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Travel Planning: Part One — You Might Want to Travel the World. Now What? Considerations for Long-Term Travel

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In part one of this two-part series, we will walk through discussions to have prior to organizing a long-term trip and the tactical steps you need to take prior to taking off for your adventure.


There are few things more exciting than translating the dream of travel into reality.

While movies lead us to believe that setting off requires little more than researching a handful of destinations, purchasing a ticket, and packing,  it’s actually more nuanced than that. 

Yes, there are people who sell everything, purchase a one-way ticket and figure it out on the go, without a timeline for return home. 

We’d bet that the majority of folks don’t fall into that category. For those who are looking to take a more structured approach, this post is for you.

It is through our learned experience that we implore you to think about how traveling for an extended period of time (however defined by you) may impact your life. We’re talking about everything from housing, career, dependents, finances and even the internal changes that can happen as you fundamentally change your surroundings.

Our story

It was over dinner in Austin, Texas, that our plan to travel the world was born. A conversation that started by reminiscing of our favorite travels together turned into what we hoped for in our future. 

When we first thought about traveling , we never imagined we’d find our way to Struga, Lake Ohrid, Macedonia

We were newly engaged, still creating drafts to as what a life with one another looked like. While we didn’t have all the specifics — who really does — we shared an enduring sense of adventure and desire to explore cultures outside of our own. 

We contemplated how long-term travel might impact our respective careers and our finances. We went back and forth about what to do with our apartment and our material possessions.

Moving from hypothetical conversation to formulating a real plan

Over the next months, the thoughts shared over that dinner in Austin turned more formal. If we were going to do this, we needed to create a real plan. A plan that considered things like how, and when, we’d inform our workplaces about our trip. A timeline of what needed to be done before we departed. Throughout our planning, we continuously asked one another if this what the other really wanted to do.

We made the decision to move forward and do the trip because we thought it was a once-in-a-lifetime window of opportunity to build a foundation for a future marriage.

The plan was as follows: we would travel in six month stretches, with two-week visits home. We wanted to travel light by living out of two Kelty 40L backpacks and a single personal item each. We would only return back to the States outside of our scheduled flights home in the event of a family member’s death. We wanted to visit a variety of countries and cultures — and in the end our trip turned into a five continent, 35 country, 250 city expedition.

It did take time to determine the specifics — everything from how long, to where, to how much we felt comfortable spending. It was an exercise that we went through multiple times — and it very much mattered because had we not understood one another’s answers, we would have been in for a world of friction and headaches later in the trip.

Assess how travel will impact you

To help other travelers get the most from their journeys, we’ve compiled a series of questions that you can think through as you consider any kind of long-term travel. We’ve kept the list to the basics for you to expand to the particulars of your own life.

If you’re planning on traveling with someone else, we can’t stress enough that you talk through these answers together. We’ve met a number of travelers along the way who discover early on that they aren’t actually compatible travel mates. It leads to quite a bit of turmoil, and unfortunately, spoiled friendships.

The goal of these questions is to get a sense of what you are looking to get out of the trip, assess your day-to-day life looks and how things might change once you’re on the road.

Work through these questions a couple of times over a month to ensure that you’ve had adequate processing time. Once you feel you’ve got a good grasp on your answers, begin pulling together a more formal plan for how you would approach this trip given your current station in life.


Questions to ask yourself before you travel long-term

Travel Style

  • What gets you excited everyday? What does a great day look like? Is it hiking for 10 miles through nature? Curling up in a bookstore and getting lost in a new novel? Exploring a bit of the sights and the outdoors?
  • What places interest you? Where would you want to go?
  • What are you looking to get out of this trip?
  • How often am I planning on going home? Will it be one long trip or broken into pieces?
  • Are you more interested in seeing as many countries as possible or getting to intimately know a country and it’s collection of townships, cities and nature?
  • How would you stack rank the importance of money spent on accommodation, experiences + sightseeing, shopping, and food? Does one category stand out as more important than the other?
  • Do you like working off a set itinerary or figure it out on the go?
  • When you get irritated, how do you typically resolve conflict? How would you expect a travel companion to work with you through the irritation?
  • If something takes a turn for the worse at home, how will you plan to approach it? Will you go home? Will you stay abroad?

Dependents (Pets)

  • Who would be willing to look after any pets you own?
  • What kinds of costs does my animal carry that you would need to include in a budget when you are away?
  • How might your relationship change with my animals by being away for so long?

Career

  • Will you plan to work when you travel?
  • How much self-worth do you derive from your job? Will you have a hard time adjusting to life without one?
  • Will you have to “start over” if you quit or can you pick up where you left off?
  • Can you work with your company to organize a position for when you return?
  • If you were to return and discover that your colleagues had been given promotions that “put them ahead of you” in the workplace, would this bother you?
  • If your interests evolve as you travel, are you in a position to change careers?

Finances

  • How much money do you have to spend on this trip?
  • How will you manage your finances when traveling? Will you leave your money in cash and investments or liquidate or?
  • If your investments take a downturn, will you still be able to afford the trip?
  • How will you pay for items when on the road? Cash, debit card, credit card, traveler’s check? 
  • If traveling with someone: Are your travel budgets aligned? If not, how do you plan to reconcile that?

Housing + Material Possessions

  • Will you continue paying rent in my apartment or will you break the lease?
  • If you own a home, what are you plans for having someone rent it out or look after it?
  • What will you do with your material possessions?
  • What items will you keep/sell/donate? 
  • If you have valuable items, where will you store them?

Health + Insurance

  • Are you in good health? When was the last time you checked?
  • Are you up-to-date on my vaccinations?
  • How will you get any medications needed when you are away?
  • What kind of travel insurance do you need to purchase to cover you while you are away?

In part two of this series, we walk through the logistical and tactical items that we completed prior to departure.

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