My Remote Year Emotional Rollercoaster

All aboard

I am Jill, a wellness coach and creator of The Jill Pill Method, my easy-going approach to wellness. It evolved after years of struggling with my own health, obsessing about what I ate and feeling generally inadequate and unhappy.

Hello, I’m Jill!

In search of bettering my life, I discovered ways to enjoy moving my body, became a fitness instructor and studied different disciplines of mental, emotional, physical and spiritual well-being.

Through my education, practice and adopting an intuitive eating mindset, I created happy, healthy, habits for myself and I help others create their own.

In 2019, my husband, James, and I traveled for an entire year with Remote Year, a company that creates 4-12 month itineraries for digital nomads. We visited 12 cities throughout Latin America, South East Asia, Europe, and South Africa, spending 4-5 weeks in each city.

The experience enriched our lives in many ways but was also taxing on our mind, body, and spirit. 

Prior to starting our adventure, I gleefully spent weeks preparing, reading advice articles, buying Digital Nomad gear, selling our belongings and getting ready to live out of a suitcase.

When the time came to leave, I felt ready! I had my packing cubes and travel insurance, but I could not have anticipated nor prepared for the emotional and physical challenges I would face throughout the year.

The nomadic lifestyle brought forth a new set of obstacles I had not experienced before including constantly changing routines, learning to navigate through new surroundings, and adjusting to foreign cultural norms.

I went through extreme emotional highs and lows, struggled to stay physically well, and got worn down from the exhaustion of excessive traveling. It took some time and trial and error, but I learned, adapted and found new ways to stay well in my life as a nomad.

Additional Remote Year Reading…

Why Remote Year?

Our trailer life before Remote Year

In 2016, James and I took an 8 month trip around the US in our renovated fifth-wheel trailer. We absolutely fell in love with the freedom of being able to move around and travel, but life on the road was not always perfect.

We would often feel lonely and isolated despite our efforts to make friends. We also spent a lot of time and energy planning our trip, figuring out where to go, where to stay, and what to do once we got there.

We knew that if we were to travel again, we would want to do it differently and Remote Year seemed like the right solution for us.

With Remote Year, we traveled with a group of like-minded individuals and had the sense of community we were longing for.

They also took care of the nitty-gritty travel details including booking our flights, scheduling our transportation to and from the airport, finding accommodations for us that suited our needs, and making sure we had a workspace with reliable WiFi.

The conveniences continued once we arrived at our destinations with the on-site city teams who helped us get acquainted with our new cities. They also curated activities and events for us to get a real feel for local life.

Even with all this assistance, we still had the ability to be independent and choose how we wanted to spend our time in each city, which resulted in the ideal marriage of support and freedom.

The Remote Year Emotional Rollercoaster

A few days after starting Remote Year, we had our orientation. It covered basic protocol, safety procedures and we learned about the Remote Year Emotional rollercoaster. It looked something like this:

Emotional timeline

This is a funny and light-hearted take on my emotional year, but, in all seriousness, I went through a lot. I don’t mean this as a complaint and feel a sense of guilt even writing anything slightly negative about our life-changing experience, but I want to give an honest perspective.

Here I was living a life others dreamed of, hiking Machu Pichu, bathing elephants in Thailand, swimming in crystal blue waters in Croatia, but I also had days when I felt depressed and did not want to leave my room.

Spending a year of rapid traveling took a toll on my health and a friend even described Remote Year as “an attack on our emotions.” Here are some of the ups and downs I went through the year.

The Honeymoon

Month One: Lima, Peru

Honeymoon phase “they see me rollin’…” Photo Credit: Brenton Cozby

After a tearful realization at the airport that I wouldn’t see my family and friends for a year, I arrived in Lima. Sadness quickly turned into excitement as I met my traveling family, aka tramily.

Instantly, I felt a strong connection with our kind-hearted Program Leader, Helena, and enjoyed getting to know the 42 other dynamic and unique individuals I would be spending the year with.

The month felt like a honeymoon where everything seemed wonderful, everyone got along, and we were on cloud nine. I ate my way through Lima, participated in as many group activities as I could attend and visited the Kennedy cat park when I missed my cats at home.

Month 2: Medellín, Colombia

Hanging out in Medellín

The honeymoon phase continued in Medellín. My apartment had a hammock which I used regularly to relax, I found a gym that kept me motivated, and had lots of vegetarian food choices that kept my belly happy. This was one of my best months for me because I was able to easily establish and stick to a routine.

Check out the Nomads Nation Digital Nomad Colombia Guide

The Dip

Month 3: Santiago, Chile  

A little help from my friends. Photo Credit: Brenton Cozby

The dip is what Remote Year calls the period after the honeymoon effect wears off and reality sets in that you have committed to a year of this. It usually occurs around months three and four and like clockwork, this is exactly when it happened to us.

For me, the dip took shape in the form of me hiding in my apartment. My tank had been running on empty from the previous two months of cramming my days with events and outings, trying to see and do as much as possible.

To recover, I spent more time in smaller groups or by myself and turned down going out to eat and instead, focused on cooking at home. Unfortunately, there weren’t any good gym options that month, but I went on morning walks with friends to stay active. 


Month 4: Mexico City, Mexico

Homesickness = a trip home

Still stuck in the dip and more homesick than ever, many of us opted to take a short trip home. Most of us were US residents and since we were in Mexico, an easy flight away from the states, many of us flew home for a few days, including me.

It was rejuvenating to see family and friends, kiss my niece and nephews and cuddle with my cats. Surprisingly though, after four days, I was ready to go back to Mexico which oddly felt more like home than my actual home in New Jersey.


Working night hours in Asia. Photo Credit: Brenton Cozby

Our four months in Asia were our most challenging. Many of us had to work US hours which meant working through the night. This made quality sleep nonexistent and being in opposite time zones from friends and family made it harder to communicate with them regularly.

On top of all this, we were experiencing culture shock, we couldn’t communicate with locals because not many of them spoke English. Simple tasks like reading labels at the grocery store were difficult even with Google translate.

Furthermore, there was a whole new set of cultural norms to adjust to.

In Hanoi, many cafes required you to keep your voice down and we would often be told we were being too loud.

Similarly, in Japan, if you did not follow proper “code of conduct”, a local would cross their fingers or arms and give you the “X”, shaming you for not acting appropriately.

The combination of these factors led to us feeling out of our element and solidified the notion that we were far from home.

Month 5: Hanoi, Vietnam

Hanoi chaos

Hanoi was noisy, crowded, and crossing the street felt like a death wish. You were expected to walk into traffic and hope that cars and scooters would go around you. They did, but it was still terrifying.

To escape the hustle and bustle of the city, I joined a local gym and took their yoga classes. The classes helped release tension, aided with improving my flexibility and provided the quiet time I needed to give my mind a break.

At the end of the class, I would enjoy a hot cup of tea, courtesy of the gym, and it was the perfect ending to my “me time”.

Month 6: Chiang, Mai

Learning meditation with Phra KK, a Buddhist monk

Chiang Mai was a month of spiritual awakening. I spent time with a Buddhist monk called Phra KK who taught me about the Buddhist way of life and different ways to meditate.

Of his many teachings, his perspective on suffering really impacted me. Throughout my life, I had been conditioned to avoid pain and suffering, but he reminded me that suffering was a part of life and that it was better to accept it than to try to avoid it.

He brought up the sad truth that most of us will outlive our parents which was a hard reality to think about but also led me to strengthen my relationship with my parents.

In order to continue nurturing my spirituality, I went to a Crystal Sound Bath where the instructor rubbed the rim of different crystal bowls to create vibrations, energy and a symphony of high pitched sounds. All I had to do was lay down to meditate whilst basking in the harmony.

Month 7: Kyoto, Japan

Rainy days in Kyoto

We arrived in Japan during the rainy season and most days were filled with grey skies and scattered showers. The lack of sunshine combined with night-time working hours had us feeling down and seasonally depressed.

James, my husband, worked New York hours which meant he didn’t finish his workday until six in the morning, long after the sun had risen. In contrast, my work did not require me to have such extreme hours and I normally went to bed by 2 AM.

I was happy to get to bed at a reasonable time but our conflicting sleep schedules meant we had less quality time together which caused friction in our relationship over time. 

Japan did not have great gym options, so instead, I rented a bike for the month. As a bike-friendly city, I easily rode to various locations including Buddhist temples, Shinto shrines, and zen gardens. These were my favorite places to find peaceful moments and focus on living in harmony with others and the natural world.


Month 8: Kuala Lumpur, Malaysia

“Over it”

By the time we landed in Malaysia, we were ready to leave Asia. We were over working night hours, hot humid weather and noodles.

This month felt especially foreign to me because it was the first Muslim country I had visited. Most women were dressed very conservatively and wore hijabs or burkas. I, on the other hand, wore my regular summertime attire of shorts, tank tops, and dresses.

Walking around the city, I would often get stares especially from men which left me feeling uncomfortable and intimidated.

This month was also a critical time for James and I who had not confronted the growing rift between us. We were hoping to get through these odd work hours and have everything return to normal next month.

No longer able to avoid the elephant in the room, we started peeling apart the layers of resentment, insecurity, and unhappiness we had been feeling.

The conversation would continue on for months to come but ultimately, it brought us closer together and helped us improve our communication skills.  

The Home Stretch Love Fest

The last four months felt like a breath of fresh air. We were no longer working night hours, we remembered what a good night’s sleep felt like, and we could find our favorite foods at the grocery store again.

These months I focused on recovery and life felt easy breezy until the realization set in that this amazing year was coming to an end. 

Month 9: Split, Croatia

Floating away our worries

Living on the coast, I spent lots of time in the Adriatic Sea, floating, literally and figuratively feeling the weight of my worries lift.

A few ladies within my tramily created a Spiritual Sisters group where we talked about manifestation, cleaning our auras, and self-love.

James and I spent a lot of time together and took a solo trip to Italy for our own version of Eat Pray Love.

Month 10: Lisbon, Portugal

Cheesy romantic picture

This month, James and I lived alone in a cozy studio. It had been a while since we didn’t have roommates and it was the ideal situation for us to continue to work on our relationship.

We joined a local gym which we went to often and got into a good routine.

We took another solo trip, this time to the most romantic place on earth, Paris. 

Month 11: Valencia, Spain

Sliding through the rest of Remote Year. Photo Credit: Brenton Cozby

I quickly embraced Spain’s siesta culture which emphasized taking a long break and nap after having lunch. At this point in the year, I was really feeling the wear and tear of traveling and siestas were necessary.

I rented a bike for the month and rode around the scenic Jardin del Turia where I would often stop to play on the most epic kids slide located in Gulliver’s Park.

I also started to practice grounding, or earthing, in which I would remove my shoes and socks and place my feet on the natural ground.

We had spent a lot of time this year in big cities with limited green spaces and spending time in nature was nurturing and healing.

Month 12: Cape Town, South Africa

Soaking in all the quality time together

We settled into our apartment and noticed a pigeon had set up a nest in the flower box right outside our window. She laid two eggs which we watched hatch and grow into young adult pigeons.

It brought us joy to check on them each day and served as a metaphor for our current stage in life. We were getting ready to finish Remote Year, spread our wings and flee the nest.

It felt surreal that the program was coming to an end so I focused on my friendships, spent a lot of time with my tramily, and soaked in these last moments together.

Post Remote Year

Where to go from here… making sense of life after Remote Year

Our final farewell was on the 27th where we reminisced about funny moments and made sense of what an unbelievable year it had been. We also contemplated what was next for us.

The next day, much of our tramily boarded planes and as said our “see you laters” holding onto hope that we would see each other again soon.

The next few weeks felt odd, I had a sense of emptiness and sadness. Ironically, we could not have prepared emotionally for the end of Remote Year just like we could not have prepared for what this year would bring.

As I write this, I am still processing everything and adjusting back to life in the states. 

Reflecting back on this bumpy ride, I am thankful that it taught me to be more resilient, adaptable, and open-minded.

I am incredibly grateful for my tramily who rode this ride with me, allowed me to be honest when things were rough with James, listened to me talk about feeling homesick and forced me out of bed when I wanted to shut out the world. If not for them, I would not have made it through this year.

I am also thankful to have found ways to take care of my well-being which I refer to as my “seat belts”. They include:

  1. Relationships: Staying in contact with my loved ones at home, having quality time with my husband and tramily
  2. Physical movement: Walking, biking, taking classes, moving my body in some way to help feel energetic, strong and clear my mind
  3. Spirituality: learning different ways of life and religions, giving myself quiet time, practicing meditation, grounding
  4. Rest: getting enough sleep, allowing myself to say no to activities and giving myself time to rest and relax
Relationships, physical movement, spirituality and rest got me through this year

In the end, I know these challenging moments of being out of my comfort zone, lead to my personal growth. It was an accomplishment to make it through this year and to find ways to stay well through it all.

If you are planning to do some extensive traveling whether through Remote Year or another way, know that it will be mentally and physically challenging but you can get through it.

If you need any help finding your happy healthy habits, I am here for you and you can book a complimentary discovery session with me here.