How to Work Remotely and Travel

Yes, work sucks, but now, more than any other time in history, you don’t have to be shackled to a desk or a job you don’t love.

You don’t have to stay in one place fighting for every measly promotion for 45 years while you wait to retire. You don’t have to endure another unbearable work meeting with a micromanaging boss and co-workers ready to throw you under the bus just to make themselves look good. Now, with the internet flourishing in the gig economy, you can create the work and the life you want.

Have you been told since you were little that you should go to school, get a good job, and climb the ladder? Whether it is a cubicle, office, classroom, shop, or a service job, not everyone is cut out for working in the traditional way.

What happens when you follow the path laid out before you and it just doesn’t feel right?

Some people suffer in their jobs for years and even decades trying to find the illustrious dream they were told would happen. This can result in damage to their health, their relationships, and their sense of self.

The reasons for not leaving a crappy job and not trying something else are ingrained in us from a young age. Maybe you have been told it is flighty, irresponsible, or selfish to want to experience another side of life. Maybe you have been told, or you tell yourself, that you will fail if you go out on your own into the world.

I’m here to tell you that none of that is true.

I’m here to tell you that you have other options.

But first, I want you to get an image out of your head.

Working remotely, being a “digital nomad,” or being “location independent” is not about working on the beach with your laptop while sipping an umbrella drink or a beer.

Sure, that’s what you see on Instagram and Facebook, but that is not the daily life of a remote worker. Will you ever get to do it? Yes, you will, but you won’t like it. Sand will get in your keys, the glare will kill your eyes, and you won’t want to leave your computer to get in the water.

But you will have amazing adventures, and you won’t regret not having the beach laptop picture.

Let me tell you what the real remote working and traveling life looks like for a few actual people I know.

Hugh – The Hotel Adventurer

Hugh has been working on his own since he left the military over 15 years ago. He was just a few years away from retiring from service when he realized he didn’t want to give up one more second of his life being under someone else. Many people told him he was crazy to give up the military retirement benefit, but Hugh’s independence was more important to him.

He started working for himself and found an independent contractor position selling hotel advertising. He would travel to a hotel, work hard for 4-5 days meeting with local businesses, and spend the rest of his stay, about 2 weeks, sightseeing, eating good food, and working his own online sales business.

Now, Hugh doesn’t need to sell hotel advertising because his business grew to a full-time income within a year. But he still loves staying in hotels. He takes any time off he wants, travels all over the world, visits friends, and enjoys his traveling lifestyle. His favorite trip so far? To the top of Table Mountain in Cape Town, South Africa.

Liliana – The Graphic Artist Grad

Chang Mai, Thailand is considered the “digital nomad” capital of the world. It is a beautiful area with inexpensive housing costs, great wi-fi, delicious food, and a bustling community of entrepreneurial dreamers working to make it happen. Liliana is one of them.

When she graduated college, she took all the money she received and booked a flight to Chang Mai, against her parent’s wishes. She knew a friend who had gone a few years before and also gained some insight by following the blogs of successful nomads. With a degree in graphic arts, she was ready to take what she learned and apply it to traveling and making money on her own.

Liliana soon found graphic arts was going to be a challenging endeavor on its own and started taking free courses available online in digital marketing. Once she combined the two skills, her business took off and she has since been to three more countries. For now, she is happy with her business and while she says she may “go get a job one day,” she would never trade the experience she has had going out on her own.

Her typical day consists of about 2-3 hours of work. She spends the rest of her day taking a yoga class, getting a massage, eating great Thai food, and making friends with people from all over the world.

Allison – From Retail to Remote Writer

Allison’s path is a perfect example of using the tools you already have to become a successful remote worker. She worked on her high school newspaper and finished one year at her local community college. She was ready to be done with school and her full-time job in retail. More than anything, she wanted to travel.

Small trips to Canada and Mexico didn’t appease her and only intensified her travel bug. She created a travel blog to document her two trips she had taken with the hopes that she would be able to add many more trips in the future.
In a Facebook group, she came across a company looking for a travel writer who could write about the city she lived in. She shared her blog with them and her knowledge of the area from working for her school newspaper. They hired her to write one blog per week and Allison’s freelance writing career was born. Now she teaches other writers how to find jobs and currently lives in the UK. She is filling up her passport with monthly train and bus trips around Europe.

If you don’t already know it, you will learn soon enough that life is short and we have to make the most of it while we are here. This means taking risks, big risks, but taking them in sensible ways to make the life we want. Here are a few tips to help you on your remote travel journey.

1. Go with what you know.

   So many nomads transitioned from the job they were doing into a remote lifestyle. Marketers, financial representatives, teachers, psychologists, web designers, students, artists, and medical coders all have skills that can transfer to a remote lifestyle. Start by making a list of all of your current skills. This is a great springboard to see which direction you want to go.

2. Figure out your passion.

   This is one that is sometimes elusive to people. You may be one of the lucky ones and know instinctively that your passion is definitely gerbils or motocross. Others struggle with having too many passions, or not feeling stirred enough by any one thing to nail it all down. That’s OK! Make a list of things you like and don’t get so tripped up on the “passion” word. One question that helps with this is thinking about how you would live each day if money were no object?

3. Start living online.

   Join Facebook groups, follow Instagram influencers, and start learning some of the lingo related to working online. Soak up as much free content as possible. Many travel bloggers give tips on how to get clients, types of remote work available, and how to make the transition from job to travel.

4. Ask all the questions.

   Whenever you find someone who is doing what you love, or at least something similar, ask them for advice. Send them your list of skills and interests and ask them where you might fit in the remote world. Ask them what they do and how they do it. You may be surprised at the incredibly supportive community among digital nomads. As a group, they want the concepts of the gig economy and remote working to work not just for them, but for anyone who wants something different from a cubicle.

5. Learn new skills.

   Once you start to narrow down type of work you want to do or the business you want to create, start learning new skills to fill in the gaps. Take free courses to help build up your portfolio.

6. Dip your toe in.

   Maybe you aren’t ready to move half-way around the world just yet. Some remote workers start out with options like housesitting, volunteer experiences, study abroad, and teaching English. Perhaps your current employer would allow you to work remotely a few days a week? Start experimenting by taking on a few clients in the evenings and on weekends. See where it takes you. You’ll be building skills and increasing your confidence to take a larger plunge when you’re ready.

The goal when you are beginning is to learn what’s possible. Once you see other people thriving as remote workers, you will be able to imagine yourself breaking from your job, forging a different path, and finding success as a remote traveler.