Money at 30: The Appeal in Becoming a Digital Nomad

As I’ve probably mentioned here before, one of the main reasons my wife and I decided to leave Los Angeles and move to Springfield, Missouri two years ago was so that we could save our money and do more traveling. However, before the city Springfield came to our attention, we had briefly considered relocating to Toronto, Ontario. Mind you the potential move to Canada had no politics behind it like many who (at least threaten to) move up north have — we just thought it would be fun to experience life outside of the U.S. and in a city that, while sizable, seemed to be more affordable than our current California home.

Alas, pesky things like visas got in the way of that plan and we decided to stay domestic for the time being. Still, I do harbor dreams of living abroad for at least some length of time (Japan in particular tops the list) and getting to truly experience foreign cities and cultures in depth. That’s why I’ve become fascinated by a site called Workationing, which follows two friends on their year-long adventures as digital nomads. After listening to their adventures on a recent episode of the Reason podcast, all I have to say is: I want in.

What is a digital nomad? Workationing?

Going back to my big move to Springfield, the thing that sealed the deal was that my job could go wherever I went. This meant that I could at least keep us afloat financially while my wife got settled in our new town and found a job of her own. Similarly, my ability to work with only a computer and some decent Wi-Fi means that not only can I work from home but that my home can be pretty much anywhere.

That’s the basic logic behind being a digital nomad: using technology to earn a living from wherever. Workationing site founders Kari DePhillips and Kelly Chase take that concept one step further by setting up shop in locales that interest them or offer experiences they can check off of their “bucket lists.” Specifically, the two friends are currently spending a month in several different places around the world throughout this year while still keeping up with their respective businesses and paying the bills.

The benefits of not staying put

One thing about Kari and Kelly’s concept that really opened my eyes was that they were living in places for one month at a time. In their case this means booking an apartment or other dwelling on sites like Airbnb. What’s interesting about this is that, in most cases, it means that they won’t need special work visas or other approvals beyond their regular passports to stay in the various countries.

In my mind this is a game-changer. For example, Japan allows American passport holders to stay in the country for up to 90 days without a visa. That means I could rent an apartment on Airbnb and experience Japanese life for about three months before disembarking, which sounds pretty amazing. From there we could either choose another destination like Kari and Kelly are doing or just head home to Springfield. Perhaps we could even head back to Tokyo the following year (sakura season is quite nice, after all).

The costs of workationing

Recently Kari and Kelly wrote a post looking at how much this year-long adventure was going to cost them. As they point out, renting an Airbnb for 30 days means a discount on the nightly rate, which can potentially be negotiated even lower. Additionally these rentals include utilities that would also bring up the cost of most other apartments. Thus, by their estimates, they’ll spend around $40,000 each on lodging, travel, food, and entertainment this year.

Now $40k may sound like a lot and it is — it’s certainly not something I could afford right now. But, as they mention, they’re going all out on this trip. In fact, their last abode was a luxury penthouse in Medellin, Colombia, so there are surely some cheaper options out there to bring that number down. 

Of course, with the dollar still going strong, now is actually a great time for such a workation trip as your money will go further.

While I have to admit that the thought of workationing has me pretty excited, such a dream is still a ways off for me. First, my wife enjoys her “regular” job and we have yet to hit upon a strong work-from-home opportunity for her. Not to mention there are also tons of logistical considerations to make before simply packing up and hitting the road air(?). That said becoming a digital nomad at some point is not only something that appeals to me but I suspect may interest you as well.



Kyle Burbank

Kyle is a freelance writer and author whose first book, "The E-Ticket Life" is now available on Amazon. In addition to his weekly "Money at 30" column on Dyer News, he is also the editorial director and a writer for the Disney fan site and has recently starting publsihing his own personal finance blog at

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