Working Remotely: 3 things I struggled with in Hawaii

Hawaii wasn’t just a three-month holiday for me. Despite what it may have seemed, I was actually working my usual business hours whilst venturing around the islands. In fact, my trip to Hawaii wasn’t even the first time I’ve worked whilst overseas. In December, I traveled to New Zealand and lived out of a car for a month, all whilst running my business, often from whatever McDonald’s restaurant I visited that day.

Working remotely might seem like a dream, but often it’s more hard work than one would imagine. Sure, you get to travel and earn a living simultaneously, but you also need to put in the hard yards before, during and after your trip. Keeping clients happy whilst you are also traveling is tricky. Time zones, adventures calling your name, and an endless to-do list can be hard to navigate – but also very rewarding! 

Below are three things I found challenging whilst working nomadically, and how I tackled them.

1. Switching out of the tourist mindset

When you’re working nomadically, you’re not a tourist, and it was getting out of that mindset that was the most difficult thing for me when I was in Hawaii. As I stayed mostly in hostels, I was surrounded by people who were traveling for weeks at a time, not months. And when you are traveling, there’s a feeling that you have to fit as much sight-seeing as you possibly can within a designated period. Whilst my friends were all off adventuring on a daily basis, there were times where I had to turn down a hike I really wanted to do, or the invitation to go out drinking in favour of doing work, and it was really fucking hard.

I tried to stay ahead of my work as much as I could so that when an opportunity arose, I knew that I could take a day off to go and enjoy myself with my friends without feeling too guilty. And when all else failed, at least I had a cellular connection so that I could get emails and messages from clients, just in case.

Working from a hotel bed is definitely a big perk about working remotely!

2. Getting distracted by people

When you’re walking around on a photo assignment, hanging out at your hostel, or sitting in a Starbucks all set up with your hard drive, headphones and notebooks, you’re going to get some curious people. On a daily basis, people would talk to me about what I was working on. Sometimes it would be a five-minute conversation, and sometimes I would look at my watch and realise that I had been talking for two hours... and I had a pressing deadline.

Eventually, I realised that at times I really needed space when I was working on something that was time sensitive or intense. So, one afternoon I spent a couple of hours walking around Waikiki looking for a quiet space to work, and I found it. On the rooftop of a shopping mall, no less! Whatever works.


3. Working around time zones

I still haven’t figured this one out. Part of the reason that I picked Hawaii to travel to, was the fact that the time zone is complementary to Australia’s. Four hours ahead but a day behind (or 20 hours, whatever is easier for you to wrap your head around) sounds easy, but it ended up sometimes being a hassle.

Before I left I spent a great deal of time trying to work out when I would be working whilst I was away. In the end, I decided to work to Australian business hours, instead of Hawaiian hours. This meant that my work day started at 1pm and finished at 9pm, and I worked Sunday – Thursday.

Sometimes this tactic worked a charm, but at other times I really needed to be flexible with my schedule. The one thing I found to be most annoying was waiting on clients to email me important documents/information and not receiving it until 2am Hawaiian time. There were a few nights where I actually got up to work at 3am because I had a deadline and let me tell you, it was not fun - but all part of the journey!

My office whilst living on the North Shore, O'ahu

In the end, I discovered that personal organisation goes a long way when working remotely. I crammed in as much work as I could during my down days so that I could go out full ball when I wanted to step away from my laptop and enjoy everything that Hawaii had to offer me!

Do you work remotely? What do you struggle with when you're traveling and hustling? Let me know in the comments below.