In my last annual review, I declared my intended theme for 2021 to be leverage:
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.
While 2020 was intense, doubling down on my commitments in 2021 pushed me to my limits in new ways. My honest reflection is that while I didn’t accomplish all that I set out to do, I still took away meaningful lessons.
At the beginning of the year, I was planning to move apartments with Lily, expand my community in Singapore, grow my product teams, launch new products, increase my coaching revenue, and find new hobbies that stick. By December, while I checked off some items, for others I struggled to make “good enough” progress. I had to confront the reality that I hit bottleneck with my time.
Determined to crank up my leverage, I tried various methods to scale up my output for my day job and creative projects. However, as much I wish I could report that I found a game-changing secret to scaling my time, I felt that I came up short. A humbling experience.
What I realized is that I struggled to navigate the explore-exploit trade-off this past year. I heavily invested in exploiting my existing opportunities, so I didn’t have much time to explore greener pastures. And when I did explore, it felt a bit too random and aimless. As a result, I felt like I hit a local maximum in my day job, side projects, and relationships.
That’s why in 2022, my theme is going to be creativity.
What creativity means to me is shifting back to an exploration mode — but with intention. I want to spend a higher proportion of my time on purposefully testing new ideas. By doing so, I believe I can move faster towards fulfilling my life-long vision of building enduring businesses that make lives better, achieving financial freedom, and cultivating community.
What were highlights of my last year?
Strengthened my relationship and Singapore community in spite of the pandemic
Growing up as an only child, I can recall numerous lonely moments when my parents needed to work overtime and I would heat my leftovers for dinner by myself. As perhaps an overreaction to this childhood trauma, I resolved I wouldn’t ever be “absent” for loved ones.
This past year, I feel like I honored this promise. I’m proud of how much Lily and I grew together. Despite Singapore’s sporadic lockdowns, we would consistently go on weekly date nights. We crossed life milestones like moving from our small, dingy Chinatown furnished apartment to a spacious, modern Rob Quay unfurnished condo (note to self: moving is a full-time job). We even helped Lily go from (f)unemployment to securing a well-paid tech role.
Additionally, I’m grateful that I’ve gotten to know amazing friends in Singapore. From brunches to board game nights to a Thanksgiving feast, we jumped on the chance to hang out whenever Singapore lifted its socially-prohibitive lockdowns. Good conversations and company are key ingredients to my happiness. Certainly this past year, they’ve definitely helped me feel more seen, grounded, and reenergized about life whenever I felt stuck.
Increased the resiliency of my mind and body
This past year, stressors came from all directions, but I never burned out thanks to the lessons I’ve learned over the year about my mental and physical health.
For my mental health, I practiced the same morning routine since 2018: taking a brisk 20 minute bike ride or walk before I start working. I’ve found that physical movement through a stimulating scenery delivers a feel-good chemical payload to my brain that helps me start the day with mental clarity. During work hours, I’ve also created more focus by blocking out maker time on several days of the week.
For my physical health, sleep was the biggest change I could make to increase my energy. Since I was 11 and staying up until 3 am playing Runescape, I can recall struggling with getting enough quality sleep. While I’m still far from perfect, I’ve improved after starting to track my sleep using an Oura ring (birthday gift). Seeing the numbers helped motivate me enough to be more disciplined about sleep, extending my total time slept by ~30 minutes per night.
Finally, finding new fitness activities also helped my energy levels. Since I couldn’t surf or dive, I took up bouldering instead, which I’ve found fun, a mental break, and physically rewarding.
Built product teams & shipped new products at a growth-stage startup
When I took my new job with Xendit, I wanted to gain 3 new career experiences: building product teams, launching new products, and working in our local markets (Indonesia & Philippines). While I couldn’t fulfill the 3rd experience due to Covid, I fulfilled the first two experiences.
I’ve built my product group from 3 PMs to now 11 staff (8 PMs, 2 APMs, 1 Product Operations). I’ve worked closely with cross-org partners to grow an entire business line. My teams have shipped several new tools for our SME merchants: Merchant Mobile App, Online Store (like a mini-Shopify), and Multi-Channel Sync. Some have gained solid traction.
It’s the first time a leadership team entrusted me with so much responsibility, so I feel grateful for the experiences. No matter the outcome, I feel like I’ve grown the breadth and versatility of my product, growth, and management skillset.
Continued coaching clients to tech job offers, got invited to be an industry speaker, and made my first angel investment
Outside of my day job, I continued coaching clients on getting job offers from companies like Google and Nubank up until July, when I paused accepting new clients due to capacity.
This past year also marks the first time I’ve been asked by startups to do fireside chats (3 product AMAs & talks for APAC startups), made my first angel investment (wrote a check to a LATAM edtech startup), and received positive feedback on my product content on Linkedin.
The above are small wins, but I can see the potential for these items to snowball into something much larger (e.g. helping more startups in emerging markets build great products and businesses).
Learned enough about crypto/NFTs to develop a keen interest and read 9 books
While I was already invested in a variety of tokens, it wasn’t until July after Lily shared her enthusiasm of a few NFT projects that I started taking NFTs more seriously.
That moment spurred me to read about the new financial models and tech underpinning the space. I also set aside some money to experiment with NFTs & DeFi, which led to mostly a lot of learning. What I’ve found most personally exciting is the business model innovation — i.e. the opportunity to help creators and entrepreneurs to monetize their creative output (music, writing, art) more easily than ever before.
Aside from exploring crypto, I still kept up my reading habit. This past year, I read 9 books across business, culture, and history (vs 11 books in 2020). My favorites included:
- The Culture Map by Erin Meyer
- In the Dragon’s Shadow: Southeast Asia in the Chinese Century by Sebastian Strangio
- How to Change Your Mind by Michael Pollan
- No Filter: The Inside Story of Instagram by Sarah Firer
What were lowlights of my last year?
Experienced intense ups and downs in my day job as a product & business lead
As a product lead and manager for the past 2 years, I’d say the biggest chunks of my time have gone to: 1) recruiting/hiring 2) coaching 3) managing interpersonal & performance issues 4) setting direction and 5) communicating & coordinating with other teams
While I’ve learned that I generally enjoy hiring and coaching duties, managing relationship dynamics, performance issues, and cross-org communication have felt like necessary evils that come with the managerial territory. Half the battle for people-related concerns has been asking the right questions and reading in between the lines of stakeholder feedback to get to the heart of the matter.
As a business lead for our customer growth goals, I discovered multiple obstacles to our success, which require the action of different teams across the organization. As a result, I spent a lot of time wrangling cross-functional partners to move faster towards these goals but faced organizational inertia along the way, which felt draining.
Building new products for emerging markets was humbling
A few of my product teams build 0-to-1 products for Indonesia & Philippines and are measured based on real customer validation, traction, and growth.
Racing to product-market fit in a developed market is already a hard problem. It feels akin to guiding a trekking expedition towards the summit. Operating in emerging markets is doubly hard because you have to consider other constraints like low tech savviness, price sensitivity, high fraud, and predominantly offline behavior. Needless to say, facing these challenges head-on has been a tough but humbling learning experience.
Achieved less creative output than I desired
Despite feeling resilient, I felt fear of failure continually linger in the back of my mind due to bigger bets I took in my day job. This fear impacted the mental space I needed to be creative, which slowed down my side projects.
For example, starting in July, I made a conscious effort to step away from 1:1 career coaching so that I could produce more scalable content instead. However, I’d sit at my laptop on Sunday mornings trying to squeeze a blog post out from my brain while feeling quite unmotivated after the intense weekdays. In another instance, I started making a few NFT trades and got sucked into their volatile movements, which distracted me from my creative work.
Fell short on my goals for living in Southeast Asia in the first place
When Lily and I first moved to Singapore in March 2020, one of my main personal goals was to use Singapore as a home base for traveling around the Southeast Asia region.
However, lately I’ve felt disappointed and a bit anxious that I couldn’t achieve this goal — due to factors outside of my control (ie strict pandemic-induced border control policies). I’ve felt cooped up on the island. Singapore is a gorgeous urban metropolis, but it also feels small, hot and humid, and lacking in nature. I’ve missed outdoor activities like surfing and hiking, which are hard to do in Singapore but so easy to access after a 1 hour flight to Indonesia or Vietnam.
Set overly ambitious targets for myself on the health and fitness front
Even though I’m happy with my improved sleep and fitness habits this past year, I initially set too high of targets (sleep before 11:30pm; achieve <10% body fat). I believe that if I were working a less intensive day job and had more headspace, I could have hit these targets. However, given my circumstances, I should have refined my expectations to be more realistic and motivational. On a related note, I also picked up a weekday wine habit, which while very enjoyable didn’t help me progress towards these ambitious goals.
What did I learn?
Focus on the right priorities (not work harder) to unlock more managerial output
I’ve learned that working harder on the wrong priorities inevitably feels like wasted time, which was frustrating. Instead, when I got the priorities right, execution seemed to fall into place quickly.
To set the right product priorities, I’ve learned that it’s valuable for my product teams to not just ship features, but optimize for speed of customer learning. Tactics might include narrowing the target customer definition, spending time in communities (especially if they’re not our existing customers), and aiming for 10 super-happy customers.
To align with peers faster, the biggest lever I used was soliciting 1:1 feedback from peers immediately after meetings. Collecting feedback using this method is more time-consuming than group sessions. However, in a Southeast Asia work context, 1:1’s have brought out a lot more honest opinions about what’s working/not working and needs to be actioned.
For levers outside of my direct influence, I’ve learned that it’s more practical to reduce my time spent unless if there’s sufficient alignment to execute. Otherwise, my time is more effectively spent on helping my teams succeed and letting their success influence the priorities of other teams.
Delegate and block out deep work on your calendar to scale yourself
When I first started managing, I liked to get my hands dirty in execution but it’s no longer scalable (and worse, comes off as micromanage-y). For new projects, I’ve learned it’s nearly always more effective for my staff spearhead the project execution, not me. My staff learn much faster; plus, 95% of the time they deliver high-quality output. I’m also freed up to think more long-term.
I also faced the problem of being overwhelmed by constant Slack/communication and last-minute meetings — which prevented me from getting my real work done. As a solution, I started blocking out 1-2 hours / day of deep work time on my calendar to finish 1 high-priority item. As long as I can finish my top priority during this committed time, then I’m happy and don’t need to worry about the rest of my chaotic schedule.
In 2022, I’m excited to continue scaling myself at my day job so that I can spend time on fresh challenges related to new products, platform development, and GTM/product marketing.
Work remotely to alleviate feelings of being stuck in one place
My environmental context is very important to my motivation and overall energy levels. While Singapore was a comfortable home base, I often asked myself, “why haven’t I left Singapore?”
At the beginning of the year, I had reasonable answers (Lily needed a visa, we both were waiting for our vaccines). However by August, I started running out of justifications. I would constantly feel anxiety over when travel lanes would finally open up. Interestingly enough, after working remotely from the US — especially Hawaii — in December these negative feelings mostly vanished. I suspect my mind and body just needed a change of scenery.
This year, I’d like to work remotely from places like Hawaii & Australia for a few months could help me feel like I’m fulfilling my sense of freedom and adventure.
Carve out dedicated creative time to feel more fulfilled
As mentioned in the lowlights, I neglected my creativity a bit in 2021, which led me to feeling less fulfilled with my self-expression and impact I wanted to have on the world. I’ve learned that I can feel more creative if I regularly schedule 60-120 minute blocks of uninterrupted time where I have no goal except to experiment and go down new rabbit holes.
Use daily/weekly habits (not goals) to expedite your health & creative projects
I originally learned this lesson in 2018, but I re-learned it this past year. One thing I consistently observe about myself is I make bigger leaps in my health & creative projects when I can build momentum around a daily habit instead of striving for a far-off goal.
For example, what works well for me are daily habits like meditate for 1 minute, do 1 push up, write 1 word in my journal, etc. Keeping the barrier to entry low motivates me to stick with the habit, since the tasks rarely feels like a hassle. Over time, I end up hitting higher and higher outputs anyway — eventually breaking my previous records.
One of my biggest intentions for 2022 is to continue dreaming up big visions for my health and creativity but measuring progress through daily/weekly habits instead.
Build shared finance systems (e.g. joint accounts) as a couple to achieve financial freedom faster
In 2021, Lily and I began tracking our personal finances together. We’d have a discussion every 1-2 months about how we were tracking towards specific savings goals but would run into conflicts on how we’re tracking expenses and planning future finances.
That’s why I’m excited for us to clarify our joint money lens this year so that we can build automated financial systems (e.g. replace Splitwise) that help us move faster towards our travel, health, and business goals.
Use novel shared experiences with friends to create unforgettable memories
For the past two years, I’ve missed my favorite ways to create cherished memories with friends and loved ones: travel, half-marathons, outdoor/adventure sports (e.g. diving), novel activities (e.g. meditation retreat), and concerts & shows.
This year, instead of just engaging friends over dinners, I intend to create deeper connection and memories by suggesting fresh activities that we can do together.
Simon T says
Great year in review – really appreciate the transparency about both the positives and negatives!
Your yearly themes reminded me of theme journaling. Cool, possibly valuable example of this here: https://youtu.be/fSwpe8r50_o?t=269
Woah that journal is neat. I don’t do the Ideal Outcomes bit, but I can see why it’s there. Thanks for your support and sharing that video Simon!