How I perfected traveling the world and working remotely

How I went from a type-A publicist in Manhattan to a freelancer who learned to slowdown in Croatia and enjoy lunch breaks from work in Italy.

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I thought about working remotely for five years before I did it. I wanted to travel and a mentor of mine where I worked had said that his best experiences in life happened when he was away from home and he loved the challenge of adapting to other cultures. According to a Citrix report, 50% of the workforce will be working remotely by 2020. We have technology to thank for this. Countless apps like Slack and Asana have been created to help professionals stay connected from anywhere in the world. I read in a Forbes article that among U.S. workers, 27% said they “might” become digital nomads in the next 2-3 years while 11% said they “definitely” would. The truth is most of them will not be able to make the switch. That group could have included me.

Here’s a little insight on how I went from a type-A publicist working for agencies in Manhattan 80% of my time to a freelancer who learned to: slowdown in Croatia, enjoy lunch breaks from work in Italy and set boundaries in Lisbon; I also learned a new definition of kindness for oneself and others in Japan, how to paint a mural in Thailand, a hike in Peru and stargaze in a desert in Colombia.


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Prior to becoming a digital nomad and working from 15 different countries in just one year, I sat behind a desk for nearly 10-hours a day for eight years. I spent a lot of my free time daydreaming about traveling and screenshotting pictures of places I wanted to see. In 2014, I clicked on an Instagram ad for Remote Year, a service for digital nomads. I followed the company for two years before applying. I acknowledged I was deeply unhappy, but the predictability of my daily routine provided a weird sense of comfort.

One day I found a quote that really spoke to me: be just as excited to fail as you are to succeed as there are lessons to be learned from both. I identified my goals and wrote down everything I was currently doing that was aiding them and what was holding me back. My main goal was to find a work-life balance to be happier, one that allowed time to appreciate the small things.

After an unsuccessful attempt to convince my employer at the time to let me work remotely, I gave my notice and accepted an invite to Remote Year. Even with some uncertainty, my life feels more permanent now. I no longer screenshot images of other people traveling, I just go. I’m living in the moment and soaking up every triumph and failure I experience.

Do you think working remotely might be for you? Here’s what you need to ask yourself:

1. Can I manage the unpredictability?

Traveling, like anything else in life, is fraught with unknowns, even more so if you’re traveling often. Some may find it too stressful to manage expectations. The reality is that your workspace Wi-Fi might not be strong enough for your office VPN, the hostel might not have air conditioning, you may be a target for pickpockets, your computer charger might stop working in a city where you can’t find an electronic store. You need to make sure that you’re ready to cope with the shortfalls. Since this was all so new to me, I chose to transition with the support of service for digital nomads. All I had to worry about was work, and Remote Year handled everything else.

2. Does my profession allow for working remotely?

This is a simple question for an individual, but a complicated question for a corporation. If you work deals simply with communication and you’re at a desk all day with a laptop and cell phone, you can work from anywhere. If you’re in a profession that centers around relationships say for example, as a congressional staffer, working remotely would be a challenge. Once you’ve confirmed that working from anywhere in the world is possible, identify how you’re going to make the transition.

3. Do I want to work for a company or work for myself?

Convincing an employer who’s not familiar with the concept of working remotely can be more difficult than convincing yourself. The fact is, remote workers are 13% more productive than those working in an office every day. You’re cutting commute time, unnecessary meetings and distractions. You have options. You can work with your current employer to come up with a plan that works best for both of you, find a full-time remote position using job boards (i.e. We Work Remotely, FlexJobs and Working NoMads), or work for yourself as a freelancer in your own field. It will surprise you how many of the connections you’ve already made in your career can lead to a new opportunity. Businesses are always looking for quality help without having to pay steep agency prices.

4. What are my personal and professional goals?

Write down your goals. You don’t need to wait to make a certain amount of money or wait until your next promotion to start taking baby steps towards achieving them. Identify if each decision you’ve made to date is bringing you closer or taking you further away from realizing them. Create a plan to make changes. For me, working remotely and traveling the world allowed me to take control of my own schedule, meet new people, practice new skills and learn about different cultures. I hope that wherever your next decision takes you, you enjoy the journey of getting there.

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