Digital Nomad Checklist: How to Prepare for Your First Remote Work Trip

Heading out on your first digital nomad adventure is incredibly exciting! It’s the chance to try something new, see the world, test your willpower, and enrich your life.  

But it can also be a bit daunting—because if you find yourself unprepared, you may jeopardize your reputation and good standing at work.

When I first set out to work in Portugal, I really didn’t know what I was doing.  I spent money out of panic on things I probably didn’t need, but I also discovered tools and resources along the way that were entirely worth the money.  Finding your work/travel groove requires testing, pivoting, and being flexible.  And you’re probably going to make mistakes once in a while (I know this is hard for my fellow perfectionists to hear).

It’s now been almost a year since I set out on my first remote work experience and I’ve definitely learned a thing or two to help me feel more secure and prepared when working in a foreign country.  Whether you’re already in a location-independent role and want to travel concurrently, or maybe you are just dreaming of remote work, I want to share with you some useful tips on how to prepare for a digital nomad adventure.

Let’s get into it!

Tip #1 - Choose a Digital Nomad Friendly Destination

There are a lot of amazing places out there that are fantastic travel destinations, but the wifi is awful, making work nearly impossible.  You want to be smart about your location.  You can approach this either by researching a destination that is already of interest to you or, if you are flexible on the location, just looking into “top digital nomad cities.”      

Whether I know where I want to go or not, my first stop is to look at NomadList– a website that ranks destinations for digital nomads, shares useful stats (like cost of living, average wifi speeds, things to do, air quality, etc.), and includes reviews.  This will generally give you a good sense of the destination’s digital nomad compatibility. 

The next thing I like to do is utilize the digital nomad Facebook groups to ask questions and gather further insights.  Two of my favorite ones are:

Female Digital Nomads(59K Members)

Digital Nomads Around the World(121K Members)

This can range from questions about specific destinations (coworking spaces, wifi speeds, sim cards, etc) to just generally asking about the best places for digital nomads.  This information is often more up to date than anything else you can find on the internet and a highly valuable resource.

Make sure to consider the time zone if your job expects you to keep regular business hours.  For example, Asia is hard for LA business hours because you would essentially be working overnight - a routine that may be miserable for some people!

Tip #2:  Make sure you have a credit card with zero foreign transaction fees and a bank with zero ATM fees

When you’re planning to be gone for an extended amount of time, you really want to plan ahead for this and make sure you aren’t getting hit with additional fees as a result.  

My favorite travel credit card is the Chase Sapphire Reserve.  Its little sister, the Chase Sapphire Preferred is a good option as well.  There are zero foreign transaction fees on both of these cards.

Most banks also charge a $5 foreign ATM fee (on top of fees from the ATM itself, and potentially horrible exchange rates).  I paid over $100 in ATM fees last year….which is very annoying. A way around this is to switch to a bank that has zero ATM fees, such as Charles Schwab.  

Tip #3:  Make sure you are protected in case of emergencies!

Once you know where you are going, make sure you get travel medical insurance.  The last thing you want is to get sick in a foreign country and have to stress about cost of care.  For peace of mind, I would always recommend getting a travel medical policy. 
I’m currently using SafetyWing, a travel medical insurance company that specifically suits the needs of digital nomads by providing coverage for unexpected illness and injury (hospital fees, doctors visitors, prescriptions, etc). It’s really affordable ($37/4 weeks or $1.32/day), easy to stop/start whenever you’re traveling, and even covers medical care in your home country for 30 days (non-US) or 15 days (US) every 3 months of service.  In addition, it provides emergency travel-related benefits such as emergency medical evacuation, bedside visit, travel delay, and lost checked luggage. A nice added perk!

No matter what type of nomad you are—full time traveler or part time / short term traveler, SafetyWing has flexible purchasing options for everyone.  For the full timers, there is a $37/4 weeks option (auto-renews, can cancel anytime), whereas short term travelers can sign up at a rate of $1.32/day.  At that rate, you’d be crazy not to be insured.

Tip #4:  Understand time zone differences and map out your work/play time

One of the hardest things when you’re a digital nomad is getting into a routine to work.  When you first start out, it can feel like you’re on vacation and so you have to retrain your brain to understand that you’re working and that starts by mapping out a schedule.

I like to take a screenshot of my new time zone vs LA and NY (the two cities most of the people I work with are in).  WorldTimeBuddyis an easy to use resource for this—screenshot below!

Make the time zone conversion your screensaver (or easily accessible on your desktop) so you can easily reference from your computer what time it is back home. 

After I understand what the time zone differences are, I will come up with a plan for what times I will work each day and map that out.  When I was in Lisbon, I would generally work 5PM-1AM (which is 9AM-5PM).  I’ve always liked working from Europe/Africa because you have the whole day free to explore your new city, and then can work in the evening, and still go to bed at a somewhat reasonable time (midnight/1am ish). Per my earlier callout, Asia is a little tougher for those of us who work US business hours because the time zones are so off.  Alhtough if you are committed to trying to work it out with your work, more power! I chose to go to Asia when I knew work was going to be light.

Whenever I’m traveling to a destination, I also like to make a list of activities that are doable in shorter amounts of time (possible weekday activities) and activities that will take up a full day (weekend activities).

Tip #5:  Scope out strong wifi in coworking spaces & accomodations

I always look up coworking spaces when I’m working in a new city, although I also MUST have strong wifi in my accomodations—because I often just end up working there, since I work late at night.  

I will only stay in a place that I have confirmed through multiple reviews that the wifi is good.  Many booking sites like Airbnb, TripAdvisor, and Hostelworld will allow you to search the reviews for specific phrases or words.  So I always do a search for wifi and check out what people are saying.  It’s not worth taking a chance and not being able to get my work done due to faulty wifi!

Tip #6:  Make sure you are also set up to make and receive calls 

Who has ever travelled internationally before, only to receive a huge bill from your cell phone company?  I have.  And it’s NOT cool.  Learn from my mistakes and make sure you have a good system for making and receiving phone calls.

I’m currently using  Google Fi – activated with an esim on a Google Pixel phone, so that I can ALSO input a local sim card and switch between wahtever is working best. Google Fi is great for digital nomads because international data is the same price as it is in the US. International calls will cost you, but it’s significantly cheaper than ATT and many other carrier rates.  Most are .20 cents per minute.  What I usually do, is try to call people over Skype (rates as cheap as .01/minute)  and just accept incoming calls thru Google Fi.

I used to travel with a TEP wireless device….but it found it wasn’t as reliable as one would hope.  There was a daily maximium on the fast wifi, and after you hit that it slowed to a speed that was utterly useless. It also didn’t work at all in Panama, which was very stressful.

Tip #7:  Stay connected with your clients & colleagues with video conferencing

On a similar note, video conferencing is so so important for digital nomads.  Facetime allows us to stay close with those back home—which just feels more personal. I use 8x8—it’s free to download and has great video quality.  Screensharing is also really helpful when you can’t be in the same physical space with your team.

Tip #8:  Pack clothing based on a theme and be prepared for different types of weather (if necessary)

When it comes to packing, I usually like to stick to a general theme – mostly black with a few pops of color, mostly neutrals, bohemian, etc.  This way it’s easy to mix and match items to create different looks

The other thing you need to think about is how long you are planning to be gone for and if you will see a change in weather (either because you are going to destinations with different climates or you are planning to be in one place long enough to see the seasons change).  If you are going to be traveling across climates, I try to think about layers and warm fabrics that fold up small so they don’t up too much room in my suitcase.  

The other thing that I usually do (but maybe not everyone wants to!) is just accept that I’m probably going to need to purchase things once I get to my destination and the weather is different.  And that’s ok!  A lot of times it’s hard to predict exactly what you are going to want/need in that destination until you get there and you are better off packing light and just picking up a few items along the way.

Tip #9:  Choose your luggage and gear wisely

I used to travel with a backpack all the time, but now that I have more gear with me, I’m shifting back to a suitcase with 4 wheel drive. I’m obsessed with my pink Away bag….it’s light, has an ejectable battery to recharge your electronics, wheels easily, and really maximixes space (I can cram so much into it!)

I’m a very light packer initially, but dpeending on how long I’m gone will sometimes purchase a cheap bag to check on the way home.

In terms of my electronics, I always travel with my Macbook Pro….I also take an extra charger (just in case I lose it….I don’t want to be in a position where I can’t find an Apple Store!). 

I also have my iPhone (US phone) and Google Pixel phone (international phone).  I take both phones since it’s easier for my friends to text my regular phone and it doesn’t take up much space.  I also have a mini phone tripodwith a bluetooth remote so that I can take pictures myself, since I frequently travel alone!

I also make sure I always have at least one portable battery (two is better!). So that I can be charging devices even if my accomodations have limited outlets.

Make sure you have multiple adapters, so you can charge several devices at once AND in case you lose any (which tends to happen with me a lot lol).

I also carry a mirrorless system camera with me – the Panasonic Lumix with a 20mm prime lens and 35-100mm zoom lens.  So I have something a step above a phone to capture great travel photos.  But it’s still much lighter than a DSLR!

Tip #10:  Share your location & keep in touch with those back home

Before you leave, make sure someone back home has detailed information about where you are staying and how to get in touch.  And call your mom….she needs to know you’re alive and well J.

Well those are my top tips for preparing for a digital nomad adventure – I hope they were useful and aid you in feeling good about your foray into this fantastic lifestyle!  As always, reach out with any questions!  And if you are a digital nomad yourself already, I’d love your thougths on this list and anything else you find helpful before you set out.

Xoxo

Lauren