my negotiating lowered the price. The $31,274 represents the total reduction from all fifteen Rome negotiations. The row at the top (highlighted in green) is the AirBNB that we ended up staying at.

Lessons, tips & advice

11 – If you had to do it again, what would you do differently?

1. We would have done it sooner (in hindsight, there was no real reason we could not have started this adventure years ago).
2. We would not go to Europe during the winter months, it gets much too cold for us.
3. We would plan our nomadic route with the seasons (following the warmth). This means Europe in the Summer and South America in the Winter.
4. To find the perfect Airbnb, when you arrive in a new country, rent an Airbnb (or hotel) for a few days so you can research the best spots in that city. Spend those few days walking/driving/biking all around to find out which area of the new city best suits your needs. Then find a more permanent AirBNB in your desired area (as opposed to finding an AirBNB from thousands of miles away). You can only learn so much from YouTube videos and Google Maps Street View.
5. Focus more on recurring passive income. This is something that we’re putting a big emphasis on now.  By having more passive income coming in, we would be able to spend more time exploring the place we are in. Currently, we are tied to our laptops for many hours each day but a large stream of passive income would decrease the number of hours per day that we have to spend working.
6. Be a more mindful consumer.  This advice is applicable to everyone, no matter their life goals (unless your goal is to become a massive hoarder).  We can’t speak for other cultures, but as Americans, we’re taught to consume…the more the better. The message that we’re “sold” is that there’s a positive correlation between happiness and the more stuff you own. We think that the opposite is true. In our opinion, when you buy stuff that doesn’t add any value to your life (as in it doesn’t serve an actual purpose in your daily life, nor does owning it bring you any joy) it tends to lead to overspending and often debt. This creates financial stress, causes you to have to work more and leaves you without any disposable income to spend on the experiences and things that will actually bring you happiness. 

We wish that we had been more mindful consumers early on. While we fortunately never got ourselves into any major debt, over the years we definitely have blown money on things that we didn’t really need. Instead we could have spent that money on more experiences (or even invested it for our future). Even if blowing money on things that you don’t actually like / need isn’t getting you into debt, it’s probably getting you into loads of clutter.  If this is you and you’re thinking about becoming a digital nomad, having loads of clutter to get rid of will be an extremely time-consuming project and will delay you from starting your journey.  So we recommend that you start getting rid of stuff now! Sell and donate anything that’s in good shape and then throw the rest out.

12 – What advice do you have for others who are considering going through a life design exercise?

Ian: In no particular order, here are seven pieces of advice on designing your life:

1. Determine if you can earn enough money through your laptop to cover (and preferably exceed) your monthly expenses. If you can do that, then you can travel around the world, join the “digital nomad” community and never stop traveling.
2. Find ways to make recurring and passive income through your laptop. Making money through your laptop is a requirement for this lifestyle but there are different kinds of money you can make, so focus on the recurring and passive revenue builders for a lot more free time in your life.
3. Don’t buy a lot of “stuff”. This is a waste of money and holds you down. Think of each little trinket and shelf decoration like another hook in your body tethering you to your current lifestyle. Sell or get rid of anything that feels like a hook.
4. Make sure your significant other is on board for traveling around the globe. I remember telling one of our clients what we were going to be doing and he said “My wife would never go for that! You are so lucky”. Yes Mr. Client, I am. If Amy was not interested in traveling around the world, then I would not be writing this.
5. Don’t have kids: You know that analogy about the “hooks” from a few lines up… that was great wasn’t it? Well, imagine a kid as the BIGGEST hook in the world and one that you can’t sell or get rid of for about 18 years.
6. Don’t get attached to your local community. Skip the community meetings, cancel your newspaper subscription and resign from the Playground Planning Committee. Instead, focus on the larger world you can explore, and don’t worry, the Gluten-Free Bake Sale will still need organizing when you get back.
7. Figure out what type of travel works for you. While I love to travel, I hate “travel” days. These are the days when we have to change countries. Doing this requires a complicated dance of the following terrible activities: repacking our life back into suitcases, getting a ride to the airport, going through security, flying for hours, landing in a new country, going through immigration, waiting for our bags, getting a ride to the next Airbnb, getting the key, getting a tour of the new place by the Airbnb host, figuring out the new WIFI password, finding the closest grocery store, buying the “essentials” again and finally before crashing into my new bed… trying to find my toothbrush because it’s never “where I packed it”.

That list was exhausting just to type never mind actually accomplish. I’ve seen some digital nomads on YouTube spend just a few days in one place and move on to the next. That sounds awful to me, but that pace of travel works for some people. Figure out what you want to experience by becoming a digital nomad and work backward from there to make it happen.

Amy: If you are looking to redesign your life, regardless of whether you are interested in becoming a digital nomad so you can travel the globe, or simply want more control over your daily life; my biggest piece of advice is don’t buy into the philosophy of  “follow your passion” or “do what you love.” Instead, strive to find a blend between a skill that you are reasonably good at (or can learn to be reasonably good at) and an industry that actually has a demand for that skill.  From there, figure out what type of work you can do with your skill (to meet the industry demand) that also aligns with the lifestyle that you desire.  Once you get this right and start to have more control over your life, you’ll likely have more free time and at that point; follow your passion on the side.

That “formula” is 100% how I was able to get to where I am today. I’d be lying if I said that web design is my passion.  I don’t hate it, but I don’t love it either.  What I love about it is the lifestyle that it gives me.  

So how did I choose web design? The honest answer is that Ian was already working as a freelance web designer and had the ability to work from home. So I asked him to teach me how to make websites, simply because I hated my job and wanted to be able to work from home. When I first started out in the world of web design, it met my simple goal of being able to work from home…that was almost 12 years ago. Since then I’ve been able to relocate from Massachusetts, buy a home in sunny Florida, and best of all rent out that home and travel around the world with Ian, all while still earning a good living creating websites. By applying the “formula” of learning a skill that I could be reasonably good at and is in an industry that has a lot of demand, it allows me to have much better control over the design of my life. Being a web designer still isn’t my dream job, but it’s helping me get closer to my dream life.

Note: Just because I’m suggesting getting into a line of work that you’re good at, but may not love, doesn’t mean that I’m saying do it half-assed. A big part of the success that we’ve managed to achieve is not only by being great web designers but also by delivering great service to our clients.

13 – What is one resource (blog, podcast, book beside your own) you recommend for those that want to design their own life?

Ian: NomadList.com – This site has an incredible amount of useful travel data for popular locations around the world. This data includes the best taxi app in the area, average internet speed, power outlet type, water quality, walkability, the average cost for dinner, and a lot more. Before you go to your next destination, be sure to check out that site.

Amy: I recommend the book “Get Your Shi*t Together” by Sarah Knight. The author (Sarah) talks about how she went from being an overworked, corporate employee but didn’t realize just how bad it was affecting her, until one day she had an extreme panic attack at work. This caused her to re-examine her life which resulted in some major changes. She realized that she wanted to work for herself and knew that lifestyle would give her the freedom to do it from wherever she wanted… and eventually she got to the point where she was able to relocate to the Caribbean.  It’s a quick and easy read, filled with simple, yet practical ways to tackle things like managing time, chunking down big tasks, hitting seemingly impossible deadlines, finances, decluttering…and a bunch of other things that are really important to sort out when you’re trying to take charge of your lifestyle.

Looking ahead

14 – What is next for you?

For our business:  We are starting to focus on more passive revenue streams which will allow us to simplify our lives, so we can enjoy them even more. While creating custom websites is very profitable, it takes up too much of our time. I know you’ve heard it many times before, but your time is a lot more valuable than money. To fully grasp this concept, know that most people (and this includes us) would be thrilled to make half as much money per year if it was 100% passive or recurring.

For our travels: When our time in Montenegro comes to an end our plan is to head to Greece until mid-August. Greece is closed to travelers right now but they are planning on opening up in the middle of May which lines up perfectly with our nomadic timeline.

15 – Is there anything I may not have asked that you would like to share with us?

If you are reading this interview that means you have already thought about living a location-independent lifestyle and that idea, at least somewhat interests you. But don’t fall into the “Instagram trap” where every hour of every day looks magical and exciting.

It’s not.

You will have shit days where everything goes wrong. But remember this: no matter where you are in the world… sometimes you are going to have those types of days. What you need to ask yourself is, would you rather have those shit days in your crappy apartment in the city you went to high school in, or would you rather deal with those days in some exotic city in a far away land?

Thank you so much Ian and Amy for sharing so much details and useful insights into your transformational life design journey with us. It is quite inspiring to see how two people who started working with average 9-5 jobs managed to become their own boss and are now building passive income sources to become financially independent and do what they love: traveling the world and enjoying every second of it! We hope that you will safely making it to Greece and hope to have a chance to cross your path 

Rapid-fire questions

We like ending every interview asking some fun rapid-fire questions to our guests

What is your superpower & why?	We’re unemployable.  That’s right…we consider being unemployable our superpower.  We learned early on that we hate most of what comes along with being an employee.  Fortunately, we’ve learned how to become successfully self-employed. Even though we still have to work hard many days, we love the lifestyle it gives us and will continue to do whatever it takes to never have to deal with 9-5 BS again…so I guess you could say that we’ve been inoculated against the “employee syndrome,” which makes us unemployable 🙂
What is your favorite travel destination & why?	Ian: The next one. Because in my mind, “the next one” is going to be even more amazing than the most amazing one we’ve experienced so far. Amy: Costa Rica. In the spring of 2019, we spent a week at a beachfront hotel in Playa Hermosa, Costa Rica and by the middle of the week, I had pretty much fallen in love. I was immediately drawn to the gorgeous landscape and enjoyed the food, but the thing that I was the most drawn to was the Tico’s (that’s the nickname for Costa Rican locals) motto of “Pura Vida”. Pura Vida roughly translates to “Pure Life” or “Simple Life” but to the locals, Pura Vida is more of a lifestyle…where you take the time to slow down and enjoy life.  I even found a place called Aqua Sport where it was easy for me to embrace my inner “Pura Vida.’ Aqua Sport is located right on Playa Hermosa and not only has beachfront dining (with the freshest fish tacos ever) it also has beachfront lounge chairs to lay back and soak up the sun, read a book and just plain relax; all while the food and drinks are delivered straight to your beach chair.  It’s perfectly paired with tropical music and the Pacific Ocean is waiting nearby for when you need to cool off. I enjoyed the vibe at Aqua Sport so much I found myself spending some time there each day of our trip. I’ll admit that I sometimes have a lot of “Type A” tendencies which can make it hard for me to relax, even when I desperately need to.  But I found that there is just something about Costa Rica that made me be able to relax…as in completely chill out to the point I felt like I didn’t have a care in the world.  I still don’t quite know what made Costa Rica so special to me, but I do know that I consider it my happy place.
What is the best Amazon (or online) purchase you made this past year?	The best Amazon purchase is also the one we use the most (besides our laptops) and that is a pair of Takeya Bottles (32oz). Amy’s is Pink and Ian’s is Black. We use these bottles throughout the day to drink tons of water. These bottles are on our nightstand when we go to bed and near our laptops when we are working. Using these bottles also cuts down on dirty dishes!
What is the best Airbnb you ever lived in and why?	The Airbnb that we currently are staying at is the best one so far. It’s this penthouse suite in Budva, Montenegro with a great view of the Adriatic Sea.  And using Ian’s awesome AirBNB negotiation skills he was able to negotiate a much lower price (than what’s shown in the listing). Everything in this apartment is updated, it’s nicely decorated and it’s located between Old Town Budva and Becici Beach, so walking to either place is very easy. Because all of the restaurants are closed (due to COVID-19 restrictions) we have to cook a lot, so it’s nice that there is a grocery store on the bottom floor of our building as well as another grocery store in the building next door. Having two grocery stores so close (and our private Penthouse elevator) makes grocery shopping really easy. Sometimes when I really want a deal on Airbnb, I throw in a 360 video for them to use as a promotional piece in their marketing efforts. (Scroll up to see the video about the Budva apartment in Montenegro as an example)
What’s something you can never live without?	Ian… and good wi-fi… and maybe coffee and wine 😉
What’s the best piece of advice you’ve received?	Ian: It’s hard to pick “the best” but a really amazing piece of advice is “Yesterday I was clever, so I wanted to change the world. Today I am wise, so I am changing myself” ~ Rumi. Amy: Many, many years ago (as in back when I still had a “day job”) Ian and I got to spend a couple of hours with a pretty successful real estate investor who was nice enough to share some business insights with us. One piece of advice that stuck with me, is that he said “don’t ever get into a business venture or partnership with anyone other than your significant other.” His reasoning was that anyone other than your significant other (whether it be a parent, sibling, friend, or even someone that you purely have a business relationship with) is not always going to have the same goals or priorities as you (even if at the time that you started the business you were both in the same place).  As time goes on, it’s likely that your personal life situation/business goals will change (and so will theirs). One of you may decide to have kids and don’t want to work as many hours, maybe your business partner’s significant other gets a new job in a different state and they now need to relocate, or maybe one of you wants to take the business in a very different direction than the other does.  Keep in mind, the other person’s goals are always going to be more important to them than your goals. This can become a recipe for chaos, ruin relationships, destroy the business and leave you scrambling to figure out what you’re going to do to earn money. But with your significant other, because you’re building a life together, it’s more likely that you will have compatible life goals and therefore make decisions that benefit the both of you…which is why getting into business with your significant other is more likely to succeed than if you were to get into business with anyone else. Not only do Ian and I share our lives together, but we 100% share all of the income that we earn, we have the same financial goals and also the same life goals…which plays a big part in why we’ve been able to create a successful company and life together.

Our Bottom Line

Wow. That was quite an inspiring story! Here are the main lessons we took away from this interview with Amy & Ian:

• Lesson 1 – “We wish that we had been more mindful consumers early on. […] Over the years we definitely have blown money on things that we didn’t really need. Instead, we could have spent that money on more experiences.” – Amy and Ian realized that consumerism wasn’t bringing them anything useful in their life. Amy actually confessed to me that she once spent $400 on a Coach bag that pretty much became a “closet decoration” that collected dust! By focusing on experience they get to always discover something new which is a great hack if you always want your brain to release a steady flow of dopamine (the hapiness hormone).
• Lesson 2 – “Realization [that] International travel would decrease our expenses.” – By taking advantage of geo arbitrage and living in wonderful countries outside of the United States, you will realize that it can actually be quite cheaper to live what is usually a similar (or better) life while exploring new and wonderful places. (This is actually the reason why we started this blog in the first place and came up with our tagline!)
• Lesson 3 – “Don’t buy into the philosophy of  ‘follow your passion’ or ‘do what you love.’” – This is so true but can be counter intuitive, especially if you’ve been paying attention to social media where people would promote themselves as living their dream lifestyle. As Amy said, you probably want to find something you are skilled to do and can be hired from before hitting your dreamlife and not making any money out of it.

Special offer for our readers: 

Are you still paying full price for AirBNBs? You don’t have to. You can save thousands of dollars and stay in better quality rentals by negotiating a lower AirBNB rate. Take a look at Ian’s new video course on negotiating AirBNBs (which was filmed in Croatia). Use the discount code “nomadnumbers” to save 15% off your purchase (discount code valid until May 1, 2021). The course has one of the best guarantees of any course available: if you can’t save at least what you paid for the course, you’ll get a full refund. Plus, if you get stuck, Ian will personally help to negotiate the deal for you!

Do you want to share your story?

Sometimes we need to hear about others making unconventional decisions before we can have the confidence to make our own. If you have (or are on a path to) an unconventional journey to improve your life that has a nomadic component to it and is interested to share it, please reach out to us as we would love to consider your story for our blog.