“Happiness Depends on You”: On the Road with Scott Bold and Michelle Eshleman

This is a traveler case study. (Read others or nominate yourself.)

Dreams can change, as was the case of Scott Bold’s childhood dream. The younger Scott wanted a good job and decent salary, but his adult self wanted something else. So along with his girlfriend Michelle Eshleman, they set out on a different course.

Introduce yourselves.

I’m Scott, and my girlfriend is Michelle. We were both working successful but stressful jobs (engineering for me, counseling for her) in Washington, DC. I had worked my whole life to have a job I liked, and was disappointed to instead feel like I was slowly dying. We decided we wanted to get away from our jobs and lives and backpack from Nicaragua all the way to Torres Del Paine, Patagonia by land or sea only (no planes), learning Spanish and volunteering along the way.

What inspired you to travel?

After I achieved everything I had dreamed of as a child – a nice car, high-paying job, good friends, fancy meals, and gadgets – I still wasn’t happy. I looked at everyone higher up than me at my job and didn’t see my happiness reflected there (not to mention they didn’t seem happy, either). So I questioned what made me happy, and realized what I wanted was freedom, new experiences, and exploration.

Michelle had considered traveling in a two-week per year sort of way until we met. She supported my dream, and decided focusing on herself and changing the way she worked might be for her, too.


Michelle in the San Blas Islands.

How did you transition away from full-time employment?

Once I saved enough money to leave my job, Michelle still needed more time. We road-tripped down the east coast of the U.S. to find the perfect, relaxed beach town to finish saving money and stumbled upon Wilmington, North Carolina.

But a few days after we moved, Michelle’s job fell through. With a seven month lease and no income, we fretted that we’d have to go back to the life we were trying to escape.

However, Michelle was always an artist and I was always a creative, business-minded hustler. Michelle started to create paintings with inspirational quotes and tried selling them on Etsy under the name Paintspiration Art. Within two months, sales were strong enough that she stopped looking for a “real” job.

Simultaneously, I turned our apartment into a thriving Airbnb rental which allowed us to pay most of our bills, host great people, and meet travelers from all over the world.

After a short time home for the holidays, we bought one-way tickets to Nicaragua.


Crossing from Costa Rica into Panama over a bridge on the Caribbean side.

Did traveling chase away your inner feelings of unhappiness?  

About 4 months in, I started getting sick of backpacking. I missed home, was exhausted, and wished I could take a break. I couldn’t believe I felt that way – it was akin to how I’d felt at my job. I had been so sure that once I was in charge of my life, I would never wish I was elsewhere, dreaming of the future. But there I was with that exact feeling.

That moment really hit me. I understood my sense of happiness and contentment had nothing to do with external circumstances and everything to do with what I was focusing on.

And I was focusing on the negatives: the bad food, the questionable living conditions, the difficulties of communication. I was doing it so much that I forgot about all of the amazing positives.

The same thing had happened at my job. I focused on the fact that I had to be there and didn’t like what I did. I could have focused more on the great friends I had and the awesome lifestyle I was able to live.

From that point forward, I practiced catching myself when I was focusing on the negative and switched it over.


Scott with the kids at the Milagro School in Peru, where we volunteered for 6 weeks as Teachers/Coordinators.

What was it like to pause your traveling and volunteer? 

It was my idea to volunteer teaching English in Peru, and I went into it with high expectations. I’d never taught anything formally, but I liked teaching and am good with kids, so it seemed like a good fit.

But my first day was rough. I wound up leading my first class alone – it was trial by fire. Despite appearing confident, I was terrified. My Spanish was conversational, but that didn’t mean I felt comfortable in my abilities to engage and entertain a roomful of 34 hyper Peruvian kids.

Walking into the classroom, my heart was pounding. Why did I volunteer for this? Travel was supposed to be fun.

The class was out of control, kids literally bouncing off the walls. The door fell shut. I was officially trapped. I’d be teaching this class whether I liked it or not. I don’t know who wanted to be there less, me or the kids.

I said my first greeting, “Buenos Dias, Clase!”


Thirty four sets of eyes glued on me: blank, suspicious stares. They were not amused. I was just another white guy volunteer that knew a couple of words of Spanish. They’d seen people like me before.

I was nervous and it showed. I was certain they could smell the fear from the moment I walked in.

At this point I was panicking. A thousand thoughts, all at once, racing through my brain. My already fragile ego was crumbling and I didn’t think I could recover.

But I did recover.

Not so much that day (my first class was admittedly bad), but over the course of the next 6 weeks I learned and started to look more like a teacher. I shifted my focus from trying to change the world to building meaningful relationships with those kids and my fellow volunteers. I spent less time ‘trying’ to teach and force English on them and more time just being there for them and teaching them what they wanted to know.

And with those shifts, the teaching became a lot easier. The kids started to trust and even like me. And I learned to relax and laugh at the silly mistakes I made. We all laughed together and I think we learned too.

By the end my time there, it was hard to leave. The kids had taken to calling me “Professor Thor” because I had long blonde hair and liked to work out. I could barely leave my apartment without hearing the calls of children, “Professor Thor! Professor Thor!” as they laughed and played in the streets.


Scott in Calafate Patagonia.

Tell us about a memorable moment from the road. 

As we got close to the southern tip of South America, we were excited to hike in the famous Torres del Paine National Park. Several people told us to skip the 62 mile “W” trek we planned because the weather was unpredictable. Then, we met another American couple who just finished the W trek – and told us about the beauty they experienced. They made us promise not only to start the hike, but not to quit.

We were nervous the night before we left. We could hardly sleep through the howling winds, pouring rains, and freezing cold temperatures– and we were inside and under a pile of blankets! How in the world would we survive the Patagonian winter weather armed with nothing but a tent and sleeping bag?

Come morning, we saw countless rainbows on our drive to the park – and we mistook them for good omens. We hiked 10 miles with freezing rain whipping in our faces. Everything we brought was soaked – our clothes, sleeping bags, packs. That first night in our tent, Michelle woke up shivering and was certain in her half sleepy state that she was getting frost bite on her toes. The next morning, toes intact, we were greeted by the most beautiful sunrise over a brilliant aqua blue lake. We had to keep going.

Over the next 4 days we encountered snow so thick we couldn’t see the mountains and valleys along our path, winds so strong they literally knocked us off our feet. At some of the higher elevation look-outs, we had to literally crawl to the edge because we couldn’t stand up. The 100 mph wind gusts ripped bridges apart and viciously snapped at our tiny tent. But we pressed on, sleeping in our little tent each night and huddling together for warmth – and seeing the sunrise over the famous Torres the park is named for was absolutely worth it.

How do you pay for your travels?

Originally, savings. We travel on the cheap and slow: couchsurfing, volunteering, independent hiking, camping, hitch-hiking, and homestays allow us to reduce costs considerably. During 9 months in Latin America, our average daily costs were around $25 per person.

Now though, I’ve been using investing strategies to make my savings last longer, and have income from my personal blog. Michelle’s paintings cover her daily expenses and she manages her shop from the road.


Crossing the border from Peru to Bolivia (it was a zoo that day!).

You’re travel hackers. Tell us your favorite programs!

I started travel hacking a few years ago and passed on that skill to Michelle, who is a skeptic turned travel hacking pro. We focus on big credit card bonuses and put as much of our spending as possible on our cards. Typically, we each open 1-2 credit cards a year to take advantage of sign-up bonuses.

We’ve used various programs and airlines (United, American, Starwood, Chase Ultimate Rewards), but more recently Chase has become our favorite due to the signup bonuses and flexibility. United Airlines is my favorite for booking award travel because they have great availability, even on ridiculous flights like NRT to SXM (only 37,500 miles).

In the last 5 years, we’ve earned somewhere between 500k-700k miles.

The great debate: aisle or window?

Michelle loves the window, and I prefer the aisle.


Michelle about to gnaw on me and the rest of tour group in the Salt Flats (Salar de Uyuni) of Bolivia.

Best travel tips. Go:

Travel is 90% attitude.

Learn to appreciate each experience for what it is and to remind yourself that it’s only temporary. I’ve noticed discomforts and challenges, when taken with a light attitude, tend to become my best stories.

Book on arrival.

We’ve found it’s cheaper to book as you go. When you book online or in advance, the price is often inflated. Don’t pay the premium for convenience (and miss the chance to haggle!).

Where are you headed next?

Our plan is spend the first half of 2015 in India and SE Asia. We are buying a one way ticket but will return by the summer for several weddings. After that we plan to settle for a year and focus on creative fulfillment through the small businesses we plan to run.

Follow Scott’s travels on his site, For the Ride, or via Twitter @scottbold.


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