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To Fly or Travel Overland from Colombia is Catch-22

CARTAGENA, Colombia- I looked over a map of Latin America, plotted my position in Colombia, then looked for my next move. I would like to go to Mexico or Buenos Aires, but I have no exit strategy. I am going broke, I need to be in a place where my wife can teach English and [...]

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CARTAGENA, Colombia- I looked over a map of Latin America, plotted my position in Colombia, then looked for my next move. I would like to go to Mexico or Buenos Aires, but I have no exit strategy. I am going broke, I need to be in a place where my wife can teach English and get paid a decent wage. How to get to Mexico or Buenos Aires?

This was the question.

Would I go north to Panama, Nicaragua, El Salvador, Guatemala, Mexico, or south through the Andes, and cut across South America bound for Buenos Aires? Both overland routes seemed arduous — it is getting difficult to take long bus journeys with my daughter, and one right after another would be a horrible experience. I thought of flying, but buying three full priced plane tickets is costly even if you do find a cheap flight.

I felt stuck, buried deep in a hole in Colombia.

To add to this, my cash reserve is dwindling fast —Colombia is not a cheap country to travel in, and I am spending more here than I have ever regularly spent anywhere in the world. As an additional topper, our 60 day tourist visas were running out, and renewal would mean paying $120 for each additional 30 day period that my three person family stays in this country.

Perhaps for the first time in my travels a clear path was not evident, I felt as though I was in a Catch-22 were each solution to my problem was unattainable in my present circumstance.

Catch-22 defined:

A Catch-22, coined by Joseph Heller in his novel Catch-22, is a logical paradox arising from a situation in which an individual needs something that can only be acquired by not being in that very situation; therefore, the acquisition of this thing becomes logically impossible. Catch-22s are often spoken with regard to rules, regulations, procedures, or situations in which one has knowledge of being or becoming a victim but has no control over it occurring (i.e. heads you win, tails I lose, output is the input…) –Wikipedia, Catch-22

A Catch-22 of travel:

When staying in a location is a poor option but leaving only presents poor options as well.

My Catch-22 in Colombia:

I could not afford to leave Colombia nor stay in Colombia. The longer I stay in this country the less money I will have to leave it, but I cannot afford to leave until I have more money.

Catch-22 book cover

I grew annoyed with myself for flying into a country without firmly thinking out my next two moves, for not having plotted out a firm exit strategy. I felt frustrated, angry over my lack of income, for not being able to give my family the freedom of motion and comfort that I once envisioned. The entire Vagabond Journey project seemed to be a Catch-22 in its own right: my family can live off this web site indefinitely if we never step foot on an airplane, but long distance overland travel is becoming a real pain in the ass. If I’m working on this website, I am not selling articles and writing for other publications whereby I could make more money.

What do you do when you are going broke? When the road seems either too arduous or too expensive in all directions? When the relations of your traveling group appear to be breaking down? When the life that you built begins to crumble around you? When you know that you need to get out of the country you are in, but do not see a clear path ahead of you? 

“In any moment of decision, the best thing you can do is the right thing, the next best thing is the wrong thing, and the worst thing you can do is nothing.” -Theodore Roosevelt

The traveler’s solution:

You go to where you know you can live well, make money, and re-stabilize. At the cost of going completely broke, you make it to one of your safety hubs — a place where you know you can repair.


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Filed under: Colombia, South America, Travel Strategy

About the Author:

I am the founder and editor of Vagabond Journey. I’ve been traveling the world since 1999, through 91 countries. I am the author of the book, Ghost Cities of China and have written for The Guardian, Forbes, Bloomberg, The Diplomat, the South China Morning Post, and other publications. has written 3720 posts on Vagabond Journey. Contact the author.

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VBJ is currently in: New York City

4 comments… add one

Leave a Comment

  • David October 11, 2011, 2:01 am

    So where are you going then??

    Link Reply
    • Wade Shepard October 11, 2011, 9:01 am

      Read today’s entries to find out!

      Link Reply
  • brandon October 11, 2011, 6:24 am

    Is teaching English not possible in Columbia because of highly restrictive work permit laws?

    Link Reply
    • Wade Shepard October 11, 2011, 8:50 am

      I am not sure about this. Though I can’t say that I have yet met anyone teaching under the table. Will check into this, as it would be good to know.

      We are all pretty much ready to get on from here though. We came to Colombia to look for a few places to stay for 2-3 months, but we just didn’t find anywhere we wanted to stay for this long. Funny stuff, truly atypical.

      Link Reply

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