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7 Expert Tips for Freelance Writers Who Want to Work From Anywhere

by | Jan 4, 2018

Imagine waking up to a sunny day in the mountains of Mexico. You sip coffee as you type a rough draft of a story, then head out to visit your favorite tamale lady. Later, when it starts to get hot, you return to your apartment and continue writing.

If, six years ago, you said that would be my routine, I wouldn’t have believed you. At that point, I’d just started my travel blog, with the dream of someday earning an extra $100 per month.

Without even knowing what “location independence” meant, I’d begun working toward it. I already had the travel part down; it was the remote work I needed to build up.

These days, however, I often hear from writers with the opposite problem. They’re technically location independent, and can work from wherever they wish — but aren’t sure how to integrate travel into their lives.

If you want to travel and write — either to mix things up for a few weeks, live abroad for several months or become a lifelong digital nomad — the process can certainly seem overwhelming.

The good thing? As a writer, you already have the hardest part figured out: how to make money from anywhere.

Beyond that, it’s just a matter of taking the leap. No small feat, I know — which is why I wrote this post. Hopefully, it’ll help you take your writing on the road (with as few bumps as necessary!).

1. Crunch the numbers

Yes, MATH.

Although I did my best to avoid math classes for years, I actually like budgeting — probably because I view it as a tool to help me travel more. And if you want to go away for any length of time, you need to make a budget.

First, determine your net monthly income — whether that’s from freelance clients, blog affiliates or a remote writing job. If you have recurring monthly expenses like your mortgage, cell phone bill, student loans or retirement, subtract those.

The remainder is what you have to play with on a monthly basis: your budget for food, activities, lodging, etc. From that, you’ll also need to subtract one-time expenses like immunizations, travel health insurance and plane tickets.

Use those numbers — and tools like Budget Your Trip, Nomad List and The Earth Awaits — to determine which locations you can afford.

2. Start small

You don’t have to sell all your possessions and go halfway around the world on your first trip.

In fact, I highly recommend taking a trial run to see how you like running your business from the road.

Where you go is totally up to you. Choose somewhere that calls to you (and that’s within your budget) — and don’t allow anyone else’s opinion to matter more than yours.

For her first solo adventure, writer and content marketer Jaclyn Schiff went to San Miguel de Allende, Mexico.

“I deliberately chose a place that attracts a lot of foreigners and where English is widely spoken,” she says. “Some travelers look down on this because you’re not having an ‘authentic’ experience, but I wanted to be in a place where I could easily get my bearings.”

Once you’ve figured out your destination, book a short stay: between a week and a month. Most Airbnbs offer discounts for weekly and monthly stays, and have the added bonuses of full kitchens and reviews (so you can read up on the wifi before booking).

And, if you start to get nervous, remember: Everything’s reversible. You can always come back.

3. Think about where you’ll actually work

That rental might have a dreamy view and a cute kitchen — but where are you going to write? And are you going to be comfortable while doing it?

“As boring as it sounds, you want to think about ergonomics when you’re working from the road,” says Helen Anne Travis, a Tampa-based freelance writer who recently spent time working from Peru and New York City.

“Look for a rental that has a table, comfortable chairs and space for you to spread out. I always bring an external keyboard and mouse when I travel so I have flexibility when trying to create a comfortable work space.”

4. Expect things to go wrong

No good story is free of conflict, and travel’s often the same way.

You should expect things to go wrong — from missing the bus to finding something strange in your soup.

Happy travelers don’t have better luck than the rest of us; they simply manage their expectations.

So instead of hoping to find the perfect cappuccino halfway around the world, be happy to find coffee at all. Instead of assuming every day will be perfect, be grateful for any moments that are.

“The best way to avoid frustration when embarking on a new endeavor like this is to let go of any and all expectations,” says Leah Davis, a writer who’s been location independent for four years.

“Working from the road probably won’t turn out exactly how you imagine, but that doesn’t mean it won’t be worthwhile. You may lose clients unexpectedly or find it difficult to maintain a healthy work/life balance at first, but it’s important to think of these as opportunities for growth rather than setbacks.”

View the entire experience as an adventure, a story waiting to be told, and you’ll enjoy it far more.

5. Separate work and leisure time

I’ve heard this advice over and over from friends, and I totally agree: Expecting to get work done “when you have time” is a one-way ticket to stress and burnout.

“I always fell in the trap of thinking I could get work done in the hotel in the couple of hours between travel and activities,” says Dana Sitar, a freelance writer who spent several years crisscrossing the United States. “That was terrible for productivity, and it made work stress seep into any fun I tried to have.”

Now she sets aside vacation days, just like with any other job. By doing that, she says, “you’re totally focused on work when you’re working and on experiences when you’re not.”

If you don’t want to take off days at a time, try setting aside certain periods every day. Since I work best in the morning, I try to get most of my writing done before lunch.

Stephanie Zito, a writer and travel rewards expert who’s been semi-nomadic for nearly 20 years, works for two “solid hours” before breakfast, then two again in the evening.

The knowledge of what’s waiting outside her doors motivates her to work hard during those short bursts. “I get a lot done and still have the day to see amazing things,” she says.

Eileen Guo, an independent journalist who’s reported from several countries, says it’s also important to remember what your goal is.

“Working from the road is very different from traveling as a tourist,” she says. “So don’t feel guilty about not visiting all the sites, taking time off from travel, or doing whatever it is that you do at home to relax.”

6. Don’t be afraid to go solo

One of the most common worries I hear from aspiring globetrotters is they don’t have anyone to travel with.

I understand why that seems like a deal breaker, but I’d urge you not to wait until you have the perfect travel buddy to hit the road. Getting outside your comfort zone will expose you to new thoughts and new people, and will surely inspire your writing.

Even if you’re not outgoing, you can find ways to meet people: I’ve used Couchsurfing and Meetup, and friends of mine have used Tinder. I also made great friends when I volunteered in Nicaragua and Mexico.

Or you can try one of the slew of startups that combines co-working and co-living, like Roam, Unsettled and Selina.

Schiff, who went to Mexico on her own, admits that even though she likes “the experience of navigating unfamiliar surroundings,” she was “definitely nervous” about going solo.

She didn’t know anyone at her destination, but told people about her plans and ended up connecting with a friend of a friend. Then, once there, she joined a coworking space and attended the local synagogue.

“You can’t be shy and you need to make an effort to put yourself in different situations where you can start a conversation,” she says. “You have to be comfortable taking initiative. But I found that if you do that, people are pretty receptive.”   

7. Travel light; travel slow

It’s tempting to bring everything with you — but the whole point of traveling is to do something different, to leave your regular life behind.

So remember: If you need it, you can buy it. It’s way better to purchase a $3 umbrella when it starts raining than it is to carry one around Thailand for weeks (not that I’m speaking from experience or anything).

And, more importantly, travel slowly. I try to stay in new destinations for at least a month.

Freelance writer Jamie Cattanach, who’s currently bouncing around Spain and Greece, has met many travelers who think it’s “bonkers” she stays in a single place for weeks.

But “they’re not splitting their attention between seeing the world and working — both of which are time-consuming and energy-draining,” she explains.

“You simply can’t always be on; sometimes, you need to spend a night vegging out in front of Netflix. By giving myself ample time at each destination, I get a chance to catch my breath, see the sights at my leisure, and do my work well without the pressure of FOMO.”

In the end, planning an adventure is pretty similar to tackling a big writing project.

You’ll have some crappy first drafts, and some moments when you want to pull your hair out — but if you take it one step at a time, you’ll get there. And will be so glad you did.

What other questions do you have about life as a location-independent writer? Leave them in the comments below.