10 year reflection @ 32 years old.

Most of this post was written next to my wife on a return flight from our honeymoon. My choices were to watch movies with no earphones, or write. Easy decision.

I just turned 32. I call the Bay Area home. I’m married. I work from home. I almost have an MBA degree. I play tennis regularly. I’m riddled with physical injuries. As I contemplate how we got here, I reflect on the past 10 years leading up to the present, and I envision how the next 10 years will pan out.

How did we get here?

Significant Events


I had spent the summer studying abroad at Peking University. I visited my family in Taiwan for a week before returning to The Bay Area for my final year in college.

Taichung with cousin

My goal was to graduate, move to Washington D.C., and pursue a career that leveraged my skills in the Chinese language. My mindset very suddenly shifted towards the future. I recognized how privileged I was to have the bank of mom and dad financing my education and living expenses. I did not want to be dependent on them after graduation, thus the focus on career.


I landed an internship at a non-profit in D.C. months before graduation, cementing the move to the east coast. The stint was short lived; I did not enjoy the east coast culture nor the non-profit sector, and I found employment at a software company as a sales and customer success associate. Back to the Bay Area I went.

Watching first ever tennis tournament, the Citi Open in Washington D.C.

From the very first paycheck, my goal was to minimize discretionary spending and invest as much disposable income. At $48,000/year, it was rather difficult to save a meaningful amount. I lived on Terisa and Crispin’s couch in Berkeley for $400/month. The commute to and from San Francisco was a brutal two hours per day.

Living on a couch was not sustainable. I found solace in the work travel which took me to places such as Stockton, Denver, Detroit, and The Netherlands, but such experiences were momentary. An opportunity presented itself in the Taipei office, and I uprooted my life and moved across the world in the pursuit of financial freedom. Little did I know this to be the first of 7 career-related relocations in my 20s.


I developed a goal to amass $1 million by 30, and I was rather single minded in this pursuit at the expense of my health and relationships.

During this time, I received several performance- or promotion-based raises, cash bonuses, and performance-based equity grants. I lived well below my means. Having read that people should spend no more than 1/3 of their income on rent and to invest 10-15% of their paychecks, I wanted to beat such benchmarks and spent <10% on rent while investing 70% of my net income.

The financial gains came at a cost. 60-hour workweeks were normal; 80+ hour workweeks were not irregular. I took multi-week business trips to Indonesia, Hong Kong, India, Sri Lanka, Bangladesh, Singapore, South Korea, Thailand, Italy, Turkey, Ukraine, and China. I’ve written about most of these trips, but only through a lens of glamour, curiosity, and joy. The trips were draining and took a physical and mental toll on me. I rarely exercised and hovered 25-30 pounds above my normal weight. I often traveled on 24-hour notice, even internationally, and I did not have enough energy to be a good romantic partner to anybody.


While working full time, I consulted on the side and earned an additional $50,000. The chairman of a wholesale shoe company hired me to build a software division to enable them to sell directly to consumers.

Towards the end of 2017, I started a “business” mining Ethereum. I opened an office in Las Vegas with $25,000 in startup costs and $600/month in operational expenses, ultimately earning an additional $50,000.

These were ultimately distractions from depression. I had poured my everything into my full-time job, and the company had all but ran out of funds. I was rather dismayed that my efforts would not culminate into financial freedom; that my (significant) chunk of stock options were valueless.

Though heartbroken at the time, the company’s downfall was good for me. I was so single minded in making money that I had neglected my physical and mental wellbeing far too long. I spent most of 2018 and 2019 trying to take better care of my body. I found a doctor to surgically remove a bone spur that had been impacting my foot since 2013. I began playing tennis. I formed some non-financial goals. I exited positions in several risky investments so that I would not expend as much energy looking at market conditions. I began dating with a serious mindset.


I met Bonita. And we got along well (duh). In 2020, my then employer gave me a choice: relocate to Austin or get laid off. For the first time, I found myself consulting a romantic partner on a big life choice. Her response was firm but rational. “If you think this job is life changing, take it and I will move there with you.” But we both knew that the job was not life changing, and that to take the job would mean I move to Austin a single man. For the first time, I found myself not chasing money. I gave up a $197,000/year job and was laid off for the first time (perhaps for love?!). I was filled with anxiety during the early stages of the COVID-19 Pandemic. And for the first time, I moved in with a romantic partner. So many firsts.

Bonita and I tried to be creative in creating memories together. Prior to the pandemic, we traveled together to Nashville and The Big Island, Hawaii. We desired wanderlust and made a few weekend trips. Our day-to-day comprised of taking walks and learning new food recipes to cook.

Hawaii Volcanoes National Park

The layoff was not immediate, but my work responsibilities rapidly dwindled. With the additional time, I applied to the Berkeley-Haas part time MBA program while searching for jobs. To my surprise, Berkeley admitted me. As I hit 30, my day-to-day living comprised of spending time with Bonita, starting a new job remotely, being a student once more, and playing tennis.

This went on for a while. In 2021, in the months leading to the renewal of our apartment lease, Bonita and I seriously contemplated buying a home. We toured about 12 homes, placed two offers, and won a bid, thereby cementing the Bay Area as home. Homeownership has been greatly rewarding. Some things are less fun than others such as repairing the foundation, hiring arborists to trim the previously neglected redwood tree, or caulking the bathroom and kitchen to seal holes. Other projects have been way more fun such as replacing a chain link driveway gate with an automatic one, making the entire home smart, and setting up various gathering “destinations” in the home and yard. Such endeavors are not only fulfilling, but also improve our quality of life.

In parallel, I was playing a tremendous amount of tennis. Given the relative safety of the sport during the pandemic, I was on the courts 5-6 times a week for 2-3 hours per period. I developed profound friendships with these individuals, making shelter-in-place feel less painful. I also admittedly developed a motivation (or obsession) to compete at the highest levels in tennis leagues, influenced by a friend who incepted the idea of winning Nationals. We achieved that goal in October 2021.

I cannot understate how good it felt. Man, it felt good. As sweet as victory was, it came at a cost. Given my motivation to win it all, I neglected my health akin to the tunnel vision I had between 2014-2017. I now have incurable arthritis in the area where I had foot surgery. In addition, I have Achilles tendonitis on both feet from overtraining, and a torn right shoulder from poor tennis serving technique. Day-to-day life now comprises of 45 minutes of physical therapy, which I expect to continue into 2023.

My biggest takeaways from these events

I need to set the right goals

I am generally able to set and meet goals. However, some goals are too broad and/or challenging where achieving them comes with significant costs. I achieved my financial target at 30 at the expense of physical and mental detriment.

Given that I’m extremely driven by checklists, I don’t think this was a good “list item” to have. It wasn’t very actionable in the sense that checking off that box brought no satisfaction. It felt like crawling through a marathon.

When it comes to tennis, my goal was to win Nationals. I did have two sub-items that I felt would help me achieve the goal: (1) improve serve, and (2) improve backhand volleys. However, I didn’t clearly define how to check off those items, and therefore the items were not achievable. I believe that the ambiguous “improve serve” item led to improper training, resulting in the shoulder tear.

Home is where relationships are

It took about 10 years for me to finally think of the Bay Area as home. Throughout my 20s, when I imagined settling down, it was in Orange County. Whenever I looked at real estate on Zillow, it was in Orange County. That is where my nuclear family lives. I have no blood family in the Bay Area.

Bonita helped me realize that my family was by and far the main reason why I was drawn to Orange County. Family is what continually draws me to Taiwan. Without family, I have few valid reasons to want to visit each location. On the contrary, the Bay Area is where I have developed friendships from school, work, and various other communities. This realization was what ultimately led us to search for and purchase the home in Santa Clara. Home is simply where you are surrounded by those you care about; those who matter to you.

I believe we made the right decision. Bonita’s family and friends are here. Many of my friends are here. We enjoy modifying the house to make it ours. All that is missing is my nuclear family (more on that below).

I find great enjoyment from experiences

Despite the Pandemic, ages 29-31 was very experiential. I visited my family several times, attended professional tennis tournaments, and explored different states and countries with Bonita. The occasional change of scenery from the Bay Area is very fulfilling and is something I would like to continue to do.

Crispin & Jen’s wedding, Colorado, 2020

I find great enjoyment from being healthy

Playing tennis regularly without issues in 2020 was, to put simply, incredible. Getting the heart to beat fast feels good. Feeling the adrenaline rush from competition is satisfying. The team camaraderie upended memories of college rowing, which are among my most profound memories from undergrad.

Whether it’s tennis or another activity, I want to use my body the way I want. The injuries I am facing now greatly impact the life I want to live. I want to be healthy. I need to be healthy.

Vision for the next 10 years

Per Lin Manuel Miranda’s genius storytelling, Alexander Hamilton was always writing like he was running out of time. There were so many things left for him to do. I identify with that character and am slowly learning just how precious of a commodity time is.

I just turned 32. There is so, so much more I want to do in my 30s. So much more I want to accomplish. But I want to accomplish them in a healthy manner that does not kill me or hurt Bonita along the way.

The overarching goal for the next 10 years: (1) build comfort around family, and (2) to be setup to meaningfully contribute to communities I care about.

Regarding comfort around family, our home is sufficient space for 2 people but will quickly become small once we have one, let alone two children. Should we continue to call the Bay Area home, a property that allows us to raise two kids the way we want, in a large enough lot, in a safe enough neighborhood, in an accessible location, with above average schools, costs well over $3 million. Given these characteristics, our incomes and/or investments need to outgrow the Bay Area’s appreciating rates of everything. I would like to purchase this “forever home” without selling our current home.

I wish to see my parents and sister’s family more often than I do now. I would like to see them at least 30 days a year because it will make saying goodbye each time less painful. There are several ways to ameliorate this situation.

Wedding day with mom

I would like to maintain a meaningful relationship with my family in Taiwan. Growing up, my parents ensured that my sister and I built a strong connection with them, and I wish to be able to see them at least every other year.

I would like to continue creating experiences with family. Whether that’s with Bonita, our kids, our families, closest friends, or a combination of everyone, experiential living is something I would very much like to do on a regular basis.

Honeymoon with my forever date @ Slovenia

To avoid distractions, I will allocate investments in a way that is consistent with our risk appetite, and to do so in automated fashion. Currently, we automatically transfer funds into various accounts, and the proceeds are automatically invested into various funds that match our tolerance for risk. I aim to minimize the frequency in which I manually purchase securities. I will aim to rebalance our portfolio no more than twice a year.

In my 40s, I would like to be well positioned to start a foundation so that I could donate my time and resources to materially benefit communities I care about. That may be the Taiwan American community, or the greater Asian American community, or tennis, or maybe even video game programmes.

I want to accomplish the above in good physical and mental health. Physically, I need to strengthen my body to compensate for the foot arthritis, foot tendonitis, and shoulder tear. Since 2013, I have not been able to run 30 consecutive seconds without pain. That needs to change. I have not been able to sit cross legged since childhood. That too needs to change. Mentally, I need to balance my time and energy in a sustainable manner. This area has been a lifelong struggle for me, and I often find myself regressing to obsessive behaviors, so I foresee this to be a challenge.

Lastly, I miss writing for myself. Gone were the days where I semi regularly wrote on this platform. There have been so many beautiful memories that I have not been able to properly put into words. I aim to write about these experiences, to remember the joy it brought, and to remind myself that such positive memories could always be repeated.

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