Being a traveling freelancer is awesome. You get to live on the road, see beautiful places, get numerous physical and mental benefits and find unexpected inspiration. And today there are more reasons to leave than ever. At the same time, it is not the same as a never-ending backpacking trip. This is a life, not an escape from one. And let’s face it, for most people backpacking is far closer to the latter than the former.
That means that though having traveling experience certainly helps, just because you’re good at backpacking, doesn’t mean you’re necessarily also a good traveling freelancer. A little more is needed.
I learned some of these skills the hard way – through trial and error. That meant it took me a while. To make the learning process easier and faster for you, I thought I’d collect the attributes I feel are important all together here so that you can read them, think about them and start developing them.
But that is only the beginning.
I’ve also written up numerous additional articles and provided links to them so that you can develop these skills and talents yourself. There will be more to come in the weeks and months to come. That means that this post – unlike many slow traveling freelancers – will not be static.
Instead, as those other posts go up, I’ll be sure to update this one with links towards these newer articles. So bookmark this page and check back often! Alternatively, sign up for the newsletter and I’ll let you know as they’re put online.
Okay, enough about that, let’s take a look at these characteristics you need, shall we?
1. Have a marketable skill or at least a passion you can turn into one
Yes, it’s kind of obvious, but that doesn’t make it any less necessary. That said, you don’t need to be a star yet. For one thing, in many places you can actually live quite cheaply while you launch your freelance writing career. For another, you can always take time out to build up your finances again.
While I was working at becoming a writer I worked all over the world in lots of other jobs. I organized parties, worked bars, wrote technical manuals, taught English and even did the occasional modeling gig.
When you do that, however, make certain that you don’t give up on that one skill that you want to turn into a career. Yes, you might be talented, but there’s a lot of competition out there. And if you want to stick out from the crowd, you’ve got to work at it. So never stop thinking about it, studying it and above all doing it.
2. Enjoy doing it (or be really disciplined if you don’t)
It can’t be just about the money, either. At least for me, it can’t. I have to enjoy what I’m doing. The reason is simple. When you’re on the road your consistently and constantly surrounded by distractions – far more so than at home.
For example, if you keep to the backpacking trails – and you probably will at least some of the time, as they’re easy to travel along, have cheap accommodation, take you to beautiful places and have at least some of the comforts of home – you’ll constantly be surrounded by people having parties and adventures.
As a traveling freelancer, you have to be able to separate yourself from that to look for work, teach yourself how to write better or write more, or hit that 8 o’clock deadline. That often means you need even more discipline than you do at home, where you’re surrounded by other people working at careers.
It doesn’t just end there, either. Often, you’ll find yourself in places where the internet and the power are iffy. That means, you can’t leave things till the last minute, as then you an outage can sink you!
3. You can market yourself
Skill alone is not enough. You have to be able to find people who need what you’re producing and then convince them to buy it from you. That means you have to market yourself (and your content)to prospective clients. I myself struggled with this skill (to be completely honest I sometimes still do). I’ve always found it hard to push myself onto others.
That has only served to make more aware of how vital a skill it is, however. It’s quite simple, really. Push yourself and you’ll have work. Don’t and you’ll go hungry.
4. You can be alone
It’s going to happen. You’re going to spend time alone – far more than if you’re just backpacking. How else are you going to get any work done?
Personally, I think the travelancer’s life is probably better suited to introverts. That said, I’ve met extroverts who manage to pull it off, so don’t be discouraged!
Whatever the case, if you can’t be alone, if it makes you uncomfortable to sit in silence without other people around you, and if you can’t sit still for hours working on your projects, then you’re probably going to struggle with this way of life.
5. You can meet people
At the same time, it’s important that you can start conversations with strangers. After all, we all need to connect with people. Otherwise, we’ll end up very lonely indeed.
Could you just travel with other people? Sure. For a while you can. The thing is, how long do you expect to do that? Traveling together – particularly with no end in sight – will strain any relationship. It is probably harder than living together because you often inhabit a smaller space.
It becomes even more difficult if you isolate yourself and don’t hang out with other people. It might sound ironic on the open road, but you’ll end up suffering from cabin fever. The best antidote to that is other people.
6. You need to be proactive
Proactivity is a skill that you should cultivate in every walk of life. Those who aren’t proactive are reactive. And they will let the problems that life throws at them balloon out of proportions before finding the energy to tackle them.
Being reactive is worse on the road, however. If you’re living in one location then often you’ll have people who care for you to badger you into dealing with your problems. Admittedly, it’s annoying (No mom, I haven’t called Dr. Michaels about the strange bump, I’ll do it tomorrow) but it works.
You don’t have that on the road. Out here it is just you squaring off against the world glove to glove. And the world is a heavyweight. The only advantage you’ve got is that you can anticipate the world’s punches and step out of the way. Not being proactive squanders that advantage.
My life philosophy is, a smart person can get themselves out of problems that a wise person would never have let themselves get into. And I try to make certain that I never have to find out if I’m smart enough.
Of course, if you’re not proactive then you’ll probably never actually venture out onto the road and instead only dream about it. So there is that.
7.You have to be skeptical
In fact, proactivity isn’t really enough. You also need a certain amount of skepticism. So if you’re one of those people that get scammed, tricked or hoodwinked – or if you often come home believing the stories the guys at the bar told, then that’s something you’re going to need to take care of if you want to be a traveling freelancer.
Yes, believing in the goodness of other people is a far nicer way to look at the world. The thing is this one of those cases where ‘wrong’ is far more powerful than ‘right’. You can be right a thousand times and only be wrong once, and yet you could lose all your money, or worse.
For that reason, it’s better to be safe than sorry.
To be clear, I’m not advocating pessimism. They are not the same. Pessimists will complain about the glass being half empty. Skeptics will take out a ruler and start a debate on whether you should measure from the middle or the edge of the meniscus.
To put it another way, pessimists base their decision on their held beliefs. Skeptics base their decisions on the facts on the ground.
8.You have to be a good judge of character
You do. It is vital that you take time to get better at reading people. After all, you’re not going to be in the safe bubble of friends and family that you’ve got at home. You’re going to be meeting new people all the time. That’s really exciting, offers a lot of opportunities and is often tremendous fun.
It also means, however, that you need to be good at figuring out who you can and can’t trust.
Now, to be clear most of the people you meet on the road aren’t bad – in fact, you meet plenty of absolute angels. The thing is, not all of them are good either. There are a few rotten apples out there and they can turn the whole barrel rotten.
To re-appropriate a common saying, you’ve got to be able to tell the diamonds from the rough. Because if you can’t separate the good from the bad, then the bad will gladly separate you from your money.
Want to know more about how to prevent that? I explain that in the post how not to get robbed while abroad.
9. You have to self-motivate
Sometimes life kicks you in the teeth. The life of a traveling writer can be hard – much harder than many of the websites let on. The question is, how do you react to life’s boots? If you’re one of those people who depends on other people to pick them up again, it’s going to be hard as a traveling freelancer.
Friendships come and go on the road. Sometimes you’re going to be around people who can help you back on your feet when things go sideways. Sometimes you’re not.
Then you’ve got to be able to do it all on your own. So make sure you can, so that you can stay productive.
10. Are technologically literate
When you’re out in the middle of the jungle and your laptop dies, you’re going to have to at least have some rudimentary technological abilities. It really is quite vital if you’re trying to freelance from the road, as your equipment is your gateway to everything – your work, your family, your friends, your research and your finances.
The better you are with technology, the better off you’ll be.
Similarly, you have to make certain you know your way around the internet. All the information is out there, but that isn’t much use to you if you don’t know how to get to it, or don’t know how to separate the knowledge from the nonsense. So make certain you are internet savvy.
11. You can maintain long-distance relationships
I don’t mean with a partner. I mean with everybody, be it family, friends or clients. It is far harder to maintain relationships online than it is face-to-face, so it is really helpful if you’ve got a natural aptitude for this. Otherwise, your relationships will dwindle and your opportunities will be fewer.
Take it from somebody who’s been quite bad at it in the past.
Your connections are vital for your sanity, for your work, for advice, for places to stay and for new adventures.
In fact, your social network is your security. So learn how to maintain it. You’ll regret it if you don’t.
This isn’t who you are?
That’s quite a list, isn’t it? Don’t feel intimidated!
These are all things you can learn. I did. Many of these skills I didn’t have when I first started out as a traveling freelancer. I was an undisciplined, reactive, lazy lout who was terrible at maintaining connections, accepted too much on good faith and was horrible at marketing his skill set.
And I’m still out here.
Admittedly, I did have some tough times and close calls. I even gave up on the traveling freelancer life at one point and tried my hand at the ‘normal’ life. I’ll tell that story somewhere down the line.
What I’m trying to say is that most of this can be learned. And as I already mentioned, I will help you learn it (with, for example, articles like this one). So do you want to be better equipped for a life on the road? Then be sure to come back frequently. Better yet, follow me on social media and sign up for the newsletter so that you can be sure you don’t miss out!
Think I’ve missed something?
Then post a comment below and I’ll add it in! In that way, this will become an ever more useful resource for everybody that wants to live the travelancer life.
My dream is that we work together. That way, we can steer each other down the right paths. We can help each other avoid the potholes of the open road. We can create a digital nomad community. Heck, maybe we can even build a real one. How fantastic that would be, right?