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I always enjoy hearing about other people’s travels because I think they are inspiring. I’m a firm believer in “you travel how you want to travel, and I’ll travel how I want to travel”, but even reading about people who are traveling much differently than I would I find interesting.  So when I got a chance to catch up with Steve, who is about to embark on a one year trip around the world, I thought others might find it interesting.

Steve had originally planned to sign up for Remote Year, a program where you pay ~$27,000 and go with 50-80 likeminded travel enthusiasts to one city a month for 12 months.  Instead, he decided to do his own Remote Year himself – here is his story

1) Tell us a little bit about yourself

Hi Dan! Thanks for taking the time to interview me. I’m a technology consultant specializing in mobile development with a passion for travel among other things. Traditionally, I’ve lived in the midwest, though that is about to change for the next year. I’m taking to the road and making the world my home with a full year of working remotely while traveling internationally.

2) What has your life been like, in terms of travel. Did you travel much growing up?

I have kind of an interesting perspective on travel. The wanderlust was instilled early. Until I was a teenager, my mom worked for Delta Airlines in International Reservations. This meant that the immediate family had access to a great perk – the travel benefit. We would fly non-rev standby, and do so often. A few examples:

  • Chicago for the afternoon for the auto show.
  • Phoenix in the throes of winter for a day of sunshine. (This trip coincided with a massive winter storm that took down the east coast’s airports for several days, resulting in 24 hours of sun followed by 72 hours of attempting to get back to Cincinnati. Always an adventure!)
  • Numerous short vacations to the Caribbean where I learned a love for the ocean and water sports including wind boarding, snorkeling and scuba diving.
  • Even more trips to visit family in San Diego, which served as a second home to me in those years.

a beach with trees and water

3) What got you into traveling recently? How have miles and points helped with that?

That wanderlust, the desire to see other cultures, experience different food and see what the world has to offer never went away. I just choked it back thinking it was prohibitively expensive to travel frequently.

(SEE ALSO: 14 of the best travel books guaranteed to inspire wanderlust and road trips)

Recently, I discovered the miles/points game, several really great resources for cheap tickets and the sharing economy. These coupled together have made international travel more approachable than ever for me.

Miles and points have helped as an enabler for expensive to reach destinations. For example, with my upcoming travel for a year, the start of the journey is a one way to Prague, a ticket that is north of $800. I intend to use points to purchase that expensive first ticket. From Prague to Split, Croatia clocks in under $200. I’ll balance use of cash for inexpensive flights and miles/points for more expensive ones (likely those crossing from one continent to the next).

All expenses will be funneled through credit cards that are paid off monthly, paying attention to maximize points. For example, airline tickets will likely be purchased on the Amex Platinum (5x mile bonus) while restaurants will go through the Chase Sapphire Reserve (2x bonus).

a city with many tall buildings

4) What made you start considering doing a remote year?

I consider myself a collector of experiences. I really enjoy doing unique and different things. So, I was predisposed to the idea of traveling for a year – who gets to do that?! Also, the ability to pack a lot of experience in to a relatively short time frame is appealing.

In addition I had a kind of aligning of the stars in my personal life that cleared the path for going remote. The obligations that tethered me to a physical location were removed, and I felt a freedom to consider exploring the world.

My mom was suffering the loss of her husband. While we were in hospice by his bedside, I got a notification from Scott’s Cheap Flights for a $420 flight from MSP -> HNL over our shared birth week. I jumped at the chance and booked tickets for the two of us. I thought it’d be a great way for her to pass what would be a very difficult birthday for both of us. We used miles to snag flights CVG -> MSP and off we went. We were staying in a bungalow in the woods on the big island when I got word of Remote Year ( After researching a very little bit, I jumped and applied. Much to my surprise, after rounds of interviews and so forth, I was accepted. reviews vs. do it yourself

5) Why did you decide against Remote Year and to just do it yourself?

If there’s one thing common about Remote Year participants, it’s their love of social media. There’s a lot of Remote Year reviews out there written by those on the trips. It’s not all flattering. Some of the reviews share a lot of the great – things like the community of 50-70 fellow remoters sounds amazing. Quick and lifelong friendships are forged in the pressure cooker of a year on the road together. That looked beautiful.

The reviews also reveal the less glamorous side – 15+ hour bus rides moving from city to city. Questionable living conditions – one remoter indicated that one month they were in seaside luxury apartments and the next they were in a high school basement dormitory with a number of bugs.

The lack of control over accommodations, travel arrangements and itinerary led me to “roll my own remote year”. For me, the tradeoff was the freedom and control over my own logistics.

a view of a valley from a cliff

6) What are you most looking forward to for your Remote Year?

The adventure of it all! It’s funny, some folks fret things like airline delays and flight cancellations. For me, it’s like a childhood memory. The scramble to find another flight, to standby, it’s like being a kid again!

I’m also looking forward to a year with no winter! I plan to head for warmer climates as winter approaches. How’s January in Bali sound? Seems like a good idea to me!

7) Anything else we should know? Is there anywhere we can follow along with your Remote Yearadventures?

First, a shout out to my family, my company and my client. Being able to take my job on the road is really key in this being possible, and I’m grateful to them for the opportunity.

The aforementioned stars lining up mean that I’ll not be traveling alone! My girlfriend Missy just finished up her degree, and finds herself free to also travel. She’ll be joining me on the road. That pressure cooker of travel I mentioned, we’re hoping it forges a strong relationship with a year of unique and shared experiences.

Follow along with our journey at We’ll be blogging our way across the world.

Readers – had you heard of RemoteYear or seen any reviews?  Any comments or questions for Steve?

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