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How This Woman Left NYC To Start A Business & Travel The World

Ludmila Leiva

This time of year, you might be finding yourself in a work rut, and any rest you managed to squeeze in during the holidays is starting to feel like a distant memory. Do Mondays seem tougher than ever and weekends shorter than you remembered? Well, you're not alone.

Maybe you’re thinking of looking for another job or fantasizing about taking off on an open-ended trip around the world. And while the idea of travel can sometimes seem antithetical to career growth — unless you’re a travel writer or an influencer or something — there are plenty of people who manage to travel or live abroad and also have a flourishing career.

Today, companies are realizing that remote work options are tied to increased employee satisfaction. In fact, Gallup’s State of the American Workplace report found that the most engaged workers spent between 60 and 80% of their week working from home and a minority of their time in the office. Today, remote jobs are becoming easier to find, and many of them don't require you to sacrifice a steady paycheck.

Even as more people are opting to spend less time working in a traditional cubicle, there are others like Amna Shamim, 35, who have decided they'd rather skip the office altogether. Shamim, who works as a writer and visibility consultant, has been traveling and working from abroad for over four years. After leaving her job in New York City, she finessed the art of nomadism while building a business and cultivating a successful career.

We chatted with Shamim to learn a bit more about how she has managed to make this lifestyle work for her — including the apps she uses and the tax exemptions she's discovered. If you’ve ever wondered about how to make the jump into full-time remote work, or how to travel the world without breaking the bank, then this Q&A is for you.

Can you give us a brief description of what your career path has looked like so far? How did you come to be a digital nomad?

I have a degree in French and Spanish literature (double major) from Bryn Mawr College. I graduated in 2006 and promptly moved up to NYC. The first six months were a hodgepodge of jobs like nannying and babysitting and some personal-assistant work. I wanted to pivot into corporate event planning, but the 2008 recession happened right as my résumé started to build, and the industry disappeared.

Before I started traveling, I had settled into working as a freelance editor, with plenty of babysitting and bartending and even some promotional modeling to earn a little extra money.

I didn’t mean to become a digital nomad. I left NYC to explore other cities where I might want to live, starting with Chicago, San Francisco, Portland, and Seattle. But I soon started looking internationally, and within six months knew I wasn’t moving back to NYC.

How often do you change locations, and how many places have you been to since you first started living as a nomad? What's your favorite city?

I used to change locations every week or two, which was super exhausting and not conducive to growing my business. I’ve slowed down in the last year to about one to three months in a location, with random weekend or weeklong trips here and there. Don’t tell my business coach, but I’ll be in five different cities in the month of March.

How can I have just one favorite city? I have several that I adore, including Barcelona, Spain; Buenos Aires, Argentina; Medellin, Colombia; Timisoara, Romania; Penang, Malaysia; Lisbon, Portugal; Larnaca, Cyprus; and of course, New York City.

How has technology helped you? Are there any resources that have been particularly helpful?

Technology has helped me immensely. I’ve met some of my best friends on the road through local Facebook groups and Slack groups. In Buenos Aires alone, my first friend came from a Slack group, another I met through a writer in a Facebook writers' group, and a third, my “Spanish language exchange buddy,” came from the Buenos Aires expat group.

Technology makes it easy to meet people on the road and to stay in touch. Numbeo.com has been helpful for getting cost-of-living estimates, with the understanding that there is some delay in cost estimates because they rely on people volunteering information.

My accountant has been very helpful and keeps suggesting financial-planning stuff, but I just use my spreadsheet. I monitor the currencies for where I’m headed in the next six to 12 months in the XE app. I use TripIt to keep track of my travel plans, with each year counting as one trip. It’s a lot to scroll down by the end of the year, but I enjoy it.

How do you think your lifestyle has impacted your career?

My lifestyle has massively impacted my career by way of my mindset. I care much less about the acquisition of objects, as my suitcase is full anyway. Now, I’m much more focused on quality of life — sleeping enough, eating well, having adventures. I need less money to meet my basic needs, allowing me to take risks that I couldn’t have before.

For example, I worked on a startup for equity for many months, and while I never earned a penny, I did learn and grow a lot. Being able to choose equity-only compensation, knowing it was likely never to turn into tangible dollars, was a luxury I could not have afforded before, but one that has helped grow my skill set and accelerate my career.

I’ve invested in my business by working with a coach, which is something I never felt comfortable doing before I started traveling. Now I know I absolutely need it, and I happened to find someone I adore working with and who gets me to do the scary things.

Now, work is less about money and more about impact. The work I do helps companies grow and better serve their audiences, and that makes me so happy, especially as I intentionally choose to work with companies whose missions I believe in.

I never take on a project that doesn’t have a clear learning takeaway for me, whether it’s about an industry, a new skill, or even a geographic location. For example, I’m working with a content agency right now, and apart from money, what I’m getting from that project is learning how to write faster while still writing well.

Just a few months in, I can already tell I’ve gotten faster, and that makes me happy because it’ll make future projects, like my books, so much easier. Of course, now that it’s less about the money, I’m poised to make more than I ever did before.

Time differences can be a drag, but I’m sure they can be especially challenging when you’re moving around constantly in relation to your clients. How do you deal?

This answer isn’t glamorous. I have calls at weird hours, including times like 1 a.m. on a Tuesday because I’m in Romania and they’re in San Francisco. I generally try to limit the number of calls I have on a monthly basis, especially with ongoing clients, by delivering regular monthly reports and responding to emails within 48 hours, even on weekends.

What has surprised you most about your digital-nomad lifestyle vis-a-vis your professional life?

How many of my clients love that I’m a digital nomad! I thought they’d be annoyed I couldn’t easily show up at meetings as I used to do when I was living in NYC, but most are more than happy to let me Skype in or skip the meeting altogether.

What’s your income been like, and was this a big shift from your job in NYC?

Right now, I earn less than I did in NYC, but that’s fine because my expenses, especially my taxes, are less. I expect in the next few years to be earning substantially more, because I have pivoted careers and the earning potential is much greater for me now.

How do you deal with fluctuating costs of living in the cities you’re in?

I deal with it by having an overall annual budget based on last year’s income. I have a spreadsheet where I log every time I swipe my credit card or pull money from the ATM, and the spreadsheet tallies it up and tells me approximately how much of my annual budget I’ve spent so far this year.

I also set a monthly budget based on how much of my annual budget I think a city will cost, but I have wiggle room on that if the currency goes nuts or I have a really good reason to splurge — like buying a dress for my brother's faux-wedding.

You found a pretty cool loophole through the Foreign Earned Income Exclusion. Can you explain how this works?

It’s pretty fantastic! The way the Foreign Earned Income Exclusion (FEIE) currently works is that you can be exempt from paying federal taxes if you meet one of two criteria: being a resident in another country or being physically present in another country for 330 days per 365.

I’m doing the FEIE through the physical-presence test, which means spending 24 hours in international waters, like cruises, is out. I also have to be aware of when my flights arrive and leave the U.S.A., but it’s worth the savings.

My accountant, Mark at WayFare Accounting, can explain this much better than I can since he’s actually the one checking all my details and preparing my taxes (thanks, buddy!).

You celebrated your "nomad-aversary" in October 2018, which now makes it over four years that you've been on the road. What have you learned in this time?

What I have learned are things like: I can’t be productive and country-hopping every week, I need a lot of sunshine every day, and walking a few miles a day makes me feel sane.

I’ve learned that I don’t mind showing up in a country where I don’t know anyone and barely speak the language, that I really dislike poorly stocked kitchens, and that I am far more productive in coffee shops than at coworking spaces.

I buy far less stuff now than I did when I lived in the U.S.A. and had somewhere to put it. I still love shopping, so I’ll happily go window-shopping with friends, but purchases are rare and usually gifts, as I simply have no more luggage space. I’ll plan purchases for months and enjoy the entire process. If I need something, I’ll buy it, but if I’m tired of one thing and looking to replace it, I do so very carefully and with great enjoyment.

I am a lot healthier now than I was living in NYC. It’s partially due to lower levels of stress and not being miserable due to the weather, but it’s also because as soon as I’m done with work, I can close my laptop and embark on an adventure, even if it’s just exploring my new neighborhood.

FOMO is a good thing in this case, because I know my opportunities to do that thing are limited, so I’d better go do it now, while I can. This has led to climbing Machu Picchu and sand boarding in Huacachina. I took a day off to make a day trip to the Guggenheim in Bilbao and rerouted my European plans to take advantage of a seat at Dîner en Blanc in Paris. I calculate more in opportunity cost than in hard dollars and cents, and that has made my life so much richer.

How have your experiences changed the way you think about home and work?

Home is now where I feel at ease and am surrounded by people and food I love. Good weather helps, too. Work is now the stuff I do for money, but also which challenges me to grow.

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