A year ago, on Jan 1st, 2020, we were just out of Antarctica, finishing an unforgettable family trip. Little did we know, back then, that 2020 would unfold as the year of the Pandemic. What I did know, however, was that my professional future was in jeopardy. The nature of my job changed overnight since the summer of 2019. While I stayed, for the time being, to keep the team together, I could not see a path to a sustainable future.

Antarctica is tranquil and magnificent, a perfect place to have an inner dialogue. On the cruise, I happened to listen to David Brook’s “The Second Mountain.” The title resonated with me deeply. Hearing stories of people whose work genuinely touched others’ lives, I knew that my work paled in comparison in meaning. While my first mountain was in limbo, there was an even deeper question of where the first mountain would lead to. I felt that even if I somehow managed to reach the top of the first mountain, something would still be amiss.

That was my state of mind at the start of the year. Fast forward a year later, I am proud to announce that my first mountain is back on track. And I have found a new sense of direction as my second mountain starts to materialize as a lofty 10-year goal. 2020 ended up being one of the most fulfilling years of my life. But how did that happen?

I realized that while my transformation was well underway at the start of 2020, reading books, being mindful, or even building habits could only get me so far. To ensure lasting changes, sometimes, we have to take the leap and emerge ourselves in completely new experiences. In 2020, I had four such experiences that led to where I am today.

Developing V8-RISCV

In January 2020, we were asked to port V8, the popular JavaScript engine, to RISC-V. There was much uncertainty regarding how long the project would last and what impact it would generate internally. While some teams started half-heartedly, I saw a short window of opportunity to establish a space in an up-and-coming ecosystem, so we moved swiftly.

With minimal resources, we had to be extremely careful in the execution of the project. Instead of plunging right in, we focused first on figuring out the best approach to minimize the development time. Throughout the project's execution, we applied the same disciplined approach to analyzing the situation first and then developing. While the course we took was not obvious at the time, in hindsight, those design decisions proved to save months of development efforts and probably the project too.

One of the potential risks had always been resources. If we lost one more team member before open-sourcing, the team was so small that the project would not have sustained. So I decided to join in the development (despite not having coded in the last couple of years), starting from writing tests, doing code reviews, developing features, and debugging issues. By focusing on improving my development skills, I was as good a C++ developer as anyone else in two months. We did lose a team member along the way, but our tiny team sustained the loss, open-sourced in July, and ready to upstream to V8 at this moment. V8-RISCV became the first, and only production-level JIT enabled on RISC-V to date.

V8-RISCV was a personal triumph at a critical time. It was one of the smallest projects I have ever managed but one managed with great clarity. It was the first application of my newly developed system of disciplined decision-making in a project context. It was the project where I re-experienced deep work and regained my development skills. Not only did I find myself pretty good at it, but I also really enjoyed doing so (IMO, coding is one of the easiest ways to reach flow states, the optimal experience). Unbeknownst to me at the time, V8-RISCV laid the path for my transition to the new job as a senior IC later that year.

In 2020, I found standing on my own and trusting my ability to learn quickly to be a recurring theme in all my new experiences. For those who have “moved up” the corporate ladder, I knew first hand that much of the insecurity of mid-career stems from the worry of being hallowed out of marketable practical skills. It turns out that if we master the fundamental skill of learning how to learn and have the mental toughness to practice deliberately, we can re-learn any practical skills quickly.

Changing the job

In mid-February, another team member decided to leave. It had happened a few times in the past few months, but this one was dear to my heart. I cannot delay the decision any further — to leave or not to leave?

The decision may be a no brainer for an outsider. But, for me, I just felt really uneasy about facing the uncertainty of job searching. This is not uncommon among mid-career people, where the discomfort of uncertainty often keeps one at the same place for a very long time. To break the indecision, I wrote down my thought process and slept on it until I was absolutely OK with the decision to leave regardless of how my job search would turn out.

Once the decision was made, it brought clarity to set me off on a path of action. Interviewing at mid-career could feel especially vulnerable (which I will describe in detail in a series of posts). But in essence, I treated the job search as a project and applied the same disciplined approach as in V8-RISCV. Instead of getting over the job search as soon as possible, I realized that the uncomfortable place is exactly where we should stay to learn the most out of it. So I took the time to prepare for the interview, experimented with different learning methods, went deep into my whys, and explored all the emotions stirred up by this vulnerable process. The “project” lasted 6 months (from the day the recruiter reached out to me to the day I started at the company). One can learn so much from such an experience — most notably on decision making, effective learning, emotional management, and self-understanding — I would recommend anyone to go through it as an enriching (albeit uncomfortable) learning experience. It is fair to say that the person who showed up at the company orientation in November was a much stronger candidate than the one being contacted by the recruiter six months earlier.

Starting Pen{g}sieve

While finding the new job put my first mountain back on track, I felt that the real transformation happened in my finding the direction to the second mountain.

Defining my second mountain is really about figuring out what kind of work is most meaningful to me. I have long concluded that being successful but lonely is not a good life, not to say that “success” could evaporate overnight when one changes jobs or retires. It becomes clear to me that fulfillment has to come from within and meaning has to come from caring beyond oneself. I increasingly feel that my second mountain has to do with connecting with people in a meaningful way and helping lift others in whichever way, large or small.

To get started, I figured that sharing my thoughts in long-form writing would make others know me better, a necessary step towards building meaningful connections. I sat on that idea for a long time, never feeling quite ready to start a blog.

The inflection point came when I decided to take an online course on digital notes-taking, called Building a Second Brain (BASB). It is hard to explain why a note-taking course could be transformative. Perhaps it is because life is formed as fractals, so pearls of wisdom can be found everywhere if one drills deep enough. I am grateful that I met BASB at the right time. It exposed me to a community of people that I had not crossed paths with before (e.g., writers, bloggers, (small) influencers), helped me overcome the psychological barrier of becoming a content producer, and gave me the necessary tools to start writing. Pen{g}sieve was the final course project for BASB.

The experience of writing Pen{g}sieve was totally transformative. Writing added a rich new layer to my life as an engineer. I understood that art is about self-expression, and sharing is an innate human desire. Nowadays, I have so much more to offer — when the knowledge or wisdom is inside you, it flows out naturally. My conversations with people became a lot more meaningful and a lot less superficial or transactional because they knew me at a deeper level through Pen{g}sieve.

Starting Pen{g}sieve also taught me how to face my vulnerabilities. To share or not to share had been a constant struggle for me. Believe it or not, one of my bravest acts last year was sharing one of my posts on LinkedIn. While sharing true thoughts in one’s professional circle felt really exposed, I also know first hand that the best way to connect is to share from a place of vulnerability and authenticity.

“Staying vulnerable is a risk we have to take if we want to experience connection.”
— Brené Brown

Learning to be a health coach

Perhaps the most surprising experience of 2020 is joining a group of part-time entrepreneurs to learn to become a health coach. My decision was as surprising to me as to anyone who knew me.

One of the main motivations for taking the opportunity was because I saw a connection between coaching (in whichever form) and my second mountain. I have just defined the goal of transitioning from a high-tech career to a more people-oriented high-touch career in ten years without having any clue how. I can’t help but marvel at the power of the law of attraction. This side hustle is a perfect opportunity for me to learn the essential skills of service, sales, marketing, and interpersonal skills needed for my future “high-touch” career.

Mingling with people from a very different background is mind-opening. Having worked in large corporations throughout my professional career, I marveled at how a team of loosely franchised part-time owners was cultivated and saw examples of true leadership without titles. I met with people whose work was aligned with their values (Yes, they found their second mountains). I have learned to interact with people without being judgmental because, as a coach, you are supposed to meet people where they are, not where you are. I saw myself sending warm check-ins and small gestures of kindness to friends and even helped a couple of friends/relatives with their health issues. More importantly, I saw myself working on something that I did not believe I could do but showed up to do it anyway.

How do changes happen?

“First private victories, then public victories”
— by Steven Covey, The seven habits of highly effective people

Most lasting changes eventually have to take place in the public sphere. As my state of mind, at the beginning of 2020 showed, no matter how mindful I was, I could not stay in the same job of uncertainty and find inner peace. At some point, we have to leap.

The trigger for leaping is decision-making, which is the process of deciding when to change course, whether to take a risk, or whether you are staring at an opportunity in disguise. So let’s talk about decision making.

Among all triggering decisions to my 2020 experiences, the decision to change the job is the only high-stake one. In this case, the barrier was my fear of not finding a remote position that fit my specialized skillset and my caliber. Whenever I thought about interviewing, I felt a butterfly in the stomach — my gut was literally telling me to stay. This was when I realized that I needed a methodology for decision making. I eventually figured out that I should separate the decision of leaving this job from figuring out how to find the new one. I wrote down my top reasons for leaving:

I am still able to learn, but it is despite this job not because of this job;
I am staying for the wrong reason, i.e., fear of facing job search;
After receiving so many strong signals of the job’s uncertainty, inaction is plainly irrational.

When I stared at my list above, I could not help but make the decision I made.

The same disciplined process played out in the other two triggering decisions. On deciding whether to take the BASB course, the psychological barrier was the price tag. My old self would have immediately dismissed paying $1500 for an online course, but the new self reasoned that, since I could afford it if the course could give me a new experience and teach me a new essential skill, I was willing to take the risk.

On deciding to be a health coach, my old self would have dismissed it because I did not have the time or skill. But upon listening to the information, my new self followed the same methodology of decision-making. I reasoned that the potential of finding a good resource (products, knowledge, and support network) to boost the health of my family, having a completely new experience, and acquiring new skills that are essential for the pursuit of my second mountain far outweighed the cost of a couple of hundred dollars. Looking at my logic, I could not find any reason not to give it a try. Even if I did make the wrong call, the mistake would be a perfect opportunity to re-calibrate my decision-making process — What did I miss? Did I get the wrong information? Was my information incomplete? Were there flaws or gaps in my reasoning? When one applies disciplined decision-making, risks are a lot more manageable, and even a wrong decision can serve its purpose as a learning opportunity.

Looking at the four triggering decisions of 2020, I realized that changing the job was the only decision in plain sight. The other three were all “un-glorified” decisions that were easily dismissed or overlooked.

The decision to join the development of V8-RISCV was so implicit that it felt like doing the right thing at the moment. But that experience laid the foundation for my easy transitioning to my new job role.

The decision to take BASB and learn to be a health coach set off my pursuit of the second mountain. While its lasting effect may not materialize for many years, I already feel a new sense of purpose. People around me felt my changes too — being kinder, more resourceful, and perhaps a bit wiser.

I believe that my second mountain not only ultimately defines who I am; it also gives me a slight edge in the pursuit of my first mountain. For instance, the seed of practicing the beginner’s mind at work was sowed from my learning to become a health coach. At work, I used the same writing skills to share my technical ideas in the long-form, which helped me jump start connections in a new remote workplace. And I suspected that being warm, open-minded, and clear-headed would make my colleagues a little bit more drawn towards me, just as many of my friends did.

To conclude this year-end summary, I found the following quote capture the essence of my 2020 experiences:

“Leap, and the net will appear.”
― by Julia Cameron, The Artist's Way: A Spiritual Path to Higher Creativity

In 2020, I leaped and fully embraced new experiences. It felt fantastic!

Pen{g}sieve Vol 6: 2020 I learned to embrace…

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