If you’re anything like me, travel is one of your great loves. So in the age of remote work where there are so many of us who already work from home or who’s jobs allow a certain amount of remote work as long as you have a good internet connection, the possibilities for integrating travel into your life have significantly expanded.

So when I realized I was ready to leave New York City but didn’t know where I wanted to live next, this reality made it possible for me to seriously consider becoming a digital nomad and if you’ve been following along, that’s what I’ve been doing since March - trying out different places I might want to live and fitting in some travel and time on Nantucket in between.

The thing to understand is that there are so many different ways to do remote work/digital nomad life and that it’s entirely up to you to craft an experience that feels good to you. Becoming a digital nomad is an exciting idea, especially if you’re a woman in your 20s or 30s, yearning for a life that blends work with adventure. The idea of working remotely while traveling can feel like the ultimate dream, but before you dive in, it’s important to get clear on why you want this lifestyle and how to make it work for you.

But let’s take a step back before we dive into how to take that first step toward becoming a digital nomad—and feeling confident while doing it!

What does Digital Nomad mean?

This phrase is thrown around in a lot of different ways. You’ll also hear “remote work,” “location flexible,” and many more. All these phrases are basically meant to describe people who’s work can be done from anywhere via digital means (usually wifi and a computer) that take advantage of that flexibility to be different places throughout the year.

Some Digital Nomads are in each places for 3-6 months at a time, indefinitely. Others, like me are treating it more as a short term experiment and are moving around roughly every month. Others are living more like backpackers, traveling very lightly and with few plans staying in places for variable amounts of time (maybe some longer and some shorter).

One of the benefits of this lifestyle are you can craft your life in terms of what works for you. With that comes with a lot of decision making and the onus is on you to have clarify in what you’re looking for!

What Are You Looking For out of being a Digital Nomad?

Before you embark on your digital nomad journey, ask yourself: What are you looking to gain from this lifestyle? Is it the freedom to explore new cultures? The chance to immerse yourself in new places? Are you looking for a new place to move (like me) or maybe a place to spend part of the year away from your current home base? Are you passionate about a hobby (like surfing or climbing) and want to be able to be in different places throughout the year that allow you to prioritize that thing?

Clarifying your reasons for becoming a digital nomad can help you shape your journey in a way that makes it more likely you enjoy the experience. It’ll also help you inform key decisions like where to go, how long you’ll stay in each place and what type of lifestyle you’ll make for yourself while you’re therer. For example, if cultural immersion is key, you might look for countries with rich traditions or unique local experiences but with cost of living that could enable you to stay there longer. If you’re, like me, seeking out a place you might want to invest in longer term, you might move through your stops at a faster pace to get to try out a few, while still giving yourself enough time to get a feel for each spot.

Take it from someone who’s done this - do not skip this step! As soon as you dive into the planning of this type of adventure, you’ll see how unbelievably overwhelming the many decisions are and the guiding light of why you’re doing this is crucial for your ability to narrow down the decision-making into a manageable set.

Who is a good fit for being a Digital Nomad (and who is not)?

I’d say there are a handful of key factors that make you a good fit for this lifestyle:

• Independent - whether you’re traveling solo or with a friend/partner, this lifestyle requires that you are an independent, resourceful, problem solver. Whether it’s in the planning process or just figuring out a new place, if you really depend on creature comforts and your community, this will likely make digital nomad life feel very uncomfortable

• Flexible - whether it’s with travel plans changing or routines switching or simple things like sleeping in different beds, the ability to adjust to new places is crucial for a successful digital nomad experience; those who are highly particular in terms of lifestyle or their schedule could still make a digital nomad life work but it’d just likely be more expensive (if you have more restrictions on where you’d stay or what time of day you travel, this is where costs can really start to add up)

• Curious - you wouldn’t want to do this at all if you aren’t curious but it’s worth repeating that the whole point of being a digital nomad is experiencing new places and things and the curious spirit will help make these times of being out of your comfort zone more valuable. Separately, there’s natural time in any digital nomad journey where you’re just not having fun and curiosity will help you introspect and reflect internally to help you learn more about yourself through the experience

This is certainly not a comprehensive list but if you have these three traits and are considering digital nomad life, you’re already certainly on the right track!

How to Make the Digital Nomad Life Work

Once you’ve decided to take the leap, it’s time to figure out the practical side of being a digital nomad. Here are some tips on how to make it work for you.

How Does Your Work Accommodate Remote Work?

The remote work life sounds glamorous (trust me, it isn’t always!) but it’s not a reality for everybody. Before you start booking flights, take a second to think about if you can actually pull this off in your current role. Does your work accommodate remote options? If you’re already working remotely, you’re one step ahead. If not, could you explore options like taking a vacation or a sabbatical? Consider time zones and how they might affect your work schedule. Can you shift your hours to align with where you’re traveling?

If you know this is something you want to do, you can consider negotiating for the option in an upcoming review or just ask permission to do a test run in a nearby city or during a holiday to get a feel for how it impacts your productivity and lifestyle.

How Are You Going to Balance Your Goals with Your Finances?

Depending on where you live and where you want to go, the financial reality of being a digital nomad can vary dramatically. Short term rentals (under a month) are a way higher per night cost than rent in almost every city and even when you take advantage of discounts for booking over a month long stay, it’s still likely you’ll be paying more than your rent (and that’s not thinking about travel costs, rental car, etc.). Spending time in Southeast Asia where cost of living is dramatically lower would be very different than spending 3 weeks in LA.

Coming from NYC, I was used to my cost of living being high and I was able to get subletters into my apartment so I wasn’t floating an existing apartment back home. But even so, my stays in these relatively cheaper cities, if you were living there full time, were often close to my monthly expenditures in NYC because of the nature of the short term rentals.

I truly believe that if this is something you want to do that you should find a way to make the finances work, even if it means a shorter adventure or taking on a side hustle in the 6 months before you leave to give yourself cushion but it’s important to keep these things in mind so you set reasonable expectations of what you’re going to spend while you’re on the road.

Don’t forget to plan for emergencies, unexpected costs, and any new expenses that may arise while on the road (like travel insurance or a virtual mailbox). Having a financial cushion will help you feel more secure in your decision to take on this lifestyle.

How Do You Deal with Uncertainty and Being Alone?

This is probably the most common question I’ve gotten from friends and family since I started this journey. Because let’s face it: the digital nomad lifestyle isn’t always easy. If you’ve never traveled solo before, it’s natural to feel uncertain or even a bit lonely at times. Candidly, I was an experienced solo traveler long before I made this digital nomad decision and I would strongly encourage you, if you’re thinking about it, to go do a solo trip first to test how you feel. (If you’re like me, you’ll become obsessed and all the sudden you’ll realize how much you love solo travel! But it’s not for everybody.) But once you’ve gotten a little experience being alone while in a new place, you can consider whether being a digital nomad would be right for you. At this point, the biggest thing I can say to you is…

Embrace uncertainty—learning to cope with unknowns is part of the process. The stretching of your comfort zone is some of the most valuable part of the experience and you can never out-plan real life. Some of the magic of the flexible lifestyle is the ability to let chance happen to you and have the unknown take you in new and exciting directions.

In my digital nomad journey, I like having the structure of where I’m going to be, where I’m going to be and my transportation (rental car, flights, etc.) booked and then within that structure, try not to over-plan or worry too much about what’s ahead. Plans with friends in those cities, people I met there or even solo adventures to try out new restaurants or explore new neighborhoods always seem to develop. You might not know everything about your destination, but with every new place, you’ll figure things out as you go.

Also, remember that feeling alone at times is completely normal. As a solo traveler, you’re often filling in an odd seat at a bar between two couples, figuring out transit systems on your own and you don’t have to ignore that being the case. I always remind myself of all the pro’s of being solo - I get to read my book, I always get to order exactly what I want, my schedule is 100% what I want it to be and so on and so forth. Over time, you’ll get more and more comfortable and it’s also totally okay to have a night in solo, just like you would at home, especially if you’re doing long term travel. Finally, if you’re really feeling lonely, FaceTimes and calls to your friends at home are always there for you!

Planning for your Digital Nomad Adventure

So you’ve decided this is something you want to do, let’s dive into the key questions I asked myself and that you should be thinking about in planning your digital nomad adventure!

Picking where you want to go

We don’t just travel to be in motion - the whole point is to go to places that you want to see. This may be places you’ve wanted to travel to, or in my case, places you thought could be a good place for you to live next. You may already have tons of ideas and if that’s the case great but it’s also okay to ask around.

When I decided I wanted to leave New York, I had a short list of the reason why I didn’t feel the city was a good fit for me anymore and even more importantly, what I was looking for in a place to settle down next. I had a few ideas in my head but also started giving those couple of data points to trusted friends and family (keyword: trusted - don’t ask just anyone or you’ll get overwhelmed with unsolicited opinions) and it turns out that my friend and family had almost identical list to the one that I had in my head. This was great confirmation of what I had been thinking and solidified my plan.

Think about time of year in each of these places and when you want to see them - high season? shoulder season? off season? This will affect pricing, crowds and also the energy of the place.

If you’re overwhelmed with options, pick a few that you’re most excited about and start there and you can fill in the rest as you go.

Determine Length of Stay

This piece comes back to the “Why” of your digital nomad journey - if cultural immersion is your goal, you might be planning longer visits. If you’re testing places (like I am), then maybe mid-length (like a month to 6 weeks) makes sense. If you’re truly sightseeing, some places may need longer or shorter.

One of the beauties of being a digital nomad is flexibility. Note that you don’t need to commit to long-term stays right away—start with a month or two, then assess how you feel.

When you have a list of places and general sense of how long you’d like to be there, you can think about a rough order of when it might make sense to go to each which will help you prioritize your planning.

Take One Step at a Time

When it comes to planning, the most important tip is to take it one step (or chunk) at a time. When I was planning my two months in Europe (more of the travel leg of my adventure), I backed myself into analysis paralysis with all the different options of where I could go. My therapist had to talk me back to earth, reminding me that there’s only so many variables the human mind can hold. Once you’ve gotten the general structure of your plan tackle one stage at a time - I recommend looking for accommodations and narrowing it down to a top 2-3 then cross reference with flights/travel (so you avoid booking an AirBnB just to realize that the flights are 300 cheaper if you arrive 2 days earlier). This can easily spiral into playing with all the various options of which order to go place etc.

For example, when I was planning Europe, I discovered that a dream hotel of mine was crazy affordable in April, so rather than my original itinerary, I switched and spent time in the French Countryside first to take advantage. But once I made that call, I tried not to engage with too many other what if’s about those two weeks of the trip and just start filling in the pieces. I challenged myself not to get too deep into planning the following two weeks of the trip (other than making sure that I could reasonably easily get from the end of the leg of travel I was planning to where I wanted the next leg to start).

Candidly, I got overwhelmed to the point of tears more than once while I was doing this more rapid tourist style travel, so don’t be too hard on yourself if it feels like a lot. Even when planning my longer stays, which inherently have fewer variables, it still takes me 5-7 research sessions before I comfortably feel ready to book a stay.

Where should you stay as a digital nomad?

Finding the right place to stay is one of the most important—and stressful—parts of being a digital nomad. Here are a few things to consider:

What Type of Living Situation Do You Want?

Think about your ideal living situation. Do you want a private apartment, or are you open to shared spaces like co-living arrangements or hostels? Co-living spaces risk more noise and you run the risk of not liking your neighbors but they can often be significant cost savers.

For my European travel, because my stays were generally 2-5 days, I chose hotels for the ease and comfort but this was certainly the more costly option. To test out cities to live next, I really wanted to simulate the experience of living in the city so I prioritized more apartment style rentals through companies like AirBnB and VRBO where there was a living space, parking, full kitchen, etc.

Neighborhood

But how do you even know what neighborhood to stay in? Google can help somewhat here but if you know anybody who lives in the place you’re headed, ask them! A quick text of “hey where’s the best neighborhood for [describe your trip goals].” They’ll save you much time googling. Get curious about safety, walkability, density of restaurants or nature, and transport options. If possible, talk to people who live in the area to get insider tips about where to go, eat, and hang out. Local recommendations can make your experience richer.

Will you be cooking most of your meals, or are you planning to eat out frequently? Consider a place with a kitchen if cooking is important to you. Think about walkability—if you like being able to explore the area on foot, choose a neighborhood that’s easy to get around without a car. And don’t forget about laundry. Depending on the area, it might not be as easy as hopping down to a local laundromat.

Other Logistics to Think About

Before you go, there are a few logistical details to tackle:

Renting a Car

Whether or not you need to rent a car depends on the city you’re in and how you want to experience life there. In some cities, public transport is excellent, and a car isn’t necessary. But if you’re heading to a remote location or somewhere with limited transportation options, a car can make life easier.

Mail and Medication

Some short term rentals will let you accept mail to the address but others don’t have a safe way to do so. So it’s important to think about how you’ll manage your mail both at home and away, so you don’t miss an important bill or have no place to send that Amazon package. If you’re doing more traveling, it might make sense to have your mail forwarded to a family member back home who can review and take action on things for you if you need to. If you’re staying in one place for a while, you can setup a PO Box or virtual mailbox with a variety of companies so you’ll still have a mailing address. You can also leverage both of these options!

If you take regular medication, make sure you can fill prescriptions in your desired location or have a plan in place to manage refills while traveling!

Just Before You Arrive

When the date is set, and your trip is approaching, it’s time to get your final preparations in place.

Start Talking About It

Let your friends and family know about your upcoming journey. You might be surprised by how many connections you can tap into once you start talking about your plans—people who know someone in your destination or who’ve been there themselves can offer valuable insights. Don’t forget to mark down these recommendations (I use Google Maps to flag the places I want to go so on the day I arrive I have places I want to see)!

Plan for Travel and Packing

Do you know how to get to your destination from the airport? Have you figured out your transportation options once you're there? As for packing, remember that you need less than you think. I always try to generally pick a color scheme while I’m traveling that enables me to pack lighter because of my “capsule wardrobe.”

But on the other hand, when I’ve been doing these longer stints trying out places to live next, I tend to bring more things to enable me to feel more at home - a few more clothes, bigger sized toiletries so they last me the whole trip that I’m there. But let me tell you, the amount of baggage adds up fast and I have rarely used even half of the things I thought I’d bring so be judicious.

Dating Apps (and Social Media)

If you’re single and staying some place for a reasonable amount of time, moving your location on the dating apps to your new spot can be a great way to meet people and learn more about a place. I don’t think you need to put in your profile that you’re a shorter term visitor but I do recommend being upfront about it relatively promptly into messaging. In my experience, most men were totally fine to still get to know me even though I wasn’t necessarily staying long term but a few opted out and that’s totally fair too. If you can, always better to be upfront with that information so the other person can do with it what they wish!

I also recommend posting on social media where you are (by this I mean city! For safety purposes, better not to tag your hotel/hostel or wherever you’re staying until after you leave! Better safe than sorry!) because people might have missed previous posts/announcements about you being in town and this can help you have more people to see while there!

Once You’re There

Now that you’ve arrived, here’s how to get settled:

Initial Grocery Run

For longer stays, your first day should include a grocery run to stock up on essentials. Don’t stock even close to a full pantry - we’re talking your most used items ONLY because you’ll hate yourself when you’re moving out and have to toss almost full bottles of soy sauce or that second pack of freezer rice you didn’t use. Again, speaking. from. experience. The fun of being in a new place will probably encourage you to be out and about more than you think so the basics for whatever breakfasts or lunches you know you’ll be eating at home but less is more.

Check-in to your goals for this stage of your trip

When I arrive in a new place, I try to ask myself - what do I need to do to feel accomplished when I leave? For me, it’s always about understanding the local neighborhoods, visiting a good number of restaurants, and I try to go tour a couple of apartments in each city so I can get a real sense of what life would look like here.

For you it might be at least one night out or one cultural sight, but whatever it is, getting clear at the beginning can help you check in with yourself througout your day to stay on track.

The Explore Day

One of my most cherished day at each stop is what I call the Explore Day. Early in your trip give yourself a couple hours to try to just get familiar with your new city. This usually looks like me taking a low key drive to visualize what different neighborhoods look like and acclimate to how the streets/traffic in the new place works. Of course, it usually ends with a restaurant I’ve been wanting to try but rather than spending your first stretch of time making bee-lines straight to places, it helps to get your bearings and you’ll feel more comfortable in the new place sooner as you’re navigating.

Advice for anyone considering being a digital nomad

All in all, I think trying out digital nomad life is an incredible experience to have, if its something you’re curious about - I’m very aware that it’s not for everyone. If you are moving toward this time, here’s a little summary plus a couple miscellaneous things I think it’s probably helpful to hear:

• Figure out your “why” for remote work/digital nomad before you start planning to help yourself narrow down the plan

• Filter where you want to go, for how long, and where you want to stay through those goals, balanced against your financial realities

• Accommodations are a big part of your nomad life - think about the experience of each type of accommodations then research, research, research

• If you are a picky sleeper, it’s totally okay to be strict about this in your search - I have to be cold when I sleep so for long term stays, I am fully okay saying that air conditioning is a dealbreaker and by not compromising on it, I’m way happier each night on the road!

• Nomad life is full of decisions and uncertainty - the more you can embrace this the more you can enjoy the journey

• Kindles are a god send for reading solo at a bar but not having to carry a bunch of books with you

• Having some plans are nice but leave room for spontaneity and adventure - those are the stories you’ll probably be telling people years later!

Good luck!

SUGGESTED READING

The Dallas Guide

The Nantucket Guide

The Paris Guide