Lessons Learned from Six Months as a Vagabond

At the beginning of January I packed up all my things into a storage unit, left my stable tech job, and said goodbye to my friends in San Francisco to pursue a life-long dream of traveling the world with just a backpack for one year.

I had flirted with the idea of a vagabonding adventure for almost a decade but never had the savings, time, nor courage to pull the trigger. That is, until recently.

Growing up as the only child of hardworking immigrant parents from a middle-class Midwest suburb, I had always viewed international travel as a luxury. My family had never vacationed overseas aside from visiting relatives in China.

Even though I loved my first experiences traveling abroad after high school, I never felt comfortable with pursuing travel in lieu of advancing in my career during my 20’s.

Then last year I had a few personal wake-up calls — including going through a break-up and professional burn-out — that prompted me to question my life priorities. With the help of close friends, mentors and coaching, I started to clarify what was truly important to me. I learned how to better align my actions with my core values.

What followed was that I began to listen to the needs of my creative, adventurous self, which I had often neglected while chasing the goals of my logical, achieving self. I made friends with my fears of feeling left behind and walking an unknown path.

These mental shifts enabled me to create the space in my life I needed to pull the trigger on my Year of Adventure.

Six Months Later

Fast-forward to mid-July.

I’ve traveled through seven countries in Asia: Indonesia, Myanmar, Singapore, Vietnam, Taiwan, China, and Japan.

There were many highlights. I rode a motorcycle 2500km across Vietnam and worked on tea farms in China and Taiwan. I took surf lessons in Bali. I finished a Mandarin language intensive in Taipei and completed a six-day spiritual pilgrimage through the Kii Mountains in Japan.

Even more importantly, I befriended countless other travelers as well as locals along the way. Several of whom I now count as good friends. I also crossed paths with friends from home, our shared experiences in new contexts bringing us closer together.

After these past few months, I feel more joyful, energized and appreciative of living in the present moment. My heart and soul feel full from the delightful memories and meaningful connections that I made throughout my journey.

I feel deeply grateful for the rare privilege to travel freely without the constraints of full-time employment. I recognize that without my passport and economic security, none of this would have been possible.

My only wish is that I had pursued my long-term travel aspirations sooner.

Lessons Learned

Vagabonding has been fun and exciting but also mentally and emotionally challenging. I learned several lessons while addressing these challenges on the road.

Real freedom comes from owning your whole experience

It’s common to think of freedom as freedom from something extrinsic (location, person, government, job). However, the most empowering kind of freedom for me is the freedom from limiting beliefs.

Back in San Francisco, I had a bad habit of reacting to situations with a victim mindset. When things wouldn’t go my way at work or in my social life I would often feel slighted at the injustice. Then catching myself in the act I’d feel self-critical of these unhealthy thoughts — starting a negative feedback loop.

Looking back, this toxic cycle became my Achilles heel, making it harder to stay motivated in the face of life’s obstacles.

During my solo traveling I noticed the same reactions would bubble up into my consciousness, but my new context made it easier for me to challenge them. After all, traveling independently meant that I was in the drivers seat of my own experience. There was no one else to blame for my present emotional state.

Starting a regular mental practice, every time I noticed myself slipping into feelings of victimhood, I tried stopping these thoughts in their tracks and reframing their underlying assumptions.

For instance when I got caught in a few massive downpours while motorcycling in Vietnam during its monsoon season, my first reaction was feeling self-pity and snubbed. How could I be so unlucky? I wanted to blame someone or something for my discontent.

After noticing my negative thoughts, however, I made it clear to myself that I was the one who decided to ride a motorcycle during monsoon season in the first place. Strangely enough, taking responsibility made me feel better — like I had gained newfound respect for myself.

Countless repetitions later, I felt like I had carved out a new pathway in my mind and started feeling more responsible for creating my own happiness.

While travel is no panacea for mental woes, I believe that thrusting myself into a new environment helped me break free from old, harmful patterns of thinking and cultivate new, positive ones.

The beauty in the world unveils itself to those who look upon it with curious eyes

Intention and perspective greatly influence the kind of travel experience you have.

Like how a fictional tale is shaped by the author’s mindset when writing the narrative, the story you tell yourself about your journey is a product of how you see the world.

If you view the world as just a checklist of attractions, it’s no surprise that traveling will start feeling like checking off the boxes at work after the initial rush of adrenaline wears off. Chasing the beauty you find on Instagram is setting yourself up to be disappointed. There are many visually stunning places, but social media has distorted our expectations of what we can see in the world.

However, I learned that by traveling with an open mindset I could be pleasantly surprised by what I might find. Maintaining a beginner’s mind helped me create my own luck, leading me to opportunities I wouldn’t have otherwise.

For example, I had never heard of eye gazing ceremonies prior to staying in Ubud. These intimate gatherings bring strangers together for long sessions of making eye contact with one another — making meaningful connections without words. I would have thought of it as a rather peculiar, touchy-feely exercise back in San Francisco.

However, when my buddy shared his positive experiences with me, I became intrigued and decided to try it out. I’m so glad I did because I found the experience to be emotionally profound, revealing to me a whole new dimension of the power of body language.

If I hadn’t led with my curiosity during this journey, I would’ve missed out on so many of my favorite experiences — maybe even all of them.

Our fears aren’t as intimidating as we make them out to be

Fear is a funny thing. It hasn’t fully gone away during my journey, but I’ve gotten better at making friends with it.

Preparing for the trip, I felt afraid of several aspects of vagabonding. Being thrown into unknown situations, feeling lonely, and getting lost or hurt while traveling alone.

Once I actually started solo traveling, I quickly realized that many of my fears were unfounded. While I’ve consistently faced unknown situations, I’ve discovered that I actually enjoy the challenge of making new friends, navigating through unfamiliar territory and coming up with a creative solution to problems I encounter on the road.

After a few months of collecting data points on my behavior, I’ve learned that I can trust myself to carve a path forward no matter what the situation is. This self-belief has become a part of my identity as a traveler and explorer.

While fear will always exist in my life, my relationship with it has improved during my time in Asia.

Letting go of judgment helps you appreciate people different from yourself

While I’ve always tried to approach people non-judgmentally, it felt hard to give up this mindset completely in my fast-paced, pressure-cooker life in San Francisco.

After having started traveling, however, I’ve done my best to shed these assumptions.

Living in San Francisco everyone I knew and met worked in tech. My mind could lazily put people into boxes based on their employer, college, age and/or hometown. Ironically, I also found it hard to feel close with people.

While traveling, I’ve met people from all walks of life — chefs, artists, designers, farmers, teachers, students, retirees, police officers, and entrepreneurs. It’s felt refreshing to escape the tech bubble. I never know what kind of person I’ll encounter, so I’ve practiced more openness and curiosity. Connection has gotten easier.

What I’ve found is that ordinary faces sometimes hide the most extraordinary stories.

The 64-year-old Canadian grandmother and recent divorcee who decided to backpack solo across Vietnam, aspiring to explore the largest cave in the world. The 38-year-old Cambodian-French woman who sold her house and finally pursued her dream to visit Southeast Asia after a bad car accident nearly took her life.

Everyone travels for a variety of different reasons. What’s incredible is to see how traveling unites people from all over the world through a cohesive common experience.

My dear travel companions also taught me this lesson. Being together 24-7, you quickly learn about each other’s quirks and needs. You learn about compromise and treating each other well as you walk along the same path.

By spending time in close quarters with someone totally different from me, I’ve grown to appreciate the unique qualities that make someone special.

Thanks to this new perspective that my environment has brought forth, I feel more connected with people than I did before I started traveling.

Going Forward

For the rest of this year, I’m continuing my journey in Europe and South America.

There are many aspects of this next segment that I’m excited about. The potential to explore history, connect with new cultures, and practice Spanish.

But most of all, I feel eager to see what new lessons I’ll learn.