aka. A confession: How we fund our travels
aka. Another confession: When traveling wasn’t my dream
I’m just going to get it out of the way: traveling was never my dream.
It was never my dream simply because it was never an option. I grew up in America, and I’m Chinese, which means that “a good job = a good life” is doubly drilled into my head. Which was exactly want I had. And so I was taught to hold on to it, at all costs. I didn’t even dare to dream of a life outside of the cubicle walls, and only took short weekend trips like a good dedicated employee. I did feel like something was missing, and yet, I thought this is what life was about… how smart, successful people lived. I thought I had achieved what I worked so hard for all my life.
Sure, I wanted to see other countries… but I thought it was only possible 2 weeks at a time. And plus, I also had the slight problem of not having anyone to go with, so I didn’t (lame, I know).
Then I met D. He had dreams, he had freedom, he had ambition. In other words, he was the complete opposite of me. He lived his life on the outskirts of the confines of society. He owned his own business and didn’t answer to anyone but himself.
By the time we met, his crazy start-up years were already behind him, and he was probably only spending 3-4 hours a day in the office. The rest of the time, he spent on working out, long lunches, happy hours, hours of TV… (or so it seemed to me, and yes, I kinda hated him).
In actuality, it wasn’t all sunshine and rainbows. Soon, I learned that he also spent plenty of nights abating server shut-down disasters, fixing other people’s screw-ups, and worrying about google search engine rankings. This past year has certainly been a testy one (with the recession and all that), constantly hovering between finally achieving the dreamed of success and falling back so hard as to practically start over.
This is the story of how this dream of travel started, how it almost died, and how it finally came to be.
Blame all this travel nonsense on a little book called The Four Hour Workweek, by Tim Ferris. Perhaps you’ve heard of it. We were researching for a vacation to Costa Rica, which led us to a travel blog, which led to another one, the author of which was once featured in this little book. With hardly a second thought, D purchased the book right away. Basically it promises to teach what the title suggests: how to cut down your working hours to 4 hours a week instead of 40, while increasing productivity and efficiency. That’s right… 4 hours a week.
And guess what the author suggests you do with all the newly earned free time? You guessed it: travel.
This ignited the first spark of the idea that such a life could be possible. D really bought into that. If you read the book, you would too. It has a way of making you believe that the impossible could be possible, that the crazy could be reasonable, that dreams could be reality. From that point on, he worked hard to implement the strategies of the book.
March 2013 was a particularly good month for his business. His sales were the highest they had ever been. And fresh off the inspiration from The Four Hour Workweek, D had turned his little humble business around to be a sleek-running automated machine. The future looked bright. The dream of total freedom and traveling the world was not so distant anymore.
But all that would change. After the super successful March, sales took a nosedive and kept on going downhill from there. It was getting scary. A few straight months of falling sales later, the business was barely even turning a profit. But that wasn’t all… the worst was still to come.
At the end of August, D’s best friend and office manager, who he had trusted to manage the daily office operations for 9 years, inexplicably went AWOL. D never found out why (though we could guess it involved a crazy girl and a mental breakdown).
After that, things became unsure. D and his business partner absorbed Rich’s duties and went back to working 8+ hours in the office. It seemed almost impossible to leave the business behind now. Meanwhile, I was dealing with some demons myself, including serious stress about quitting my job. I even offered to keep on working in case his business falls apart (as much as that would crush my soul). But D didn’t want to hear about it and never once did he say “we can’t”.
All we had to do was look at things a little differently.
As horrible as it was, Rich leaving turned out to be a blessing in disguise. Having lost the glue that holds the office together, and yet refusing to give up on the travel dream, D was forced to look to more creative ways to run the business, using many of the strategies from The Four Hour Workweek. In the end, this even allowed him to reduce overhead costs by using overseas assistants. D was once again, able to break free from the ties of the office.
All this became a bit winded, but what does this mean? We are still making our travel dream happen. It just means that we cannot travel as freely as we originally anticipated. D is still picking up the pieces a few days a week, working with and training the overseas assistants. And so on those days, we stay put in our rental, both of us working away on our laptops. And because we do need to be constantly attached to the internet, we won’t be adventuring in the Amazon rainforest or hiking Patagonia anytime soon. But who can complain when we are still living the dream!
Because we do have a source of monthly income to fund our travels, this blog isn’t exactly a budget travel blog, (though there are few things that make us happier than delicious cheap street food). And of course, as D’s standard middle-class income is not showering us with money either, this blog also isn’t a luxury travel blog. You won’t see us staying at 5 star resorts, nor at $5/night hostels with cold showers. Rather, we prefer the happy medium – private apartment rentals that allow us the privacy we need to work.
If any of you even read this far, you rock! Seriously. And thank you to all the readers who are following along on our travels!
And oh! We never did take that vacation to Costa Rica. What was originally a one-week vacation has turned into a new full-on nomadic lifestyle, which will hopefully take us on many adventures around the world. For how long? For as long as we remain curious about the world, share this crazy dream that was never even a dream, and can stand each other. :)
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Check out D’s blog here.

Ah, this makes me so excited! I currently freelance (writing, photography, marketing, anything I can get my hands on really). My boyfriend also owns his own business, and hopes to have the freedom to step back and let employees do the work one day. Then we want to travel the world, living off our little businesses. Although I would have to work a couple of days a week, but I’m sure that just means you take travelling slowly.
Thanks for sharing your story Anna!
Chalsie | The Workshop Co. x
Thanks so much for reading Chalsie! I’m loving your blog!! :D
If you guys already own your own businesses, then you guys will be just fine! Since your boyfriend has employees, I recommend The Four Hour Workweek (he’s probably already read it!). That book was what made D realize that travel was possible! And it didn’t take that long to step back and rearrange his duties to be online only. He’s not exactly down to 4 hours a week, lol… maybe like 4 hours a day, or a little more. But that’s doesn’t matter because he now gets to work from wherever in the world in wants! Best of luck to you guys! I’ll be following your adventures. :) x
Wow. I just came across this post… what a story you two have! I’m amazed by what you do and am so glad to be along for the adventure! xoxo
I’m thrilled to have you along too, Daisy! I have to attribute our life to my boyfriend. It still amazes me that we’re able to do this and that he’s really able to run his business from thousands of miles away!! He works hard, but it’s so rewarding to be able to work wherever we want!