Have you dreamt about quitting your job to travel the world?

Yi Shan
17 min readJan 30, 2020

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I did that in 2019 and here’re the 11 lessons I learned.

In April 2019, I quit my product manager job at Stack Overflow to travel the world. My partner left Big Law to join me.

By Thanksgiving, we had traveled to Jamaica, Norway, Denmark, Germany, Sweden, Italy, Switzerland, Burning Man, China, and Nepal. Then we took a 40-hour multi-leg flight via Bangkok and Tokyo and flew back stateside.

Biking in the street of Copenhagen, Denmark
Biking on the street of Copenhagen, Denmark (July 2019)

After months of traveling, we missed having a set routine, we missed the U.S., we missed our friends and we missed our dear kitty cats, and so we dropped our plans to visit South America and instead ended the trip early… In December, we picked up our kitties from New York City and moved to Colorado.

Hiking towards the Everest Basecamp (Nepal, November 2019)

2019 was one of the most challenging and daring years of my life.

Reading at the tea house in Namche, Nepal (November 2019)

While traveling, I continued my habit of reading every day. At the end of 2019, I had finished 51 books and learned a ton. I grew tremendously on all levels — physically, emotionally, mentally, and spiritually.

First time snowboarding (New York, February 2019)

If my old, unconscious habits and patterns were like deep tracks in the snowy landscapes of my mind, the new environments, impressions, and experiences served as a layer of fresh snow. They obfuscated the existing tracks and created a blank slate that allowed me to consciously redraw the patterns. Now, I want to share with you the most significant insights and lessons I gained from this process:

Part I: Know thyself

1. Working till we’re old and accumulating material goods is not the only way to live our lives

When I was growing up, every adult around me had a job. All my grandparents worked until they reached age 55 or 65, the legally-mandated retirement ages in China. When I played make-believe adults with friends, we all pretended to go to work every day — because what else did adults do?

Feeding birds at Gothenburg, Sweden (July 2019)

Before I left my job, my ego knew no other reality than the 9-to-5 life. For a while, the thought of not having a job and traveling the world petrified me. I believed I was making a gigantic mistake and my ego began looking for reasons not to pull the trigger.

“What if I can’t find protein powder in other countries?” When my ego presented this excuse as the last resort to protect itself, my partner and I burst into laughter and started packing immediately. The nonsensical nature of that statement had made it clear that I was out of excuses and it was time to take action.

To our amazement, our lives didn’t end after leaving our companies. Rather, we started to thrive. We began to explore with more freedom. We no longer had to spend our most precious time and energy at work. We gained more mental space for new experiences, ideas and the desire to start a new company.

Napping at sunset in Jamaica (June 2019)

2. Actual work is easier and more enjoyable than procrastination

The 9-to-5 schedule has trained me to comply with the adage known as Parkinson’s law: “work expands to fill the time available for its completion.” Without the structure of a job, the unexpected freedom paralyzed me. For weeks, I couldn’t write one email without dragging my feet in agony.

Slowly and painfully, I started to discover that two parts of me were constantly at war: a primal self always craved instant gratification; another, rational self tried to optimize for the future. When I procrastinated, the primal self overindulged in unhealthy short-term satisfaction. On the other hand, the rational self reacted with anxiety and fury over being caged by the primal monkey mind. Neither was having a good time.

Whenever I finally overcame the initial resistance and began doing productive work, the primal mind happily accepted its fate and went for a nap. The rational self could then work happily with focus and determination. Afterward, the monkey woke up relaxed, the rational self felt accomplished. Both were ready to have real fun together.

With this dynamic in mind, I began telling myself that I only needed to work for just five minutes before I can stop. This pleased the primal mind, who felt happy taking a quick break knowing that she could soon get back to short-term satisfaction. The starved rational mind would take any opportunity to work toward a better future. But once I had begun working, the primal mind was already napping and not easily awoken. And so the rational mind could continue working undisrupted for hours.

After I finished the work, the rational self was happy that the important work had been done. The primal mind felt excited that she could now recommence the pursuit of short-term satisfaction without complaints from the rational self.

Over time, the feedback loop of “finishing work early” = “having more fun, guilt-free “ was established. Both minds developed a positive relationship with the promise of a rewarding work session.

This is how I cured my late-stage procrastination disease.

The stunning sunset without filters in Norway (July 2019)

3. I am a limited person and that’s fine

During the continuous pursuit of growth and development, I always have high standards for myself: I aim to become fully enlightened and lose my ego completely. I want to survive in any environment I encounter, get along with everyone, and be with my family with full presence and love without ego or PTSD. As you might expect, it didn’t work out well:

Throughout my travels, I ran into breakdowns after breakdowns. The ever-changing cultures and environments deeply challenged me. As I grew more aware of the state of the world, the gap between reality and my ideals widened. I then fell into a shame spiral for not being enlightened enough to accept the what-is.

Amidst a breakdown after fighting with my family, a good friend enlightened me, “Oh, that’s normal. After all, you’re an ordinary human.”

Yes, that’s right — I am just an ordinary human. I’m not a god, Buddha, or a saint. I make lots of mistakes. However hard I work on growing, I will always have my limitations.

And so I started learning to accept my limits and shortcomings. The shame dissipated. Amazingly, I stopped forcing myself into a perfect shape and I got much happier and kinder.

I recognized that my energy is extremely limited. I can’t be everyone and everything. I cannot improve, cure or control everyone and everything. To create the life I want, I need to consciously choose areas to devote myself and let go of the rest.

Rather than aiming to bring the stars down to earth and then beating myself up for my failure to do so, I can light a candle to add a little light to the world. And that is enough.

Little Yi

Before visiting China, I got in touch with my father with whom I had lost contact for years. Upon my arrival, he reached out and said that after looking at what I had shared on WeChat (mostly about my life, personal development, and gender equality), he no longer wanted to see me for the rest of our lives. Before I could reach out for clarification as to what had triggered him, he blocked me and cut off our only way of communication.

I was devastated. I cried for days on end. I repeatedly asked what it was about me that made my father reject me. I also got angry that he left without giving me a chance for answers.

As I battled these demons, I gradually acknowledged the limitations of my father: he also is an ordinary human. He grew up with extensive trauma and little love. If I had lived his life, I might have done the same things he did. If I were him, I might have also yelled at, beaten, and rejected my kid and never showed remorse.

Consequently, I started to accept that he might never become the father I wanted. But this might not have anything to do with whether I’m good enough. And if this is true for my father, it could also be true for my mother, my family, my friends, and even strangers.

Over time, as I learned to accept my limitations, I began to accept the imperfections of others. This acceptance, in turn, created the space for the world to be just the way it is. And I finally made an important step toward finding inner peace.

First-time skydiving (New Jersey, June 2019)

4. Thyself ≠ thy country.

“Patriotism is your conviction that this country is superior to all others because you were born in it.” ~ George Bernard Shaw

We visited 11 countries on this journey. I discovered that people from each country attach their self-identities to that of their countries to a varying degree.

For example, during the three weeks of hiking up to the Everest Base Camp in Nepal, the locals almost always asked me, “Which country are you from?” Whenever I answered “China”, they concluded their inquiry as if they had learned everything there was to know about me. At times, I answered “the US” to see what would happen. Every time, they got confused. “But you don’t look American,” they’d say. “Are you Korean? Japanese? Chinese?” They were determined to trace my origin, to place me in a neat little box that fits into their worldview.

You and I are humans with unique experiences, stories, beliefs, and consciousness. “China“, “the US“ or any other country name does not and can not define us.

After connecting people from all over the world, it’s ever more clear that we are not our countries. The most wonderful country can give birth to extremely unconscious people while the most insane country can host noble souls.

Mentoring at StartingBloc in Durham, NC (May 2019)

5. New experiences are a magical time machine

Maybe you’ve had similar feelings: Time moves at snail pace when we were young. As we grow older, time runs faster year after year and never seems to slow down. We definitely felt this way before our trip.

As we started our adventure, we almost never had the same day twice. Every single day brought its surprises and challenges. Magically, these colorful events stretched out the feeling of time. Months of travels made it seem that two or three years have passed.

If you felt 2019 passed you by way too fast, try doing something different: learn new skills, make fresh memories, visit places you’ve never been to, try out exotic food, and get out of your daily routine and comfort zone.

Our life is super short. If we can make it richer and longer, why not?

Performing on stage at Improv Camp (June 2019)

Part II. On others and the environment

  1. Our environments shape us

As much as I’d like to believe I’m the complete master of my behaviors, that’s simply not possible. Our environments deeply influence our behaviors, beliefs, patterns, and who we are as people.

When we remain immersed in one environment or culture for too long, it’s easy to forget what a stronghold it has on us. I traveled from Hamburg, Germany to Copenhagen, Denmark, from Lillyhammer, Norway to Tuscany, Italy, from Burning Man at Black Rock City, the U.S. to Inner Mongolia, China, from Shenzhen, China to Kunming, China, from Kathmandu, Nepal to Denver, U.S.… I witnessed and often lived how different people lead their lives around the world. It amazed me to see what a big impact our environment has.

Some of the best Italian dishes I’ve ever tried (August 2019)

For instance, among the beautiful mountains of Norway, it’s as if everyone lives in harmony with nature. We took baths in lakes and hiked almost every day. My partner’s grandpa was the fittest 80-year-old I’ve ever met. He was in such great shape that I couldn’t keep up with him down the mountainsides. The mountains seem to slow down the pace of society and instill people with a sense of gratitude for their existence. The experience provides a stark contrast to how New York City can make people’s stress levels soar while leaving them craving more power and material possessions.

One of our favorite activities while traveling is to eat street food. We’ve tried the weirdest (the word “weird” is generally a compliment in my book) street eats in countries like Cambodia, Colombia, China, Thailand, and Vietnam. My stomach has always held up until we neglected all warnings and tried the street foods of Kathmandu, Nepal. I got food poisoning for the first time. While I was battling the stomach bug, the horrendous air in one of the most polluted cities on the planet made me only want to hide in our room and watch TV all day. In contrast, during the three weeks hiking in the Himalayas, I didn’t watch TV a single time and hiked over 105 miles (170 km) with a 20-pound backpack at altitudes up to 16,200 feet.

Fun photoshoot in Shenzhen, China (October 2019)

At Burning Man in Black Rock City, I felt freer to exist as my self than ever before in my life. Whereas in Inner Mongolia, China, I got intense judgemental stares everywhere we went merely because I’ve chosen to spend my life with a white foreigner.

At Burning Man, Black Rock City (September 2019)

Constantly experiencing new environments and consciously reflecting on them rather than being unconsciously shaped by a single environment accelerated my growth.

I used to live a comfortable and yet anxious life in New York City working as a Product Manager in a white male-dominated industry. The culture stressed me out. And yet the stability and security incentivized my ego to prevent me from taking any actions that would drastically alter the situation. After taking a leap of faith, my ego had to accept that it could no longer rely on the old snow tracks. And my growth radically improved as I was free to carve new paths.

As a lesson for the future, we need to learn to consciously choose places that support our growth and who we aspire to be. Staying in a stale and comfortable environment can be a trap. Few things jumpstart our growth as rapid changes in our environment. It can be scary to take the initial step, but once you’re already walking you realize it’s all worth it.

2. Real belongings and friends are essential ingredients of happiness

“Sometimes life is too hard to be alone and sometimes life is too good to be alone.” ~ Elizabeth Gilbert

Quitting my job to travel the world has been a life-long dream. However, after my dream came true, I felt depressed. Long-term travels can be extremely isolating. Despite a constant bombardment of new inputs from new environments, life felt meaningless. I was missing deep and nurturing connections with interesting people

We, humans, are social animals. High quality, loving relationships are the sources of much of our happiness. It’s critical to cultivate and nurture them.

Friendsgiving in New York (November 2019)

3. I don’t have to take anything personally

During our travels, I encountered varying levels of racism, sexism, and xenophobia. For example, a waiter at a local restaurant in Cinque Terre, Italy let another Italian jump the line in front of me and then started pointing and talking about me in Italian with contempt. Later, I went back with my partner, and the same person was nothing but polite towards us.

These experiences bothered me a lot at first. I felt humiliated and angry, “How could they do that to me or anyone just because of how different we look? This is so unfair!” Then I would get all frustrated and defeated, unsure how to handle it all.

After repeatedly encountering similar situations, I’m gradually learning to make my peace with these issues:

You see, I’ve realized that these types of reactions never have anything to do with me. Even when it seems that I’m the one that triggers them, people’s reactions to me are mere products of their own experiences, beliefs, values, biases, and projections. They are often completely unrelated to whether I’m a wonderful or a terrible person.

Going back to my discussion above regarding forgiveness and empathy, if I was the waiter and shared his background, memories, genes, stories, and worldview, I might have behaved the same way. Understanding this allows me to not take other people’s projections onto me personally. It lets me react with compassion rather than contempt when someone treats me poorly.

Going through challenges without light through “Dialogue in the Dark” to empathize with the blind (Oct 2019)

Part III. Contemplation about society

1. Sexism is very much prevalent most of the world

Yes, the status of women around the world is gradually rising. Unfortunately, we still have a long way to go.

When it comes to gender equality, the Scandinavian countries are leading. I felt the safest and most respected in these countries as a woman during our visit. And the progress is well reflected in their policies. For example, Norwegian law regulates that the Norwegian parliament and company boards must have at least 40% women. After the birth of a child, the government mandates that both parents get separate paid time off to take care of the baby.

In contrast, in the tech industry in the U.S. where I used to work, most companies’ executives are men. Once in a blue moon, a woman or two would make it to the top, but they were rarely able to stay in the Old Boys Club for long. When I connected with them one-on-one, they often shared with me the numerous struggles they encountered as a woman leader in a man’s world, struggles that eventually made them leave their companies and sometimes abandon their careers.

In China, I played around the Chinese app Tik Tok (抖音), one of the two most popular social media platforms in the country. (Note: the Tik Tok app outside China comes with completely different user bases and rules.) Many of the top videos with tens of millions of views are openly sexist. For instance, they joke about sexual harassment, normalize the behavior of stalking, and rate women solely based on their physical appearance and how well they can cook. Most female friends I have in China experience enormous pressure to focus solely on their looks and housework skills. The plastic surgery industry doubled its size from 2015 to 2017 and is continuing to rise. Almost every picture shared by young women on social media and even review sites is heavily photoshopped to the point where they barely look human anymore.

In Jamaica, the locals, mostly men, ignored me. Even when I asked a question, they would often answer to my partner. When I took out my credit card to pay at restaurants, my partner got the bill instead.

On the road to gender equality, we human societies still have a long long way to go.

With the Mosuo (a matriarchal ethnic group in China) women in Yunnan (October 2019)

2. Poverty is a human invention

The divide between the poor and the rich upon birth is a unique and horrific invention by our species. Traveling made us witness severe unfairness of resource distribution around the world.

By way of example, Norway has 80 times the GDP per capita of Nepa. Whereas Norwegians can quite literally bathe in endless bodies of freshwater, people born in Nepal generally lack access to clean drinking water. According to the World Health Organization, “more than 1000 Nepali children under five die each year from diarrhea-related to poor water sanitation.” On the other hand, those among us lucky enough to be born in countries like Norway receive free healthcare and 25 days of paid vacation each year.

We are all humans, but the most significant differentiator in our quality of life is the random birth lottery that determines our family, gender, race, country of origin, socioeconomic status and a myriad of other factors outside our control. Dr. Dan Ariely, Professor of Psychology and Behavioral Economics at Duke University asked in his Ted Talk, “What are the characteristics of a country that would make you want to join it, knowing that you could end randomly at any place?” In other words, if you were to be reborn today and could randomly end up in any socioeconomic strata, any race or any family in a given society, how would you like that society to look like? It’s safe to say that such a society would be a lot fairer and egalitarian than the societies we have created thus far.

A porter carrying goods weighing up to 200 lbs in the Himalayas (November 2019)

3. Economic prosperity ≠ happy people

At the end of our trip, we were able to travel around Nepal for four weeks. Nepal has one of the lowest GDPs per capita in the world, only two-thirds of Cambodia’s GDP, half of India’s and Kenya’s, one-seventh of Thailand’s, and one-tenth of China’s. And yet the people there were amazingly conscious and present.

Kids performing during Diwali on the street of Kathmandu, Nepal (October 2019)

For instance, in the most polluted, crowded, and heavily trafficked areas of Kathmandu, a motorist gently let me walk first while he turned around. Another time, my partner dropped his bottle while walking. A stranger picked it up, handed it back to him with a smile and walked away.

Even in Thamel, the most touristy district of Kathmandu, we found wonderful and present people. On one morning of the Diwali festival, the travel agency we urgently needed to see was closed. Next to the agency was a store that sells handmade T-shirts. Upon seeing our distress, the owner kindly offered his cell phone to reach the travel agency for us. As we were on the phone, he left for the bathroom and trusted us alone with the store, i.e. his entire livelihood. Upon return, he refused to take any money as a reward.

The kind T-shirt maker in Kathmandu, Nepal (October 2019)

I recall an experience while I was working in Hong Kong a few years ago. After work, I crossed the border to Shenzhen, the metropolis next-door. My cell phone battery suddenly died and I couldn’t reach my mom who was picking me up by the border. I asked about ten groups of people for help and yet not a single person dared to lend their cell phone to me.

In that small store in Nepal, I felt waves of conflicting emotions — touched by the unconditional kindness of the owner and saddened by the loss of humanity and trust in Chinese societies.

On the subway of Shenzhen, China (October 2019)

I used to believe that culture always grows with the economy. After visiting places like Nepal and Thailand, I found out how wrong I was. Economic growth might bring forth the development of some cultures. However, an over-emphasis on economic growth often comes at a price.

New York City PRIDE parade (July 2019)

In 2019, I visited 11 countries and 30+ cities, read 51 books, quit our jobs, started a company remotely. I also skydived, snowboarded, learned archery, attended Burning Man and improv camp, got a six-pack, and participated in CrossFit open all for the first time. 2019 was a glorious year filled with challenges, joy, and growth.

What did you learn and receive in 2019? I’d love to hear about your experience. Feel free to share in the comments below.

Wish you a wonderful and fruitful 2020!

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Yi Shan

Productivity Coach for Startup Leaders and Creator of the 30-Hour-Workweek System (30hourworkweeksystem.com)