One of the downsides to freelance writing is that you often have to spend money to make money. Samantha has funded many work trips out of her own pocket, and at times she barely makes back what she spends. Other freelancers I've met say that working on the road can be tough logistically. They could be in a dank hotel in Thailand just minutes away from an important business meeting when the WiFi unexpectedly crashes. Or they could be sitting in a hostel bed trying to desperately finish a piece of work with a pumping party pounding away next door.
Choosing to work instead of join a party full of friendly foreigners is a disciplinary act even Deepak Chopra would struggle to master. I found this tough when I was freelance-writing in Bali (I know, woe is me). Don't get me wrong - I absolutely loved that experience, but when the beach and $2 beers were calling my name, forcing myself to stay indoors was a true act of mind/body unity.
Despite these challenging realities, being a digital nomad allows people like Samantha to experience so much of the world, and it's a job she and many others wouldn't trade for any cushy office chair.
If you don't fancy globetrotting and would rather freelance for the sole purpose of never having to take off your Pokemon onesie, there are still a few challenges with working at home. As mundane and petty as offices can be, they do provide people with a sense of community and purpose. You can talk about your day with your workmates or even bounce ideas off them, which is something people who slave away at home would probably miss.
But, and I can't lie, it's a pretty big but, freelancing gives people the option of working (or not) whenever they want. This is great for parents who need to stay at home with a sick bub or for yuppies who want to go on spontaneous trips to Bali twice a year. In their Mercedes. While watching Sky TV.
As well as computers and the internet, the reason so many people are able to freelance is because businesses are demanding it. There are many advantages to companies hiring contractors, the main one being cost-cutting. Let's face it, people spend a lot of time at work not doing work. In fact you're probably reading this now at your desk (no judgment). So paying people on a task-by-task basis can be a lot cheaper.
There are also a whole bunch of extra costs employers don't have to fork out for. These include company cars, sick leave, or extra milk for the office fridge (all costs add up). Also, getting work as a freelancer can be tough, so they will likely want to do great stuff to keep companies coming back for more.
Work can be hard to come by because freelancers compete in a global market. This means that some, especially those in IT, have to compete with salaries as low as $2 an hour. Some companies avoid these dealings because of language barriers, but some don't, making it tough for workers wanting Western wages. On top of that, the biggest struggle with freelance work is almost so obvious it barely needs to be stated - it's not guaranteed. That means if you don't find work one week you won't be able to eat or pay rent. It can be a risky business, but if you're good at what you do and can save for the slow weeks, it's a worthy way of making a living. However, it probably won't earn you enough to buy a home in Tamaki Makaurau any time soon (what would?).