On a 24-hour train from Hong Kong to Beijing, I made about $100 on board that smelly, electricity-and-internet-free compartment. Let me tell you something, that money goes a long way in Asia. While I couldn’t technically access my invoice on Ballpark or submit it for payment, I was able to complete a project, from start to finish, during an otherwise boring-yet-affordable train ride.

This is what I love about freelance writing. I can fill my waiting time with work, and feel productive anywhere I go.

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That’s not to say freelancing is easy. I spend a lot of time not making money. From wasted pitches and inquiries to endless hours of research that never come to fruition, you do a lot of work you don’t get paid for.  

You spend a lot of time (and money) in coffee shops, and there are times when you’d sell your left foot (not arm, never an arm) for “free” WiFi. As a freelance writer, you experience serious bouts of writer’s block, especially when you’ve accepted a topic you know nothing about, or when you’re distracted by anything from next month’s rent to the endless construction next door.

On a recent jaunt around Southeast Asia, I was stuck without internet for 3 days. Not because it wasn’t available, but because my MacBook Pro’s AirPort decided to take a break. Of course I didn’t have an Ethernet cable, nor did I have access to the outlet.

Unfortunately, I’d had reliable internet for the first few days, so I’d committed to quite a bit of work over the next few before heading off to a deserted island of the coast of Bali. Let me tell you, it is not fun doing research on an iTouch, writing on a MacBook, and borrowing a PC to find a way to send in your work, especially when efficiency is the only way you can really make a reasonable hourly wage.

Another time, I worked with a company that turned out to be completely disorganized, underfunded, and over budget. Much like people who go out to eat despite not having enough money for a tip, the company decided the last person they had to pay was their content writer. It didn’t matter that I’d completed thousands of dollars of work for them, or that I had all the authorization passwords to every corner of their website, they still thought it was okay to stiff me. What makes matters worse is that I was a friend and colleague of one of the partners.

How do you handle the business-personal relationship when things get messy? I considered logging in and removing the content I hadn’t been paid for yet, but couldn’t bring myself to do it. Instead, I bugged and nagged as best as I could, and was able to weasel most of the money out of my friend — but still left with an unpaid invoice of several hundred dollars.

The worst part of freelancing is that you’re always working, and you’re never really on vacation. When you’ve always got a handful of pitches in the works, and the possibility of an awesome last-minute project, it’s not possible to really shut down.

There’s always something to be done. You can’t leave your work at the office because the world is your office. You can’t ignore your work emails because they’re linked to your personal email account, and connected to your smartphone or tablet. You’re never fully at ease because of this lifestyle you’ve chosen.

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Relying on your own fickle internal discipline, the unreliable internet, and flaky clients is enough to make scores of people shy away from freelance writing. There are times when I want to throw my computer out the window and give up on this lifestyle all together.

Then I think of myself slumped down in an office chair, staring at a lifeless computer screen, chained to my desk and email. I remember being forced into useless, time-wasting meetings, and eating microwaved leftovers at my desk (the highlight of my day) for about the same meager paycheck I currently receive. I quickly click to my TripIt account and see my recent and upcoming itineraries, and I check my anger.

Every job has frustrations, but when you can work in Central Park, at home in your pajamas, or in a rambunctious youth hostel in Tokyo, you remember to smile.

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