Travel Advice, Writing

How I Traveled to 40 Countries in 10 Years Without Quitting My Job

I really enjoyed reading this post from Girl Tweets World, How to Live a Life of Travel and Not Give Up Your Day Job, and appreciated Jayne’s honesty, so I thought I’d share my story as well.

A lot of travel bloggers advocate “quitting your job to travel the world”, and while that’s all fine and well if you have the means to do so, it isn’t necessary. You can live a life of travel and still keep your day job. Here’s how I did it:

1. I made travel a priority

Sounds too simple, right? But it’s amazing how it easy it is to let a dead-end job or bad relationship railroad your travel dreams. Before you know it, you wake up middle aged and wondering where the time went. I remember when I was 19 and a sophomore in college in New York, I made a list of all the things I wanted to do in my 20s. Some of the items included running away and joining the circus (ha!) but other far-fetched items on the list (like running away to work on a cruise ship) would turn out to become realities. I continued to stay focused on my travel goals and never wavered from seeing them through to completion. I was determined.

2. I went to work as an au pair abroad

I wanted to study abroad in Europe but didn’t speak enough German, so I went to work as an au pair in Austria in order to gain the necessary language skills to do so. Austria had a cool law that allowed all immigrants to study German for free, so I was able to take weekly German lessons free of charge while getting paid to babysit two young girls. The job didn’t pay well, but I had free room and board, which helped me save money for my travels. The family also took me on trips with them around Europe (free travel! Ye-ah!). Afterwards, I went to study for a year in Eastern Germany, where I visited more than a dozen countries, traveling mostly on the weekends and working as a nanny and English tutor to pay for my trips. I found my au pair job online, through a free au pair matching website.

2. I landed a job on a cruise ship

reannon cruise ship
Here’s me and my parents in San Diego, standing in front of a cruise ship I worked on in Mexico.

I knew the best way to travel on the cheap would be to land a job in the travel industry. One of the items I’d put on my dream list when I was 19 was “get a job on a cruise ship”, which I knew would be a challenge. Cruise ship jobs are in high demand. After analyzing my skill set (the most work experience I’d had at that point was babysitting), I decided that childcare would be my “in”. That summer, in order to make my resume cruise ship ready, I got a job with kids at a sleep-away camp in New Jersey. The following year I took a 7-month paid internship at Disney World. When I returned back to New York from Florida, I worked in several local resort gift shops. Thus, by the time I graduated college, I had professional childcare experience as well as hospitality experience. Plus, I spoke German. I was ready to apply for a job as youth staff on a cruise ship.

Getting a job on a cruise ship wasn’t easy. I applied to every cruise line and only heard back from two, but that was all I needed. Two days after I’d graduated from college, I was working on a cruise ship in the Caribbean. I did that off and on for two years, sailing around the Caribbean, Mexico and Canada.

3. I taught English abroad

Japan Reannon


In between contracts on the cruise ship, I took a teaching course and became certified to teach English as a Second Language (I got my CELTA). I wanted to return to Europe but ended up in Japan instead, because a friend from college was living in Tokyo and looking for a roommate. Plus, I’d heard it was far easier to find a job teaching in Japan than it was in Europe. Sure enough, less than a week after arriving in Japan, I had found a job teaching children at several daycare centers and cram schools around the city. Tokyo was expensive, but my job paid well and I compensated for the high rental costs by sharing an apartment with 8 other people. This allowed me to be able to afford to travel to Singapore, Hong Kong and South Korea.

4. I got a job with an airline

Working for an airline

After returning to the US from Japan, I went to work for an airline as a customer service agent. This wasn’t an easy job to land, and I had to beat out 2,000 other applicants for that one, seasonal position. Having interned at Disney World and worked on a cruise ship, however, helped. My language skills and experience abroad set me apart from the other applicants as well. Working for an airline allowed me to travel for free. During my time with the airline, I traveled to Mexico, Puerto Rico, Columbia and to numerous US states.

5. I became a freelance writer so I could work while I traveled

After my contract with the airline was up, I moved to Central America so that I could live cheaply and launch my career as a freelance writer. For four months, in between Spanish lessons and hikes up volcanoes, I wrote and submitted my work to various publications. At the end of my stay in Central America, I’d developed a fairly decent portfolio of travel writing samples. It took a lot of work but slowly, I was able to get enough writing clients to be able to earn a meager living.

6. I moved places where the cost of living was low (more money for traveling!)

Although my family lives in the San Francisco Bay Area, I knew that I couldn’t afford to live there and still travel, so I relocated to Las Vegas, Nevada. Although there’s a lot not to like about Vegas, it has several things going for it including:

1. Homes are cheap (I bought a 2-bedroom house and my mortgage is only $500 a month).

2. The airport is centrally located (only 10 minutes from my house), and there are a lot of flight options in out of and Vegas.

3. Vegas is close to a lot of cool places. Vegas is only 4 hours from LA (by car) and the beach and only a few hours drive from several national parks, including The Grand Canyon, Zion and Bryce. Plus as someone who loves to write about travel, there are no shortage of cool restaurants and hotels to write about.

7. I worked at a marketing agency that offered a “work remote” option

After living in Las Vegas and working as a freelance writer and part-time ESL teacher, I landed a job at an internet marketing company that allowed its employees to work remotely. I frequently opted to work from San Francisco and New York and during that time, traveled to Argentina, France, England and Sweden and Finland.

8. I started my own social media consulting company, officially becoming a “digital nomad”

This past February, I left my job of three years and launched a social media marketing company, Skylark Media Consultants. I now do social media and content marketing for several companies in the travel industry including Smarter Paris, a digital travel guide ap (check it out! It’s pretty cool), and Escape Adventures, a bike tour company.  Although being self-employed has been stressful at times (a lot of long hours!), it’s been worth having the flexibility to work wherever—and whenever—I want. Plus, being my own boss is pretty sweet!

But that’s not the whole story…

I’ve also had help, too

It wouldn’t be fair to stop the story there, because I couldn’t have done a lot of what I did without help from my parents. Though I’ve worked and paid for my travels myself, I did live with my parents briefly in between contracts on the cruise ship. When you work on a ship, you work for several months on the ship and then you get a month or two (or sometimes more) “off”. During that time, I was fortunate to have a home to return to. Some of my friends were left living in hotels or having to pay for short-term rentals. Although I paid my parents rent during this time, I would have had to pay a lot more if I’d had to go out on my own. I don’t know that I could have worked on the cruise ship if I’d had to live in New York solo. Cruise ships offer free room and board but they do not pay their youth or cruise activities staff well. It is not a job that will make you rich.

I also had help paying for rent when I lived in Germany during university. Although I worked during that time, I wouldn’t have been able to afford my school and living expenses without my parents’ contributions.

What’s more, in the last few years, I’ve been able to travel for free, thanks to my mom’s job working for a major US airline. Although 99 percent of the countries I’ve checked off my list were visited prior to her job with the airline, a few of them—Argentina, China and Japan—were visited using her free flight benefits.

I’ve been lucky

Though I’ve worked very hard to be able to travel, I’ve also been lucky as well. I’ve made my share of mistakes and have been fortunate that none of those mistakes have had any lasting, long-term effects. I also know that I lucked out being born into a developed, westernized country. Having a US passport, not to mention a middle-class upbringing, has afforded me options that billions of people will never have, no matter how hard they work.

Should you quit your job to travel?

As someone who has done both (I once quit my job to spend four months backpacking in India), I would say that I prefer working and traveling at the same time. Those months in India were amazing, don’t get me wrong, but I think for me, perosnality-wise, I’ll always prefer having the structure of a job. Continuous travel can grow tedious after a while.

If you’d like to keep your day job and still travel, I recommend you choose a career that affords some flexibility. Many jobs now offer “remote work” options that will allow you to work from anywhere. I also recommend you live somewhere that’s inexpensive but also close to a major airport. Trying to fly out of small, regional airports can be limiting and expensive. There’s a reason I live in Las Vegas now; the cost of living is low and the airport is only a 10 minute drive away and you can fly direct from Vegas to numerous international destinations.

Whatever your preference, I hope this post will help you see that quitting your job does not have to be the only way you conquer your travel dreams. If you’re willing to forgo the tradtional career route and willing to travel slowly, you can keep your day job and see the world at the same time.

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