Even though I’ve famously started this post with a “how to”, I am not actually going to focus on instructing our readers of the various ways one can seek income when traveling abroad. I’ll save that for the experts who have actually traveled abroad already and know firsthand. We never seek to be a “you should do this” blog, trying to tell you where you should and shouldn’t go, what you should and shouldn’t do, etc. It’s just not useful, and its just not… us. Who are we to tell you how to travel? All we really seek to do with making our adventures public is inspire others to travel in the first place – and should we succeed in at least causing you to consider more travel in your own life, then we are happy. What we hope to teach is that though travel is not easy, it is in fact much easier, cheaper, and rewarding than what we generally assume.

What I am referring to in the distracting title is a recent question that Emily and I have been trying hard to answer these past few months. It’s no secret that traveling costs money. Back before we knew we were going to have Carter, we assumed that we had time to save up enough to be able to pay a year’s worth of gear and in-country living expenses, while collecting enough frequent flyer points to travel between countries for free. Thanks to some nasty debt we acquired early 2013 we didn’t save up quite enough frequent flyer points to get all three of us around the world, so we had to add expensive plane tickets to our list of things to pay for, and thus severely offset the amount we were going to use strictly for living expenses. This left us with some pretty wide assumptions, such as, “Things will work out with Scott’s job.” The thought that everything would politely fall into place was a tempting ideal, but ultimately naïve.

As early as July I had announced to my “boss” that I was going to be traveling around the world within the next year, and that we would be moving out of state for a few months prior to going. I assured him that I would work the same as I always had been—after all, I was already working from home and had worked remotely all the previous summer when we were living on the east coast. He seemed at least okay with the idea after the initial shock, and that was that—I would work about 30 hours a week while traveling and our income issues were resolved.

Then things with work started to really suck.  My “boss” got weird.  He started making really awful business decisions and had major health issues that slowed the whole company down.  It went from “young, hot tech startup in growing pains” to “feeble old company with back problems and no insurance” in no time at all.  I had some serious questions I needed answered, questions about whether I could really trust this as a source of continual income for the duration of our trip.  It got to the point where I wasn’t really sure it would last us even till we left to our first country.

We began to think of other solutions.  Photo shoots around the world?  Naw.  Kickstarter?  Doubt we could pull that off.  I looked into other employment opportunities, particularly ones that would allow me to work remotely.  None trusted that I would be able to work while traveling (and I can’t exactly blame them).  It seemed I was stuck.  It was at this moment that a window opened.

Throughout the past several years I’ve been blessed to be introduced to and gain experience in a lot of skills that can be used remotely, namely: expertise in Photoshop, Illustrator, online marketing, writing, research, front-end coding (and minor back-end).  The combination of these skills have led me to believe I might have a chance as a freelance web developer / marketer. Only thing I needed now was to prove it.  Over the course of the summer, a friend and I tackled a few small website projects that we had stumbled upon, and it seemed to go well.  Later on in the year we were able to score a few other larger projects that have given more income than we ever expected from a side business.  We decided to make it official. We created an LLC, built our own website (goodbay.co), and set up everything that we needed to in order to run a web design/marketing studio online.  It was an immediate success.  It also immediately started making me lose even more of my hair than usual.

I found myself swimming in 60 to 80-hour work weeks trying to juggle the job I had already plus these new clients, stretching from 7am to up to 10pm with no breaks, 6 days a week. It was actually really awful. It was sapping my life away and making Emily’s life much, much harder as she involuntarily became a single parent.  Something had to give.  Thankfully, it all happened in a flash.

The “boss” from the older job had decided to pull some interesting shenanigans that me and my friend (who also worked with me at this job) found was beyond what we were willing to be a part of.  A messy dialogue and series of unfortunate events ensued, and in the aftermath my friend quit his job and I put in my two-weeks notice, bringing the official count of the number of employees in the company back down to 1.  The good news in all this is that we were ready to put full force behind our new business and leave our worries behind, and we could do so without working 60 to 80-hour work weeks.  Or at least that’s how it looked on paper.

Several weeks into it, my friend was offered a chance to work with an amazing company.  Being just weeks away from becoming a father himself, it was clear that it was the best decision for him to make the jump, as it was a bit more secure than the income we were counting on for our own business.  We agreed that he would help me finish up the current projects and then fully focus on the new opportunity while still remaining a passive part of the company.  Ultimately I think this was a really good move, as it would force me to learn some of the skills that he had in order to still function as a proper web development agency.  But the realization was now that my source of income, and therefore my travel plans, was solely dependent on whether I could run a consulting business on my own.  From the other side of the world.  Without a phone.  Looking dismal yet?

Well the verdict is still out.  I’m in a scramble to increase my development skills and am not taking on new clients until I can trust my abilities more.  I’m using the whereweroam.com website as a playground for writing new code and experimenting with newfound skills.  I’m doing everything I can to see what it will be like operating a business overseas when communication is tantamount (skype might be my saving grace), or whether or not web development is going to be my golden ticket at all.  The amount we have saved will last us well into the 2nd leg (between 4-6 months of traveling), but what do we do after that?  Do we come home?

As much as I want to say that the goal of hitting 12 countries in 12 months takes precedence over everything in our lives, we have to think about our future. We have to think about what we are going to do after our travels, and how we can best provide for our current and future family. When it comes down to it, the goal isn’t what matters after all. What does matter is the value behind that goal (as we’ve written about here). And what is that value?

That travel. Is. Awesome.

There may come a time in our journey where going to a new country every month may not be financially plausible. We might have to stay in a country for longer than a month (gasp!) to work out some way to move on.  But after several discussions about what we should do when we’re out of money, we’ve decided we’re not interested in coming back here. The world is our home from April 2014 till March 2015, and we will do whatever it takes—teaching english, spending a couple months learning how to code better, becoming a sign twirler—to be submerged in experiences we might never have again.

May we reach the goals that we’ve set, but at the least, stand true to the principles and values we believe in.

Oh, and if you need a website built, here’s my shameless plug.