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How We Travel & Work

Travel and work in Montenegro

Want to Travel? Need to Work? This is How We Do Both.


It seems like every couple has had the “travel and work conversation,” and it usually starts like this: hanging out on the couch, scrolling mindlessly through an Instagram feed looking at people’s beautiful travel pictures, and someone comments, “I wish we could work while we travel all the time - looks far better than our daily grind!”  


Well, we were there, too.  After years of daily commutes, long hours in the corporate grind, and military deployments, we decided to take action.  Travel shouldn’t just be for the mythical “influencer” (still not sure what that even means…).  We wanted to travel - but need to work - and came up with the following plan to make it happen:  


How We’re Able to Travel and Work 


  1. Remote Work to Cover Daily Living Expenses While We Travel

  2. Real Estate Investments for Building Long-term Wealth While We Travel and Work

  3. Travel and Work Projects through

  4. Extended Stays to Build Solid Travel and Work Routines

  5. Make Sure You Travel and Work - Not Work and Travel  

  6. Making the Decision to Actually Go Travel and Work


1. Remote Work to Cover Daily Living Expenses While We Travel


While plenty of people approach work and travel as a work, save, travel, repeat cycle, we weren’t comfortable at our age with blowing through all of our savings while traveling.  Instead, we wanted a way to make enough while on the road to at least cover our daily living expenses.  Unfortunately, LinkedIn and Indeed don’t have any job openings for “Trust Fund” listed yet, so we knew we’d need another way to keep some money coming in while we were traveling.  

One of the perks of international travel is that the cost of living in many spots around the world is significantly less than that of a major US city.  As such, we knew we wouldn’t need to replace 100% of our US income - just enough to cover our budgeted daily spending (which we knew would fluctuate but would, when averaged out, remain fairly consistent).  


To work remotely, the first step is making sure you’re in a line of work that actually allows for remote work, that is, something that only requires a laptop and WiFi connection.  For Jenna, the digital media planning world inherently lends itself to remote work, so she was good.  For Chipp, leaving the military with a background in security studies, things weren’t as clear.  So, back to school it was - three years and a CPA licensure later, accounting (and writing about accounting-related topics) became the skill of choice for remote work.  


NOTE: If you have a skillset conducive to remote work, here are some resources for connecting with clients as a freelancer -,,, and


2. Real Estate Investments for Building Long-term Wealth While We Travel and Work


As stated above, we felt too young to start blowing through savings to travel.  While kids weren’t an issue when we first started traveling, they were definitely in our future plans.  Plus, who knows what’s going to happen in life?  Bottom line, we wanted to ensure we had a means of building wealth while on the road, especially as income from remote work would just be covering our day-to-day expenses.  


Solution?  Rental real estate.  You don’t need to be a real estate tycoon to take advantage of the wealth-building aspects of rental income while traveling.  While having a portfolio of rental properties helps, just renting out your home while traveling goes a long way, too.  If you’re able to rent out your home, a little cash flow from the rent payments is great, but building equity is the primary goal.  Even if you just break even, with rent payments covering your mortgage and associated costs, someone else is putting money into savings for you.  Every month as that rent payment goes towards your mortgage, your equity in your house - and your overall wealth - increases.  


Is rental real estate absolutely necessary for traveling?  Certainly not.  But, it definitely provides some peace-of-mind knowing that your savings aren’t completely on hold while out seeing the world.  


3. Travel and Work Projects through  


Need to provide some background on this one - directly from “A Workawayer is: A traveller willing to help out for a few hours a day in return for a place to stay and food to eat. (Some hosts also offer a wage.)”  This awesome platform links hosts who need a hand around the house or farm with travellers willing to help out in exchange for a place to stay - the ultimate win-win!  


The benefits of embracing the community are two-fold.  First, from a financial perspective, spending time working with a local host significantly cuts down on your travel expenses, as room and board are included.  Second, these are absolutely priceless opportunities for cultural immersion.  Sure, staying at a hostel is great, but you’re not truly immersed in the local culture.  As a Workawayer, you have the opportunity to join the community, meeting awesome locals and like-minded travellers in the process.  

4. Extended Stays to Build Solid Travel and Work Routines

We expected this would be the case before leaving, and we absolutely confirmed it once on the road - working while traveling is extremely difficult when you’re moving all the time. 


If you’re moving every few days, settling into a solid remote work routine becomes next to impossible.  So, we decided on the following rule of thumb: except in rare situations, don’t stay anywhere for less than two weeks, with the ideal stay closer to a month. 


With this amount of time, you have at least two full work weeks to establish a routine - figuring out where in a place you’re physically going to work, where to grab groceries, what a good local coffee spot is, etc.  And, staying for multiple weeks gives you the added bonus of actual weekends to provide a semblance of structure to your lives (though most of our weekends start closer to noon-ish on Thursdays).  


We’ve found these long weekends A) provide us a sense of work/life structure and balance, and B) are great opportunities to take longer day trips and overnight excursions in a new area - without the guilt of feeling like you should be on the clock. 

5. Make Sure You Travel and Work - Not Work and Travel 

This may just seem like it’s semantics, but you absolutely need to remember why you’re traveling in the first place.  If you don’t, you’ll end up falling into the same grind you tried to escape by heading out to travel.  

When we set up in Istanbul - our first stop on our initial year off to travel and work - we fell victim to these backwards priorities.  We both spent essentially a full, 9 to 5 (plus some) work week, tied up in our Istanbul apartment, working away instead of exploring this incredible city.  And then, after working full days, we tried to jam a full day’s exploration into just a few hours.


That first weekend, thoroughly burned out, we realized this wasn’t why we were traveling.  Our goal was to get out and see the world - with work covering the expenses.  We didn’t want to just work our normal jobs from another apartment.  

So yeah, make sure the emphasis stays on the travel, not work, part of the travel and work equation. 

6. Making the Decision to Actually Go Travel and Work


This is the hard part.  The above may seem overwhelming, but with a few-year outlook and ability to stick to a plan, hitting the above wickets is definitely achievable.  Where people get hung up is actually doing it, that is, buying that first plane ticket and heading out.  


It’s extremely easy to rationalize not traveling.  Actually carrying out your plans is, unfortunately, far more challenging.  We’d been talking about quitting our full-time jobs and traveling for years, and we still had second thoughts and doubts about whether we were doing the right thing all the way up until our first flight.  


The “ten-year rule” put us over the edge and convinced us to go.  When in doubt, look at a situation and ask yourself, “ten years from now, will I look back and wish I hadn’t done this?”  We knew that there was no chance that, ten years down the line, we’d ever look back and say, “wow, I wish we hadn’t taken that year to work and travel the world together.”  No regrets about our decision.  


Here are our stories!

Remote Work to Cover Daily Living Expenses
Real Estate
Extended stay
Make sure
Making the decison
Travel in Porto
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