Hi, I’m Jeffrey. I graduated from MIT in 2019 and was on the early teams of Scale AI and Gather.Town. I spent over 20 years going through the motions of what was expected of me and working towards goals other people set. I’m fully aware that when we lack conviction in our career, relationship, or life directions, we lose motivation, experience perpetually low mood, and get overwhelmed.
Unfortunately, this rut can be hard to escape. Most people construct narratives to justify their unfulfilling life directions. This complacency kicks the can down the road by temporarily delaying future existential crises and anxiety.
It wasn't until I began looking inwards that I gained the conviction to explore my true interests and take my life in entirely different directions: as a hip-hop dancer, an early employee at a multi-billion dollar startup, and a co-founder of a company. I’d like to share my story as I learned to incrementally explore my values and experienced the fulfillment that comes with living according to them. Learning to follow my inner compass helped me make multiple consequential life decisions with clarity and conviction, including twice deciding to step away from tens of millions of dollars.
The sections below are organized by into distinct stages in my conviction journey. If you currently resonate with a section below, my work is definitely meant for you.
I had no internal convictions at the start.
Like many, I grew up wholly focused on adhering to societal expectations, and was rewarded for doing so. I buried my intrinsic desires and curiosity to chase “success.”
Public High School
My primary value was to follow the consensus playbook of success in my community: get good grades, take lots of advanced classes, pursue a handful of extracurricular activities with the goal of standing out for college applications, apply to US News Week’s top universities and hope to get in.
Instead of real, internal passion, my only goal was achieving validation and admiration from my family, friends, and community, and getting into a top college was the only prescribed way to do so. As a result, all of my responses to the college application essay prompts designed to glean a bit of what made me a unique individual were manufactured to sound passionate but devoid of real passion.
Writing those essays, I felt like a fraud and wished I had instead led an interesting life made up of decisions made from personal conviction, but recognized that doing so probably would have hurt my chances at getting into a prestigious university, especially as a public school student with no generational wealth or family legacy at any university.
First two years at MIT + Snapchat (2 years)
Entering MIT, I knew what the consensus playbook of success expected: select a major with high-paying career prospects, get good grades, get top internships or research positions, go to a prestigious graduate school, and then go work for decades at a prestigious household-name company, demonstrating company loyalty and gradually climbing through the ranks to retire as a senior-level director or equivalent.
However, being at MIT quickly exposed me to a number of prestigious career paths that I had never been exposed to growing up in tech-heavy Seattle. I learned about banking, trading and more on Wall St., about Management Consulting, about Product Management, and more. I didn’t know what path to take, so I chose a major that would leave the greatest number of prestigious career paths open: Computer Science.
Once again, I didn’t pick my major from a place of intrinsic desire or passion – had I done that, I likely would have pursued Mechanical Engineering or Architecture, as I enjoyed the mechanics side of physics and had an inkling that I would appreciate building tangible products that would impact people’s lives.
My first year was wholly focused on getting an internship at a name brand company – I grinded Leetcode and relentlessly networked on LinkedIn and through acquaintances until I landed a software engineering internship at pre-IPO Snapchat. The work itself was not particularly fulfilling (working on an API for programmatically buying ads within Snapchat), but it was an engineering role at a name brand company – a taste of the promised land that the consensus playbook said would win me the utmost validation and admiration from my family, friends, and community. And that validation did come, and it was a pleasant sensation for a while. But it didn’t last, and I entered my Sophomore year reflecting on that experience and realizing I didn’t feel that personally fulfilled from the work. Maybe it was the nature of the work itself, or maybe I just didn’t produce enough impact to feel like I mattered.
My second year was wholly focused on getting an internship on a specific team I felt interesting, once again at a name brand company. I felt personally intrigued by quant trading and by computer vision, and dedicated my year to taking classes and preparing for interviews for roles in these two areas. In the end, I was fortunate to land a computer vision research internship meant for PhD students, coincidentally once again at Snapchat. This was me pursuing a direction based on my intrinsic desire and passion, albeit still in a way that was compatible with the consensus playbook. The work was definitely more personally exciting than my first internship, but I gained even more nuanced understanding of my values for work: I didn’t like the pace of research, nor did I find much fulfillment from developing a particularly elegant solution to a software problem. What I did enjoy was sitting on the intersection of product and engineering, with the ability to wear both hats and choose what to build and how to build it based on direct conversations with target customers. I was able to experience this while building out a prototype for a standalone computer vision feature, and knew that it felt fulfilling to me. And maybe I always knew this inside even though I hadn’t explicitly articulated it, because the same intuition likely drove me to want to study Mechanical Engineering or Architecture.
I tried listening to my inner wants for the first time.
My first step towards following my inner compass came after I first felt disillusioned, and gave myself permission to adhere to my intrinsic desires instead.
Third and last year at MIT
My third year started off with low motivation. I had finished most of the four year Computer Science degree in my first two years as part of my quest to quickly land name brand internships, so there were no more prescribed courses I had to take. In addition, I struggled to identify any one prestigious career path that neatly captured my newfound desire to sit on the intersection of product and engineering. Product Management felt too isolated from the development of the product, while Engineering felt too isolated from the direction of the product. I fell into a bit of a rut and didn’t apply to any internships that fall, only fielding interviews when peers referred me to their companies or when companies reached out after seeing my experience on LinkedIn. It was quite a low point in my motivation, as I also didn’t know what classes to take that would bring me closer to a prestigious career path that satisfied my desire to sit at the intersection of product and engineering. Instead, I turned my focus towards new non-academic activities (such as joining a competitive hip hop dance team and getting sucked into K-Pop fandoms) that I had always been interested in but never pursued before college since they didn’t feel optimized for college admissions. This was my first clear departure from the consensus playbook for success, but I was learning to live for myself and adding unique texture to my life that felt genuine to my intrinsic desires.
I started diagnosing my dissatisfaction with my inner values.
My second step towards following my inner compass resulted from realizing my burnout and low motivation stemmed from a newly-emerging value of mine not being catered towards.
Scale AI (2 years)
The end of my college experience was sudden – a friend reached out about an opportunity at Scale AI, a fast-growing startup labeling data for enterprise ML teams, valued at $90M at the time. The company was looking to hire a generalist with strong product and engineering skills to build out a new team, and my friend referred me. This felt like such a uniquely perfect opportunity that once I got the job offer two months before the end of the school year, I immediately signed and notified my family, friends, and university that I would be graduating early at the end of the semester. My family, friends, and university advisor were all shocked and asked me to reconsider, but I had such strong conviction that this opportunity was one I had to pursue to stay true to the one career value I had gleaned about myself: a desire to sit at the intersection of product and engineering.
During my time at Scale, I was extremely motivated because I had been given outsized opportunity as a 21 year old new grad. I was asked to start a new team critical to Scale’s mission of becoming a generational titan in AI and ML, and take it from concept to product-market-fit. After successfully completing my mandate in 1.5 years, I had proven to myself that I was capable of creating real business impact while sitting at the intersection of product and engineering, and also grew more confident that when I optimize for intrinsic values, my motivation is lasting and rewarding.
However, I also realized that sitting at the intersection of product and engineering wasn’t my only value. I was feeling burnt out, and a large part of it came from the fact that I wasn’t at all motivated by the impact of my work: making the lives of ML Engineers at large enterprise tech companies easier. Once I had completed my mandate with the new team I was brought in to start, I decided to leave Scale AI.
This was a difficult decision that took over a month of contemplation, discussions and negotiations. I discussed my burnout with managers, coworkers and peers. I took extended paid time off to get away from the daily whirlwind of Scale and think more clearly about my values:
- Of the values I’d identified, which were being met at Scale?
- What new values was I being exposed to, and would I able to explore them deeper at Scale?
I returned confident that I needed a change, and luckily my managers were eager to help me explore new opportunities within the company across a number of different roles, responsibilities and teams. However, deciding between all these options was very overwhelming. Coworkers, family members and peers all had opinions about which opportunity was best, and I found myself growing confused and paralyzed to decide. And furthermore, I felt like a hypocrite for now being burnt out from my misalignment with the company’s mission because I previously didn’t mind when I joined the company over a year prior.
Clarity only came when a close friend helped me recognize that values are dynamic, and while joining Scale satisfied my values at the time, it was worth considering whether old values had died or new values were emerging. By focusing on how my values had shifted, I was able to articulate a new emerging value that was not being catered towards, and made a commitment to explore it by leaving Scale AI: building delightful experiences that provide real value to people I care about.
My decision cost me to lose out on:
- $10m+ in company shares left on the table.
- a tangible promotion to senior role, a new high-visibility product and a flattering compensation package.
- a community of bright and hardworking people with whom I had built a strong reputation.
- the respect and admiration from family and friends that I gained working at a high-flying venture-backed startup.
- reliable financial security in the form of a six-figure salary and benefits.
Stepping away from all of the things I once was told I should aspire for and was now being handed to me wasn’t just challenging. It was terrifying. But I gained the clarity of mind to leave Scale by adhering to my known values and committing to explore other emerging and undiscovered values. And because I acted according to my intrinsic desires, I still feel proud of my decision to this day. This was a crucial step in my journey to take control of my life direction.
I began making life decisions using my inner values.
My third step towards following my inner compass happened once I realized the value of articulating and adhering to my values.
Gather.Town (1 year)
One of my closest friends growing up is the very talented, very focused visionary Phillip Wang, CEO of Gather.Town. Phillip asked me to join Gather as a cofounder in the earliest days at the start of the Covid-19 pandemic lockdowns, and I spent time turning the very timely video-conferencing prototype into a software business.
As we scaled during the first year of the Covid-19 pandemic lockdowns, we saw our friends use the platform for birthdays, hangouts, movie nights, and more. We saw people get married on the platform. And I had the privilege of pitching Gather.Town to the MIT professors in charge of the core freshman classes that I had just taken a couple years prior. Building a product that was able to provide great value to people I knew and cared about was an incredible feeling that gave me a sense of purpose and self-fulfillment, confirming the value I wanted to explore after experiencing burnout at Scale: building delightful experiences that provide real value to people I care about.
Once Gather was growing so fast that we needed to bring on outside help, we each had to decide whether to make the 5-10 year commitment to be a formal cofounder. And while I found enjoyment building for people I care about, it was clear to me that Phillip had something more: a passion for building a responsible metaverse. This passion didn’t just give him lasting motivation and tremendous focus but also gave his life rich “texture” – he found a purpose and was fulfilled by working towards it. I didn’t share this passion, but seeing his deep conviction first hand meant I now desired to similarly find a passion I could work towards. Thus, I made the tough decision to leave Gather to explore my intrinsic desires and find passion in my professional life. I set out to test a third potential value: working on a product I am emotionally attached to as a way to gain lasting motivation and give my life rich texture.
Gather has gone on to grow rapidly, enabling millions of users to uniquely interact online, hiring a hundred bright and earnest believers in the metaverse, and raising millions of dollars from Sequoia and other top funds. I lost out on the ability to fully experience this once-in-a-lifetime journey, the opportunity to work closely with one of my closest friends and cofounder-level financial upside (likely another $10-100m+ in company shares left on the table). But similarly to my departure from Scale I acted according to my intrinsic desires and I still feel proud of my decision to this day. These experiences were growing my intuition for how to take control of my life direction.
I committed to iteratively exploring and exploiting my inner values.
Since then, I’ve been learning to live according to my inner compass in a healthy and productive way. It’s been daunting, but incredibly rewarding, fulfilling and satisfying. Because life is dynamic and our values are constantly evolving, this journey is never complete.
Sabbatical (2 years)
By leaving Scale and Gather.Town, I had formally departed from the consensus playbook for success, and with it went validation and admiration from some members of my family, friends, and community. But having experienced the sharp contrast between how I felt in high school applying for colleges only focused on the consensus playbook for success and how I felt at Scale and Gather fully embodying intrinsic values that I had identified, I knew it would be worth it to take time, explore more of my values and interests, and gain strong conviction in my life direction.
I started by making up for all the years spent following the consensus playbook for success at the expense of my intrinsic desires. I set aside six months to explore less prestigious industries I had always been curious about, such as real estate, e-commerce, cannabis, and digital content creators. In each one, I deeply researched, networked, and prototyped to gain insight into the spaces, and while doing so, validated a third value: working on a product I am emotionally attached to and pursuing my intrinsic desires gives me strong and lasting motivation, and gives my life rich texture.
Putting it all together, I knew the following about my work values:
- I like sitting at the intersection of product and engineering. This evolved more generally into I like wearing multiple hats by interweaving cross-functional insights together, and this was most abundantly needed when building a pre-product-market-fit business.
- Building delightful experiences that provide real value to people I care about gives me motivation, purpose, and conviction.
- Working on a product I am emotionally attached to and pursuing my intrinsic desires gives me strong and lasting motivation, and gives my life rich texture.
I’m now building the Inner Compass resources I wish I had.
I would have greatly benefitted from support, guidance and skills for learning to follow your inner compass, especially in tough life decisions. Now I’m compiling my insights to help my future self, peers and others do the same.
Inner Compass Work (Present)
The biggest value I had personally created for myself over this entire journey since public high school was creating space for exploring my intrinsic values and learning to make life decisions according to them.
When talking with peers around me at MIT, Scale, and Gather, my story resonated deeply and my journey inspired them to want to invest similar energy into articulating personal values and finding purpose and conviction. However, most were unsure where to start and scared to take the risks I had taken by taking a two year independent sabbatical: loss of financial security, loss of social validation and loss of belonging and community.
It was clear to me that the value I had created for myself could also be very impactful for the people I care about, which satisfies my second value. It was also clear that the other two values would be satisfied if I turned my attention towards providing this type of value to my peers.
Thus, I decided to try building upon my learnings and methods to offer my peers a way to gain the same sense of self and conviction without the confusion and risks I endured.
Even though I originally set out only to solve this problem for myself and my peers, seeing the clarity of mind and confidence my peers and I have gained motivated me to expand my horizons and help more people with similar struggles.
Now, a group of us are trying to share the merits of values-based living and enable others like yourself to follow their inner compasses to lead more genuinely meaningful lives.
Do you resonate with my story?
If you see yourself in any of my past experience, I may be able to help you resolve your angst about life or career direction. I’ve spent the last couple years carefully curating a method for value-aligned living: Inner Compass Work. We married our method with an AI-guide to tailor the experience to your needs. As a result, you'll identify your desires and gain the confidence to make life-changing decisions, without the time, cost, or awkwardness of working with a life coach.
Quotes that inspire me
