Living the Digital Nomad Lifestyle

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I’ve been obsessed lately with the idea of a digital nomad lifestyle. Although I pretty much have my dream job right now, and I enjoy living in Seattle, part of me is drawn to the idea of not being tied to one location for work. In this day and age, working remotely is much easier than you think. All you really need is a computer and a good internet connection.

I recently met up with a former colleague of my husband’s, Tim Farley, a web developer who lived the digital nomad lifestyle for several years before moving to Colorado with his wife. My husband and I enjoyed drinks and a rousing game of pool with him as we talked about his experiences traveling. Later, he emailed me some more stories of his travels.

Here are some highlights from our email conversation:

Can you tell me about your experience living the digital nomad lifestyle in New Zealand?

After finding out about New Zealand’s Working Holiday visa, I dreamt of taking some time off while I was still young and before I needed to be too career-driven. I decided to apply online and had a visa within 24 hours! Then I somewhat impulsively bought a one way ticket and sold off a bunch of my stuff. I consolidated a small amount of savings, and moved the rest of my stuff back to my parent’s basement (thanks Mom and Dad!). Before I knew it, I was boarding a plane to New Zealand.

How did you make money while you traveled?

I found a non-paying job at a free-range chicken and pig farm north of Auckland, in return for meals and lodging. Then I bought a used car and found a couple on the North Island that was sailing around New Zealand and needed a “deckhand.” I did that for 2 weeks. It was unpaid, but they fed me, gave me a small space to sleep in the boat, and taught me to sail. After that, I ferried my car across Cook Strait and found a temporary job bottling wine in Blenheim.

I did some backpacking on the Great Walks of the South Island and found a job as a pizza chef in the small tourist town of Te Anau. I loved it there and worked for about 4 months. Then, I went back to Wellington where I spent a month unsuccessfully looking for a job as a web developer. Desperate, I found a job picking kiwi fruit in the Bay of Plenty (Mt. Maunganui). My year in New Zealand ended by me eventually finding a “real job” at a small ad agency doing web development. I spent 3 months doing that while living in a small hostel and learning to surf at the same time. I applied for a visa extension, but didn’t get it. So I ended up having to leave New Zealand in a mad rush.

A digital nomad visiting a chicken farm in New Zealand
Free-range chicken farm: Paparoa, NZ (photo credit: Tim Farley)

What did you do after New Zealand?

I went to Australia for a few weeks. And then flew home to Pennsylvania with a plan to return to Australia and do the same one year working holiday there. Instead, I got back together with my ex-girlfriend (now my wife). The two of us decided we’d build up our freelance businesses and become a “digital nomad” couple. We would be traveling the world while working as freelancers.

What made you decide to go on a big trip like that?

The main thing the New Zealand experience did was made me realize how easy it would be for me to continue to do things like this. When I returned home from Australia, I decided I would build up a freelance business. This process took some time, and I was lucky to be able to ease into it. I initially stayed basically rent-free with different friends and family. I did this as I ramped up my business and got my name out. At the same time, I spent time back and forth between Pennsylvania (where I crashed with my parents or my sister) and Peru (where I stayed with my girlfriend). Eventually we rented our own place in Cusco, Peru (for 6 months). And then we stayed in Puerto Varas, Chile (3 months) before deciding to tackle SE Asia. We spent 7 months in a bunch of different countries in Asia.

How long were you doing the digital nomad lifestyle?

In total, it was a little over 4 years. I left for New Zealand in September 2009 and I came back from the SE Asia trip in February 2014.

How hard was it to get freelance jobs while traveling? What kinds of strategies did you use to make sure you had a steady stream of income?

This is without a doubt the hardest part of the work-travel lifestyle. I found a combination of two strategies worked best for me: strategic partnerships and passive income. I spent some time forming strategic partnerships with design agencies. I’m a web developer, so I contacted some agencies and studios that specialize more in the design aspect and began to do work with them. This worked out very well because they were already established and had a relatively constant stream of work coming in – some of which required development expertise that they didn’t have in house.

The other key is passive income. This is the real golden ticket, but is very had to do. For me, it took the form of hosting reselling: whenever I did a web project, I always offered the client web hosting as well. Clients would pay me yearly for the managed hosting of their websites. I would then consolidate these hosting accounts to a single reseller account and was able to earn a small profit. Other ideas for passive income would be stock photos or icons, WordPress themes, web or email templates, music, podcasts, eBooks, or an Amazon Associates account. Passive income is hard to do right, but if you’re successful at it, it is the ultimate way to fund your travels.

A digital nomad kayaking in New Zealand
Kayaking Doubtful Sound (photo credit: Tim Farley)

How did you manage your income streams?

One final piece of advice regarding funds, and this is true for freelancing in general, but especially for someone who is a digital nomad: your income will fluctuate, but your expenses must be managed by a strict budget. I had months where I had a lot of invoices come in and others where I hit a dry spell and had relatively low income. The way that worked best for me was to have a separate account where all my business income went to, then I would cut myself a monthly salary from there – so in good months the business account would swell and in bad months it would shrink. As long as you’re realistic about your salary and rigidly strict about your budget, this works out well.

What’s your biggest piece of advice for someone considering the digital nomad life?

My biggest piece of advice is to choose fewer places to visit, and visit each for longer periods of time. There are several benefits to this, but the main ones are that when you are more stationary, you can save money on lodging and food, guarantee that you’re available to do work (this routine is essential), and it allows you to get to know the place as a local.

Here’s the sad truth about work-travel – you have to be available to work. Most of the people that I met while traveling fell into the category of long-term travelers: people who had spent some time saving up money and then took one long trip to many different areas in a region while slowly spending the money they had saved up. This is the traditional backpacker mentality, but it is very difficult to take this approach while work-traveling. If you’re work-traveling, you will need internet connection and will have to be available to, you know, work!

A digital nomad hiking in New Zealans
Hiking the Kepler Track, Fiordland National Park (photo credit: Tim Farley)

Resources for digital nomads

Here are some great resources to check out for those interested in the digital nomad lifestyle:

Trip Advisor – user-generated reviews of locations, hotels, etc, and can be a good resource
Capital One 360 – online banking makes it easy to create new accounts for budgeting
Capital One credit cards – this card has no foreign transaction fees and offers good rewards
Earth Class Mail – I prefer online payments, but if you receive paper checks, this is a great resource

To read more of Tim’s stories during his travels to New Zealand and his life as a digital nomad, check out his blog at

Living The Digital Nomad Lifestyle | The Wandering Daughter

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Hi, I'm Astrid

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I'm a travel-loving mom of three from Seattle. Join our adventures as we explore the Pacific Northwest and the world!

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