So you’re planning your first trip as a digital nomad, eh?
You’ve heard all about the amazing co-working spaces with unlimited coffee and friendships waiting to be made and seen the photos of nomads chillin’ poolside with their laptops (which, let’s be honest, is mostly just a front for the ‘gram because who actually takes their laptop to a pool, but I digress).
It all looks incredible… and it is!
But before you can have your own “office anywhere” moment, you have to actually figure out where to go and how to get there … and that’s where the anxiety sets in.
Let’s face it. Wrapping your brain around everything you need to do to prepare for your first foray into the wild world of digital nomadism can be totally overwhelming.
But fret no more, mis amigos! In this post, I’m going to walk you step by step through the entire process of planning your first trip as a digital nomad so that you can focus on the epic experiences you are about to have without stressing.
Sound good? Okay, great! Let’s get into it, shall we?
There is a huge difference between traveling abroad for vacation, where you can disconnect from the demands and responsibilities of everyday life, and traveling abroad to actually live and work. When it comes to choosing your destination, this very important distinction that requires a different approach.
Ultimately, the key is to ensure that your chosen location aligns with your specific goals and needs.
For instance, let’s say one of your primary objectives is to scale your web design business to six figures this year, and you have your sights set on spending the next three months on one of Thailand’s enchanting islands. While they offer incredible natural beauty and many opportunities for fun excursions and parties on the beach, they may not be renowned for their reliable wifi connections or accommodating workspaces.
Getting clear on what is MOST important to you and what you’re seeking to gain from this experience will help you make a decision that supports both your personal and professional goals.
Before you even begin planning your trip itself, take some time to think about WHY you want to embark on this journey and what you hope to get out of the experience. Your answers to the following questions will help inform all of the decisions to follow:
Alright, have you figured out why the heck you’re doing this?
Great! Let’s dig into the details.
This can be tricky if you’re a freelancer whose income may fluctuate from month-to-month or if you haven’t actually figured out how you’re going to make money on the road yet, but regardless, do your best to estimate your average monthly income.
Next calculate your total recurring monthly expenses. This number shouldn’t include your living expenses abroad, only the bills, subscriptions and financial obligations you already have that you’ll still be paying for while on the road, such as streaming subscriptions or student loan payments.
*Pssst… this is also a good time to do an audit of your expenses and see if there is anything you’re paying for that you don’t actually need or that doesn’t make sense for life abroad. Cancel those now and save that moolah.
Finally, take your monthly income, subtract your monthly expenses (also taking into consideration your savings and investment goals), and voila! You have your monthly living budget!
INCOME – EXPENSES – (SAVINGS + INVESTMENTS) = MONTHLY BUDGET
Easy enough, right?
*Pro Tip: It’s a good idea to always travel with a savings fund of at least 1-3 months of living expenses in case you are unable to maintain your income or something unforeseen happens (Case in point: When my laptop, aka the key to my business, died without warning while I was on vacay in Phuket… hellooooo unexpected $1,700 expense! )
Review all of your current bills and subscriptions. Cancel or pause anything that won’t be needed while you’re living abroad. Then calculate your total amount of recurring monthly expenses. This number will give you a general budget to work with which, taken in conjunction with your travel preferences, will help you decide where to call home.
Next, it’s time to brainstorm all of the characteristics of your ideal living environment and lifestyle.
What does your dream digital nomad life look like?
Are you traveling solo or with a friend or significant other?
Do you want to be surrounded by people, such as in a hostel or co-living environment, or do you need your own space?
Do you prefer to work at morning or night, and will the time difference of your destination affect that?
Do you have a way to make money while you travel or do you need to figure it out along the way?
What’s the weather like in your ideal location?
Don’t worry about your budget in this exercise or if some of your “ideal characteristics” seem to be in conflict (i.e. up in the mountains vs. by the beach), just set a timer for 10 minutes and GO!
Set a timer for 10-20 minutes and brainstorm a list of all of the qualities you’re looking for in your ideal destination. Don’t overthink it – it doesn’t matter if some of the items in your list seem unrealistic or conflict with each other – just get it all out on paper!
Now that you’ve identified your goals and travel preferences, take a moment to make a list of your Most Important Things (MITs).
These are the features or characteristics a location MUST have to even be considered.
For example, for me this includes:
What are the things and resources you need to live your most happy and productive life?
Using your list from the last step with everything you want in a location as a starting point, create a condensed list of the things that are MOST important to you and/or that you need, ranked (roughly) in order of importance.
Now you may already have some locations in mind, but if not, here are some lists and resources to get you started:
Nomad List is hands down my favorite resource for scoping out new destinations.
It’s a crowdsourced database of cities in the world where digital nomads rate different aspects of the places they visit and live including cost, internet speed, safety, quality of life – pretty much everything you can imagine!
There are also multiple forums and slack channels where you can ask any questions that you have and connect with other digital nomads who are traveling to the same location. ‘Tis truly a gift from the heavens!
Reading about a place can only get you so far. I prefer to try and get a feel for the vibe of the place by finding YouTube videos of the location, particularly videos that have been created by other digital nomads, as they tend to focus more heavily on the details that will be more important to you as opposed to videos aimed at tourism which tend to focus more solely on sightseeing.
Many of the more popular digital nomad destinations (and yes, I do recommend choosing a place where there is already a thriving digital nomad community for your first trip as it will make things wayyy easier) have Facebook groups for digital nomads in the area.
Join groups associated with the locations you’re interested in living and see what people are saying, what events are happening, and what the general vibe is.
This is the perfect place to ask any questions that you might have, connect with people in the area prior to your arrival and can also be helpful for finding housing opportunities.
ONLINE BLOGS & FORUMS
Trip Advisor is one of my go-to resources for learning about a potential destination (they always seems to have all the answers!) but there are tons of forums and blogs dedicated to travel.
I’m also a fan of The Blonde Abroad’s website!
Do you have friends who are already living the digital nomad lifestyle that you can reach out to? If not, do you know anyone who has vacationed in the area you’re interested in who can provide some insight?
If this is your first trip, there’s a good chance you may be the pioneer in your friend group and don’t have anyone you know personally to turn to for advice. However, as you travel and get to know others who are living a digital nomad lifestyle, their insights, recommendations and experiences will become invaluable for choosing future destinations!
Use an app like Google Drive or Notion or a plain piece of paper, create a table. Along the side of the rows, write each of the potential locations you’re considering. Along the top of the columns, write in your “MITs” from the previous step. Then, in each corresponding box, indicate if the potential location meets your requirements (you can also use a ranking system like 1-10 vs. yes or no) as well as any additional notes that you want to remember. Use this chart to determine which location(s) have the highest overall score and to rule out any locations that are missing any of your non-negotiables.
First, figure out if you need a visa to move to your top locations. If so, what are your options? Can you get a visa on arrival or do you need to apply for one before-hand? How long can you legally stay in the country (or countries in the case of Europe and the Schengen Area)? Do they offer visa extensions?
Next, gather any necessary documents for your visa application. This will vary by location but usually includes things like passport photos, proof of sufficient funds, proof of accommodation, proof of an outbound flight before the visa expires, etc.
*Pssst… If you don’t actually have an out-bound flight ticket yet and are not sure when/where you’re headed next, you can rent one for about $10 using Onward Flights. Pretty nifty, eh?
You can also visit Skyscanner.com, then:
Make sure to apply for your visa with PLENTY of time before your trip. Do a little investigating to see whether the embassy where you’ll be applying for your visa is generally fast or slow. The time it takes for you to get back your visa (and consequently your passport) varies wildly by location, so do your research!
If you’re planning to live somewhere for an extended period (longer than a visa exempt stamp or tourist visa allows), do some research into how flexible the country is about granting back-to-back visas. Can you just cross the border and come right back in? Or is there a limit on how many days you can spend within the country during a given time period (i.e. 90 out of 180 days)? Do you need to investigate longer term options (i.e. a volunteer or education visa)?
Spend some time looking up the visa options and requirements for your top destination candidates. You can begin by Googling around, but always be sure to confirm the information that you find on the U.S. Bureau of Consular Affairs website (or the equivalent for your country, if you are not a U.S. citizen)
Okay, so you’ve done your research, narrowed down your list of potential destinations and have ensured you can meet the visa requirements.
Now it’s time to use all of this data to choose a location and make it official by booking your flight.
If you can be semi-flexible with your dates of travel, you can score some major savings.
To find the best flight deals with Skyscanner, type in the airport you’d like to fly out from >>> type in the city or country you’re headed to >>> set your departure date to “whole month” >>> select the month you’d like to leave >>> Press “search flights” >>> and voila! You can see an entire calendar of airfare prices for the month. Choose the cheapest date that works for you and that accommodates your travel needs.
A few tips:
Make a final decision on where you’re headed, book your flight and make it official!
Now if you’re anything like I was, you’re probably staring at your flight ticket confirmation pinching yourself like, HOLY SH!T I’M ACTUALLY DOING IT, THIS IS NOT A DRILL, I REPEAT, THIS IS NOT A DRILL!!! and about to burst from a combination of overwhelming excitement and crippling anxiety.
Put the squeezy stress ball down my friend, we’re gonna put those worries to rest!
Every time I’m headed somewhere new I make a list of EVERYTHING I’m the slightest bit nervous about or that could go wrong (what if my luggage gets lost, what if nobody around me speaks English when I land, what if one of those creepy not-real taxi guys hovering outside every airport kidnaps me (you know the ones lol), etc).
I usually set aside 20 minutes or so to brainstorm and then let the list marinate for a few days, adding to it whenever a new worrisome thought makes its way into my consciousness.
Then, around a week later, I go through my doc and tackle my fears one by one.
The beauty of the internet is that any question you have, someone has likely had before you and they probably asked it somewhere publicly online.
And if they haven’t – YOU can ask it and it’s likely that someone out there will have an answer they’re willing to share. This is where Facebook groups and online forums like Trip Advisor come in handy. Even reaching out to YouTubers or travel bloggers who have covered your destination can be helpful.
I’ve found this approach to be super therapeutic. When you capture your fears on paper, you get them out of your head so that you don’t waste time being distracted or uselessly worrying in the present moment, and have peace of mind knowing that you’ll address it later when you actually have the proper time to dedicate to it.
Preparation is truly the antidote to fear! If this is your first time traveling alone or to a new destination, a little extra preparation can go a long way and make your experience much more enjoyable. Don’t skip it.
Set a timer for at least 20 minutes and start brainstorming everything that you feel nervous, scared or uncertain about for your upcoming trip. Once you’ve completed your list, let it sit over the next few days and add any further concerns to it as they come up. Then, set aside some time to address each fear one by one. Of course you can’t mitigate all fears or guarantee that everything will go perfectly accordingly to plan, but addressing these worries now will make for a lot less stress in-the-moment if these things DO happen because you’ll have done your research and have a plan of action.
Every city has their good and er… not-so-good neighborhoods.
Do some research into the better areas (particularly for foreigners) to live in your destination.
Also do some research into cafes, co-working spaces, gyms, etc. that you think you might like, and try to find a residence that is near those locations or else is conveniently reachable.
First things first, when moving to a new location, you need a place to live!
Make sure to do research into what the rental process is like in your destination country. Is it best to book an apartment online in advance? Or can you show up and find a short term rental once you get there?
For example, in many places in Southeast Asia you can just roll up, walk into an apartment building, ask to see their available rooms, and if you like what you see, sign a lease for as little as 1 month and move in that same day. Easy peasy.
In these cases I recommend booking a hostel or Airbnb for the first few days after your arrival so that you orient yourself and get a feel for the city before going around to local apartment buildings and finding your future home.
In other places it will be nearly impossible to find a lease for under 6 months, so in those cases, I usually just suck it up and use Air BnB (which is typically highly inflated compared to local rental prices, but has some pretty great deals if you can stay 28+ nights and get the monthly discount).
IF you want to live non-traditionally or need some extra support financing your trip, consider one (or a combination) of the following options:
Take some time to research what the options are wherever you’re headed and determine what appeals to you the most given the resources that you have available.
Yes, yes I know bad things always happen to “other people”, but you? You’ll be fiiiiine. Cool. Got it. Now go buy some anyway.
I personally always use World Nomads. They cover a wide variety of potential accidents beyond standard health issues ($5,000 for dismemberment, say whaaa!? ?).
Especially appealing is that if your stuff gets stolen, they will cover up to $3,000 in replacement costs.
If you do ONE THING in this post before setting out on your trip, make it this.
BOOM! Now even if you’re service-less and wifi-less when you land in your new location, your maps and navigation will still work (which is even more comforting than you can imagine when you touch down in a new place).
Another alternative that lets you download offline maps is the app Maps.Me.
if you’re reading this post, you’ve likely chosen a country where there is some level of English fluency.
Even if speaking the local language isn’t necessary wherever you’re headed, you should still make a point to master at least a few basic words.
Here are a few suggestions:
In my experience, “hi” and “thank you” are definitely the ones you’ll use the most.
However, I encourage you not to limit yourself to what is necessary. Even if your speaking skills aren’t perfect, a little bit of effort goes a long way. Locals will usually be more helpful and accommodating when they see that you are at least trying.
Also, be sure to download Google translate if you haven’t yet.
Find out what dress customs are like where you’re headed and respect them. Does this mean you have to radically change your style if you’re headed somewhere that is more conservative? No, not at all. But there’s a big difference between wearing a flowy sundress somewhere where the locals tend to be more covered and wearing short shorts and a crop top, ya feel?
Dressing in a way that can be considered offensive not only screams “tourist” and makes you a huge target, but also can be seen as ignorant and arrogant by the locals and draw their hostility. You’ll get a lot farther (and be much safer) by dressing in a way that demonstrates respect.
PACK LIGHT. In my opinion, traveling with hand luggage and a carry-on bag is the only way to go.
But HOW, you say? How can I possibly fit my entire life into two teensy little bags?
The truth is it’s a lot easier than you think. Traveling with a carry-on saves you tons of time, money, and overall hassle.
And with each new trip you take, you’ll get better and better at honing in on what you really need to live comfortably and productively on the road.
To get you started here’s my list of digital nomad travel essentials, that come with me wherever I go.
As equally important as what you pack, is how you pack it. Check out my post, How to Travel Carry-On Only: 19 Packing Tips for Digital Nomads for tips on how to make the most out of limited space when moving abroad.
Also, be sure to confirm your airlines weight and baggage allowances before packing so you don’t get slammed with surprise fees at the airport!
Before your flight, there are a few things that you should be sure to do:
The best part of travel is getting to immerse yourself in what makes each destination unique. Is there a certain local food you need to try, or a special style of dance originating from the country? Maybe natural wonders like waterfalls or man-made architectural masterpieces? Figure out what makes the country you’re visiting special and make a point to experience those things.
I recommend scouring the internet for:
There are a lot of things that you’ll have to learn as you go, but it’s helpful to try and discover what you can ahead of time ‘lest you accidentally offend you’re new friends!
Whew! If you’ve stuck with me this long you should be feeling a lot more confident about your trip.
Go back to the list you made at the beginning and see if there is anything that we didn’t cover in this guide, and then put your super sleuthing skills to use and get to googling or feel free to drop me a line with any questions.
Now, I must know, where did you decide to start your digital nomad journey? What are you most excited about?
If this isn’t your first time around the digital nomad block, what are your tips to ensure a smooth trip?
Let me know in the comments below!
And if you know someone who would find this post helpful, please feel free to share it with them!
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