2020 Annual Review

In my last Annual Review, I declared my intended theme for 2020 to be architect:

Going forward, the theme I’ve decided on for 2020 is architect. I see architecting a new home as a fitting analogy for what I want to do this year — lay the foundations for an expat lifestyle in Singapore, and more broadly speaking, a sustainable life path that relentlessly prioritizes my long-term fulfillment.

What actually transpired was shocking, like it was for everyone else around the globe. While I spent my 2019 backpacking relatively care-free across the world, 2020 was nebulous, intense, and stressful.

Reflecting upon this past year, I feel proud that despite all the uncertainty and chaos that I had to navigate, I stayed committed to my chosen life path and forged ahead.

In January, after Lily and I moved my items into long-term storage in San Francisco, we flew out to Shanghai to spend Chinese New Year with my extended family. I couldn’t have expected that we’d take a flight to Sydney (where Lily’s parents live) in under 48 hours after news of the pandemic spread caused both our families to panic about travel bans.

Afterward, it was a long-winded journey to secure employment (thank you Xendit!), housing, and a work visa in Singapore. There were several scarily close calls along the way — nearly getting rejected at the Singapore border, almost getting stuck in Indonesia during my first week of work, and multiple delays with my work visa application.

Although I didn’t choose these turbulent experiences, I’m grateful that my year of travel in 2019 taught me a new toolkit of resiliency, adaptability, and creativity that I used often to navigate them.

Now at the end of 2020 (and the close of my 20’s), even though I’m living with more uncertainty than ever before, I feel fulfilled in realizing my architecting theme.

I’ve architected the foundations of my new expat lifestyle for my early 30’s. I didn’t back down from pursuing my dream to live and work abroad despite the risks. Now Lily and I are living in Singapore, safely and happily. And once borders open up in Southeast Asia, I’m thrilled about the opportunity to explore this dynamic region again.

For 2021, my theme is going to be leverage.

Why leverage? I want to think and dream bigger than ever before. Yet it’s become increasingly apparent to me that I have limited time and resources to direct towards goals like building long-lasting businesses, financial freedom, and community. Leveraging my scarce time, energy, and money will be the key to unlocking these larger-scale visions.

What were highlights of my last year?

Successfully moving to Singapore with Lily and building a new home in the city amidst the pandemic

The crowning highlight of my year is how Lily and I executed our goal to move to Singapore in spite many roadblocks — thanks to good fortune and decision-making.

In February, as Covid started spreading across borders and immigration policies became strict, I was still flying in and out of Singapore and Jakarta for job interviews. I got lucky, receiving an offer letter from my manager at Xendit by the end of the month.

Signing the offer gave us enough security to fly to Singapore in early March to lock-in an apartment lease (Lily already had an EP from her Singapore-based startup). The timing was impeccable because if I had flown to Singapore even 2 weeks later, I would have been refused entry at the border due to more stringent Covid policies.

After seeing how the US federal administration botched their handling of the pandemic, I’m enormously grateful to live in Singapore where community spread is contained and I can meet friends and colleagues face-to-face. Even though living in a new foreign city can be lonely, I’m fairly sure it would have been even more isolating to reside in a locked-down American city.

I’m also very fortunate to have spent the earlier lockdown period with my significant other. Having Lily by my side during this time made the whole experience much more manageable. It was a blessing to be able to go on nightly walks and cook together. When I felt down or isolated, her warm support was always the pickup I needed.

Returned to the tech industry, stepping into a new role as a manager and product leader

One of my career goals this year was to grow my skills in building high-performing product teams as a manager and coach. I’m very happy to have received the chance to do so at Xendit thanks to belief from my manager and leadership team.

I currently manage 5 product managers (PMs) in my Merchant Experience product group, which is responsible for reducing friction and creating new engaging hooks for our overall merchant base. My PM reports range from junior to senior levels of experience. I love what I do as a manager, helping each of my reports double down on their unique strengths and level up in terms of their impact on the product and business.

We shipped a lot together, such as Xendit’s first self-serve onboarding flow, third-party integration enhancements, new go-to-market (GTM) tools & processes, and foundational Data tools. We also started validating hypotheses for new products, defined more clear processes, and even helped one of my reports win support to build his own team.

Over the next year, I have plans to add at least 3 more PMs to my group and help the whole product organization scale faster and more smoothly during a high-growth period. At Dropbox, I was an individual contributor, mostly consuming what my leads communicated as the organizational strategy and process. At Xendit, I’m taking on new challenges as a product leader, driving the creation of some pieces of our product strategy, processes, and alignment with GTM teams. I’ve just started this next phase of my career journey, but I’m learning fast.

Expanded my tech career coaching service offerings, leading to a five-figure business

I’m proud of sustaining my US-based career coaching services throughout the year, still delivering as much value as I possibly can for my clients. While I’ve had to cut back on a few initiatives around content creation and 3rd-party coaching platforms due to my full-time job commitments, I’ve continued to coach for my private practice.

What surprised me was that even though I couldn’t make as much time for marketing as the past year, I received a still large flow of inbound inquiries from potential clients referred to me by previous clients, third-party sites, and LinkedIn. These new inbound inquiries have turned out to be the source of most of my current clients — the rest being returning clients.

Building my coaching business continues to be a source of energy and inspiration for me. I love being a part of my clients’ career journeys and seeing the meaningful difference that I can make for them. It’s also been a delight to be able to grow sales throughout the pandemic as well — and I aim to reinvest the proceeds to continue improving my products and services.

What were lowlights of my last year?

Feeling stressed as I navigated Singapore immigration during the height of the pandemic

After we left China in January, most ASEAN countries including Singapore had issued a Covid policy to block entry to any visitors who had visited China within the past 14 days. I had just booked a flight from Sydney to Singapore for 15 days after I left China for a few in-person interviews (several of which ironically got canceled or moved). I took my chances at the border and felt my heart stop when the immigration officer did a double take looking at my Chinese visa stamp and asked me for date of last entry. After I said “15 days ago”, it wasn’t until he called over another officer and got his second opinion, did he let me through the gate. My heart started beating again.

Later in March, I applied for an Employment Pass. Typically the process takes ~2-4 weeks, but I heard from other expat friends to expect a longer process during Covid times. It wasn’t until 4 months, 2 resubmissions, and 1 short-term visa extension later that I finally received my approval letter in the mail. During this springtime period (while Singapore was also in lockdown ), I had this anxiety-filled thought about getting deported from the country constantly lingering in the back of my mind, which was a huge distraction.

Feeling self-doubt and uncertainty about navigating my role in a new workplace

I started a new job at Xendit in March just as the pandemic kicked into high gear. I spent 1 week onboarding in our Jakarta HQ, but had to leave shortly afterward and still haven’t met face-to-face with most of my Indonesian colleagues.

The role that I started out with (operations) was significantly different in responsibilities than the one I’m doing now (product). While I was excited to try my hand at something new, the role never quite fit like glove and I constantly questioned myself if I was making the most use of my strengths. I spent the first month wrestling with idea of telling my manager that perhaps I was in the wrong seat on the rocket ship. I was scared that her response would be “take it or leave it”, which would have forced me to enter a complicated Singapore labor market due to a perfect storm of Covid-induced hiring freezes and not having a work visa (a blocker for anyone still hiring).

Thanks to Lily’s constant support and encouragement, I communicated my request anyway. Fortunately, my manager and the leadership team responded well to the idea of putting me back into a product capacity, given that I first proved myself through a 2-month testing period, which felt fair.

Fast forward to today, I’m much happier about my role and responsibilities building and growing the product org at Xendit, but there was a dark cloud hanging over my work life for a couple months.

Feeling disappointed that I didn’t build as much community, healthy habits, and creative habits as I desired to at the start of year

After settling into my new home, I intended to build a community, healthy habits for sleep and fitness, and creative habits for writing and building my coaching services.

During the past 9 months in Singapore, I’ve neglected to make as much progress in these areas as I would have liked. The reason why was partly in my control (prioritizing work > social life) and partly due to external factors (lockdown making it difficult to meet people).

• Community: Since I arrived in Singapore during the lockdown period and was still in my first 90 days, I chose to double down on my work instead of actively reaching out and cultivating my personal relationships. I still made a few good friends along the way, but I fell short of my expectations for the tight community I’d cultivate.
• Healthy habits: I recovered my weight from 150 to 160 lbs during Singapore’s lockdown (still down 25 lbs from 2 years back), which was the kick I needed to get a gym membership in July. I’ve maintained a relatively healthy diet and frequent gym habit (2-3x / week), but I aimed to achieve a lower body fat percentage (e.g. <10%). My sleep schedule has also been more inconsistent than I wanted.
• Creative habits: I was writing on a daily basis during my travels, but now feel lucky if I have enough time to quickly scribble down a review of my last week in my Notion journal.

Feeling stuck that I didn’t get to travel as much this year as I had originally planned

I didn’t leave Singapore from March to December — the longest duration I’ve spent in one city without traveling for as long as I can remember. This period is a noticeable contrast from even the first 2 months of the year where Lily and I were still bouncing to and from Cartagena, San Francisco, Shanghai, Sydney, Singapore, and Jakarta.

At the start of the pandemic, I was tired of constantly being on the move so I welcomed opportunity to stay put. However, by December, I grew antsy. One of the perks of working for an Indonesia-based startup was the opportunity to travel every 2 weeks or so between Singapore and Jakarta, but alas, I haven’t had the chance to fully take advantage of this perk just yet (crossing my fingers for 2021). I will certainly be one of the first people jumping on the next flight out of Singapore once a travel corridor opens up.

What did I learn?

Being ruthlessly disciplined about how I manage my time and energy

When I prowled the Singapore job market for new roles in January, I realized that I wanted to step back into a high-growth work environment. There were a few reasons:

• I was feeling well-rested coming off the tail end of my travel sabbatical and ready to work hard to quickly make a real dent on the business. I didn’t want a chill corporate environment.
• I wanted a real challenge — to be pushed to grow faster as a manager and leader. Even though I’m not a big sports guy, I try to view my career like a professional athlete. What would it take for me to grow and reach the top of my field? I felt that a high-growth startup would be the best place to find this type of challenge and motivate someone like me.
• I also wanted to put my new post-sabbatical mindset to the test. Did I actually become more resilient, adaptable, and creative or was I deluding myself? Would my refreshed mindset extend to my work life?

The great news is that I’ve noticed shift in how I used my knowledge about myself to manage my psychology, draw better boundaries, and create positive feedback loops to use my time and energy more wisely than previously.

For example, I’ve observed in the past that I perform much better during the day after I’ve already physically moved in the morning. So I started doing morning cycling and gym sessions to kickstart my day with a full tank of energy. In another instance, I learned that I’m much less effective if I don’t mentally compartmentalize my work, so I blocked out Saturday entirely as a personal day to recharge, e.g. date night with Lily, meeting friends, and tending to my veggie patch.

Despite having higher expectations and more workload than ever before, I’ve still made progress by optimizing how I leverage my time and energy instead of simply “grinding it out” at all costs.

Building and coaching high-performance teams

Over the past few months, I’ve focused a large chunk of my time on coaching my PMs and building my product teams.

What I’ve learned to be the most effective on-the-job coaching tools with my direct reports so far have been 1) Best practice emulation 2) critical thinking questions and 3) just-in-time feedback:

1. Best practice emulation: When I worked with my PMs to train them on a new skill (e.g. cross-team projects), it wasn’t enough to verbally communicate the expectation because they still couldn’t model the expectation. They learned much more rapidly when they could first watch me (or another senior PM) take lead and show examples of real output, explaining why I was making certain choices. Then once they had a clear mental model of the expectation, I’d hand-over the meetings and docs to them to drive while still checking in on their progress towards milestones.
2. Critical thinking questions: After my PMs started getting the hang of a skill, I’d ask them more “why”-type of questions to assess if they could understood the reasons behind what they’re doing, not just performing rote tasks. I ran this exercise a lot during our 1:1s so they could practice guiding me through how they connect the dots more convincingly. Sometimes they’d also share great reasons that I didn’t think of, which goes to show that I’m still a work-in-progress as well!
3. Just-in-time-feedback: When I noticed an opportunity to improve performance with feedback (e.g. delivering presentations), I started providing it immediately instead of a week later because the clearer context enabled PMs to respond immediately Often times when I saved feedback for our monthly feedback-oriented 1:1, my PM needed to really mine his/her brain for the context. For my PMs who were really hungry to learn, this immediacy gave them fuel to grow quickly.

These tools are just the tip of the iceberg, and I’m eager to further develop my coaching toolkit.

I’ve also started exercising my organizational muscles by spearheading strategy and structure to provide clear direction for my product group, spinning up new teams to fill certain gaps in our strategy, and building cross-company processes to improve how various functions operate together.

Accepting that friendships and community take time to build

One of my chief aims after arriving in Singapore was building my social circle. While I’ve made a couple of good friends, I still feel a general sense of lack of community.

Part of the issue was a Covid-triggered lockdown made it difficult to meet new people face-to-face. Another part of the issue was that my intense work schedule made it challenging to carve out a lot of time for making new friends.

The biggest learning for me though was accepting that I connect well with people who are values-driven, nerdy, and fairly independent thinkers. The reality is that these type of people are hard to come by anywhere, let alone Singapore. Even though I’m meeting friends through friends of friends, colleagues, product circles, and online groups like Lunchclub, I realized I need to have a bit more patience to find and/or build my community.

Navigating expat life, including immigration, finances, and taxation

Living as an expat, as an particular American expat, can get complicated. Earlier I mentioned the challenges of getting my work visa approved. In addition to the immigration piece, managing my personal finances (e.g. which country’s bank accounts should I keep my paycheck?) and taxation (e.g. what type of taxes are an American expat liable for?) are also complex.

For the tax piece, in previous years I’ve always handled my own US federal and state taxes. However, 2021 will be the first year in my life that I’m recruiting a professional to help me file my American taxes to avoid making any rookie mistakes as an expat.

Exploring various hobbies like reading non-fiction and urban farming

Lily has called me an “old soul” given my passion for books, whiskey, and nature.

Over the past year, I finished reading 11 books (compared to 26 books in 2019) that spanned topics like management, product, psychology, and history. A few of my favorites were:

• Peak: Secrets from the New Science of Expertise by Anders Ericsson
• How Asia Works by Joe Studwell
• High Output Management by Andy Grove
• What Customers Want by Andrew Ulwick
• No Rules Rules by Reed Hastings

Business books contained practical lessons that I could apply immediately to the workplace. Other books helped me further my broader understanding of humans and our societies.

Aside from reading, I’m very proud to have grown and harvested my first batch of vegetables this year including kang kong, dwaf bok choy, red byam spinach, and siam queen basil. This was a hobby I wanted to try out for a long time and finally did. Lily and I cooked dinner using my first harvest, which felt satisfying (as well as tasty!).

What am I looking forward to this year?

Sustaining and cultivating my closest community

Relationships take time and I want to make sure I’m proactively putting a generous heaping of time into the right relationships. With Lily, this means scheduling weekly date nights and planning fun novel activities to do with each other to keep the spark alive. With friends in Singapore, this means organizing small social dinners and events as a host to form tighter bonds. With friends and family back home, this means scheduling weekly or monthly catch-up calls.

Hitting milestones related to long-term financial freedom

Lily and I both care about achieving enough financial stability, so that we can make career and life choices that are 100% independent from our finances. This year will likely be focused on expanding our income streams and diversification. There’s still a long road for us to go, but we’re headed in the right direction and it’s exciting to go on this journey with my partner.

Learning to grow my product teams and tackle more complex challenges for the company

Over the next year, I’ll be growing my team in size and scope to solve a breadth of problems related to growth, scaling, and product-market fit expansion. I’ll also be working closely with our leadership team to set clear direction for navigating our markets. I’m excited to learn fast and hard on how I can create more leverage on my time, energy, and knowledge to achieve my desired outcomes along this journey.

Finding hobbies and physical activities that stick

I enjoy experimenting with varied hobbies, but I’d love to find a couple that really stick throughout the year. What I’ve discovered is that I love doing physical activities and/or being outdoors when I’m not working, so my hobbies need to have me moving my body. The other criteria I have for my hobbies is I’d like to do them to also meet new social circles. I’ll likely test the waters with cycling, rock climbing, and basketball next year.