What I Learned from Being a Digital Nomad

Here at Cardwell Beach, we’ve made it a priority to encourage our team to work in a borderless work environment. Team members routinely vary working from home offices, traditional office settings and wherever inspiration strikes, especially during CB INTERNational, our intern-abroad program. So it’s a pleasure to introduce our friend Dan Englander, a New York-based author and sales consultant. He’s the founder of Sales Schema, which is home base for his books, courses, and articles about sales and marketing. Dan was the first employee at IdeaRocket, an explainer video animation studio, where he won business with Fortune 500s and startups like Venmo. More recently, he has spent months living and working abroad as a digital nomad. He shares his insights below on the benefits and challenges of the nomadic life, as well as some practical tips for those ready to take the leap.

I ordered my third Old Fashioned as the clock struck midnight at the Strand Hotel in Yangon. Talking with a Hong Kong-based journalist, I lapped up stories of corruption, political intrigue, and the wild west landscape of local entrepreneurship in Myanmar, a society experiencing rapid change as its controlling military junta loosened its grip. My girlfriend Casey and I were two months into a longterm Asia trip. Having quit my job and nearly completed my first book, I was a digital nomad.

Bagan, Myanmar (Source: StellarRegions.com) Bagan, Myanmar (Source: StellarRegions.com)

We moved through Vietnam, Cambodia, Thailand, Myanmar, and Indonesia. The big highlights: the street food of Hanoi, motorbiking through Hue, the thousands of quiet and mystical temples of Bagan, and scuba diving with sea turtles in Sumatra. I could go on, but if you’re like me, you’re bored by gushing stories about how “incredible” everything is on an exotic trip. If you’re interested, Casey’s blog visually captures the experiences.

What is a digital nomad?

The role is defined by those who use technology and telecommunication to earn a living and, more generally, live a traveling lifestyle. The digital nomad community is typically made up of web-based entrepreneurs, designers, developers, writers, and other freelancers.
The long-term traveler counterculture has existed for decades, first with the beloved travel manifesto Vagabonding by Rolf Potts, and next with Tim Ferriss’ digital spin in The Four-Hour Work Week. It’s tough to talk about digital nomadism without at least mentioning these two books.

Is the nomadic lifestyle at your fingertips? It depends…

The centerpiece of the argument for the nomad lifestyle is that it’s easier to achieve than we’re lead to believe. Movies and pop culture train us to envision long-term travel as accessible only for the uber rich or extremely rebellious. In Vagabonding, Potts examples a scene from the movie Wall Street, where Charlie Sheen daydreams about racking up the millions needed to motorcycle across China. In reality, as he notes, it’s a feat achievable on a custodian’s salary.

This agrees with my experience. For one, there’s the well-known lower cost of living in Asia, Latin America, and other regions outside the US and Europe. Also, when you make yourself rich in time, you gain a ton of flexibility. That high-priced plain ticket drops exponentially when you fly when no one else does. I used to think that Ferriss might have exaggerated the absurdly low travel costs he recounts, but then I spent $300 to fly from Jakarta to Washington, DC. We enjoyed months in Asia spending less than we would living in small apartment in a rural area here in the States.

Although the nomad lifestyle requires much less dough than most people assume, you do have to save up several thousand dollars, which will vary based on your region and timeframe. The common argument made by nomads, which is that everyone should jump on a plane and be like them, is out of the question for the many people who live from paycheck to paycheck.

Ferriss tells a story about a family who enjoyed an amazing world travel experience after pulling their kids out of school and teaching them on the road. This feat is possible, and I’m sure there are many parents who are unfairly pushed by social pressures and myths into ditching their travel dreams.

At the same time, most (though not all) of the of the digital nomads are childless, if not single people. This is not surprising. Getting yourself to leave behind a comfy and consistent lifestyle is one thing, but making that shift as a family is an entirely different matter. For that reason, you won’t find me encouraging my friends with kids to quit their jobs and jet off to foreign countries for months at a time because I have no idea what that really entails.

Meaning > relaxation

When we arrived in a new city on our travels, we saw sights, relaxed, and had fun for a few days. Then the malaise set in. If you eat candy exclusively you will feel crappy. Lounging on a beach or touring museums all day is ideal for short conventional vacations, but it gets pretty unfulfilling after a while.

Nomads separate themselves from tourists by deriving meaning from their travels. They work towards goals and they create things. I wrote a business book. Your work will fit your skills and affinities. Maybe you have a blog concept in mind, an online course idea, or plans to build a more badass cheese grater. On the other hand, you might not be interested in starting your own venture. You might convince your boss to allow you a sabbatical for the purpose of revamping your company’s communications strategy. This is similar to how college professors take time off to write celebrated books that rain accolades on their departments.

Whatever you choose to work on, make sure to do as much setup as possible before you head out. Do research, talk to experienced parties, go through draft stages, and get constructive criticism. The idea is to hit the ground running as soon as you start vagabonding. Whatever your end product is, work towards something that will open doors for you when you return, even if you have no plans to become the next Zuckerberg. Best case: you have the groundwork for a successful business or major career upgrade. Worst case: you’ve added a resume booster. And don’t worry, you’ll still have plenty of time for relaxing and touring.

Entrepreneurship in exile

Getting a new business off the ground is much less intimidating when you shrug off Western-level expenses. The biggest travel costs come from moving between cities. When you dig into a single location, especially one where a dollar buys you a decadent meal, your river of expenses shrinks to a trickling stream.

Bangkok, Thailand (Source: StellarRegions.com) Bangkok, Thailand (Source: StellarRegions.com)

For this and other reasons, close-knit entrepreneurial communities are thriving in countries like Thailand, Vietnam, and the Philippines. In Saigon, after doing tai chi in my underwear and smashing mirrors to the soundtrack of The Doors, I holed up with my MacBook Air in many of the city’s eclectic cafes. I met expats who were living in the “Pearl of the Orient” for months and years. Many ran niche content sites and e-commerce operations. I observed that the unconventional entrepreneurial community inspires in these founders more experimentation and camaraderie than their peers in cities like New York or San Francisco. Immersion in a foreign market can stimulate fresh ideas that competitors back home might not be considering.

Making it happen

All that aside, you don’t have to be an entrepreneur to go full nomad. I met Europeans and Australians doing a few months vagabonding in the middle of major career changes. I know freelance specialists who make it a point to travel three months out of every year.
But maybe you have a fulltime job and that’s not possible. Perhaps you can repackage vagabonding as a 3-12 month sabbatical. What’s the worst that can happen if you ask your superiors to entertain the possibility?
Or maybe you have eventual plans to switch jobs. Why not starting saving up for a buffer period sooner rather than later?

The hard part

Leaving a stable job is never easy. That’s a given. What’s less obvious is that you don’t have to worry about the terrible soul crushing gigs, but rather the ones you enjoy. If your job sucks, you will do everything in your power to make a change. If things are going well and you find the work compelling, you can do it forever. But doing it forever might mean neglecting major opportunities for personal growth. Also, what’s enjoyable today might become monotonous five years from now, if you’re able to maintain that sort of professional longevity.
I was hired as the first employee at an explainer video animation studio. I handled sales, project management, bookkeeping, and many other duties. Over the course of three years, we grew to a ten-person team after starting with two. We upgraded to a large studio space in midtown Manhattan. We did business with 16 Fortune 500s. I enjoyed the work, and we were going strong when I left. I learned more from the experience than I could have possibly imagined.
Departing the company was one of the hardest things I’ve ever had to do. But it was worth it. Now I work with my alma matter in a more flexible way doing business development remotely, an aspect of the job that I especially enjoyed.

A nuanced perspective

Long-term travel affords its practitioners a fresh perspective. By staying in a place beyond a two-week “whirlwind,” you get a much deeper understanding of how people live in a foreign society. This makes you rethink commerce, relationships, work, leisure, and other aspects of life.

Phnom Penh, Cambodia (Source: StellarRegions.com) Phnom Penh, Cambodia (Source: StellarRegions.com)

That said, I often observed the rose colored glasses problem among fellow travelers, and I probably fell into too sometimes. Backpackers say things like, “The people are so nice here!” or “Everyone is so real!” Poverty and political upheaval aside, travelers often express a sentiment that the foreign culture is better or more noble than the homeland. Of course, that’s never completely true or untrue.
It’s healthy to open yourself up to a place, but it’s important to keep a critical eye. Without knowing the language, there’s a ceiling to what you can possibly understand. I’m a native English speaker, and there’s plenty that bewilders me about UK culture and even aspects of my own American culture for that matter. Admitting that you don’t really know what’s going on is a lot more empowering than assuming that the smiling Bangkok cab driver genuinely likes you, or that the stone-faced Moscow museum guide despises you.


Let’s get into the nitty gritty. Here are free-floating tips and tools that will allow you an easier, cheaper, and much more enjoyable nomadic experience:

1. Pack light

Regardless of cultural differences, almost everyone in the world does laundry around once a week. Washing clothes is cheaper and more convenient than carrying a lot of extra stuff, which weighs you down both physically and mentally. Among fellow travelers, I noticed a direct correlation between the amount of stuff people carried and their level of stress and group bickering. For specific packing recs, check out this article from Tortuga’s Packsmith blog.

2. One bag to rule them all

The 70-litre silo bag is for outdoor trekkers and masochists. If you want to get your flip flops from the bottom of that thing you have to unpack and repack everything. It’s all about the 46-litre pack, which is the largest you can carry-on. Checking bags is convenient on long international flights, but it’s an unnecessary drag for shorter regional jaunts. Bags get lost and luggage wait times are unpredictable. To avoid digging, make sure your 46-litre opens from the center.

3. Street food can be safer than tourist food

Despite what my not-so-traveled travel doctors instructed me, the solo street vendor, whose livelihood is based on the quality of his product, is a safer bet than the well-trafficked, Lonely Planet-vetted establishment. The cook at the back of the big eatery, which probably isn’t scrutinized to the standards of your local health department, has much less skin in the game. Both businesses will use similar ingredients, washed in the same water, but the difference is accountability. Plus, street food is cheap and delicious.

4. Bank fees: brought to you by Satan

Bank fees are the worst thing on which you can spend your hard-earned money, especially the sort that are levied for the simple act of withdrawing your own funds. These fees are compounded when you go international. I’d rather be pickpocketed on the street than at the ATM.
To avoid this, open a Schwab High Yield Investor Checking account, which reimburses you at the end of each month for ATM fees.* I assume they can do this by passing customers some of the savings they enjoy from not running brick and mortar locations. I’ll take it.

5. Know the payment hierarchy

To get the best conversion rate, your first choice is a credit card (as long as it doesn’t charge a foreign transaction fee), because credit card companies have the most leverage to secure the best rate. Second choice: ATM’s, assuming the bank is legit and you’re withdrawing from an account that reimburses your fees. Worst choice: currency exchanges. The little guys have less muscle at the exchange table, so you pay more.

6. Haggling doesn’t have to mean being a douche

Many westerners come from cultures where haggling is rare. When they travel to places where a bit of wheeling and dealing defines most street transactions, they feel insecure, so they turn into Gordon Gecko. They make unreasonable demands, walk away from 50-cent-too-high items, and generally act like meanies. I used to fall into this habit, but then I started matching the rhythm and demeanor of the seller. I avoided emotion, removed the phrase “general principle” from my lexicon, and I started getting better results at the bargaining table.

7. Accept your limitations

Don’t feel guilty for homesickness. Uprooting permanently isn’t for everyone. All the benefits aside, I don’t think I’m cut out for the permanent expat lifestyle. After a few months, I start missing friends, family, that pizza place on my block in Queens… I have future plans to go abroad for six months at a time, but I’ll always enjoy the consistency of a homebase. Maybe you’re in the same boat, or maybe you’re fit to be a perpetual nomad…
Only one way to find out!

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