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  • Writer's pictureEddie & Megan

An Interview with The Happily Homeless

In October, Megan's sister and brother-in-law visited us in Croatia. We were staying in Zagreb at the time, but planned a 4-day trip to Dubrovnik since we'd heard and read such good things about it.

On our second day in Dubrovnik and we were sitting at a cafe bar built into the cliff facing the sea, watching the most beautiful sunset, and enjoying a few too many beverages, when a young couple passed our table and noticed one of us was wearing a Chicago t-shirt. We chatted for a bit, found out they were also traveling full time, exchanged Instagram handles, and went on about our days.

This is how we first met Lydia & Matt (The Happily Homeless). Since then, we have been lucky enough to meet up with them in Zagreb when our paths crossed again a couple of weeks later. These two are so interesting we talked for FIVE. HOURS. STRAIGHT. (right through dinner). And one of us is, in fact, a straight-up introvert believe it or not.

Today we're sharing a Q&A we did with Matt & Lydia to share a different-yet-similar perspective on full time travel.


By way of introduction, the bio on The Happily Homeless blog reads...

"Hi! We are Matt & Lydia, Indiana native’s that recently quit our jobs to travel abroad. In March 2019, Lydia and I left Chicago after 5 years where we lived the typical American Dream. By “typical,” I am of course referring to the upper 5-figure student loan debt and 60+ hour work weeks. We realized pretty quickly that this wasn't the life we wanted in the long term."

1. How long before you left on your trip did you come up with the idea to travel full time?

Lydia: Long-term travel wasn’t really on our radar until Matt obtained his dual citizenship for Italy. He was eligible to apply because of his Italian great-grandfather, but the process was extremely lengthy and difficult. The citizenship appointment at the Italian Consulate in Chicago had to be made more than a year in advance and it took that entire window to obtain all the proper documentation. Putting in this amount of time and effort sparked our initial interest in the possibility of spending an extended period of time overseas. All of these “what ifs…” eventually shifted into a sincere “why not?” Matt and I eventually took this momentum for travel into an actionable plan. In short, we put together a “check list” of items that we had to complete before we straight up quit our jobs and started traveling. The list (below) made its way to our fridge and stayed there for over two years. Once we hit that final goal, it was time to leave!

  1. Savings and Retirement

  2. Education (Matt was getting his MBA)

  3. Career Progression

  4. Learning Italian

  5. Steps towards my own citizenship

2. How did you prepare financially to take a year off work and travel the world?  Do you mind sharing your monthly budget and how close you have been thus far? 

Matt: I think the fact that (a) we put our plan for long-term travel together over three years ago and that (b) we lived fairly modestly in Chicago, it wasn’t overly difficult to map out a savings goal and timeline to fund our travels. I sincerely believe that a lot of people don’t realize (especially our network in Chicago), how much easier it is to increase your savings if you cut out some of the day to day expenses of going out to eat. We found that our friends in Chicago spent an average of $350+ per week on food (breakfast and lunch during the week and a nice dinner on the weekend). Since we’ve always been “Sunday meal preppers,” it was a breeze to hit our savings goal of $48,000 ($4,000/mo. budget) for travel while still staying consistent with maxing out our 401(k)’s as well as additional investing.

3. Your social media handle is "The Happily Homeless" but you do actually own a home, don't you?   

Matt: Touché! Yes, we do own a condo in downtown Indianapolis. However, since it was a last-minute purchase before we took off for Europe (and since we’ve never actually lived there), we’re viewing it more of an investment vehicle than an actual home. So, for all intents and purposes, we’re very much homeless (and happy about it)!

4. How have friend's and family's reactions at home surprised you?  

Matt: To be honest, there was a lot of push back and judgement before we left for our travels. In hindsight, I believe that this “judgement” was coming from a place of love more than anything else. For many of these people, they simply didn’t want us to leave because it would be the furthest that we’ve ever been from them. Others were simply afraid for our safety. And some simply believed that we were being irresponsible to leave stable and well-paying jobs.

fishing boats in a harbor on a sunny day in Split, Croatia
Reminder: Your dreams don't have to wait until retirement.

Fortunately, within a few weeks of being gone, there seemed to be a tangible shift with all of these initial feelings. Safety concerns almost disappeared overnight when they realized that every major city and country that we were visiting was safer than the streets of Chicago. The “it’s irresponsible” concerns shifted to new levels of excitement about our travels and adventures. And for those that would simply miss our company have found that they’re actually talking to us more than before!

5. What would you say to people who think your current lifestyle is only for "trust fund kids?”

Lydia: Maybe it’s my own naivety, but when I meet or hear about people in our age group traveling long term, I don’t immediately jump to the idea of “trust fund” kids. For most people, you don’t need a budget of $4k/mo. (or more) to travel. There are a number of options and places that allow a budget to actually be much smaller.

However, despite my own vantage point, I do understand where that perception comes from. For most societies, the idea of “not working” and exotic travels is reserved for the ultra-wealthy. For those people (and even those that are interested in long-term travel), I’d HIGHLY recommend two books:

  1. Vagabonding by Rolf Potts

  2. How to Travel the World on $50/Day by Matt Kepnes

Both books outline a number of ways that long term travel can be relatively easy to accomplish at any point in an individual’s life.

6. Tell us about your packing list and luggage.  If you could do it over again, what would you do differently?  

Matt: Oh man! I have to imagine that everyone who travels long-term and lives out of one or two bags will give you the exact same answer: It is an ongoing struggle to pack the right kind, and right amount of items.

For Lydia and me, we spent our first two months in Central America, and we laugh at ourselves often about those first packed bags. We had ponchos, multiple swimsuits, first aid kits, antibiotics, water shoes, etc. – you would have thought we were planning a permanent move to the Amazon.

In short, we learned that no matter where you are in the world, you can pretty much find whatever you need at a local store. So, when we took off for the 2nd leg of our journey (Europe), we packed only the essentials in 2 - 45L Tortuga backpacks. These packs included the necessary clothes, electronics (computers, camera, Kindle, etc.), and a few miscellaneous items (resistance bands for working out, a clothesline, and a daypack). And believe it or not, some of these “essentials” seemed to be superfluous as I still find myself ditching items as we move from one city to the next.

7. We know you've done a few house sits.  Do you prefer them over rentals?

Lydia: Short answer, no. Being responsible for watching over a pet and/or property is not the ideal situation for the entirety of our travels. Believe it or not, when we set our initial budget, we didn’t even know that “house sitting” was an actual thing. So, when we found out that it was a viable option for us, we signed up as a way to use occasionally in cities that are typically more expensive (e.g. Milan, Amsterdam, etc.).

However, after completing five house sits to date, we’ve found a much deeper and richer benefit of house sitting than the original and superficial benefit of “cost savings.” Let me explain. Since we spend a huge chunk of our time in Airbnbs (versus hostels or space-sharing accommodations), it’s difficult to meet or connect with new people. Now, because of house sitting, we’re meeting and connecting with locals all over the world, creating long-term friendships and a much deeper purpose in our travels other than ourselves.

8. If you could pick one aspect of full-time travel you dislike, what would it be?    

Matt: Personally, I find myself missing the day-to-day rhythm of “normal life.” Being EXTREMELY type A, I’ve always prided myself on my to-do lists, schedules, and the go-go stimulation of life in the big city. When you quit your job and start “nomading” around the world, a rhythm – especially the type of rhythm you can find in a big US city – is virtually impossible to recreate. In one hand, this is torture to a person like me. However, after a few months of travel, I’ve decided that this current lifestyle is actually a good thing for my overall growth as I’ve become much less rigid and much less anxious about situations not going according to plan.

9. Do you intend to go back to your same careers when and if you move home?  Or would you prefer to learn new skills and make a career change?  

Lydia: When we left Chicago, both Matt and I worked in the HR technology and software space. I personally believe (well, I hope) that it will be easy to slide back into a similar career at a similar pay scale. With that being said, we both worked in software sales and I’m confident that the skills we had when we left corporate America can be transferable to a number of different industries and/or roles.

To combat some of those negative thoughts however, Matt and I have made it a priority to continue our self-education during our travels. Specifically, every day we dedicate 1-2 hours to reading, writing and online courses to bolster both the left and right sides of our brains.

10. Where do you see yourselves living in 2 years?  10 years?

Matt: That is a great, albeit difficult, question! If we were to guess, we’ll probably end up in Chicago or Indianapolis in the short-term as the majority of our professional and personal networks are between those two cities. With that, one of the things that we’ve identified as a real possibility in the long-term (10-15 years out) is buying land in Eastern Italy and slowly (over a few years) building our dream home!


By now it should be clear to anyone who knows us why we got along so well with Matt and Lydia from The Happily Homeless. We admire their sense of adventure and their passion to create their own path in life.

A huge THANK YOU to Matt and Lydia for being willing to share more about their trip and their current lifestyle of full time travel. Be sure to subscribe to their blog and follow them on Instagram to follow along on their adventure!


Eddie & Megan

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