Centering Yourself: A Guide to Digital Nomading as a Means for Self-Exploration | Part 2

Part 2: Designing your first draft…

This is the most exciting and most challenging step: designing the first draft of your digital nomad plan. The goal here is to review all your options and craft a plan that looks and feels good to you and your circumstances on paper. Emphasis on the “on paper” part because once you arrive things may feel different and you might want (or need) make some changes to your plan. This is totally okay! Going into this process knowing that you will eventually change some details around whether it's finding a new accommodation, adding in a new city to visit, or altering some of your dates. Take the pressure off of this step because uncertainty is expected. The most important part is to build a plan that is firm enough so that you’re covered but flexible enough that you can make necessary changes without too much risk.

First, map out your professional and personal limitations. Understanding your limitations gives you concrete details to work with and prevents you from dreaming too big (or small!) for the opportunity you have right now, right in front of you.

Mapping out your professional limitations:

I’ve found it easiest to start with professional limitations since your job is fueling your trip. You’ll need to know for certain that your job (even if it’s remote in the U.S.) will allow you to do this.

For example, your employer (or even your position within your company) may restrict where or how you travel. I learned that some remote jobs may only allow you to work out of the country for a certain amount of time (i.e., 60 days). Others may only permit you to work from certain countries (i.e., no countries or regions listed at or above Level 3 — Reconsider Travel on the U.S. Department of State Travel Advisories). I’ve learned from friends that some positions or industries where you work with proprietary and/or sensitive data might not allow you to bring items like laptops or phones. A simple “plant the seed” message or conversation with your HR specialist or manager can help you understand if travel and work are a go.

Once you’ve determined that you can in fact travel and work, it’s time to think about scheduling. Do you have occasional off-sites, retreats, or meetings you have to attend in the U.S.? If you answered yes, you will need to factor these events into your plan when deciding when and where you go, as well as what you bring with you.

For example, if you have a company offsite every year in September that takes place in Colorado and you want to travel for three months starting in July, you’ll have to make a few decisions before committing to your schedule. One decision might be to see if you can skip the offsite. Maybe it’s optional or your employer is willing to grant you special permission to miss it. In my experience, it never hurts to ask, if that’s the option that could work for you.

Another option is to potentially shift your timing and dates, going with the option that allows you to make it back to the U.S. in time for the offsite. Maybe you still leave in June and come back in late August or maybe you cut back your trip ideal from three months to two months and still leave in July.

The last option, which often can be the easiest or hardest, depending on the circumstance, is to go to the offsite and then go back to traveling. Let’s say you leave in July, travel until September, spend a few days in Colorado, and then head back out for another month. This option may not be feasible if you’re digital nomading through Southeast Asia, but it could work well if you are digital nomading through Mexico and can get on an easy, direct flight back and forth.

At this step, I’d also recommend documenting the seedlings of your plan and your questions for your employer on a Google Doc or in your notes app on your phone and bringing it back to your HR colleague or manager. Sharing the basic details about when and where you’re thinking about traveling, especially how it relates to any company-wide events, doesn’t hurt. In fact, being proactive with your planning and bringing in the appropriate people to weigh in on your request might be necessary. I remember needing to get my request approved by my manager.

Example: I set up this Notion page where I kept track of all the details of my travels, leading up to and during.

Mapping out your personal limitations & setting your dates:

Once you find out what work and travel policies (or lack there of) you may need to adhere to, it’s time to weave in your personal preferences and constraints to lock in your dates. I chose to travel for the months of May, June, and July because my lease was up at the end of April. It was perfectly timed too because I got to take advantage of what my friends dubbed ‘Euro Girl Summer’ at 24 years old, where I could enjoy the influx of tourists to the region and enjoy the busy summertime energy.

Choosing your dates first allows you to align with the best places to travel. For example, if your dates are October through December, you may rule out going to Costa Rica for a beach getaway because it’s during the rainy season. But… maybe you’d go at that time if you’re looking for a steep discount on your accommodation or you just want to spend your days in the rain! The most important advice here is that it really depends on you and what you want — there’s no right or wrong answer on where to travel. By settling on your dates you can make those decisions better and decide where you’d value being.

Nailing down your exact location(s), accommodation, & starting to think about travel cadence:

Once you have your dates and country or region, it’s time to consider your location more closely. I suggest that you be open to going to places that call you and try on new ways of living but also be realistic for yourself.

After deciding on Portugal, I chose Lisbon because it had a great reputation for hosting digital nomads. Its vibrant cityscape, diverse people, and easy-going way of life made it even more attractive. What really sold me, however, was the fact that it is welcoming to digital nomads of all backgrounds, very safe, and also easy to get to or from if needed. As an anxious girl who was trying out this new way of traveling, and doing it by myself, this was essential. Choosing Lisbon afforded me peace of mind.

The view from outside of my accommodation in Lisbon. Where I’d take walks in the mornings and evenings.

I also knew how much I wanted to be immersed in nature — specifically mountains and the ocean, since it would be summer. I couldn’t stop thinking about how cool it would be to actually live next to the ocean. So I booked some time in Madeira Islands, an island 400 miles off the coast of Morocco also known as the Hawaii of Europe.

This decision was to push me in the direction of my dreams, values and also fears. And if I hadn’t reflected about or honored my values, I wouldn’t have allowed myself to have that experience. I would’ve played it safe and maybe had the digital nomad experience of someone else’s dreams.

Although my plan for when and how long I would stay in Madeira changed between drafts (more to come on that in Part 4), it really made my digital nomad experience. Looking back, there were other locations I wish I had tried out. They were more remotely seeped in nature but at the time my priority was peace of mind, stick mostly to what I know, and that was big cities. Even though, I can reflect on what I might’ve added, I wouldn’t change a thing about my experience. Because the goal within all of this is to plan and try, and plan and try again!

Now the tougher part. Setting up a trip you can afford and sustain. The biggest thing that you don’t want to skimp out on is your accommodation. If you are anxious or new to traveling, I’d go back and highlight that sentence. Traveling can be very exhausting. You’re likely navigating new languages, new customs, and new paces of life. Just trying to find your way can take time. That’s why finding an accommodation that you feel safe and comfortable returning back to every day after a long day of sightseeing and working is essential.

Across the board, I can tell you that finding an accommodation that has at least a comfortable bed, reliable internet, and a desk is everything. A place to sleep, a place to connect, and a place to work are the barebones. Once you have those, think about the other priorities you want your accommodation to have.

My top two priorities were having a reliable, stress-free place(s) to work and a network of people to get to know. There are so many options for accommodations these days, so you do have to sort through your options. You have hotels, hostels, Airbnbs, co-living houses, and more. For me, Airbnbs and hotels were knocked out because you can’t always guarantee good wifi and you’re still alone. Co-living companies like Outsite (which I used!) and Selina (learned about) include co-working cafes, desks, and high speed wifi in your accommodation fee.

Outsite also had a group chat and community managers who threw weekly events to encourage collaboration. Looking back, a quality that Outsite had that I later appreciated was their flexibility in canceling. They had a really great customer service team and you could cancel or modify your trip for a full refund as long as you made the change 14 days beforehand. This also gave me peace of mind going into booking a three-month trip, several months out. More to come on this in Part 4.

The biggest misconception I hear about digital nomading is that it’s insanely unaffordable. Finding an accommodation that has all of the things you need listed above is just not as expensive as you might think. Booking one month in Lisbon and Madeira Islands turned out to be cheaper than my Washington, D.C. studio apartment rent and I got to live in a cool place and meet tons of people that I never would’ve known. Some companies may even offer discounts the longer you stay. That’s why I’d suggest that you dream big and then crunch your numbers.

My comfy room in Lisbon! I had a lovely bed and two big windows where I could sit at my desk and work.

Once you have a sense of your dates, your main location, and your accommodation, you can dive into your travel route. If you pick Europe, for example, you can get out a map and star cities you think would be interesting to travel to and cross-reference what the options look like on whatever accommodation you choose. You can also take a look at companies like Trip Advisor or Viator that do excursions and see what kind of options you have for leisure, entertainment and exploring. This is not for you to stick to but it’s to help add some structure, some inspiration, and some ideas, around the dates and location you chose.

Travel cadence can be tricky cause it will almost always take some adjusting and/or trial and error. I’ll be discussing this more in Part 4…