NOLA to Bogotá Update: What Happens when You’re Busy Making Travel Plans

I’m starting this post while sitting on my first ever Amtrak train. I’m departing from Houston, where I just flew in the night before from Cancún, and heading back to Lafayette, Louisiana, where I visited in January on my way to Mexico. I’m back in the US, and I plan to be here for several months before jumping back on the road I was on through Central America or heading off somewhere else.

I’m not sure yet if it’s a good thing or a bad thing that I’m here, but I thought it was important to share what can happen when your travel plans don’t match up perfectly with your travel reality. So here are some thoughts on the path that took me in the last month from the DF south, through Oaxaca and Chiapas, all the way to Playa del Carmen and the Mayan Riviera, and finally to this train.

Mexico City Travel Fails

Villa de Madrid, a few blocks north of my Mexico City home, on one of my last days in the DF.

Why I Left Mexico

I had already planned to leave Mexico City around the third week of July, but when I left with two friends to rip through a one-week tour of the south of Mexico, my plans were still equivocal. I’d accompany my travel buddies to the Yucatán, to Playa del Carmen, where I didn’t particularly want to go but, meh, beats being alone, why not.

From there I’d say my last couple Mexican adioses to my travel companions and regroup before taking the plunge south into Belize and Guatemala. But despite all my proselytizing here on Globalect that anyone can travel on any budget and so on, and despite already knowing the joys of going broke on the road, I decided it was better to hop on a bus to Cancún and fly to Houston, Texas. Because logic and stuff.

Travel fail playa del carmen

Sunset in Playa del Carmen, as seen from the rooftop of my hostel, on my last night in Mexico.

I left because a shrinking bank balance and a series of goodbyes all at the same time got me down, but also because I wanted to put in overtime hours on my freelance business without the distraction of working 20-30 hours a week for my accommodation in hostels and random volunteer projects. Essentially I was both pushed away from Mexico and simultaneously pulled to Florida, where I’m now sitting as I finish editing this post.

My Mexican Travel Fails

If we’re starting with the half-empty glass, there are three ways in which I fucked up in Mexico. I mean it sincerely when I say these fuckups have formed a priceless learning experience, but they’re also the reason I’m temporarily off the road and spending my days in a home office behind two computer screens. They are money, time, and people.

Travel Fail #1: money mismanagement

Mexico is cheap. Even Mexico City, by most reports one of the more expensive cities in the country, comes in solidly under most American cities in terms of everyday cost of living, and it’s a huge step down in expenses from Western or Northern Europe.

That means I was able to enjoy a pretty reasonable urban lifestyle in the DF — eating out, going to bars, visiting museums, and seeing live music, among the other trappings of such a global city with a vibrant cultural life. But even with these kinds of entertainment expenses, I stayed most of the time within a dollar or two of my $10 USD daily budget. That wasn’t the problem.

Mercado Medellin Travel Fails

Mercado Medellin, where I did much of my cheap grocery shopping in the DF.

La Bipo Travel Fails

La Bipolar (right), one of our typical haunts in Mexico City and a great place to throw back $2 beers between shots of mezcal.

My money mismanagement wasn’t how I spent my money in the DF, but rather how I earned it, namely in a location-dependent way. Despite my efforts to become location-independent, I actually ended up spending about 40-45 hours of every week on location-dependent activities, mostly working for my accommodation and a bit of extra cash at Hostel Home and teaching private ESL classes in the mornings.

Bascially, these low-hanging fruits kept me distracted from the bigger picture, and by the time I left the DF, I had little more in my pocket than when I’d arrived there. More importantly, I had established no reliable way to earn more money while on the road. Had I invested my time instead in online income — another contract writing or blogging job, some steady translation work, etc. — then I might still be on the road.

Travel Fail #2: time mismanagement

This is my newest insight into the world of long-term travel. I’m not a fan of express travel: our three-day tour of Oaxaca and Chiapas, culminating in an overnight bus, was way too rushed for me. But where do you draw the line between ‘slow travel‘ and putting down roots?

I spent seven and a half months in Mexico, about five of which were in Mexico City. Had I spent those many weeks bouncing around from place to place then I’d call that quite a thorough tour of the world’s fourteenth-largest country. But in effect what I ended up doing was just becoming a long-term guest in the DF.

Hostel Home Travel Fails

Hostel Home, my Mexico City base of operations.

When you travel long-term, you’re constantly stimulated by the novelty of everything. The lack of routine, meeting new people every day and making opaque the transparency of daily life. But when you stop long enough that you recognize and avoid the slow cashier at your local grocery store and wear headphones on public transit because experiencing it is no longer new or interesting, well, that’s a different category.

But you’re also not, not really, living there. Especially not if you live in a hostel or otherwise surround yourself with equally temporary guests. It’s like the worst of both worlds: you put down enough roots to grow numb to the monotony of the everyday, but those roots don’t go deep enough to support a whole life, to let you integrate into the culture, or develop a regular social circle.

In the future I think I’ll keep my stays to the extremes of the length-of-stay spectrum. Four or five days in most places is sufficient, and for enormous cities like the DF or for interesting Workaways or volunteer opportunities, maybe two or three months is okay. It’s about leaving on a high note or actually signing a lease and becoming part of a community somewhere.

Travel Fail #3: social mismanagement

This one is probably my most honest reason for taking a break from the travels right now. I’ve hopped on the road with $40 or $50 to my name more than once and made it work. But even if you throw a few zeros behind those numbers, the constant goodbyes still tear you down over time.

In the DF I got comfortable enough to make some real friends, not something I think I do that often when properly ‘on the road’. There were parties and camping trips and bribing cops and weekend excursions, and it was all enough that I realized about a month and a half before leaving that I’d have to do the damn goodbyes thing again. This was something I had specifically wanted to avoid after leaving Leiden the last time.

El Imperial DF Travel Fails

Seeing some live music at El Imperial in the DF, with two of the other hostel volunteers (one of whom was performing that night).

The problem with this is comparable to that of living in a university town, but on a smaller and maybe more intense scale. I lived in a hostel and associated with travelers and expats, and while I met and befriended plenty of Mexicans, most of them were coming from and on their way to some other far-flung corner. People are constantly coming and going, and you find that rather suddenly there’s no one left — either all your friends move on to their next stops or you leave and in six months you don’t know a soul in that place you called home for all those months, because they’ve all left too.

After saying goodbye to all the Class A human beings I met in the DF, I headed south with one of my best friends from the hostel and his brother, and after a couple weeks I had to part ways with them too. Then I found myself on an empty beach in a tiny resort town on the Mayan Riviera, hanging out with this iguana and trying to figure out how to go cold turkey on my social life.

Iguana Travel Fail

This lizard (one of the best listeners I know) was there for me during a dark and lonely time.

This is the pessimist’s take on my flight from Mexico and fleeing back to the safety and free food of North Florida. But there were just as many pulls as pushes: I prefer to think of myself as flying towards rather than fleeing from something.

What’s waiting in Florida

As I said, when I started drafting this post, I was on an Amtrak to Lafayette, LA. Now, as I finish it off, I’m sitting in my newly thrown-together office at home with family outside of Jacksonville, Florida, where my big bed is in my own air-conditioned room and the free food and hot water flow more or less without limit.

So now the strategy is to get back on the road, but to do it sustainably this time. In the next few months I’ll be investing all my time and energy in my location-independent work while taking some local trips and spending time with family and friends back home.

Travel Success #1: working towards location independence

This year has been huge for me in terms of professional success, and I don’t think I’ve shared that with many people yet. When I started my Latin America trip, I had nothing remotely resembling steady work: sometimes I went a whole month without earning a penny, and other times I earned $400 in a week. Actually that one happened like once.

Since starting to work seriously on my location-independent business in Mexico City, I’ve now reached a more or less steady base income of about $200 a month from freelance editing, writing, and language and communications odds and ends. It’s modest, but it’s consistent, which is a huge milestone. The last few months I’ve made closer to around $500 sitting behind my computer screen in hostels and cafes.

Jakob Gibbons Travel Fail

My eighteen month-old baby, Jakob Gibbons Freelance Language Services, who I’m returning home to pump full of human growth hormone and let loose on the world.

This year I’ve also gotten my first paid writing job with the blog Transparent Language. I’ve also, for the first time, been approached by several organizations, from online language learning communities to travel publications, who have asked me to write stuff or review stuff or in some way use my brain and my computer to get paid for stuff. That’s pretty cool too.

I’ve met a lot of other freelance whateverers this year, and probably the only common piece of advice they’ve given has been that, if I want to get really serious about this, now is the time to start pushing that snowball uphill in the form of 40 (or 50, or 60) hour work weeks until my freelance baby grows up into a healthy online communications and language services adolescent. He won’t be buying me a house anytime soon, but I need to raise him up until he’s level-headed enough not to crash my car into a telephone poll or commit socially awkward misdemeanors that reflect badly on my parenting.

That means for the next few months I’ll mostly be blogging, tweeting, posting, sharing, writing, bidding, proposing, learning, connecting, networking, and any other gerund it takes to build a business that will one day in the hopefully not-too-distant future keep me on the road as long as I’d like.

Travel Success #2: traveling like a normal person (and writing about it)

I often completely forget that one can travel even with a 9-5 job and a mortgage. Luckily, I have neither of those things, which means my life is even more flexible.

NOLA Travel Fail

New Orleans, where I visited on my way to Mexico, then again on my way back to Florida, and will visit one more time for my birthday next month.

I’m going back home to work hard, but all work and no play makes Jake a dull boy. I flew back from Mexico to Houston because I wanted to visit friends I made there and in Louisiana, and I just finished a fantastic week with them. In the next several months I’ll also go to New Orleans to celebrate my birthday, Tallahassee for homecoming at my alma mater, and nearer-by locales like Jacksonville’s Riverside neighborhood and St. Augustine.

FSU travel fail

Florida State University campus, where I’ll head in November to show some Seminole pride at homecoming.

And of course, I’ll be writing about all that here, as well as working on the enormous backlog of writing I’ve wanted to do for Globalect and other corners of the digital and analogue worlds.

Travel Success #3: socializing like a normal person

I think there’s no way to say this that doesn’t sound dramatic or self-involved, but I’ve come to believe that travelers are among the loneliest folks around. The dozens of major goodbyes and 100+ little ones I’ve said over the last few years have easily been the saddest moments of those years, and I know I’ve always got more on the horizon.

Algiers point travel fail

Ferrying across the Mississippi in New Orleans with Daniel and Josh, just two names on a long list of friends I’ll be spending time with while in the US.

With so many of the people in my life so transient, I’m really learning to appreciate not just the old friends, but the new ones I’ve really connected with in a meaningful way. The next few months in Florida will be not only barbecuing with my uncles and playing cards with my grandparents, but also visiting and being visited by all the best people whose lives I’ve managed to stumble into while vagabonding around.

The Road to Bogotá

When I look back at the original post detailing my plans for NOLA to Bogotá, I laugh in Spanish. Jajajajaja, ¿juát was I even thinking?

Three to six months seemed like a good forecast until reality kicked in and I spent that amount of time in one single city. I’m constantly relearning the lesson that life is what happens while you’re busy making other plans, and in my case those are usually travel plans.

So when friends ask me now what’s next, if I’ll head back to Central America or maybe straight to Colombia or go spend a few years in Holland, I’m never sure what to say. Sometimes I just answer with what I’m feeling that day — “yeah man, hoping to rent an apartment in Nicaragua somewhere after the first of the year”, or, “I think it’s time to work on my debt and save some money, so I’m thinking a few years in the Netherlands.”

But really I just don’t know. And that’s cool, because for now I’m doing big things in a tiny place. And I’m gonna enjoy it until the next carefully strategized move or abrupt impulse takes me off to some other thing.

Have you ever abandoned ship in the middle of a trip, either because you had to or because you wanted to? Share your thoughts and reflections in the comments below or in a tweet to @JakobGibbons!


  1. Carla · August 24, 2015

    I’ve been reading your blog for a while now like the creepy stalker I am. You’re a wild one, Mr J. I’ve been in a similar position after four months of road tripping the US…but now my freelancing business finally feels sustainable-ish?? Anyway, I really hope you get your business together and back on the road!! Let me know what niches you write in, I’ll keep you in mind for referrals. :)

    • Jakob Gibbons · August 24, 2015

      Heeey you big creep, thanks! In terms of writing I’m generally focused on travel industry (magazines and blogs but also city tourism associations and stuff like that) and grant writing in the development/NGO sector, and I also like to do bits here and there for language teachers, learners, and professionals :-)

      What kind of work are you doing? Fuck that’s exciting that it’s sustainable-ish, totes jelly. How long have you been working on it? So many questions, I think I’ll facebook message you :-P

  2. Heather Cole · August 24, 2015

    I have to say I admire your ability to be spontaneous and see where life takes you, as that is something I could never do, being an obsessive planner, especially where travel is concerned. If a trip doesn’t go entirely to plan my whole world falls apart! But for all the tough times you’ve experienced just don’t forget the good, sure you had to say goodbye to good friends, but would you rather not have met them and shared lots of fun times with them? I can’t imagine what that really feels like as we never stay in one place long enough to form proper friendships but I do think we’re missing out! Amazing what you’re now achieving income wise per month, you clearly have what it takes :-)

    • Jakob Gibbons · August 24, 2015

      I think I’m not a very ‘naturally’ spontaneous person myself, in fact it’s something I’ve learned the hard way over the last few years from overplanning trips and leaving no flexibility to enjoy myself. Do you feel like you struggle with this sometimes?

      Thanks for the positive words and safe travels to you!

  3. Lucy · August 24, 2015

    Hello from another wanderlust soul with a big desire to see the world and no money..)
    I think it’s wrong using the word ‘fail’ so many times in just one post (ajajajja) because you actually gained…a lot! you made friends, memories ,experiences and you learned a lot.. and if you call this ‘failures’ well I don’t agree..
    I admire your courage ;)

    • Jakob Gibbons · August 24, 2015

      Haha thanks! Actually using the word ‘fail’ so many times was sort of an SEO thing :-P But yeah, in seriousness it doesn’t really feel like a failure, for the reasons you’ve said! The friends and memories and things learned are always worth it.

  4. Erica · August 24, 2015

    Hi Jakob, sorry to hear about your mishaps but I’m glad to hear you were able to turn it around. I never personally had to make a 180 and change all my plans, I’m quite OCD when it comes to planning that’s why (which I’d like to think is just caused by too much excitement), so most of the time I have plan b set aside. Anyway, wishing you luck in your business and travels. And if you ever find your way in Southeast Asia, I’ll be in the Philippines for awhile, so let me know if you have questions to avoid any future misadventures, hah.

  5. Andrew · August 24, 2015

    Hi Jakob:
    Old guy here who spent about 7 years on the road, Mexico, Caribbean and Africa. It can be a lonely existence if you keep moving, and the highs and lows can give you vertigo. But there is no fail amigo, only living and learning. You’ll still be thinking about your adventures 20 years from now and practically everywhere you go in the states you’ll be the most interesting person in the room. Even if no one knows it because you don’t want to be a bragging jerk.
    PS: You should consider Africa.

    • Jakob Gibbons · August 24, 2015

      Thanks Andrew — indeed there are no fails! I think this post came off a bit more negative than I intended, and I’ll be correcting that with another post later today ;-)

      I’m more than considering Africa; in fact a long-term trip through Eastern and/or Southern Africa is sort of my ‘dream’, something I hope to do before I hit 30! Any tips or highlights to share?

  6. Janna · August 24, 2015

    Sorry to hear about all the hiccups along the way, but glad you made it to your destination safe and sound. I defiantly couldn’t have done it that way.I’m wayyy too much of an planner, as in way too ocd about it, i like to have things planned down to the hour if I can. It gets hard doing it that way, trying to loose up a bit but doubt I’ll ever get that go with the flow

  7. Charlotte · August 24, 2015

    Sorry to hear about the mishaps, it is good that you can really turn a situation around :)
    Love your blog!

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