Lessons Learned — My Journey as a Digital Nomad

Alexandra Macias
8 min readApr 29, 2019

Over a year ago I joined a company called Selina. A hospitality platform that is developing the home for the new generation of travelers and workers: the digital nomads.

Although this concept started to gain popularity in 2014, I didn’t know anything about it up until last year.

My role at the company allowed me to travel more than I could have ever dreamed of. The travel became so frequent that at some point it became a waste for me to pay rent in Tel Aviv, and that’s really when the journey as a nomad started.

Everyone talks about how fun and awesome it is to be a digital nomad. I wanted to dedicate the next few paragraphs to speak out some of the struggles that nomads, or at least I personally went through. For the sake of keeping an orderly post, I’ve divided the “lessons learned” into two sections:

  1. Working remotely
  2. Living nomadically

Working Remotely

Working remotely is rapidly becoming a well-adopted practice. According to a Citrix study, it is expected that 50% of the workforce will be remote or office free by 2020.

In fact, the remote workforce has grown by 140% since 2005 according to Global Workplace Analytics. In the US, more and more companies are going completely remote, growing from 26 in 2014 to 170 in 2018. This is a trend that is going to continue to grow and is going to favor the younger professional generations that consider travel and work-life balance as a crucial part of their lifestyle.

When I joined the company, while I was based in Tel Aviv, my team was scattered mainly around Colombia, Panama and the US. It took roughly 3 months until I met my colleagues in person for the first time.

Photo Source: Kevan Lee, What is Remote Work? A Guide for Building Remote Teams and Finding Your Dream Work-from-Home Job (Buffer blog)

The pros are quite obvious: you get to work from home, your favorite coffee shop or even a hammock by the beach. As long as you execute, wifi works and you turn on the camera for the video calls, you are good to go. You feel empowered, responsible and accountable for your actions.

But what about the cons of remote work?

  • Working in teams: face to face interaction is crucial to building a healthy team culture and dynamic. When you join or create a team remotely, the sense of engagement is completely different. The daily “standup calls” are the replacement for the morning coffee, but instead of talking about the amazing party that you went to over the weekend, you are already talking about your tasks and struggles to execute your goals. You just know what you hear and what you read in the emails. Trusting a team with that little information is not trivial, and probably not possible either.
    It took 3 months after I joined the company when I got to meet my team. It was probably one of my happiest days, and also when the real teamwork kicked off. We spent a few days together, bonded, got to know one another in a more personal way and connected in our interests and personal goals, beyond the framework of the company. That’s how you build trust and a healthy team dynamic.
  • Loneliness: working remotely can get lonely. If you are traveling by yourself or you are in a city where there are no colleagues, it can get lonely. Yes, you do get to experience the flexible hours and all that jazz, but.. to what extent is it fun to work alone from a coffee shop? You can obviously meet random people, but you end up missing those weekly meetings in the conference room or those office happy hours.
  • Losing track of who is working where and doing what. When being part of a hyper-growth company, there are constant changes in roles, teams, and employees. When I traveled to Panama for the first time, 3 months after I joined the company, there was a company retreat. I finally got to put faces to all the voices that I had spoken to. It was a game changer. But then 3–4 more months passed and in the next company retreat so many new faces and names I had to learn. Hard to keep up.
  • Your days are so flexible that you end up fitting 2 work days in one. While I was in Israel, I had to start in the morning hours to do my work, but then when the evening came and you would normally close your laptop, the other hemisphere of the world is waking up and turns out your team is there. It becomes hard to create the so-called “work-life balance”. It happened more often than I could have hoped for that I was having drinks with friends at 2 am and a call from Colombia popped in. Gotta learn how to manage time and how to respect the timezones of everyone you work with, and in order to achieve that, your calendar becomes a part of your body. Blocking hours in which you will be sleeping, the lunch break in the middle of the day, and even what hour of your morning you dedicate to your pilates class.
Image source here

Living Nomadically

Now, it is one thing to have a flexible work model in which you work from home or the beach a couple of days a week, or even the entire week. But it is a whole different situation when you are traveling while working. I can only speak from my own experience, so this part will be way more personal and subjective than the first one.

To set the right context I must emphasize that I never formally decided: “I want to be a digital nomad”. I had a couple of 3-week trips and then planned for a longer trip of about 2 months, so before departing, and accompanied by other personal matters, I understood that it didn’t make sense for me to pay rent anymore. That 2-month trip, by the way, ended up turning into an 8-month journey.

  • I understood that you can’t have one home. Spain is home, Israel is home, Mexico could probably be home too, and the more I get to travel, the more I realize that. The way that the world is connected and how accessible travel has become, there is no reason to hold on tight to a single place to call home. But just as much as you become a citizen of the world, you become homeless too.
Image source here

Which brings me to the next point:

  • You own what you can fit in roughly 23 kg. The whole idea of a nomad is that you can move from place to place with what you have on you. You might have bought a house and then taken the time off to embark on the nomadic journey, so you have your belongings there. But if you are like me and don’t own a home and you gave up on paying rent, then all you have is what you can fit in your suitcase. How did that play out for me?
    Stressed out so much about not being able to bring enough stuff with me, that I made sure to pack those 23 kgs + the 10 kg of the carry on to the fullest, and leaving boxes of extra clothes in storage rooms between Spain and Israel.
    Of course, I had overdone it. Being a nomad teaches you how much shit we have that we don’t need. How many things we keep in our closets “just in case” even though we haven’t worn them in years, and are still hopeful that we will.
    But at some point, it becomes boring. You have used the same clothes for the last 4 months. I ended up doing something a bit stupid, or creative: every location that I would visit, I would leave an item of clothing that I hadn’t used or known wouldn’t need, and then replaced that item with something new. Silly, but you gotta compromise.
  • Back pain. You quickly learn to appreciate the mattress that your grandma recommended you to buy when you had moved out of your parents' house. Hotel rooms, Airbnb’s, couches, airplanes, buses, tents? That cocktail of accommodation alternatives end up paying off, and it hurts a lot.
  • Fear of commitment. The world is yours. You can literally live anywhere you want and move wherever you want. I have friends that have stayed in the same city for months and yet have switched apartments on a weekly basis. The idea of committing to one location and booking an Airbnb for more than a week or two is terrifying and also ends up being more expensive than paying a month of rent. But, who can commit to a short-term rental contract? That would limit your freedom to choose what to do.
  • Keeping a healthy routine becomes very difficult. I personally hate running. In fact, I am more of a Pilates person. I love going to the studio in the morning and start my day like that, but if you are constantly on the move, how do you find a studio that will take you for a few weeks? Sure, you can pay single classes instead of full membership, but then, how do you make sense out of your finances?
  • Keeping up with your life before you were a nomad. You still have a family, friends, maybe even a relationship. Traveling and moving around so much ends up creating some kind of constant long-distance relationship with what your former life.
Image Source by RawPixel on Unplash

My conclusion is that living nomadically should be a well-thought decision, with all the pros and cons that it entails, and also the sacrifices that come along with it. My personal take in it is that being a nomad and working remotely is a fun experience that makes you learn and grow in countless ways, but also something that is temporary. Temporary could be several years, but at some point, at least that’s what is happening to me, you end up missing having your own bed and a more established routine.

I’m still surprised that I am feeling this way, but now the real question for me is: what will be home for the foreseeable future?

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