Tips for Living a 'Perma-Vacation

Tips for Living a 'Perma-Vacation

There’s not much I can complain about without sounding like a giant asshole. I lead a pretty charmed life, so I try to keep my complaints to a bare minimum. I know you could give a tiny rat’s ass that it’s cold in Cancun or that the WiFi in Kuala Lumpur is slow. But one of the greatest pet peeves I have is when people ask me, “So, you’re life is, like, one big vacation, huh?”

I can assure you it is not.

Working remotely, or ‘digital nomading’ as it has come to be known, is one of the greatest life choices I ever made. My happiness factor increased 110%. There’s no morning commute (except to my couch or dedicated island workspace du jour), once winter hits New York I get the fuck out, and, most importantly, time is entirely my own. That said, digital nomading is not a career path for everyone. It's unpredictable, unstable, and requires a ton of self control. It is also a privilege that comes with certain responsibilities. Because as much as that next cliff needs jumping off of or that coral reef needs exploration, there are people on the ground counting on you to produce whatever it is that you produce. You are still responsible for being a functioning member of society. So in order to have your perma-vacation and paycheck, too, here are my tips for successful digital nomading. 


Find a Routine
Digital nomads may seem like carefree, bohemian, caution-to-the-wind souls. But the successful ones are those who hide their Type A very, very well. To be a digital nomad, and a good one, you need to have excellent organizational skills, because as much as your life may appear to be free-form, there has to be structure in order for it to function. 

I am most productive in the morning, no matter where I am. It’s 6:45am on a Sunday right now and I’m sitting here writing this. My optimal hours are from 7am-10am, so that’s when I answer emails, do administrative tasks, and make outlines for my articles. From 10am until about noon I go to the gym, because while I may not be on vacation, many of my hosts treat me as if I am. Being pampered with food and drink is one hell of a business perk, but it does do damage on the body after a while. Afternoon is when I set up a workstation, whether that's at my desk at home, a hotel lobby in Cabo, or a cafe in the heart of downtown Hanoi. I’ll stay working until about 4pm, when my brain officially shuts off. 


Make a Budget
I cannot stress this enough. You MUST be aware of your finances. If you’re someone who works remotely, but for a company, your job is a little easier because you are still earning paychecks on a regular basis, and ones whose taxes are removed for you. But for freelancers like myself it’s a little different.

As much as I try to plan for timely paydays, it can be one mega crapshoot. Checks sometimes get held up, whether for bank holidays, budget seasons, or straight up human error. Then there are the checks that take six weeks to process, or the ones who don’t arrive via direct deposit. But those bills aren't going to pay themselves, and the phone company doesn't care that you will deposit that $900 check waiting in your mailbox AS SOON AS you get back from China. 

The first thing I try to do is send all my invoices twice a month. I do a round of invoicing on the 15th of every month, and a second at the end. That way I know that at least every two to three weeks, I have money coming in. 

I also live by Excel spreadsheets. I map out how much I need to earn every month to meet my expenses, and what money I have already ensured is coming in. Then I know how much more work I need to take on in order to make ends meet.

And always, ALWAYS deduct 25% of each check from your earnings Because while you may be getting $1,000 for that assignment, what you have to play with is only $750 because, you know, taxes. Freelance checks do NOT have federal or state taxes removed for you, so you have to plan for it on your own. Pay quarterly estimated tax so that once April rolls around you aren’t slammed with a bill from the IRS for thousands of dollars. 

Trust me. This is honestly the best advice you will ever receive. Pay your quarterly estimated tax. Just do it. 


Embrace Technology
If you’re a digital nomad, chances are you already know what’s up with technology. But just in case you don’t, there are several Apps that will make your life much, much easier:

Google Drive - For all those spreadsheets we just talked about. Keeps them in a tidy place so you can access them from your computer or your phone or an internet cafe if something goes wrong with the first two.

Mobile Banking - Pay your credit card bills and track your budget from literally anywhere. I once missed an Amex payment (by one day, one time, in eight years) and was slapped with a 29.99% penalty APR fee for six months. That's interest money I could have spent doing literally anything else. 

Venmo/PayPal - Just two solid banking apps to allow you to move money around easily. 

Calendly - Schedule meetings or conference calls without the back-and-forth email chains. This allows people to enter the times they are available so you can find a common ground without clogging your inbox. 

VPNs - These are Virtual Private Networks. What they do is essentially trick your computer’s IP address to think it’s in another country. This is especially handy in a country like China, which blocks Google, Facebook, New York Times, etc. It’s also handy if you want to watch Hulu, HBO, or certain Netflix programs from the U.S. while abroad, because there can be some long nights when you just want to curl up with Michael Scott. And on a more practical note, some U.S. websites (like Con Edison) don’t function without a U.S. IP address, so you’ll need one in order to pay certain bills. Opera VPN is a good free one. (Opera is blocked in China, so try Express VPN if traveling there.) 



Stay Connected!
After you’ve embraced technology, it is important to actually use it. And not just for self organization. Make sure to stay in touch with people back home, and certainly the ones who are in the position to potentially give you jobs. Just because you’re gallivanting on the Gili Islands does not mean you’ve fallen off the face of the planet. But it can be easy for you to do so. You must keep yourself relevant in order to stay competitive and not be forgotten about. I guarantee you there’s someone closer to home waiting to take your place, so make sure that those who are counting on you can do so, and are investing in you for a reason. 

Send emails every. Single. Day. Follow up. Follow through. 

Flickr/duncan c

Flickr/duncan c

Leave Room for Improv
Sometimes shit goes wrong. It just happens. You just don’t know when a thunderstorm will knock out the power, or a gas strike will result in protesters blocking a highway, making a normally 4-hour bus ride a 16-hour one. You just don’t know. So work ahead. I always work two weeks ahead with my assignments, so should anything go wrong, and it usually does, I’m not holding up the show for everyone else. 


Never Forget Why You’re Doing This
And above all else, never lose sight of why you did this in the first place. You’re a digital nomad because you play by your own rules. Because your time and freedom are worth so much more than any amount on a paycheck. Because you are in control of your own destiny and you have a vision that you are in charge of seeing through to success. It is the most rewarding choice you can ever make. So don’t forget to see the places you are, and take advantage of the life you’ve created for yourself. Hit the road for months on end, because you can. Make polite chit chat with a surfer and his wife from Melbourne while waiting for a bus in Mexico, and end up meeting up with them in France four months later. (True story.) Eat that weird shit. Embarrass yourself. Make huge mistakes. 


This is really your life. It’s no one else’s. And as long as you never become a burden to society or anyone else, as long as you never hurt anyone, as long as you are proud of what you will be absolutely fine. Our lives may not be one giant perma-vacation, but we are luckier than most, and we must never, ever forget that. 

Meet Vaera Journeys

Meet Vaera Journeys

Say Yes to New Adventure

Say Yes to New Adventure