From Aspiring Actress to Remote Worker: In Pursuit of Flexibility

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Welcome to Location Independent Success Stories, the newest interview series on The Sweetest Way!

In each new post, I’ll be introducing you to someone who’s using their unique skills and talents to kick ass as a digital nomad and live life on their terms.

This week, I’m pleased to introduce Eva Casey, a girl whose deep-seated desire for a flexible lifestyle ultimately led her to location independence and working in a remote position with an up-and-coming travel company. Eva Explores location independence interview: remote work with a travel startup

Eva Casey travels around the world working as a writer and social media manager for the travel startup WeTravel. She is also the solo-female explorer behind the blog Eva Explores which shows women around the world how to travel despite their fears!

Follow Eva Casey’s adventures: Facebook | Instagram | Twitter

First, please tell us a little bit about yourself. What’s your background, and what are you doing now?

I actually went to university for musical theater–I’ve been dreaming of becoming an actress since the age of four! After school I moved to New York City to pursue my dreams, and, like so many before me, got discouraged and quit. There were a multitude of reasons, but the main one stems back to the fact that I simply didn’t know myself well enough yet. I was seeking approval on every audition I went on, and when I didn’t get the job it felt like a personal blow. Not the most sustainable way to live.

I have always loved to travel. I remember going on a ten-day whirlwind tour around Europe at the age of 11 with my brother’s gymnastics team. Or popping across the border to Mexico on a family trip to Arizona and seeing a vastly different culture. When I got old enough, I went on trips of my own.

Upon returning to NYC after a two-month backpacking trip around Western Europe, I fell into a depression. I kept trying to get my life to fit into the parameters I had built long ago as a teenager: Move to NYC, audition, get a job on Broadway.

One day I Googled the phrase ‘travel around the world all the time,’ and was met with page after page of travel blogs encouraging me to ditch everything and travel the world. I was still skeptical that a woman could travel the world safely by herself, so I Googled that as well. My eyes were opened by reading accounts of women everywhere (including yours, Leah!) who were traveling full-time by themselves. I decided to join their ranks.

After saving for a year and a half by working as a full-time nanny, I hit the road and traveled to Central America. Now, a year later I am in Southeast Asia working remotely for a travel website called WeTravel as their blog editor and social media manager.

How often do you travel? Do you have one city that you consider a home base?

I am fully nomadic at the moment. Over the past year, I have visited over ten countries, rarely staying in the same spot for more than a week or so.

I consider my home base to be Syracuse, New York, where my family still lives. I am lucky that if I need to I can return home and have a place to stay. I also have a sort of home base in Helsinki, Finland where my best friend lives.

Where are you now, and where do you plan to travel next?

Currently, I am in Bali, Indonesia. I came here for a work retreat held by WeTravel, the website I work for. They are based in San Francisco but flew the team out here to Bali for two weeks. Eva Explores location independence interview: remote work with a travel startup

I stayed behind in Ubud to catch my breath for a couple weeks, and kind of fell into a nice routine. After a quick jaunt to Singapore, I decided to come back to Bali for a few weeks. It’s nice to feel like I have a “landing pad” and am beginning to form a community.

How do you typically choose your destinations?

Sometimes, especially lately, they are choosing themselves for me! For this most recent trip in Southeast Asia, I had been wanting to come to this part of the world for SO long. I knew I was going to come here eventually, so when I saw that the next TBEX was being held in Manila, I bought a ticket. I flew from Helsinki to The Philippines. Then, WeTravel contacted me about going on their work retreat in Bali. I was already going to be in Asia, so they were able to fly me from Manila to Bali.

Otherwise, I get inspiration from reading travel blogs and scrolling through Instagram. Back in August, I saw a photo of a cute cafe in Prague on my friend’s Instagram account and booked a plane ticket from Helsinki that day. I try to operate with maximum flexibility because I am quite the commitment-phobe these days. But I need to balance flexibility with getting the best prices on flights. That’s why, more often than not, I book one flight and then get around by land the rest of the way. I also hate flying, so the less of that I can do, the better.

When did you realize you wanted to become location independent, and what were your reasons behind that decision?

I think I decided that I wanted to become location independent the first time I Googled ‘how to travel the world full time.’ I was already thinking of ways that I could work for myself, from home, before the idea to travel full-time even occurred to me.

As an actor, finding flexible work is usually thought of in terms of in-person work like waiting tables or babysitting. I wanted to have a flexible job that I could do from anywhere to make my life as an actor easier. I honestly had zero idea how to go about it, though. I never thought I could be paid for my writing. I never went to school for anything like that, and it just didn’t occur to me to leverage skills I already had into a paying job.

What were some of the first steps you took toward achieving this lifestyle for yourself?

When I first started traveling, I created an account on Upwork. I didn’t invest much time into applying or searching for jobs, though. At the time I was traveling using the money I had saved as a nanny. What I did do was focus on my own personal travel blog. I wrote a lot and amassed a body of work that I could point to for potential employers (though I didn’t realize it at the time). Eva Explores location independence interview: remote work with a travel startup

I also read everything I could about growing a brand and social media presence. This was simply because I was interested in the topic, and applied everything I learned to my own blog. These things led ultimately to the job I have now, though I certainly did not see the pathway at the time.

Of all the places you’ve lived and worked so far, which one was the best suited for people living a location independent lifestyle and why?

I will agree with Marissa and say that Poland, and Eastern Europe, in general, is amazing for location independence! This fall I traveled through the Czech Republic, Poland, Lithuania, Latvia, and Estonia, and found all of them amazing for digital nomads.

Another spot that I think is great for location independent workers who enjoy a tropical climate is Nicaragua. I especially enjoyed Granada and San Juan del Sur.

Currently, I am working in Ubud, Bali which is a well-known hotspot for digital nomads. So far it is living up to its reputation!

Tell us about your work. What is your primary source of income?

My primary source of income is my work for WeTravel, a travel startup based in San Francisco. I work remotely for them as their blog editor and social media manager. They are a free yoga retreat and group trip planning tool, and I am helping to grow their brand. The challenge of writing a blog in order to convert users into customers has been exciting and new for me. As their blog editor, I don’t only write articles. I interview various travel influencers for the blog, hire additional writers, edit their work, optimize the blog for SEO, and write guest blog posts for WeTravel on other publications.

In my role as social media manager, I do everything related to WeTravel’s social media strategy. In fact, I was able to create their social media strategy, implement it, and tweak it to see results. I monitor which social platforms are working better than others, and where we are seeing the most conversions. I also schedule all of the content that goes out on their social media platforms. It’s very time consuming, and I am always looking for ways to streamline and automate!

How did you obtain your position with WeTravel?

WeTravel actually found me on Upwork. I had my profile set up, with my only work experience being my own personal travel blog. They invited me to interview for the position, and I thought it was too good to be true! At first, I was only hired as the Blog Editor, but I convinced them to hire me as their Social Media Manager after a few months.

What does the average workday look like for you?

I don’t have an average workday, unfortunately! I keep trying to implement one. On average, I do my writing in the morning, as that’s when I have the most inspiration and drive. I try to save mindless activities like scheduling social media or responding to email in the afternoon. Sometimes I can work all day long, from when I wake up to when I go to sleep. That’s the problem with creating my own schedule, I also have to create free time. Eva Explores location independence interview: remote work with a travel startup

If someone else wanted to follow a path similar to yours, what advice would you give them?

Don’t undervalue yourself in the beginning. Even if you have no experience, you have skills that are valuable to potential employers. Focus on those skills and try to negotiate a fair wage.

Even if you have no experience, you have skills that are valuable to employers. Click To Tweet

How much could someone expect to earn when just starting out? How much do you earn now?

Many of the jobs on Upwork hover around $3-5 an hour. That’s out of the question for me. When I started at WeTravel I was making $10 an hour. This is why I said not to undervalue yourself in the beginning. The work I was doing was definitely worth more than that, but because I had no other experience I didn’t want to ask for more.

Eventually, I proved my worth to the company and negotiated a pay raise. It was my first time asking for a raise, and it was absolutely terrifying for me, but I definitely think that it’s something everyone should do at least once. Writing the reasons why I deserved the amount I was asking for down was immensely helpful. I was able to remain calm and ask for what I deserved.

I am still not making as much money as I could potentially make with a more established company, or even as a freelancer. However, I believe in WeTravel and enjoy having the stability of a (relatively) steady paycheck each week. Eventually, I would love to start something entrepreneurial, but at the moment working remotely for someone else is perfect for me.

Do you have other income sources as well? What are some of the other ways you earn a living?

I have no other income sources at the moment. However, I have recently begun to exchange writing and social media services on my personal blog, Eva Explores, for compensated activities and accommodations. I am very selective about who I choose to work with, so this doesn’t happen too often. Also, it’s not “free” in the sense that my time is valuable, so I try to limit the amount of sponsored activities and stays I do per month. It does help to cut down on travel expenses, though!

In your opinion, what is the hardest thing about living a location independent lifestyle?

Making my own schedule was always my ultimate goal, but I am now realizing how challenging that can be. It’s up to me to accomplish my tasks in a timely manner. No one is telling me when I “have to” work besides myself. It’s always extremely easy to slack off if I don’t feel like working, so I have to be my own boss. Eva Explores location independence interview: remote work with a travel startup

What are some of the things you like about it the most?

It’s a double-edged sword because one of the things I enjoy most about the location independent lifestyle IS making my own schedule! First of all, there’s the fact that I am able to be anywhere in the world and earn money at the same time. Then there’s the fact that if an exciting opportunity comes up, I am able to just do it. This past Monday afternoon I attended a local wedding here in Bali. Flexibility is freeing!

How did becoming location independent change your relationship with travel? Do you do things differently now?

This is a lesson I am still learning (often the hard way): I need to go MUCH slower than someone who is traveling on vacation or a gap year. It’s hard to get much work done when you’re packing up and moving on after three or four days. Also, it’s hard to form a routine or community when you’re constantly on the move. In 2017 I am going to attempt to stay in one spot for at least a month.

What do you think are some of the necessary traits or skills someone should have if they plan to pursue a location independent lifestyle?

The courage to step into the unknown and know that everything will work out exactly how it’s supposed to. When you start down the path to location independence, there are going to be times when you have no idea what you’re doing. There’s no blueprint in place. It takes trial and error and a willingness to try something and potentially fall on your face.

Productivity is a major challenge for many digital nomads. Share with us one of your best tips for staying motivated and getting sh*t done.

One of the most valuable pieces of advice I’ve received is the concept of the “shitty first draft.” Your first draft (not necessarily just writing) is always going to be shitty. Just do it. Get it out into the world. Don’t overthink your first attempts at something. After it’s “on paper” you can go back and edit.

Also, capitalize on your productive hours, days, weeks, and months. Have you noticed that you work best at 2 in the morning? Prioritize that time for your hardest work. Do you always get fatigued around a certain time of the month (ladies, I’m looking at you!) Plan for that time by working harder during your productive weeks so that you can take time off when you know you won’t get much done anyways. Eva Explores location independence interview: remote work with a travel startup

Do you have any location independent role models who have helped you or motivated you to achieve your goals?

Obviously, Leah has been a huge motivator for me in pursuing the location independent lifestyle! In particular, the idea that location independence doesn’t just have to mean being a ‘digital nomad,’ but rather having the flexibility to work from anywhere!

My cousin Susan has been living a location independent lifestyle well before ‘digital nomad’ was the latest craze. She just happens to stay in one spot. Her work online allows her to stay at home with her family while providing for them at the same time.

Some other women who have inspiring career paths in addition to being full-time bloggers are: Nikki of The Pin The Map Project, who founded a magazine and works as an editor for The Culture Trip; Camille of This American Girl, who leads yoga retreats in different places around the world; and Kristen of Hopscotch the Globe, a travel video creator who is now working with the Travel Channel on a web series.

What’s one of the most valuable purchases you’ve made for your business–something that wasn’t necessarily expensive, but provided you with a lot of value?

I tend to get most of my business information online, but a few books have really opened my mind:

You Are a Badass: How to Stop Doubting Your Greatness and Start Living an Awesome Life by Jen Sincero
Big Magic: Creative Living Beyond Fear by Elizabeth Gilbert
The Artist’s Way: A Spiritual Path to Higher Creativity by Julia Cameron

Tell us about one of the biggest mistakes you’ve made and how others can avoid it.

As I said before, a big mistake I made was undervaluing myself. Wherever you are listing your services, keep your starting wage on the higher side. If you’re anything like me, once you get an interview with someone you will have a harder time asking for more money. If they know upfront what you are really worth, it will be easier for them to negotiate down if need be. Then you can either accept or look for something that will pay you more.

Obviously, it can be worth it to take a lower paying job when you first start out to gain experience. In that case, state from the beginning that you are accepting for less than you normally would, and that you expect to review your compensation in a few weeks/months once you’ve proven your worth. Eva Explores location independence interview: remote work with a travel startup

Finally, if you could offer your younger, less experienced self one piece of advice for this journey, what would it be?

Even though you may not have experience in your desired field of work, you have plenty of skills that offer value to potential employers. Don’t feel bad for taking up space in the world.

Also, enjoy the journey. Things work out when you least expect them to. Just know that the right opportunities will come into your life exactly when they are supposed to. Appreciate what you already have, and the travels that you are currently experiencing. So many people want so badly to be doing the exact thing you are doing right now. Take the time to really enjoy the little moments. You may never be in this space again!

The right opportunities will come into your life exactly when they are supposed to. -Eva Explores Click To Tweet

Still have questions for Eva Casey about working remotely? Leave them in the comments and let’s discuss! Want to share your own location independent success story? Get in touch!