Swapping Your Cubicle for the Beach: Here Are the Secrets to Making It as a Digital Nomad

Amy Truong

1. Amy Truong

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Amy Truong

2. Mish Slade

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Mish Slade

3. Kit Whelan

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Kit Whelan

4. Andrea Holland

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Andrea Holland

5. Carl Hasselskog

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Carl Hasselskog
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Staff writer. Frequently covers franchise news and food trends.

It’s been another long day at the office. Your cubicle seems to be getting smaller. You have yet to see real sunlight for the second day in a row, and you probably won’t anytime soon. You look around the office in search of reprieve but the windows allow only a small bit of light through its shades. Not that it matters, it's another grey and dreary day.

The phone rings. You answer. It’s not an unpleasant conversation but the forced small talk and pleasantries don’t help to fill the void. Just like the paint on your office walls, everything’s gray-neutral.

When you started this career years ago, it was all so exciting and new. You liked what you did. But now, it’s all repetition. You wake up and do the same thing every day, see the same people, places and things. It’s been awhile since you’ve really felt alive since you started working for “the man.”

That’s when the daydreams of working from a laptop in faraway places, exotic lands and foreign countries start. Maybe one day you could be like the McDonald’s guy, traveling the world, eating burgers and “McBlogging” about it.

For some, the worldly escape will only ever live in their imagination. But for others, the nomad life -- new people, places, adventures every day -- is reality.

Below are insights from digital nomads on how they are making it work, and how to make the leap into this world:

Business/occupation: Github developer and founder of upandexplorer.com

What led to your decisions to become a digital nomad?

My initial thought process was “Wow, the world is awesome. I need to see more. HOW?!”

I was working in IP consulting for a couple of firms in D.C. at the time. But, I eventually got in the startup world, which brought a whole new world of opportunities.

In consulting, you sometimes work on top-secret projects that require background checks and security clearance and require you to work in the office because of security concerns, so I really loved the freedom and flexibility to work where I want and travel where I please.

I really think right now it’s not as big as it could be, but a lot of companies are hopping on board. It’s definitely a privilege and I really appreciate it.

What are common misconceptions about being a digital nomad?

People think you have to have all this money to travel and be a nomad. It’s actually a bit easier for me to be a digital nomad in terms of living expense. I don’t have to pay rent or a mortgage or for utilities and that sort of thing.  

What are some unexpected advantages to being a digital nomad?

Overall, I never thought I’d be able to live and work in Morocco on the beach and work in my bathing suit in a different country. It’s hard, but it’s worth it when you get to have experiences like that.

What are some challenges?

Sometimes you do have to miss family events like weddings, baby showers, birthdays or  friend’s events. Dating is also hard. You’re constantly on the go. That’s something to take account, too. You meet other travelers, but its hard long distance.

You also have to be a great at  time management. It’s possible to be productive, and you can excel. But it’s hard to be able to do this and travel at the same time. At the office, you have a routine, and you have to have that as a digital nomad, too. There’s still that need for balance.

Business/occupation: Author and blog writer at Making It Anywhere with her husband Rob.

What led to your decisions to become a digital nomad?

It wasn’t exactly a conscious decision, it just kind of worked out that way.  

After we got married, we took a six-month sabbatical to New York City. It was really easy to get started as soon as we realized what we wanted to do and we needed to start writing again.

Why remain a digital nomad?

It’s more about the freedom. It’s that feeling you get when you’re living or arrive in a new city, and you’ve got everything you own and could ever need in your bag, and that includes your work. It’s the most amazing feeling.

What are common misconceptions about being a digital nomad?

People who aren’t familiar with it, just have no clue what it is. My parents’ friends, they can’t quite figure out how we can work on the Internet and deal with clients and client issues without seeing someone in person, or run a business and not have an office.

However, we have a huge client base, because we don’t have to restrict ourselves. It’s a much bigger pool of potential clients and staff members.  We also don’t have any extra costs, like rent for an office space. Sometimes, it is nice to meet people in person, which is why we do have training days in the U.K.

To make it sustainable though, you need to work hard. [Being a digital nomad] is not an easy way out. It is an adventure, is exciting and amazing, but there’s a lot of hard work that goes into it.

What are some challenges?

It can be stressful. You go from being an employee with guaranteed money every month to setting out on your own. We found that terrifying, realizing if you don’t have a client, you don’t have money. We spent a lot of time setting up our pipeline.

What’s the best advice you have for someone considering a nomad lifestyle?

Do try to be familiar with the language and learn a few key phrases. It probably won’t get you far, but it shows that you’re trying.

Don’t pack loads of stuff. And, if you’re going to set up a business, have a routine.

Business/occupation: Social media and marketing consulting firm, Founder of 7in7 and Seek New Travel.

What led to your decisions to becoming a digital nomad?

It wasn’t a decision, it happened in a moment.

Other people work so hard, and planned for years to do this. It’s just sort of the way life took us, but it is something I was consciously preparing myself for over the years.

Why remain a digital nomad?

There’s a lot of fulfillment I get from my career.

I work about 20 hours a week. I could easily break six figures, but I like my life, my free time and ability to go on glacier hikes and get coffee. I work to live, not live to work.

What are common misconceptions about being a digital nomad?

In term of nomad couples, you can still have separate lives, even though physically together.

People talk about how your digital life and your real life are different. But for us, it's kind of the same. You can be physically next to someone but be experiencing a totally different day than they are, because you're plugged into your digital self, rather than your physical self.

What are some unexpected advantages to being a digital nomad?

There are nomad hubs like southeast Asia, Bangkok, Bali and Berlin. If I feel like it, I can sit around with my people, my community. It’s really about community at its core.

What are some challenges?

There is something to be said about having that balance between work and play, so you’ve got to have a lot of discipline and time-management skills.

Business/occupation: Global public relations at DialedPR.

What led to your decisions to become a digital nomad?

It’s a choice I made for the life I wanted to live and build. It really was a big risk. I left a really nice and secure well-paying, full benefits, whole-nine-yard job in San Francisco. I left because I wanted to pursue a certain life that wasn’t about the money; it was about the flexibility about the lifestyle.

Many times I’m just like “Wow, you just have to remember how very lucky you are.”

Why remain a digital nomad?

My favorite part is I can be on a beach somewhere or on a train in Morocco, as long as I have connectivity. It’s challenging at times, but there’s so many resources now.

I can't imagine going back and doing it any other way, because I feel lucky in having the opportunity to build this life and make it a reality for myself.  

What are common misconceptions about being a digital nomad?

People don’t quite understand. It’s a very generational thing, as well. For my parents it’s tough to understand what you’re doing and how you can travel anywhere and still make money. It doesn’t compute.

In client service you have to be very transparent about it from the get go, because you’re going to not physically be there. But my clients know my full attention is still available. I’m just going to be elsewhere. At the end of the day, it’s based on the trust in your relationship.

What are some unexpected advantages to being a digital nomad?

I think people are thinking that traveling is a luxury; it’s something they want to do but there’s always an excuse, even if it is rational. The number-one reason is they can’t get off work, especially in America. But traveling is a lot easier when you’re a digital nomad, because you can literally work from anywhere. My mentality is why not take advantage when you’re in your prime to have these experiences?

When you finally do get out, you have these great experiences. I’ve had the chance to go to off the beaten map-type places and these really great personalized experiences.

What are some challenges?

I can’t tell you how many times we would walk around new cities looking for hotels or hostels with good Internet. It's such a priority when you're doing what we do, and often times it can be difficult to find -- and that is definitely a pain point.

What’s the best advice you have for someone considering a nomad lifestyle?

It’s not for the faint of heart it. You have to be prepared for a lot of unknown and be comfortable with being very uncomfortable.

People see it as actually touring and doing those type of trips as a vacation, but if you’re a digital nomad, you’re actually going and living in these countries like you would be living in America.

Business/occupation: Co-founder of Degoo, a memory and backup service

What led to your decisions to become a digital nomad?

The appeal came when I realized that you can travel and fulfill so much of your needs with barely any money.

Why remain a digital nomad?

The freedom is what’s most appealing to me and the work comes more naturally.

Also, you don’t need a lot of money. You can live a fairly natural lifestyle, get lots of work done, meet amazing people and experience paradise at the same time.

What are common misconceptions about being a digital nomad?

Back home, people tend to think that traveling, like going to Bali, is a sign of laziness. But there’s another side to it. Working while traveling is hard work, and it’s about living life to the fullest rather than not doing anything.

What are some unexpected advantages to being a digital nomad?

The big benefit is I get to understand the customer base better when I work with clients from all over the world. I learn more about their cultures and way of life, and it’s easier to work with them and build a product that appeals to them.

What’s the best advice you have for someone considering a nomad lifestyle?

With today’s economy, everything enables you to be much more independent, but that can also be scary sometimes. Sometimes, it’s easier to have someone else make the decisions for you, and when you’re not happy you can blame someone else.

There’s also many potential distractions, you have to be able to balance work, so you have to have something you’re passionate about.

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