2016 in Review: A Year As A Digital Nomad

This post was last updated on 2024 April 13

If 2015 was the year of the nomad, then 2016 was definitely the year of the digital nomad.

Rather than aimlessly wandering around Australia for a second year, I decided to travel more slowly so that I actually had time to work and thoroughly enjoy my surroundings. My loose plan was to base myself in Australia on the ETA tourist visa and make a visa run approximately every 3 months to some nearby country. In actuality, I rarely knew where I’d be in a month’s time – and by the time 2016 wraps, I’ll have taken 26 flights this year and visited 7 countries.

It was far from the “settled” year I thought I’d have in 2016, but what unfolded instead was this beautiful period of time that I feel like I actively shaped myself. Everything that happened was my choice and by my doing – I moved when I wanted to, traveled when I pleased, worked when I felt like it. 2015 was like that as well, but this year was different because I felt more secure in my lifestyle: I didn’t have the stresses from last year around what I was doing with my life, where I was going, or how much money I had left. 2016’s agonizing dilemmas were more along the lines of “Should I take on this cool new project?, “Where should I go for my next visa run?”, or “Should I apply for this house sit?”. I’m pretty ok with having these sorts of problems, especially when I’m deliberating over them while on a weekday hike or mid-massage in some tropical Asian locale. I’m realizing that what makes me happiest isn’t traveling full-time; it’s all about having freedom.

Phillip Island walks

I won’t lie though, money is constantly on my mind because I travel with student loans. This year I wanted to secure a semi-steady stream of freelance work without going back to working full time. Instead of earning more, I wanted to see if I could save more money. That meant getting creative with all sorts of life hacks. I managed to score over 200 nights of free accommodation this year thanks to house sitting, Airbnb referral credits, blogging perks, and crashing with friends and family. I also negotiated about $2000 worth of travel-related freebies in exchange for blog posts, social media coverage, and/or photos.

I’ll have a future post dedicated to 2016 money matters (including the burning question of what my ‘freelancing‘ actually entails), but here’s the bottom line:

+ MONEY EARNED: $44,300

+ MONEY SAVED: $10,500 (blogging perks, free accommodation – assumes I’d have spent $40/night)

– MONEY SPENT: $34,500 ($21,000 on day-to-day; $13,500 on extras like student loans, visa-related nonsense, business expenses, insurance)

= NET INCOME: $20,300

I’m proud of myself for pulling all that off, but if I’m honest: I probably worked more to save that much money than I would have had I been living in one place and working full time earning that same amount of money. My life has been FAR more interesting and unconventional for it, but damn – I sure am exhausted.

sydney house sit

And not to beat a dead horse or anything, but the whole Aussie visa situation was a constant source of stress for me this year. Another reason why I didn’t want to work full time or commit to a long-term lease in Australia is because I didn’t have a long-term visa with work rights. I meticulously covered my tracks and made sure not to technically “reside” anywhere by hopping around from house sit to sublet to Airbnb. It was a brilliant way to save a ton of money and experience a variety of neighborhoods around Melbourne and Sydney, but it’s just not sustainable long term. I’m at the point where I’d rather work a bit more and invest my free time in building relationships, working on my fitness, and pursuing other interests, rather than in all the administrative bullshit involved in constantly moving around and selling myself for various opportunities.

So in 2017,  I’ll be slowing down even more and basing myself full-time in Sydney (hopefully with more local travel in Australia). I’m so relieved to be able to stay in Australia without fear of deportation, and extremely excited to unpack my bags for the first time in two years. The plan is to rent a room or house near Bondi Beach, continue freelancing, and go to school until I get my permanent residency. I’m signed up for a Marketing & Communications certificate program at a school in Bondi Junction which starts in late February, and though there is no guarantee of when I might get my skilled visa invite, word on the street is that June-ish is a reasonable assumption. Until then, I’ll just have to play the role of student in order to fulfill my student visa requirements.

brighton baths

And now, a little month-by-month recap on where I’ve been and what I’ve done in 2016:

January — Melbourne, Australia

When 2016 began, I had a boyfriend, a yoga studio, and a bike in Melbourne. It was the closest I’d come all year to a “settled” life, yet if you asked me what my life would look like 1, 6, or 12 months from this point, I’d have had zero idea. I was very much focused on enjoying the present, not so much planning for the future.

I remember January being crazy-hot (over 100F at times) and not having any aircon or fans at my Northcote house sit, clearly a very convenient time to be stuck inside furiously working on a massive project. I did manage to enjoy a few outdoorsy slash summery things, including quick trips down the Great Ocean Road and to Phillip Island.

App Guy and I called it quits this month, and pretty much as soon as it was over my immediate thought was: I’M MOVING BACK TO SYDNEY. Melbourne is an incredible city, but I’ve always known that Sydney is my place.

Favorite Blog Posts:

phillip island
Phillip Island.

February — Melbourne, Australia

This was a good month. I turned 31 and had my move to Sydney and upcoming trip to NZ to look forward to, which I think really allowed me to savor my remaining time in Melbourne. I did all my favorite Melbourne things (COFFEE BRUNCH STREET ART COFFEE CYCLING COFFEE) as often as possible while living in Brunswick.

February’s excursions included a Mornington Peninsula getaway where I thoroughly explored the ocean beaches, and another excursion to Phillip Island, this time to redeem a glamping trip I won in an Instagram contest. I had THE BEST TIME on both of these trips – seriously, they are way up there on the 2016 highlights reel. I love exploring Victoria!

Favorite Blog Posts:

mt. cook new zealand
New Zealand.

March — Melbourne & Sydney, Australia / New Zealand

Things got busy in March. I squeezed in a trip to Wilsons Promontory during my last week in Melbourne, then caught the train to Sydney where I dropped off my luggage and spent a few days before heading off to New Zealand for my next visa run to travel solo for 3 weeks.

I got smacked with some seriously terrible weather while in NZ, but still managed to take advantage of the glorious mountainous landscape by hiking, biking, and camping all over the central South Island. I conquered Roys Peak and the Mueller Hut trails, went stand-up paddleboarding on Lake Wanaka, and cycled the Hawea River Trail.

Aaaaaand I won another Instagram contest! This time I was awarded $5000 for my entry in the Find Your Way to Win $5k contest put on by the Mornington Peninsula tourism board. I used some of my winning to buy a GoPro later this year, totally justifiable right?

Favorite Blog Posts:

milford sound new zealand
Milford Sound, NZ.

April — New Zealand / Sydney & Adelaide, Australia

I wrapped up my NZ trip with 5 action-packed days in Queenstown, during which I hiked to the Ben Lomond summit, cycled around the Gibbston wineries, and took a scenic flight to (and boat cruise around) Milford Sound.

Upon returning to Sydney, I took on a house sit in Erskineville and nested there for a couple weeks in the most perfect renovated Victorian terrace house with an easy-to-care-for dog. I did NOT in any way want to leave this house, or Sydney for that matter, but I had a blogging event to attend at the end of the month in Adelaide so off I went again. I ate and drank my face off in South Australia and really got to know this undertouristed region of the country. I finally went wine tasting in the Barossa Valley and McLaren Vale, and soaked up the excellent weather by taking advantage of the free bike hire scheme in Adelaide.

Favorite Blog Posts:

sydney harbour bridge

May — Adelaide & Sydney & Byron Bay, Australia

May kicked off with the Tasting Australia festival in Adelaide, where I was one of the bloggers in attendance… which basically equated to lots of free food and wine and tours. I have so much love for South Australia after this trip – I’m so glad I visited!

Next, I flew back to Sydney to begin a month-long house sit in Lane Cove. Living in the suburban boonies gave me time to catch up on work, binge watch my TV shows, and explore the more residential suburbs around inner Sydney Harbour – i.e. I was a big ol’ hermit this month and gave zero f*cks about it.

I begrudgingly left Sydney again for 5 days in Byron Bay, which I LOVE-LOVE-LOVED for its laidback beach vibes and epic sunsets.

Favorite Blog Posts:

Koh Tao dive
Diving in Koh Tao, Thailand.

June — Sydney, Australia / Thailand / Malaysia

I was due for another visa run in June, so once again I left Sydney when I really didn’t want to (are you sensing a pattern here?) and thrust myself back into hot humid weather in Thailand. I went kayaking around Phang Nga Bay and then spent the majority of the trip on Koh Tao learning how to scuba dive… and ODing on coconut smoothies and massages, obviously.

On my way back to Sydney I had a 12 hour layover in Kuala Lumpur, so I figured I might as well leave the airport and see a bit of Malaysia for the first time. I found KL to be underwhelming, but I feel like I’d have enjoyed it more if I weren’t so tired and maybe was more of a foodie.

At the end of the month, I started my first of multiple consecutive house sits in Camperdown and attempted to get some routine back in my life. I finally joined a gym! And most important of all, I realized I could apply for the independent skilled visa to remain in Australia with permanent residency. I had no idea it would take me 5 months to get through the initial process, but so began my winter doldrums and influx of gray hairs.

Favorite Blog Posts:

Petronas Twin Towers
Kuala Lumpur, Malaysia.

July — Sydney, Australia

Life slowed down significantly in July as I settled into house sitting some needy dogs who I could never leave alone for too long. I worked on some projects and dug into the heinous visa process and bitched and moaned about how cold Sydney was getting. There were a few fun bits to July though, like taking a pole dancing class and doing the coastal walk to Cronulla Beach.

Mostly I remember being lonely this month. It was weird being settled down for a few months in one neighborhood and having some form of a routine, yet still feeling like an outsider – a visitor. I wanted friends, I wanted to date, but then I knew I’d be leaving again in 2 months and would have to start the whole process over after losing momentum.

Favorite Blog Posts:

house sitting australia
House sitting in Sydney.

August — Sydney, Australia

Oh god, August was kind of the worst. I house sat for two high energy dogs and just about offed myself. One of the houses was absolutely AMAZING, perfectly located in Glebe with a view of the Sydney skyline from the master bedroom. This was far and away the best thing about August.

For the most part, I spent the month chasing and cleaning up after dogs, reluctantly networking with fellow bloggers and travel industry folks, and chasing various people down about visa-related documents. Productive and exhausting, that about sums it up.

Favorite Blog Posts:

siargao sugba lagoon
Siargao, in the Philippines.

September — Sydney, Australia / Philippines

In September the sun came out (both literally and metaphorically) and I relocated to Coogee for what was basically my dream house sit. Caring for a cat while being a 10 minute walk away from Coogee Beach: can this be my real life please?

So the first half of the month was all about falling back in love with Sydney’s Eastern Suburbs and doing all the nearby coastal walks. The second half of September flung me to the Philippines, and I spent this time almost exclusively on the beach. I got my advanced diving certification on Malapascua and learned how to surf on Siargao: two islands I’m still aching for and would return to without hesitation.

Favorite Blog Posts:

el nido island hopping
El Nido, Philippines.

October — Philippines / Sydney & Adelaide & Kangaroo Island, Australia

The second half of my month in the Philippines took on a different tone. I was off-the-walls excited to finally make it to El Nido, a place that’s been on my non-existent bucket list for years and years… but it wasn’t quite the paradisiacal experience I’d imagined. Monsoonal rains put a serious damper on it and limited how much I could see and do. On the plus side, I met some lovely people there who I may not have bonded as much with had I been off adventuring every day. And I did get to island hop and dive with a sea turtle, so I can’t really complain.

The trip concluded with my first TBEX, a travel blogging conference that was held in Manila this year. Overwhelming, impressive, exhausting, inspiring – I’m still not quite sure how to sum up my experience, but I definitely felt all of those things at basically all times.

I returned to Sydney mid-October despite almost getting deported and spent 8 days living on Bondi Beach again. IT WAS THE BEST.

And finally, at the end of the month I took off yet again, this time to meet a friend in Adelaide for our Kangaroo Island road trip. We explored McLaren Vale and the Fleurieu Peninsula on our way to Kangaroo Island, contentedly wine tasting amidst beautiful landscapes the entire time. I absolutely LOVED living out of our campervan for 6 days and could have easily carried on for months with it.

Favorite Blog Posts:

fairlight beach manly
Fairlight Beach near Manly, on Sydney Harbour.

November — Sydney & Kangaroo Island & Melbourne, Australia

Our KI road trip wrapped and I returned to Sydney for a house sit by Manly Beach. With perfect weather and copious beach walks, early November really did it for me. Except then all my visa nonsense came to a head and I spent most of the time dealing with that and worrying about whether I’d even be able to return to Australia next year.

Later in the month, I put all my belongings in storage and flew to Melbourne for 10 days before heading back to the States for the holidays. Aw, I missed Melbs! I binged on coffee and street art and brunch and caught up with some friends and ended up having a lovely time.

Favorite Blog Posts:

sydney harbour bridge

December — Melbourne, Australia / Hawaii & NYC & Connecticut, USA / Mexico

On December 2 I left Australia to head back to the US after 2 years overseas! But first, a cheeky 12 days in Hawaii before heading home to the east coast. Anna decided to join me shortly after I booked my flight back in February, and we spent a couple days bumming around in Honolulu before flying to Kauai for our road trip. I was super nervous to be driving for the first time in over 3 years, but I had absolutely nothing to worry about – it was easy!

Kauai was incredible: we camped on beaches, took a helicopter tour over the island, poked around in so many cute little shops and cafes, and splurged for a night at the St. Regis Princeville (OMG PLEASE TAKE ME BACK). Then Anna left and I took on the Kalalau Trail, which was the reason why I booked this Hawaiian stopover in the first place. The hike was absolutely epic in every way, but if I had to do it again I’d allow more time and trek with a friend.

na pali coast
Kauai, Hawaii.

On the 15th I touched down in NYC after 2 straight red eyes (not my best idea) and made it home to Connecticut. Stepping straight into a cold freeze was painful: I had very little tolerance for cold before, but after 2 years of mostly warm temperatures I basically can’t even handle freezing weather now. I got sick almost instantly and hardly did anything during the 5 days I spent back in New York City because it was too damn cold to exist.

But man, has it been lovely to see friends and family (and cats) again – not to mention actually experience a proper Christmas! I may have been a pansy in the cold and spent too much time layered up inside catching up on work, but I did an excellent job at soaking up all the Christmas vibes.

And lastly, on New Years Eve I flew to Cancun to avoid the Obamacare penalty (if you’re American and you spend more than a month in the US without health insurance, you pay a hefty fee – no thanks!). I figured I’d spend that money on a trip instead (can you blame me?). I’m excited to kick off 2017 on the Riviera Maya with my sister Jamie and give my body what it needs: 80-degree weather.

Favorite Blog Posts:

christmas 2016

new york city
New York City.

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