I've been deliberating for quite some time, testing the waters with trips that have only grown in duration and intensity.
One thing I have always done however, is return to Adelaide. In many ways I think that my return ticket was always somewhat like a safety blanket to me, knowing that at some point I will go home.
I have decided this week however that I am just going to skip the Adelaide stop over I was planning between trips, and just run back to back. This time I was supposed to fly all the way back to Adelaide, stay there for 14 days and then fly on to Boston.
The more I thought about it, the crazier it sounded to me. The more I discussed it, the more I realized that it just didn't need to go that way.
I've worked hard for the last 2 years to build a business that doesn't require my physical presence in any specific place ever, simply an internet connection (a decent internet connection I should add). Every single decision for this period has been geared around giving me the flexibility to simply keep travelling without stopping,
Previous Attempts at Living the Digital Nomad Life-Style
I've had mixed results with travelling and working thus far. Absolutely had a fantastic time in most places, except one. Which i'm not going to trash online, but if you've ever drunk with me you will know exactly where I am speaking about haha
To see a cool chart with this all mapped out by the way, you can look at my profile here on NomadList.
Nomading Through the USA
I kicked off my initial experiment with a 3 week trip in the USA, attended some conferences and tried to do as much site seeing as possible. Changing city every week pretty much, combined with not really being able to get over the sensation that I can only refer to as 'holiday brain', led to a less than productive period for me and my business.
My time in the USA actually made me start to question whether I was even cut out to be a digital nomad (remote worker, geographically unbound entrepreneur, whatever term you want to use).
The hard stats of my business showed me that if i kept it up I would find myself downsizing on staff or closing my doors reasonably soon. So I returned to good old faithful Adelaide on the premise that my hometown would obviously be the most conducive place to getting more work done.
It didn't take long for me to get a little stir crazy however, between commuting to an office space that I rented just to feel more like I had a job, and the fact that every single client in my hometown wanted a face to face meeting (so that I could explain to them how it is that I can assist their business to communicate effectively digitally) I was losing a huge amount of passion and ambition.
Days became transit and work, whilst evenings became friends who were busy and Netflix. Not exactly the pinnacle of lifestyle design that I had always dreamed about.
Nomading in Chiang Mai
A really great friend of mine (who I'm confident will one day see the light, head to Asia and stop straddling 2 expensive Australian cities 😉 introduced me to a website called Nomad List and my life was forever changed.
I'm not even sure that I had ever even heard the term digital nomad before hitting this website link in a facebook message, but it immediately resonated with me.
The site systematically categorizes and scores cities around the world on how well it is to head there and be a remote worker, with metrics such as air quality, traffic congestion and the all important average internet connection speed.
I had other friends that had always extolled the virtues of Chiang Mai, one in particular who spent months answering questions in a relative circular format, and egging me on to just pull the trigger and come.
The presence of Chiang Mai sitting square at the top of Nomadlist at the time simply sealed the deal. I took a hard look at my next few months, worked out what I absolutely needed to be in Australia for and then booked my ticket, arriving smack bang in the middle of burning season. Very well researched.
Never the less, I loved it. I love the freedom, the city, the people, the night life, and I REALLY loved the average internet speed I could get in my Apartment (for which I think I paid far more than I should have, but couldn't bring myself not to book it with a site/app that I was already familiar with.
I proved to myself in Chiang Mai that as long as I don't move around too much, I totally can handle working remotely without screwing my business over. We grew during the month that I was there. I still had issues with 'holiday brain' but they were manageable, and the work was getting done.
Nomading in the Philippines
The Philippines held a very special place in my heart and my business, as it is the primary recruitment ground for most of my workforce. If this offends you, meh.
Right off the bat however I realized a few very vital things. One, I was not going to be able to work with the WiFi connection my hotel provided, and two this was not a classic tourist destination.
Never the less I found a coworking space, and I was fully productive for my first week whilst I was in Cebu, despite meeting a girl who holds a very special place in my heart.
I only booked one week in Cebu however as I wanted to spend the majority of my time in Manila. The main goal for the Philippines was to meet all of my staff in person. At the time I had 2 employees in Manila (well Quezon City is near enough to call Manila haha), one in Iligan and one in Negros.
In retrospect I wish that I had hosted our work retreat in Cebu, but oh well. It seemed to be a more economical decision (less team flights and hotels) to go ahead and host in Manila.
The time spent meeting and getting to know my team in person was an amazing experience and was an absolute highlight of the trip.
The internet connection in my hotel in Manila saw me getting an expensive cab to get into an internet cafe each day (again, super well researched, I really wish I had stayed in Makati).
I met some life long friends in Manila, and once again, my business did not suffer during this period.
I definitely felt more confident in my ability to work remotely without dooming my business, and started researching the next trip pretty much immediately, and finally decided on Ko Lanta in Thailand (although a return trip to Cebu was definitely on the cards for a while).
Not Long into My Most Recent Trip in Ko Lanta
I was deliberating on whether or not I even needed to go back to Australia.
So I finally did it, I cancelled my return flight to Australia, which brought a whole other world of different things that need to be addressed.
Actively treating this as a life style now, and not simply frequent 'workations' meant dealing with more technical aspects of life than previously needed.
Deciding to Cancel My Return Flight On This Most Recent Trip Opened Up a Whole New Can of Worms
Extending My Thai Tourist Visa in Krabi at the Immigration Center
Having so many friends who have been through the Thai visa extension process I had mixed expectations. In fact the day before I went in to extend this one a friend of mine in Chiang Mai lamented at the fact that he lost an entire day waiting in cues just to get his extension filed and sorted.
Plenty of people on Koh Lanta assured me that this was just not the case in Krabi (especially during the low season), but I still went in there expecting to lose a couple hours of my day at least.
Well its always good to build something up in your own mind to be horrible, because then no matter what you are going to be ok. What awaited me on the other side however was no line, a courtesy counter with a digital camera ready to take my passport photo for me, and friendly staff that got the entire thing done within about 10 minutes flat.
Working Out What Insurances Will Actually Suit Me Better
I'm not an idiot, so I've never traveled internationally without travel insurance. Realizing however that I was going to be away for quite some time made me realize that the insurance products I've been using may not actually be the most effective for my needs any more.
After countless hours weighing up options, I can definitely report that... this decision still doesn't need to be made yet. My current travel insurance is still good for a few months or so. There is also every single chance that I will end up sticking with them, as I've only ever had good experiences (and unlike so many glowing reviews of insurance products I've waded through, I've actually made a claim, and still have nice things to say haha)