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When the digital nomad lifestyle first began to draw my attention, it was easy to picture myself lounging in a cushy pool chair, laptop in lap, looking out over the seemingly endless horizon of where warm, golden sand meets blue-green waters. I would probably have a super feminine drink in hand, complete with a tiny umbrella as the final touch. The less sexy details of working remotely however, like dealing with WiFi connectivity issues, lack of 4G coverage, and timezone coordination, I conveniently left out of my daydreams. In hindsight, it is important to recognize the smaller, less alluring details because they are key as to why the digital nomad lifestyle—and working remotely as a whole—is a pipe dream for so many of us.

It’s true; working remotely is a dream come true in many ways. I wake up when I want, work where I want, and take breaks whenever I damn well feel like it. I have no one breathing down my neck about my KPI, adherence to their attendance policy, or putting their own agenda above the company’s success or my own. As long as I get my sh*t done, I get paid. Better yet, once I achieve that initial momentum, I’m granted the ability to be choosy with which clients I take on.

Before I get carried away though, the levels of freedom and flexibility afforded by freelancing do come at a heavy cost (and not just monetary). Let’s be honest, so many people in the 9-5 workforce sit in mind-numbing commutes and deal with their fair share of B.S., but freelancers do too. There are days as a remote worker where you want to throw in the towel and disappear just the same.

There is a dark side to working remotely (both nomadic and not) we tend to leave out of our fantasies until we experience it firsthand. You must continually adapt to external circumstances (weather, 3rd world infrastructure, travel delays, etc.) or you’ll risk becoming more jaded and bitter than Han Solo’s emo progeny.

1. Routines Suck, But Working Remotely Requires Them

This is number one because of the sheer potential this has to positively or negatively impact your success as a skilled professional. Without a compulsory, work-mandated routine, you are responsible to create and maintain your own. If you are like me and dislike any structure more than being asked about the World Cup as an American (USA is out? Who cares, REAL football is about to start), you are going to struggle at times.

2. Getting $%^& Done Requires Consistency & Effort

With the certainty of an atomic clock, intricate problems show themselves at very inopportune times while you work remotely. If you expect a solution to be any easier because of your sweet view of the Petronas Towers from your bedroom-turned-office, you’re in for a rude awakening. There are times when you just wish you were sitting face-to-face with the people you’re working with, or at least to be able to do certain things yourself.

3. Having Reliable Internet Isn’t Always an Easy Feat

While passing through Thailand, Malaysia, and Singapore, I discovered a wide range of connection qualities and speeds. Some places with amazing WiFi quickly lose it during a thunderstorm, which is pretty much everyday. In one case, lightning struck the building I was in and fried the fiber optic node–that was a fun week. Keep a data plan on your smartphone just in case you need an easy hotspot.

4. Grab a VPN Service Like VyprVPN to Get Around Blocks

Say what you will about the media in the US, but we are very blessed to have our first amendment rights. Many of the countries you pass through have strict filters to protect their own ideas and ways of life. You may need access to websites and tools that are otherwise blocked, so plan accordingly. Remember, once you step off that airplane, you are in someone else’s homeland. Even with a VPN, be conscious of your online activities.

Another important VPN feature you’ll need is called geolocation spoofing. For example, when I access a certain client’s Instagram account, I need to look like I’m in Seattle, the client’s home area. Otherwise, even with the right password, Instagram will lock and flag her account as compromised (we learned this together the hard way).

5. Printer/Scanner Combos Are Gifts From Above

This should be self-explanatory. Save yourself from future headaches and go buy a decent printer combo if you plan to stay put for a while. At the very least you would be wise to locate the nearest print shop.

6. Opening a Bank Account? LOL, Good Luck

Unless you’re lucky enough to be accepted into Stripe Atlas, you’re going to have a tough time running a US-based business from afar. Open any bank accounts you need BEFORE travelling abroad. My latest project, an online women’s clothing store called The Heritage Fashion, nearly got deep-sixed before we could even launch, because the banks were afraid of a remote account holder. If it wasn’t for the actions of my partner back home we’d be done for, which leads me to point #7.

Also, make sure you notify all your banks and credit card companies (including PayPal) of your travel plans so your cards don’t get blocked, or worse, you get locked out of online banking. Opening a bank account in a foreign country usually requires that you have a work permit/employment visa in that country, so don’t depend on that either.

7. Be Picky With Your Business Partners

Whether you’re looking for a local business partner or one back home, choose with your third eye. Your hometown or high school friends, for example, are usually terrible choices. Why? Because many of them privately envy you and your perceived success. Some will smirk when they see you going through a difficult time. You—and only you—will understand the struggles and hardships you experience. Bearing that in mind, you must choose someone who enjoys watching others succeed and who is willing to work hard to achieve their own success.

8. Save Income For Rainy Days

This seems like common sense, but it needs to be said. All those orders and revenue you see rolling in? They will stop and go like that Toyota Prius you sat behind in your last traffic jam. While everything is usually cheaper outside the States, try not to get carried away. You’ll panic way less during the slow months, I promise.

9. People Won’t Respect Your Time

Even with a solid routine, you’ll have constant interruptions when you work for yourself. Your new friends or your significant other will hit you up and expect you to drop everything to come kick it. It is super tempting, but you’re not a retiree yet (or even close for that matter). Learn how to set good boundaries. Make it clear you’re still working and you’ll hang out with them when you’re done.

There are more things you’ll want to add to your list when you live it for yourself, but the first step is believing you can actually do this. Yeah, having no safety net is f%^&ing terrifying at times. It won’t be a fit for some, especially if you have a romantic partner who wishes to stay put. But there are those of you can—and will—do it. And all the more power to you. Feel free to connect with me if you’re passing through Malaysia. You’ll quickly learn that many expats stick together while abroad, or at least have a warm community of sorts. So instead of Instagram-ing your Vegas vacation (for the millionth time), get out of your bubble and go experience what the world has to offer. I dare you.

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