Guest post written by Shira Weitz, traveler, actress and blogger extraordinaire.

Before quitting my day job and giving up my over-priced apartment in Los Angeles, I longingly scrolled through Instagram, getting a glimpse of what looked like a glamorous life of whimsically dancing from country to country, from waterfall to waterfall. I was, in short, seduced by the idea of life as a digital nomad. 

I asked myself what was stopping me from becoming one of them? It seemed like left and right, more people were choosing to give up a more materialistic way of life in favor of finding remote work. I sold most everything I owned and began my research on how to achieve location-independent work.

It’s been an amazing journey thus far, but I would be lying if I said it was easy. I’ve had panic attacks in Italy, and moments where I was shrouded in doubt in Amsterdam, quite frankly, feeling like an idiot for imagining that I could possibly be capable of this lifestyle. 

Yet, every time I manage to come out on the other side of things. If you have the guts to take the leap and join in on life as a digital nomad then you will overcome the hard times, too. 

I like to look at the preparation for this lifestyle like a trip to Morocco… you can never quite prepare yourself for the chaos, but it sure does help to know certain things in advance, like, say, that shopkeepers will try and block you in their shops until you purchase something. When you know what obstacles are likely to arise, you have a better chance of not being thrown off, and therefore, not wanting to give up. 

Finding remote work is a hustle and it comes at a cost, but you shouldn’t let it stop you. To prepare yourself for what’s ahead, here are some pitfalls to be wary of and how to avoid them.

It takes time to start a business, and your income is never secure.

Before starting on my journey, I had a side gig freelancing for a friend of mine who worked in marketing. I composed press releases and other marketing materials and she paid a great wage. She was super encouraging that I could build a career around this. 

“This will be a piece of cake!” I thought… but I was wrong. Without an existing portfolio and extensive work experience, it was incredibly hard to compete with others, even just landing an interview or a trial run. I was faced with a ton of rejection and it was extremely discouraging. 

On top of that, the jobs I was getting offers for were much lower paying than I was anticipating. Additionally, I got very excited about opportunities that seemed like a sure thing, only to have said opportunity drop off the face of the planet without a word. 

Anytime you’re starting a new business or a new career, it’s going to take time, effort, and extreme patience.

How to avoid:

Give yourself plenty of time to save and get your ducks in a row before trotting off around the globe. If you have the ability to make the ultimate millennial move and live at home for a few months before starting your journey, do it. 

It will be tempting to take on a full-time (or even part-time) job so you can save as much as you can, but I would advise against anything that will leave you too exhausted to put in the effort needed to launch your business- which is basically a full-time job of its own! 

I got a casual job, working the front desk at a workout studio for a few hours a day. The pay was minimal but added up, plus I got to work out for free!  

Stay focused and don’t let rejection shake your confidence. Keep plugging away, knowing that it will be small bits of progress that will lead you to your desired outcome. 

Since I was pursuing freelance writing I started my own blog, not for the purpose of monetizing it but for the purpose of practicing my craft, getting on a routine and building a portfolio. It became MUCH easier to apply for jobs, and I was getting a much better response rate as well. 

Start off slow. Like, incredibly slow. Make sure you have some savings to fall back on, not if, but when things slow down, or clients disappear. 

If you’re desperate to flee your homeland (or don’t have a way to live cheaply while saving) start off by picking a place that’s known for being cheap and stay for a while. Give yourself time when you arrive to settle into a routine that generates (at least) semi-steady income.

Productivity is hard when there’s so much to do and see and I don’t know what time or day it is!

Yes, especially for people who aren’t seasoned travelers, it’s incredibly difficult not to get lost in the hustle of a new city. Isn’t that the entire point, anyway? 

Self-imposed routines are hard enough to maintain when you’re in the comfort of your own home. When you find yourself in a new, exciting and beautiful place, it’s nearly impossible. Not only are you constantly meeting new people, but trying to navigate the basics, like transport and eating cheaply, can overwhelm you. 

Hostels that have a big common area for working will likely have a bunch of guests flocking in and out to socialize.  Even now, as I write this article in the lobby of a hostel, I’m listening to the other guests enjoy a card game on the rooftop terrace, overlooking the stunning Moroccan city of Fes. (Fear not, I got my haggling in early this morning.)

Distractions are everywhere when you’re traveling, and depending on your location you might not always have the resources you need to be productive. Maintaining productivity and staying motivated are among the hardest challenges to overcome when you’re always on the go.

Sometimes, I’ll try leaving work for a long train or bus ride, only to find it’s still hard to choose productivity over sleep, catching up on social media, or, ya know… doing nothing.

How to avoid:

There are several ways to increase your productivity! Sometimes, a good place to start is to figure out what kind of workspace gets you in your zone, and what time of day (or night) you’re most productive. Are you able to focus when other people are around? Do you need to shut yourself off in your room? Do you wake up early with a burst of motivation? Or is your brainpower unleashed in the night? 

Your ideals might not come into fruition immediately, but having specific and achievable goals to work towards will help you stay on track.  

Finding and staying in a co-living space is a great way to make sure your focus stays sharp, as you’ll be surrounding yourself with like-mind, motivated individuals. You’ll get to witness how other professionals balance working with playtime, and there’s less awkwardness or guilt that stems from politely asking others to bugger off at a hostel. 

Make sure when you’re heading to a new place that you’re giving yourself enough time to get work done and explore. That way, you won’t feel anxious sitting inside and buckling down for a good portion of the time because you’ll know that you’ll soon have some well-deserved freedom. 

Just by socializing with other digital nomads, you’ll learn tips about where to stay and what restaurants to go to that are optimal for getting work done. 

One last, but major way to stay productive is to make sure you’re doing work that you love, and don’t bite off more than you can chew at one time. I’ve had moments where I said yes to an assignment, and then realized that my heart just wasn’t in it, and that it was excruciating trying to focus with temptation all around. When that happens, be kind to yourself, do your best to finish your contract, but know that there are times when the money may not be worth the mental stress.

Stay tuned for part 2 of “The Pitfalls of Remote Work and How to Avoid Them”, coming soon…

Where to next? Find flexible month-to-month rentals across the globe on Anyplace.


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