Escape Artist #1: Casey from Remote Year

A big thanks to Casey from Remote Year for being the first digital nomad to allow me to interview her! Casey is from the US and is currently travelling the world while working remotely for a company in New York. She got accepted for 1 of the 75 spots for the Remote Year programme, which is quite impressive considering there were 30.000 applicants! Be sure to check out her awesome blog called A Case For Love , which she describes like this:

…what started as an anonymous dating blog when I was living in NYC has transformed into a less anonymous dating abroad blog over the past few months that I’ve been traveling.

To get to know more about Casey and her YES! philosophy to life, check out her amazing answers below. Hopefully you’ll find this as valuable and inspirational as me.

Please give a short description of Remote Year for those who have never heard about this before. How is your average day?

Remote Year is a company that was created for digital nomads to work remotely while traveling the world.  It is an incredible concept that I have gotten the opportunity to be a part of.  I have a full time job for a company in NYC but have been traveling the world for the past 8 months.  I have been with my company for 2.5 years, and was living in NYC prior to joining Remote Year.  My clients are all East Coast based, so I work in that time zone to adhere with my work schedule.  In Europe, I work from 3p – 11p, Monday – Friday and then the rest of the time is my own to explore the city that I’m living in at the moment.

How and why did you end up in the Remote Year experience?

Growing up in the New York area, I always knew that the plan was to go to college, get a corporate job and move to NYC after graduation. I followed the plan (kind of, with a quick year off after graduation to live in Paris). As soon as I got settled into my corporate life in NYC, I left to work at a start-up where I’ve been for the last two and a half years.

I’ve gotten pretty lucky with travel and have almost spent more time outside of the US than home in the past few years.  I take every opportunity I get, and when I found out about Remote Year, I knew it would be perfect for me and had to give it a try. I had been living in NYC for almost four years with a great job, great apartment, great friends and family close by, but this was an opportunity that was too good to be true. I applied for RY along with about 30,000 other people and when I was one of 75 people accepted for the March program, I pitched the idea to my company who backed me 100%. I am so fortunate to have been able to keep my same job at a company I love while being able to travel the world for a year.
I can do my job well from a coffee shop in Buenos Aires, riverboat in Prague, or even the beach in Croatia.

How did you convince your boss to let you go for one year?

I applied for Remote Year after a friend of mine told me that this program was made for me. I applied, not realistically thinking that anything would happen, but what the heck, I had nothing to lose except for the $50 application fee.  I applied, interviewed, and got accepted last fall and was faced with a big challenge of how to convince my company to be on board with me working my full time while traveling the world for a year.  I put together a document that outlined all of the aspects of Remote Year and how I would be committed to make it a complete success for the year.  My job is my number one priority, and by gaining my boss’ approval, I was able to show my dedication to my company.  I have been working there for two years and have made amazing connections with my coworkers and they knew that my work ethic would continue without being in the office.  It showed how much trust they had in me and has made me want to work even harder to keep showing them how much I appreciate their support for me on my year abroad.
October Escape Artist Casey
Casey trying on new outfits!

Best sides of working like this?

Not to sound too cliché, but traveling is my favorite thing in the world. Having been to many countries and always finding a new adventure, I knew that Remote Year would be a perfect lifestyle for me.  I’ve been given the chance to learn about so many different cultures, meet amazing new people, network like crazy and experience things in the past few months that many people don’t get to experience in a lifetime. Being location-independent means that I can do my job well from a coffee shop in Buenos Aires, riverboat in Prague, or even the beach in Croatia.

And the less glamorous ones?

As many people strive for the perfect work – life balance, Remote Year has tried very hard to make that happen.  However, there are still times when work stresses come up, despite the location. Every day is not always like the vacation pictures seen on Instagram.  What people back home don’t see are the late nights behind my computer, making this whole situation actually work. It’s not always easy to travel and have a full time job, but it’s worth the effort.
Why wouldn’t you say yes to biking down a mountain called Death Road in Bolivia?

Do you have any tips for resources (web pages, books, courses etc.) besides Remote Year?

I didn’t do a whole lot of research to prepare for what to expect before moving to Argentina for my first month of Remote Year. I’m very much of a “go with the flow” type of person, and figured that it would all work out, which, luckily it has. I didn’t’ look up anything along the lines of how to become a digital nomad and didn’t do a lot of prep before hopping on the plane to Argentina. I realized that this isn’t the case for most people, and a friend of mine actually created an online course to help people learn how to become a digital nomad. He interviewed me as well as some of my other nomadic friends, and has been teaching courses around the world which have proven to be successful to many aspiring digital nomads. Check out his course here!
Do you want to dine abroad? No problem!

What’s your top tips for people that want to work for place independent income?

Always say yes (within reason and depends on the situation, obviously…) but for the most part, say yes.  This has been quite a year of “yes” – why would you not want to learn how to play polo in Buenos Aires?  Why wouldn’t you say yes to biking down a mountain called Death Road in Bolivia? And don’t think about ever saying no to a Tinder Social date in Serbia.

What was the biggest problem you never expected to have with this lifestyle?

Before I came on Remote Year, l was living, working and dating in NYC. I was going on dates with people who were great, but not for me. I have so many friends who are starting to settle down, however, I’m at such a different point in my life. I had hoped to meet someone along the way, and I’ve been keeping a blog about the good, bad and the ugly of dating on the road. I’ve met a lot of interesting people and have had connections with a few that I felt were stronger than others, but the biggest challenge has been the constant traveling. I’ve met guys that I’ve really liked on either their last night in a city, or my last night, and it makes it tough to wonder if I’ll see them again. I should have expected this, but it still comes as a challenge each time I meet someone new to think about the fact that I may never see them again.

Do you want to continue your current lifestyle after Remote Year has finished?

I have a few more months to decide what and where I want the outcome of this year to be. My life and my friends that I’ve been traveling with for the past 8 months have been so amazing, and it’s hard to think about anything else just yet… stay tuned 🙂

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