Insightful Realities of Being a Digital Travel Nomad

Let me tell you a story!

That experience with the dentist in the Dominican Republic who shocked me with her work to get to my teeth… just wait until you read about it!

I am very blessed and fortunate to live a “boundless life.”  My only big responsibility at this point is me, and I am okay with that.

The other day, I was halfway joking when I told a friend that I “did my duty” and now it’s my turn to take care of me. I would be lying to you if I was to write that I was a devoted mom, wife and daughter because the truth is that I fulfilled my responsibilities to the best of my abilities with the little knowledge I had about how life was supposed to be. I try to be better every day even though I know I am perfectly imperfect. I am still dealing with my insecurities and my demons, but we are getting along fine!

I did not have a manual on how to raise my kids. I did not know how to be a perfect daughter even though I always sought validation from my parents, my elders, my partners, my daughters, my community, and my circle of friends. I think I developed a reputation for being “the one who is always there” and I was okay with living up to that expectation regarding of what I felt. And I felt a lot – anger, resentment, disappointment… you name it.

In May of 2023, I had some sort of epiphany. My soul was speaking to me, no – it was screaming at me, and I finally began to listen. It told me that it was time for me to be happy. It had been more than 10 years since my kids had moved out of the home we built, it had been more than two years since my divorce had been finalized, and by then, I had also done everything I could humanly do for both my elderly parents, and several other relatives. My soul was tired. So was I.

I had checked every box required by society in my life: the degrees, the house, the kids, the marriage, the divorce, the credit score, the bank accounts, the executive job, the sports car, the wardrobe, not in that order. I had achieved them all. Yet, somehow, I felt empty inside.

Ten months later, I decided to sell my house, give away or dump a lot of my belongings, and keep some very meaningful items in storage. I booked a ticket to Bali, yes, Indonesia, and on March 31st I was on a flight from New York that changed my life.

Some people thought I was homeless, but I have not been. Other people thought I lost my mind, and I did not care as I owed them no explanation. Finally, my kids told me to “go ahead and be happy”, and that, I think I am.

I have been now an official digital travel nomad for nine months and I have visited or stepped foot on at least 8 countries, which is a technicality because I am counting layovers (Saudi Arabia, Dubai, Malaysia and El Salvador) However, I have fully lived in four countries this year: United States, Indonesia, Dominican Republic, and now Colombia.

This is where it gets great. Let me tell you about what I have learned about the good, the bad and the somewhat ugly about this lifestyle and how I have managed!

The Good:

The Good – it’s reeeeeally good Trust.

1. 1. Flexibility and Freedom: I get to enjoy the ability to create my own schedule, work from stunning locations, and choose where to live based on personal preference and lifestyle. Long gone are the days when I had to be at my desk in an office at 9am – you know, getting ready, making breakfast and sometimes lunch, get in the car (I don’t miss the snowy, cold days!) Then be in pointless, useless meetings all day – time sucking vampires that drained my productivity and creativity! I don’t miss any of that!

Now, there is something to be said about having a US passport and the door open to most countries around the world. I get to choose where to go next and for how long, so I get a different environment every so many months. Some people call it “slow-mads” and I am okay with that.

I was in Bali, Indonesia for almost two months. I did not want to leave. Opening my laptop in Nusa Penida at my villa by the pool after breakfast, or working from Mertasari Beach while sipping a beer or having lunch/dinner while hanging out with the locals was phenomenal! I have gotten to create some of my best work in Medellin, Colombia, which welcomes nearly 8,000 digital nomads every month into the city!

2. 2. Cultural Immersion: I get to experience diverse cultures firsthand,I have broadened my worldview, and gained valuable insights that enhance both my personal and professional growth. Because I have gotten to schedule tours in between to sightsee and learn about each community or country, I hear and see the things mainstream media in the US never share.

I have gone into neighborhoods like Comuna 13 in Medellin to learn about its history, which is marked by a lot of violence, power struggles, unfairness, and have learned about the community’s inner strength to take back their neighborhood making it one of the most energetic ones I’ve seen.

In the Dominican Republic, I got to visit El Panteón de la Patria, for free – mind you! – and learned about the country’s historic battles against both Spain and Haiti to gain its independence. These are stories that make me often think about society’s inequalities and how each country has had to struggle to get to where it is today. I can talk about Bali *all day* so I will skip on all I did there!

3. 3. Networking Opportunities: Connecting with other people has been interesting. I don’t necessarily try to socialize with other nomads. Often, we are working as it is evident by the number of people I see on laptops at cafes and restaurants. However, I do get to share my story with locals, which tends to get them intrigued about my life, my kids, my work and this has created new friendships around the globe. I know exactly where I will stay when I return to Bali in 2025, and I know where I am getting my hair and nails done when I get to the Dominican Republic, and I know who I can call to pick me up at the airport in Medellin because that’s what happens! I connect with local people and stay in communication over WhatsApp, and I love it.

The Bad:

1. 1. Inconsistent Income: Although I am very lucky to have a steady source of income, the nature of freelance and online work makes me more cautious about when and how I spend my money. I have a budget in mind for rent and it must include wi-fi, a kitchen as I like to cook my own meals, a washer (and maybe a dryer or clothes rack), and I need an air conditioner in hot climates or at least a fan. Hey, I am glad I don’t drive – by choice. It makes no sense. In my budget, I also include potential fees to do excursions and tours at least once a week or every 2 weeks. I don’t own fancy clothes or jewelry or make up – as a matter of fact, I went down from two closets full of clothes and shoes to a suitcase and a backpack – talk about downsizing and being a minimalist! I am okay and happy with that!

2. 2. Time Zone Challenges: Sometimes coordinating emails and email responses, meetings, and deadlines with clients or teams on the other side of the world can be tricky, especially if there is a time difference of 6 hours or more. This means, I must get creative to work very late nights – as I have, taking a meeting at 1am and sleeping in or taking naps in the afternoon or early evening so I am wide away past midnight. I am perfectly okay with that as they don’t happen often, so the sacrifice is worth the reward.

3. 3. Limited Access to Resources: Depending on my location, I have encountered issues with reliable internet, power outages, or lack of workspace, which has hindered productivity. In Santo Domingo, power outages are frequent to the point that one day I counted around 5 or 6 in a span of a few hours. Luckily, most of the apartments I have rented are equipped with a backup power generator big enough to kick in within 30 seconds, which is great. Now, imagine having to reset your internet connection 5 or 6 times in just one afternoon. It gets frustrating to say the least!

The Ugly:

1. 1. Loneliness and Isolation: For some, constantly moving can lead to feelings of isolation, as it may be hard to establish deep, lasting connections with others. However, I am an introvert and this is not the part that gets ugly because I try to go out every so often. The part that gets ugly is when I do have a connection with someone, like the young woman who did my nails in Santo Domingo (Dominican Republic) who, for almost three months, shared some of her life’s moments with me. She is just about my oldest daughter’s age and her kids are a year younger than my grandkids. It was a little rough leaving the Dominican Republic when I left and she made it special. I know I will be back and I know I will see her again, but that last day was hard.

2. 2. Health and Safety Concerns: Traveling can potentially expose you to varying health risks, inadequate healthcare systems, and safety concerns in some areas. This is true. Imagine having the same dentist for most of your adult life and suddenly, you get a toothache in a country where you don’t know anyone or where to go!

You have to stay resourceful at all times. Ask the people you meet along the way to suggest a dentist or the nearest health clinic or urgent care centers. I asked the drivers all the time “Where can I find X? Where do you go to get X done?”

Heaven forbid you get “Bali Belly” or “the dengue” or worst, have to have emergency surgery… My suggestion is to get on your favorite search engine, look up providers, look at their reviews, create a “just in case list” and keeping an eye on your health.

I found a great dentist in the Dominican Republic, and she was able to get me in the same afternoon for a cleaning. After X-Rays, we were able to see I needed some repairs to some work I had gotten done years earlier. It was a fraction of the cost of what I would have had to pay out of pocket, plus she did not use anesthesia! That was a really great experience!

3. 3. Work-Life Balance Struggles: It doesn’t help that I am neurodivergent – as in, I have Adult ADD. It IS a thing! This makes the line between work and leisure blurry making it challenging to disconnect from the laptop, smartphone and email to fully enjoy my travel experiences.

Then when I do get to do any extracurricular activities, it is hard to go back to work. So, I make it a habit to break down my workweek, and I am not spending 5 days of back-to-back work. I work 2-3 days, but then I go out to a mall, on a tour, to the museum, restaurant, or park to take in the beauty of my surroundings and perform my favorite sport of all times: people watch!

It makes it easy for me as I don’t get the sensory overload, and I can find balance.

Being a digital nomad is not for everyone. I have to say that the last nine months I have spent a lot of time adapting. I spent a lot of time comparing flights, ticket prices, schedules, lodging. Finding a place to stay takes probably a good 30% of my time in a month because it is not often that I get to spend more than a week at one given apartment. I must be careful and conscious about where I’m going, the neighborhood, and pay attention particularly to the reviews from other renters.

Sometimes, I also reach out to my friends back in the US who know the area I’m planning to visit so that they can tell me what neighborhoods I should rent and where to get some of my essentials. This lifestyle is doable, even with kids. I do not recommend it unless you’re willing to take on home schooling., which makes me ask: would you want to do that full time?