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Becoming a Digital Nomad: Keys to Success

Becoming a Digital Nomad: Keys to Success

At the time of writing this, we’re in the throes of the Coronavirus pandemic. Millions of people have been sent to work from home. Several are asking themselves if they could continue working from home forever. The brave few are wondering if they can take it to the next level: working from anywhere forever. In other words, people are considering becoming a digital nomad more than ever before.

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While ‘digital nomad’ might conjure up images of millennials working on beaches, there’s so much more to it than that. The good news is, there’s no one cookie-cutter answer to ‘how to be a digital nomad’. However, I’d argue that there are a few keys to digital nomad success that people should know about before deciding to leave the 9 to 5 life in pursuit of eternal working holidays.

What is a Digital Nomad?

In short, a digital nomad is a remote worker. If you work from home, in theory, you’re a digital nomad already. However, more people would add on that digital nomads also travel while working.

How much do they travel, exactly? As much or as little as they want.

On one end of the spectrum, a digital nomad might be a parent that travels with their family and works as they travel. On the other, it might be someone that sleeps in a different bed every week, traveling to new, exotic places as often as they can.

More often, a digital nomad is someone that works full time and stays in places for a few weeks to a few months at a time.

Point being – anyone can be a digital nomad any way they want. It’s just important to know why you want to be one, and to do it in a way that works for you.

Climbed a mountain, achieved a goal!
After I became a digital nomad, I spent a ton of time hiking, road tripping, and with my family

Why I became a digital nomad

When I was in college, I was recommended a book called the 4-Hour Workweek by Tim Ferriss. The book changed the way I thought about a lot of things, including how I envisioned my future of work. I had spent the summer after my freshman year living and working abroad, so I knew that was possible. However, the 4-Hour Workweek led me to realize ‘work’ didn’t have to be in a single place.

To be clear, I didn’t know what I wanted to do. I did know what lifestyle I wanted to have.

Read that again. I had figured out (a lot earlier than most) that my happiness wasn’t going to be found in a cubicle. My idea of working was not college –> work –> retire. Instead, I wanted to enjoy my entire life, and take short ‘retirements’ at my discretion.

I didn’t want to retire in the sense that I stopped working until I ran out of money. Instead, I decided that I wanted to work to live, and that my lifestyle was going to change and flow with me. My plan was to read often, work as much as I needed to, and chase ideas.

The good news is, that’s exactly what I’m doing now. It took me five years and finally making the jump to becoming a digital nomad, but I got here. At least I didn’t wait until I was 65.

Working outdoors
A lot of my fun days are punctuated with work stuff. It’s all about balance.

5 keys to successfully becoming a digital nomad

Okay, so, how does one become a digital nomad? That’s easy. You take your computer and go somewhere. You continue to work and live wherever you want.

Like almost anything, there are good ways, bad ways, and better ways to do things. After meeting thousands of digital nomads in the past several years, here are a few things that I find the successful ones have in common:

1. Know why you’re becoming a digital nomad

The first key to a successful location independent lifestyle is getting your mind right. You should have a keen understanding of why you’re choosing this life. It’s nontraditional, and everyone thinks about going home and doing the easy thing occasionally, so it’s vital that you understand why you’re doing what you’re doing.

If you value freedom, want to travel more, or simply want to live more cheaply than in the U.S., then you might already have reasons to become a digital nomad.

On the flip side, if you enjoy the creature comforts of home and have never traveled to a place and thought, “Man, I wish I could just… live here”, then you might need to dig in to your ‘why’ a little bit more. Same goes for if you simply hate your office.

Your reason doesn’t matter as much as your conviction behind it. If you are truly interested in living a location independent lifestyle while earning enough to sustain it, then give it a shot. The worst thing that happens is you can go home and reset.

Becoming A digital Nomad: Keys to success
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2. Prepare for the emotional roller coaster

Depending on where you go, how long you stay there, the people you surround yourself with, and the work you do, becoming a digital nomad can take a huge emotional toll on you.

One day, you might be in LOVE with Rome. You don’t think you can ever get enough aperitivo and basilicas. Then, one day, you suddenly will realize how loud it is. You’ll get annoyed with people being so touchy with each other, and start looking for a way out.

Sometimes, digital nomads take on a new career when they hit the road. Many people have a sudden, crushing realization that they hate teaching English online or finding their own clients.

What I’m saying is, one bad shower can leave you really missing home. So, prepare for the ups and downs.

Bring a few comforts of home with you. Mine is my memory foam pillow and several bags of microwave popcorn. There’s nothing some snacks and a good night’s sleep can’t fix.

3. Ride the global economy

This is a major key to location independent success.

“Earn dollars. Live on pesos. Compensate in rupees.”

Tim Ferriss

When you take on a digital nomad lifestyle, you put yourself in a unique position to earn as much as you did in the states but experience twice the lifestyle. Hear me out:

Let’s say that I still lived in Dallas. In a shared apartment, I spent $1k a month on rent, $100 on utilities, $70 a week on groceries, $100 a month on car insurance, $40 a month on gas, and $400 a month dining out. Not including other little things, like going to sports games, ubers, and more, I easily spent about $3000 – $3500 a month.

Now, let’s consider another major city that expats love: Kuala Lumpur. I could live alone in a luxurious downtown apartment for $500 a month (comes with utilities and regular cleaning, too!). I’d spend about $30 a week on groceries, and maybe $200 a month dining out. I wouldn’t have a car, so ubers everywhere might cost a little more. Getting a car to the beach for the day costs about $40 per person. My life there would only cost about $2,000 a month if I wasn’t being frugal.

Moroccan Breakfast
At my place in Morocco, breakfasts were prepared for me each day along with the other people living in my building.

These examples would be similar in other nomad hotspots including Playa del Carmen, Mexico; Tbilisi, Georgia; and in Bali, Indonesia.

Therefore, permitting that I earn the same amount in the U.S. as abroad, not only could I invest my extra money, I could choose to work less, therefore enjoying the places I’m visiting even more.

Riding the global economy means earning money in dollars, while living on cents.

A note on retirement and the global economy:

Being a digital nomad doesn’t mean you can’t afford to live in the U.S. Instead, it means that you’re choosing to live wehrever makes you happy. It’s still smart to invest for retirement.

A lot of people choose to retire outside of the U.S. However, it’s a heck of a lot cheaper to retire abroad. It’s worth considering a nomadic lifestyle, even in retirement.

4. Follow technology

Before becoming a digital nomad, I would seek out vacation spots that were off the grid. I’d use my PTO to go off into the mountains of Guatemala and not use my phone for a week. I got away from my work by getting away from technology. However, it’s a little bit different as a digital nomad.

Digital nomads don’t work from anywhere. They work from anywhere that has good WiFi.

Places like Asia and Southeast Asia are known for having some of the most advanced technology in the world. Not only that, but access to 4G internet and data plans are cheap.

If you’re just starting out, be sure to make sure that wherever you decide to go has strong WiFi. You can find this information by searching digital nomad forums on Reddit, looking on nomadlist.com, and searching for digital nomad blogs.

Work from anywhere
Work from Wi-Fi

5. Know when to stop working

This is a key to success for any remote worker, but especially for digital nomads.

Imagine going to your dream location. For the sake of imagination, let’s say it’s Bali. You arrive, set up shop, and get your backlog of work done from traveling. Then, you spend the next several days getting ahead on work. A new project pops up, and suddenly, you’re spending 10 hours a day in your room on the computer. NOT ideal.

As a remote worker, you have to know when to call it a day. Give yourself time or productivity limits, and stick to them. There’s no point in choosing a lifestyle for yourself and not following through on it.

Read Next:

The keys to success for becoming a digital nomad are simple. Like anything else you do, you should root yourself in a purpose. Then, take practical steps toward finding places that you love to be and things you love to do.

If you’re interested in learning more about the digital nomad lifestyle, check these articles out:

Be Productive While Telecommuting: 3 Easy Ways

Be Productive While Telecommuting: 3 Easy Ways

Many of us were recently thrown into the teleworking world, some for the first time. It wasn’t easy for people to figure out how to do it, and how to stay productive while working from home. While everyone’s experience with staying productive while telecommuting is different, there are three things that have been super helpful for me.

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Teleworking and working remotely from a porch in Iowa
Getting some work done before a day of hiking!

Telecommuting was awesome for me… until it wasn’t.

I started teleworking, or working remotely, about two years ago. My former company started a policy that allowed us to work from home one day per week, and I jumped on the opportunity. I used the day to get my work done more efficiently as well as get some things done around the house.

As weeks went on, I started to play with my work from home days a little bit more. I spent mornings getting work done in a local coffee shop and took calls in the afternoons. Some days, I’d go work from a friend’s place.

Then, after I quit my job and went out on my own, I was suddenly working from wherever there was WiFi without ANY sort of accountability. I began sleeping in, working until all hours, and sometimes getting on my computer while still in bed. I lost any sense of structure to my days.

Stay productive while telecommuting
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Top 3 ways to be productive while telecommuting

I realized early on that I needed to give my days some structure. Here are my top tips for people who want to be more productive while telecommuting:

1. Create a morning routine

Yes, I said it. Sticking to a morning routine is KEY to being productive while teleworking.

Whether you adhere to a miracle morning or simply commit to an alarm clock and simple morning routine, find something that works for you. It’s ok to start small.

I started by simply committing to drinking a full glass of water before 8:30 every day, no matter what. Then, I added 5 sun salutations before 8:30. Then, I bumped it up to 8 am. It goes on, but now I have a morning routine that has me in to ‘work mode’ by 9 every day.

2. Prioritize your day

Not only do successful work-from-homers prioritize their days, but they do it the day before. Let me give you an example.

My to-do lists are often scattered and have things added to them throughout the day. It leaves me feeling overwhelmed at the end of the day rather than accomplished. To combat this feeling, I rewrite my to-do list at the end of each day.

Before rewriting my list, I sort out what the most important things are. Then, I rewrite my list for the following day with the most important activities at the top of the list. Then, I make sure I have what I need to get the top 3 done the next day.

When I know the day before that I am set up for success the following day, I can rest easy and walk away from my work.

telecommuting outside
Working from Vedauvoo National Forest

3. Start the Pomodoro Technique

In short, the Pomodoro Technique is short work sprints followed by even shorter breaks. The work sprints are strict: no distractions, no exceptions. There are plenty of Google Chrome plugins that help with this, or you can simply set a timer.

I’m weak when it comes to my phone, so using a phone as a timer is no bueno for me. I use the Marinara plugin on Chrome and set a timer for 25 & 5 minutes. I work for 25 minutes, then get up and do something else for 5.

When I’ve prioritized my day, I simply start with the most important thing first and set 1-3 sprints aside to finish it. For example, I know that if I need to write an article today, I’ll set aside one sprint to write it and the second to refine it.

I pair the Pomodoro Technique with the Pareto Principle and Parkinson’s Law. They’re better explained here, but they essentially say that if you have a set time to get something done, you’ll get it done.

Further reading on being productive and telecommuting:

Does Solo Traveling Mean You’re Alone?

Does Solo Traveling Mean You’re Alone?

Here’s something I’ve noticed: So many people, especially women, behave as if they can’t do something if they aren’t doing it with someone. While desiring companionship is wonderful, it also creates a sense of fear when it comes to traveling alone.

Hitch Hiking, but not alone.

Solo traveling does NOT mean you’re alone.

Solo traveling, or independent traveling, just means that you’re in control of your time. Here is what I propose:

Reframe How You Think About Being Alone

In our culture, loneliness seems to have ties to self-worth. When we feel really isolated, we seem to think that we’re less-than. We get all wrapped up inside of our heads thinking that because we’re alone, nobody wants to be with us. Loneliness makes us feel undesirable.

I’m writing this during Corona, and I can see loneliness changing people. We are being left to feel our grief and anxiety and confusion alone in our living rooms. We feel alone in the world, so we reach out to technology to connect us. We Zoom to talk about our feelings, and we feel validated by group messages.

When I say ‘our culture’ I mean you. I mean the folks who turn to the internet for conversation. It’s not a bad thing. It just means that we’re all out here, feeling connected all of the time. It helps us to combat our loneliness.

Then the question becomes, even if we’re alone, are we really, you know, alone?

I traveled solo to Sweden, but met super cool people on a Couchsurfing tour. I wasn’t lonely OR alone.

There is a difference between solitude, loneliness, and being alone.

It can be super difficult to be alone. Heck, even I’m guilty of taking my phone into the bathroom with me. Why do I need to be connected in the bathroom?

I don’t, but I am.

I encourage you to play with solitude.

Get to know yourself by being alone. Even sit in loneliness for a while. It might not be hard during Corona, but it might also be super hard since we’re now more attached to our phones than ever before.

You can become stronger through loneliness.

And, here’s the thing. When it comes to traveling solo, I rarely feel lonely. In fact, I’m rarely alone.

Not only that but the more that I’m alone, the more I come into myself; I find my center. I become friends with my solitude. We’re tight. We challenge each other. Together, my solitude, my independence, my fears, my travels, and I become stronger. We move each other forward.

We don’t hold each other back – we’re travelers.

Does solo traveling mean you're traveling alone?
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Traveling Solo: How to Be Happy Alone

Traveling Solo: How to Be Happy Alone

When was the last time you were alone?

Take that a step further: When was the last time you were happy alone? Do you know how to be happy alone?

These musings are the number one reason why people tell me they don’t want to travel solo: They’re afraid of being lonely.


As we settle into different levels of self-isolation, this question might be easier to answer than ever before. However, that’s not what I’m asking.

I want you to identify when you were not just without people, but not reachable. A time when you’ve stopped any sort of one or two-way communication with the outside world: no scrolling on facebook, no ability for someone to reach into your mental space.

Maybe your phone was off in another room and you were reading. Perhaps all you did was leave your phone in the living room while you went to the bathroom.

Was it in the last week? Longer? Were you happy?

Why People Don’t Travel Solo

When people tell me that they couldn’t travel alone, they typically give me one of three objections: They don’t know where to start the solo travel process, they don’t know how to plan a trip, and they think that they don’t want to be lonely.

If you’ve been reading my other writing for a while, you’ve probably learned that I don’t spend a lot of time alone despite traveling solo. To combat being alone, I :

  • Get a SIM card in my phone so that I’m reachable
  • Stay in hostels so I can be social with other guests
  • Take group tours or join classes to meet people
Made a friend while traveling solo
When solo in northern Israel, I met this girl. She and a friend were out taking photos, and they kind of borrowed me and decided I was their friend for the hour.

You Don’t Have to Learn Before You Go

Solo travel is something that I don’t think I learned to do intentionally. I did it a lot before I realized I’d done it.

I remember telling a friend a couple of years ago that I was planning my first solo travel experience. She looked at me baffled. In fact, she told me I’d been doing it for years. “Sure,” I said, “But I mean like really going somewhere on my own”.

A Couple of Quick Stories

Let me tell you about the times I didn’t realize I’d solo traveled.

  • After freshman year of college, I had the opportunity to teach English in France for the summer. I went not knowing anyone, but knew that I’d be with a bunch of like-minded English speakers all summer.
  • I went on study abroad to Cyprus as the only person from my university. I didn’t know anyone on the program, but I knew there were 70 other people who would only be in Cyprus for a semester, so we’d probably become friends.
  • I went to Israel and Palestine for two weeks knowing that some friends’ families would help me out when I was there. I had people to lean on, so I didn’t see it as going solo.
Solo traveling in Hong Kong
In Hong Kong, I traveled solo but Couch Surfed. A stranger became my saving grace while there. Story here

How to be happy alone:

As in non-traveling life, making friends is weird. However, it’s typically easier when traveling if you play your cards right.

In this video, I outline how to make friends while traveling. The internet is riddled with blogs and tips, but here’s the thing: when you’re traveling, you have more in common with the person next to you than not.

Think about it. The person next to you has likely come from a similar place, and something similar drew them there. They’re also away from home and likely looking for someone to share the joy of traveling with. A simple comment on their travel gear can kick off a day of camaraderie or at least some interesting stories.

I know I’m oversimplifying it. I’m basically saying, “Well, then just don’t be alone!”. It’s not that easy. However, if you go out of your way to meet people, you will. Here are a few ideas:

  • Stay in group housing such as hostels. Many have single rooms but common areas full of people looking to meet others, and some even host events for guests to do things together.
  • Go on group tours. This can be 7-day tours or activities for a few hours in the afternoon at your destination.
  • Hang out in tourist areas. It’s ok to read a book in the park or stay at a restaurant a little longer.
  • Use technology. Apps like meetup.com and Couchsurfing have meetups of all kinds all around the globe.
Solo Traveling in Morocco
“Alone” On a beach in Morocco

How Alone Do You Want To Be?

This is a real question. I have friends who go off on ‘think weeks’. They lock themselves up somewhere far from society and turn their phones and TV’s off and are intentional about their thoughts and actions.

Other friends go on cruises for singles in hopes of spending lots of time with other people. This is their idea of being alone.

Other friends show up to motorcycle rides alone in hopes of making future biking friends.

Here’s the truth nugget: If you want to meet lots of people but go lock yourself in a cabin in the woods, you’re going to have an awful solo trip. If you want to meet lots of people but stay at a hostel near the woods or a campground with lots of community activities, you might have the best ever solo trip. It’s up to you.

It really comes down to effort and mindset. So, let’s talk about mindset.

Are You Nervous About Traveling Alone?

Are You Nervous About Traveling Alone?

My aunt asked me at the Christmas dinner table, “Are you scared of anything, Samantha?”. The answer? Absolutely. But am I nervous about traveling alone? Not so much. Here’s why:

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Perhaps she meant about the people on the road.

Perhaps she meant about lifting off of having a home base.

Maybe she meant all the unknowns that come with nomadic life.

Here’s the thing: yeah, I’m a little scared of all of it. But I’m not going to let it hold me back.

The least of my worries:

I’ve been in SO many uncomfortable situations while traveling alone, but they all had a reason, and they all made me a better person and traveler. Here’s a few stories:

  • I’ve seen people in the US ask someone a question in English, and get super frustrated that the recipient doesn’t understand, so they speak English louder with hopes that they’ll find a mutual understanding. How terrifying to have a stranger yelling at you. However, while this is intimidating, both parties want to understand each other.
  • I got nervous about leaving my hostel alone on my first day in Beirut, but the truth was that I needed socks, so I ventured out on to the streets in search of the dollar store.
  • Sure, I got nervous in Budapest about going to a club alone, but it was that or not see one of the most famous bars in the world, so off I went. In the end, I had a weird night of eating carrots (apparently that was a thing at this party?) and drinking a LOT of water with new friends.

Next week, I’ll show up in Morocco as a solo traveler with the intention to stay for a month. I’m nervous to show up in Morocco alone and not really know the language. Come to think of it, I’m not entirely sure what the language there is. However, based on experience, I know it’s all going to work out.

An example of when I was nervous while traveling – 4,000 feet above the Grand Canyon, December 2019

No such thing as ‘home’

I haven’t lived anywhere for more than two years since I graduated high school. What the transient lifestyle has taught me is that people are home. Even if you’re reading this and you’ve lived in the same place or been around the same people for a long time, hear me out:

Home will be with the beautiful people I meet around the world. Home will be my mom’s house, home will be seeing my brother for weeks at a time, and home will be the WiFi Tribe I fall in to.

Home will not be my big, beautiful bed. Home will not be a closet, a garage, and the things that I’ve surrounded myself with. Home will be me. I will always be home.

Hitchhiking in Cyprus – not traveling alone, but still fun!

The Point:

Assume the best. I can only create a reality in which I am so well supported that there is no alternative. It’s the only possibility when working through being nervous about traveling alone.

So, Are You Scared of ANYTHING?

Yeah. So I go vet it out and the question marks become bold exclamation points. I get to be a digital nomad. I get to bring these stories to YOU and make it easier for you to get over the nerves of traveling.

However, I hope that the nerves, the unknowns, and the trepidation never goes away. I hope that I still feel small when I stand beside the ocean and that the waves of equanimity change me everywhere I go. I want to have a heightened awareness every time I step into a new place; we never step in the same river twice.

How To Make the Most of Your PTO in 2020

How To Make the Most of Your PTO in 2020

2020, the year of the dad joke. Ah yes, as early as 2017, dads in businesses everywhere started calling their 3-year plans ‘Vision 2020’. Dad jokes aside, January 1st marks the beginning of an entire decade, and it’s a perfect time to start living the vision we have for ourselves.

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While I live in a travel mindset, living your goals could look a lot of different ways. It’s easy to dream about all the places you want to travel, but let’s talk about really planning how 2020 will be the year during which you travel.

Jefferson, TX was a great weekend getaway!

Let’s talk do’s and don’ts when planning travel, especially as a professional:

Do:

  • Leverage holidays – One of my favorite posts is an argument for traveling during Thanksgiving. What you need to know is that you can use holidays and your floating holidays and combine them with PTO to turn them into week-long vacations. For example, MLK day is on a Monday. You could fly out on a Friday, take 4 days of PTO and return the following Sunday and have taken 9 full days elsewhere.
  • Say ‘no’ to other people – I’m 28, which means that I’m in 3 weddings next summer and am invited to more. As a nomad, I am choosing to come back to the US for those weddings, but I realize not everyone has that luxury. It is tough, but if you want your time off to be your own, decide early which events you will be saying ‘no’ to in 2020.
  • Say ‘yes’ to other people – On the flip side of that coin, decide which events you will be saying ‘yes’ to this year. Is there a wedding in Punta Cana that you can go to, and extend for a vacation for a few days? A work conference in Florida could mean you have easy access to cruises.
A long weekend Labor-Day trip to Belize a few years ago. 5 days away with only 1 day of PTO!

Don’t:

  • Travel during other people’s holidays – What I mean by this is, there are events during which people travel frequently and it causes flight and hotel prices to skyrocket. For example, spring break in Mexico. If you want to visit Mexico, you may want to save money and maximize your time there by going during the other months. Same thing with Central Europe; it can be crowded and pricey during the summer.
  • Do it for the ‘gram – When was the last time that a photo made you joyful? The answer might be ‘never’. If that is the case, then do not travel to places just because they will be good for one Instagram shot, or because you’ll get lots of likes on Facebook. Additionally, these places are typically over touristed and have little else to offer than the ‘Instagram spot’. Instead, go to places that you love, and take great photos while there.
  • Be rigid to your dreams – If your dream vacation to Rome isn’t in the cards this year, that’s okay! Keep saving money, and perhaps choose a destination that is more accessible for you. Taking steps toward your travel goals is more important than checking every place off your list!

Where do you want to jet off to in 2020?

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