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Interview Series: Traveling9to5

1. Can you start by giving us a little bit of background about yourself and your blog. How did you start traveling? When did you start blogging, and what did you expect readers to get out of it?

Josh and I met 10 years ago. We are that cheesy high school sweetheart couple that most people roll their eyes at! We started traveling in 2007 together through Europe and continued with short trips to Central America and around the United States. Josh was a technology consultant and Caroline was a personal trainer in Chicago. In 2011 we decided that we would take a risk, sell our stuff, and leave our jobs to travel. We already had savings in the bank and we gave ourselves 6 months to plan, continue saving and tie up loose ends in Chicago. With no end plan in mind, we boarded a plane to Hong Kong and have been on the road for 7 months through Asia and Africa and are ending the year in South America.

Originally we started Traveling 9 to 5 to document our own adventures. As we researched our trip online we found a lot of holes and missing information. We wanted Traveling 9 to 5 to be a resource to help fill in the blanks and make it easier for travelers to just go. Too many of our colleagues and friends would complain about their jobs with no actionable steps to improve their situation. We want Traveling 9 to 5 to inspire them to believe that you don’t have to be miserable, that it is possible to do something you love and make money to support your lifestyle!


Coast of South Africa

2. Let’s talk experiences – what has been the best experience you’ve had on the road? The worst? The most dangerous?

Our best experience on the road was our recent self-drive safari through Botswana and Namibia. We honestly had no idea what we were getting ourselves into and no expectations for the trip. We were charged by elephants, saw prides of lions and learned to drive through 4 feet of sand. The nights were spent cooking over the fire and lavishing in the peace and quiet that only the middle of nowhere can offer. The stars at night were enough to take your breath away.

While we were driving ourselves through Africa and having our best experience, we also had our worst! In Namibia we visited what the guidebooks and locals said was a must see, the Petrified Forest. This turned out to be the worst tour I have ever been on. We don’t like tours to begin with, and while we were expecting one thing, we spent half an hour listening to a tour guide while looking at rocks that kind of looked like trees.

If you can’t tell our African experience made quite an impression on us. Our most dangerous experience was probably that entire trip. We had no experience with wild animals or knowledge on their movements and activity. We had no idea what they looked like when they got angry or how close was too close. We camped for 3 weeks outside while listening to huge elephants and wild dogs run through our campsite. We were blissfully ignorant, but looking back on it incredibly stupid. I wouldn’t have changed our trip in any way, but it was by far the most dangerous thing we have done yet!

3. Your route is incredibly unique, how did you come up with it? What other countries/activities were you considering?

Josh was able to use his airline miles he saved from consulting to purchase both of our around-the-world tickets. We had 15 stops around the world and we planned to maximize all of our time while we were traveling. Thanks to the miles, we ended up getting two around the world tickets for $346.

We wrote down everywhere we wanted to go and figured out a route that made 90% of the locations possible and the rest we will be back for! We wanted to visit SE Asia because of the vastly different culture and our own love of the food.

Africa was Caroline’s dream destination. We both wanted to go on a safari and this was by far the most expensive and out-of-the-way part of our trip. South America is a perfect opportunity to practice our Spanish and we’re looking forward to the natural beauty the continent has to offer.

4. Had you guys ever traveled together before? How have you been managing on the road thus far, and do you have any advice for couples traveling abroad?

We took our first international trip together in 2007 and have traveled together ever since. We work well together, Caroline does a lot of the planning, Josh figures out the logistics on how to make it happen. Caroline loves cooking, but hates washing dishes, and Josh doesn’t mind getting dirty.

Our advice would be to figure out what you do best and what you enjoy doing and each do that. Keep the lines of communication open, if something bothers you get it off your chest instead of keeping it in and letting it build up. When you spend so much time with one person you have to be patient and understanding.


Working 9 to 5 in Barcelona

5. You’ve mentioned several times on your blog your goal is location independence – do you still consider this a reality? What are likely scenarios?

It is more than a consideration, we are currently making it happen. We are spending a month in Buenos Aires to focus on our business ideas and preparing to return back to the US in January to hit the ground running. Step by step we are working towards location independence, not necessarily in order for us to travel around the world for the next 5 years, but we want the option to be there and to be in control of our days.

Josh designs and builds websites so he is working on compiling his portfolio and marketing his work. We have different ideas for products we can offer online from ebooks to courses, and more.

6. I noticed that it seems Caroline does most of the writing, and I think Josh handles a lot of the photography. How have you guys divided up responsibilities and how has it worked out?

Caroline loves to write, it has become her meditation. When she feels inspired she writes. Josh handles all the back end stuff. He built the website and keeps it updated and looking good. He edits every post before it goes up and handles our email and comments. He’s writing a bit more, but prefers to leave it to Caroline since she’s so good at it!

7. What are some of your interests outside of traveling?

Caroline is a fitness addict. She loves running and has struggled to get into a routine between the constant travel and the heat. Josh is a voracious reader and misses his guitar at home. We both love a night spent with good friends and a glass of wine.

8. What are your upcoming plans, both travel and non travel?

We plan to spend the rest of the year in Argentina, Chile, Ecuador, Peru and Mexico (with a few surprise destinations added in.) We are looking for housesitting gigs in the U.S. (Anyone out there need to reliable, energetic and responsible housesitters for January – March?) while we work to launch our business ideas.

9. What do you miss most about being home?

We miss our friends and family the most. I miss the random Tuesday night where you don’t have anything planned so you make a quick call to some friends and end up having a BBQ out by the pool and drinking a glass of wine together.

We also miss being there for the big events. The birthdays, the weddings, engagements and the babies. We know that we are there in spirit, but we miss being able to celebrate all of the big life markers with those back home.

10. What’s your biggest fear about returning home?

I fear relating back to American culture. We have traveled light, tracked every cent we’ve spent and have loved the simplicity of our lives this year and I fear getting caught up in the craziness life throws at you. It sounds crazy, but I fear going through the boxes I left in storage. What seemed like a small amount when we left, I fear will seem like a mountainous pile to come home to.

Although I know it is inevitable, I fear failure. We are planning to work for ourselves, which is scary when you are looking for the next pay check and covering health insurance and still maintaining some what of a twenty-something’s lifestyle. It is all unknown and that is scary…but exciting at the same time!


Josh and Caroline Eaton are the creators of Traveling 9 to 5. From Chicago, IL, they quit their corporate jobs, sold (almost) all of their belongings and are currently writing and traveling around the world hoping to inspire others to say yes to their own adventure. You can follow them on Twitter, Facebook and Pinterest.

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