Happy Holidays!

I’m writing in from the Seattle airport while waiting for my connecting flight to Tokyo, which makes it the perfect time for me to crystallize my reflections on my last chapter before starting the next one.

Looking back on 2025

2025 was a crazy year for me. And a good one.

This was the year I took the leap and left the default path of a Bay Area kid by quitting my job in big tech and spending 8 months backpacking around the world.

In hindsight, it all feels so obvious. You could pick it out from any cliché story following the hero’s journey where the protagonist feels stuck, takes a leap to pursue a childhood dream, and comes out the other end changed forever.

But quitting my job was probably the hardest decision I’d ever made. It took me nearly one and a half years from when I first came up with the idea to when I actually executed it. The idea didn’t really get momentum until October of 2024, when a perfect storm of events in my life happened:

• The end of a long-term relationship, which left me free to plan my own future

• A round of layoffs at my company, and the ensuing chaos which made me question my career trajectory and what I would learn by staying

• Connecting with people who had done the thing and came from similar backgrounds to myself.

  • A special shoutout to Dexter Zhuang - who left his job as a PM at Dropbox to go on his own travel sabbatical in 2019. The articles he wrote during and after his travels provided concrete proof that you can quit your job and be more than okay. In fact, the format of this annual review is inspired by his annual reviews 🙂 If you read this, thank you again, Dexter!

What were the highlights of my year?

Gained more confidence in my ability to handle uncertainty

In the past, I was the type of person to plan my travel itinerary down to the minute, trying to squeeze in every possible activity to “maximize the experience.” But over the years, I started adopting a more flexible style of traveling, leaving time blocks open to serendipity.

However, backpacking took the novelty exposure to an extreme. For the first segment of my travels, I was hopping cities every few days, staying for up to a week at most. Just as I was getting comfortable in a city, it would be time to move on to the next. Each time, I would feel a pang of anxiety and nervousness. What would my next stop be like? Would I make friends? Would I be able to navigate the city? Would I get robbed or hit by a car or fall off a cliff?

Eventually, I noticed that even though I often feel nervous or anxious before stepping into the unknown, once I made it to the other side, I quickly figured things out, and the anxiety faded. The epitome of this was my motorcycle trip across Vietnam, which went from something I almost bailed out on to one of the best experiences of my life.

In the past, I was far more uncomfortable around uncertainty, and this showed up as risk aversion both in my personal life and at work. I stayed in the Bay Area instead of exploring other places to live. I took the big tech job instead of exploring startups or other unconventional career paths. Backpacking ended up being the exposure therapy that taught me something important.

Trusting myself.

Reignited my love for reading

This year, I finished reading over 34 books and skimmed through the contents of dozens more. This was a big jump compared to 2024, when I read 19 books, and a huge jump compared to 2023, when I read only 6.

While working, it often felt like my brain was too full, fragmented, or drained to focus on reading after a day of nonstop meetings. I limited myself to “easier” reads, like memoirs, which were usually written in a conversational voice and engaging narratives. However, after quitting, I had both the energy and time to read deeply and widely again.

Throughout the year, I dived into classic tomes like Crime and Punishment and Anna Karenina, geopolitical memoirs like From Third World to First, mysteries like The Devotion of Suspect X, and even read my first novel entirely in Japanese with また、同じ夢を見ていた.

The characters (or the narrator) of the books became my friends, and I would often feel a bit sad each time I finished a book, knowing that I wouldn’t be seeing those characters again. It was a great way to stave off the inevitable loneliness that hits while on the road, especially when I hadn’t met a group of friends I clicked with yet.

I know I won’t always have the time and space to read so much, so I’m grateful for these special chapters when I can.

Gained a broader perspective on the world - the good, the bad, and the ugly

Prior to my backpacking adventures, I only had a vague concept of the countries I was visiting, primarily from history books I read in middle school and high school.

Visiting in real life made it real, and I got a crash course in history, politics, economics, culture, and language each time I visited a new place. I began to better understand how certain historical events left enduring scars, how policy led to growth or decline, and how people adapt to varying circumstances.

I was touched by the kindness and warmth I received along the way. Both from locals who extended their hospitality and from fellow travelers, who I shared many good conversations, laughs, and meals with.

Most people in my circle of friends and acquaintances in the Bay Area are, frankly, very similar to me. Of course, this often means we get along well, since we could relate along many dimensions. But traveling exposed me to people from a much wider range of geographies, age groups, ethnicities, careers, religious beliefs, and values.

This exposure to people and places very different from what I was familiar with felt greatly enriching, and paradoxically helped me understand myself and where I came from a lot better. The ability to compare and contrast made it easier to pick out what values I resonated with, how my beliefs were shaped by my upbringing, and the privileges (and challenges) that I grew up with.

What were my lowlights of the year?

Falling into spirals of existential angst

During the beginning of my travels, I was fueled by adrenaline and the high that comes with stepping into a new adventure. However, several months in, I found myself coming to grips with the reality of being in liminal space.

I went on this trip without a clear idea of what I wanted to do afterwards, which meant that there was no defined “end date” to my travels, and no “goal” I was trying to achieve. I soon realized the downsides of letting go of the stable identity I previously had. As a product manager, it was easy to explain to people what I did for a living, and how that shaped my life direction and worldview. After leaving my job behind, I found myself grappling with questions like “do I deserve this?”, “what do I do with my life?”, and “what’s my purpose?”

This was accentuated whenever I saw people living in comparatively poorer conditions, or who had limited opportunities solely based on their place of birth, making me question the fairness of it all and whether I should be doing more to make the world a better place.

These moments were extremely uncomfortable, but in hindsight, they were probably the periods where I experienced the most personal growth. Eventually, I was able to define my values more clearly, and I developed new strategies and principles for how to cope with the existential questions of life.

Unable to fully let go of family expectations

Throughout my travels, I continued to receive anxious messages from my mom, including listings for jobs I had no interest in, unsolicited career advice, and tips on how to use AI to write cover letters.

I know it comes from a place of care, but I found it difficult to shrug off these implicit expectations as I try to pave my own path. Reading those messages often left me in a bad mood, and I eventually chose to just disengage entirely to preserve my sanity.

Perhaps I simply have to reset my own expectations. My travels helped me better recognize how my parents were influenced by their own upbringing, growing up in the chaos and poverty of Taiwan post-civil war. This left behind a scarcity mindset that highly values stability. It’s likely that until I find myself in a career that’s “legible”, I’ll continue to get anxious messages, and at this point it’s better to accept it will happen than try to fight it.

Looking forward

Going into 2026, I’m looking forward to laying down new foundations.

I’m excited to be based out of a single location again, where I can develop routines, invest in hobbies, and nurture a stable community.

I want to be mindful to not take on too much all at once. Moving to a new country will come with a slew of new challenges, and I wouldn’t be surprised if some of my plans get derailed. If I ever find myself overwhelmed, I’m hoping I can quickly course-correct!

Concluding thoughts

Honestly, I’m still figuring things out.

There are lots of open questions I don’t have answers to yet, and plenty of known and unknown unknowns. But for the first time in a while, that uncertainty doesn’t feel like a problem to solve. It feels like space. I’m grateful for this year, for the people I met, and for the chance to start the next year with a little more clarity.

Here’s to an amazing 2026!

Cheers,
Tim