Home » Freelancing » Digital Nomad FAQs

I’m aware that my lifestyle is different from the norm (I created it that way, after all) and people tend to have a lot of questions about it. If it weren’t for other digital nomads before me successfully and sustainably living this lifestyle and writing about it online, I don’t think I would have even thought it was possible. (For example, Gigi Griffis, who wrote the incredibly comprehensive post ‘Everything You Ever Wanted to Know about My Digital Nomad Life’ that inspired me to write this very post.)

So now it’s my turn to answer some Frequently Asked Questions about my lifestyle for those who are simply curious as well as those who want to follow in my footsteps.

Contents

Love & Community

How are you planning to meet a nice Jewish boy?
Do you get lonely?

Health

What about health insurance and healthcare?

Money & Work

How do you make money?
Are you just constantly on vacation?
How do you stay focused?

The Logistics of Being a Digital Nomad

When are you coming home?
How much stuff do you travel with? (And how do you live with having so little??)
How can I do what you do?

Travel

What are your favorite places you’ve traveled to?
How do you decide where to go next?
What destinations are on your wishlist?
Is it safe traveling as a woman alone?


Love & Community

How are you planning to meet a nice Jewish boy?

I’m probably not going to…? But you should know, I have never dated a Jewish guy in my life. I’m pretty happy to be exploring outside the Tribe.

As for dating in general, it is hard while living a location independent lifestyle. But I reckon people struggle with the dating game no matter where they live or what they’re doing.

Related posts:

What I’ve Learned about Sex and Romance from Travel

We Need to Talk about Tinder (a 2013 gem from when it first came out)

Guy holding girl from behind standing on a rock on an island
Not lovers we just play em on TV

Do you get lonely?

I’ve experienced loneliness while traveling and living abroad in the past so this time around I’ve been intentional about where I go and where I stay.

For example, in Koh Tao, I chose to live in a private room in a hostel. In Chiang Mai, I stayed in a coworking and co-living environment. In Sri Lanka, I traveled in a group of other digital nomads.

Social interaction and the larger feeling of being part of a community are essential to staying mentally healthy for me. My efforts have been effective: the last time I can remember feeling lonely was back in the States, before starting the digital nomad life.

Lonely isn’t the right word for this but what I do feel is exhausted. It’s painful to constantly connect with people and create a social circle for myself and inevitably have to say goodbye, over and over. I was in tears in the airport when leaving Chiang Mai over this very issue. Even if I don’t leave a place, my nomad friends will. I haven’t found a solution for this yet.


Health

What about health insurance and healthcare?

I was insured under a plan from the ACA when I was living and freelancing in the States. Since moving abroad, I have chosen to forego American health insurance. I have simply paid out of pocket for any healthcare expenses both in Thailand and in the States when I went home to visit. I calculated and I spent approximately $1130 for healthcare needs, including dental and vision, in the past year between Thailand and the US. I’m considering writing a longer post about this soon…

Related posts:

Tools to Manage Your Mental Health While Traveling


Money & Work

I don’t get it – How do you make money?

My main source of income is my freelance work. I am a content marketing strategist and copywriter; this means I strategize and write/create content and copy for businesses to help them generate more leads and sales online.

I also make a few pennies here and there through my blog (yes, this one), mainly through affiliate marketing. I link to brands and businesses I have used and loved and if my readers buy something through my link, I get a small commission.

Related posts:

How I Made $5k in My Fourth Month as a Freelance Writer

Seems like you spend a lot of time at the beach though. Are you just constantly on vacation?

No, no, no no. The first year I started freelancing, I had to make a concerted effort to plan a vacation from work. Otherwise, I was basically working 9-to-5, if not more. When you have a lot of projects on or are hustling really hard as a freelancer, you may find your work bleeds into everything you do. It’s hard to escape it or to manage your time when there’s no one overseeing you and you can do work from your couch in your pajamas if you want. It’s honestly not very healthy.

Female digital nomad working on laptop in a cafe in Sri Lanka
Candid of me working in a cafe in Sri Lanka

Once I moved to Thailand, I endeavored to have more balance in my lifestyle. And I was able to do this since the cost of living was relatively low and I had saved up an emergency fund that took some of the financial stress away. I followed the natural ebb and flow of my projects and worked when I needed to and had deadlines and otherwise spent time hiking, snorkeling, tanning, hanging out with friends, living my life etc.

Overall, as time has gone on, the meaning of ‘work’ and ‘vacation’ have simply changed for me. There isn’t as much of a line of demarcation. I seek to balance work and leisure in my everyday life and find when I do that, I don’t crave a vacation the way I have in the past when I’ve worked more traditional jobs.

 

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How do you stay focused?

Oh I’m the worst procrastinator. (Just see my post the 7 Habits of Highly Unproductive Freelancers to see what I mean.)

Otherwise, the external motivation of knowing you’re getting paid to do a project helps. Deadlines help. Also caffeine sometimes.


The Logistics of Being a Digital Nomad

When are you coming home?

*Sigh*

I’m not. For now, this is the lifestyle I’ve chosen. I went home for 6 weeks over Halloween and Thanksgiving in 2018 and I plan to make more visits home in the future. I don’t have any plans of moving back to the States. Of course that doesn’t mean it will never happen.

Related posts:

Reflecting on 10 Months Abroad and Leaving Koh Tao

Two girls hugging on top of Stone Mountain in Atlanta
An Atlanta visit in autumn 2018

How much stuff do you travel with? (And how do you live with having so little??)

I travel with a 65-liter backpack and a 32-liter “day pack”. I have a satchel purse that I can pack into my bigger pack when I’m moving between places and use as a purse once I’m settled in somewhere.

I used to travel with less (I was a strict “carry-on only gal”), but halfway into this past year living in Koh Tao, I got SO sick of wearing the same things over and over and over, I decided to upgrade to a checked bag and carry-on. So far it has been worth it to have a few more clothing (and bikini) options.

Two packed backpacks
Everything I travel with – a 32-liter “day pack” and 65-liter backpack

As far as the backpack-versus-rolling-bag debate, I think it depends what part of the world you’re traveling in. Since I’m in Asia at the moment and for the foreseeable future, I prefer having a backpack I can easily carry across all types of terrain.

In terms of living with less, I suppose what I have is the equivalent of a capsule wardrobe. It makes my life easier to not have a ton of choices of what to wear on a daily basis. That said, I tend to enjoy replacing items or buying new little things like earrings or nail polish every now and then to spice things up. (Like I said, I can get very sick of my clothes and feel the need to express myself differently as time goes on.)

I am lucky and grateful to have access to my parents’ house in my hometown of Atlanta. I still keep lots of stuff I’m not currently using there (e.g. all my winter clothing when I’m in tropical places).

Related posts:

Check out my Most-Used Travel Items here.

Here’s what I bring in my travel first aid kit.

Headed for cold weather? My winter travel packing tips.

How can I do what you do?

Oh man, this is a tough one. There is no one path to successfully becoming a digital nomad. And honestly from what I can tell, most people who attempt it either give up or aren’t really making enough money to live comfortably. That said, here is the skeleton of advice I would give to someone who wants to travel and work from their laptop:

  • Do NOT quit your day job. Start your digital nomad business on the side and get it up and running smoothly before moving abroad.
  • Explore all the options to work online and travel. For example there’s freelancing (writing, web development, social media, virtual assistant, and more…), teaching English online, Amazon FBA whatever that is, having a full-time remote job…
  • Grow emergency savings. I recommend putting away 6 months of emergency savings in case it all goes to shit.

I’ll flesh this out in a longer post at some point.

Related:

How I made $5k in my fourth month as a freelance writer

Truths and myths about being a full-time freelance writer

Reflecting on my first month as a digital nomad


Travel

What are your favorite places you’ve traveled to?

This list of my top 5 favorite places I’ve traveled to is still accurate.

How do you decide where to go next?

I’m not naturally inclined to be very nomadic honestly. I’m more interested in staying somewhere for a long period of time. That said, I consider the following when deciding where to go:

  • Weather – I tend to prefer warm, tropical weather. I’m also currently only packed for warm destinations.
  • Beach – I feel very at home on islands.
  • Cost of living – I look for a low cost of living so I can save or spend my money elsewhere besides on accommodation, food, and transport.
  • Community – Even if I can’t be around other digital nomads, I prefer for there to be some sort of backpackery community around so I can make friends and not be lonely and sad.
Girl in red bikini running on Silent Beach in Sri Lanka
Did I mention I’m a big fan of beaches

What destinations are on your wishlist?

Here’s a rough list…

To live:

  • Mexico/the Caribbean
  • Lisbon
  • Bali

To holiday:

  • Japan
  • Kyrgyzstan
  • Hawaii
  • Cuba
  • Greece
  • Norway
  • Philippines
  • Croatia and Slovenia
  • Vietnam

Is it safe traveling as a woman alone?

I think it depends where you are. So far, the only place I’ve felt extremely unsafe as a woman traveling solo has been India. I anticipated Sri Lanka might be similar and made sure to travel in a group. It’s good to know your tolerance for risk (mine is quite low) as some women have traveled through India solo and thought nothing of it, while I left the country completely because I didn’t want to be alone there.

Of all the places I’ve been in the world, I’ve felt the safest on my own in Southeast Asia. Like safer than I feel in most parts of the US.

 

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