Discover more from Game of One
#25: I quit my job! 🕊️
and how you can too :)
In one sentence: I quit my job! And I made the How To Quit Your Job guide.
After a year of toiling in the fields of my over-thinker mind and oscillating between preserving inertia and embracing uncertainty, I finally did it. I quit my job. I left my cushy product manager tech job without another one lined up… to play, to hone my craft, to wander the unknown.
Back in December 2021, during my Annual Review, I set the goal of quitting my job in 2022. I wasn’t sure what I would do after leaving. I just knew that I wanted to quit. Once the seed was planted in my head, it was an arduous twelve month journey to follow through on the intention. It was a constant mental jousting between my pragmatic, conservative left-brain and my free-spirited, open-minded right-brain. The two parts of me whispered into their respective ear like the angel and devil on either shoulder.
I was navigating an internal dilemma, but the external world was equally debilitating. I leaned on friends who previously quit their jobs to take a career break, start a company, or pursue their creative passions. But when I told my more conventional friends (the majority) that I wanted to quit my job, they would respond with skepticism and bewilderment. They couldn’t fathom why I would willingly walk away from my six-figure remote job which made me feel like I was being naive, ungrateful, and delusional.
Looking back, I was trying to seek consensus to justify a personal, divergent decision. There’s that one Robert Frost poem that we all had to memorize in elementary school:
Two roads diverged in a wood, and I— I took the one less traveled by, And that has made all the difference.
Here I was, already at the trailhead of the less traveled path. Ready to take my first step. Yet, I was looking for the approval of my peers on the commonly trodden path who all believed they were stuck or not even aware of this other path.
Throughout the course of the year, my plan changed frequently. One week I would get fed up and want to quit without any foresight. The next week I would get money worries and back away from what seemed like a cliff. The truth is there was no plan. In order to explain, we’ll have to go back to the early days. Where so much of our assumptions and beliefs were conferred and entrenched upon us.
stay in the loop with what I’m cookin up ✌️
I grew up in the suburbs outside Washington D.C. with two working immigrant parents. I remember my dad would quiz me and other neighborhood kids on state capitols at the playground. My curiosity was cultivated through visits to the National Zoo and Smithsonian museums. I was a nerdy, straight-A student, but I was never forced to play piano or go to Kumon. It was the same unbound upbringing of being spoiled with too many Yu-Gi-Oh cards and quitting Chinese school too early that led to a future sense of agency.
My parents gave me full autonomy on which universities to apply to. I naively didn’t apply to any Ivy Leagues because I didn’t want to immerse myself in dense amounts of legacy, wealth, and pretentiousness. Even if partially true, it was faulty logic and also hypocritical since I still eagerly applied to Stanford.
It ended up working out and I started at UC Berkeley as a Mechanical Engineering major. After realizing I hated physics and switched majors to Electrical Engineering & Computer Science (EECS), I still had no idea what I wanted to do. I was surrounded by a mimetic shroud which made me believe I should pursue software engineering, but after failing to brute force my way into enjoying it, I miraculously discovered this other legible path - becoming a product manager.
My first job was awesome. I landed a coveted spot as an Associate Product Manager at a Big Tech company. I was in a close-knit cohort which led to close friendships and we even got to travel around the world on a three-week business trip. But… I was drinking the Kool-Aid big time. So much of my identity was wrapped up in work with free lunch and dinner provided as well as my social life which increasingly included coworkers. When I got laid off, a lot of assumptions I had around Work and its role in Life were shattered.
Looking for a new job in Summer 2020 was tough to say the least. There was no vaccine in sight and companies weren’t hiring, let alone a new grad with only ten months of experience. After being laid off and spending the following three months cooped up at home during 100°F summer days, I wasn’t going to let my new job stop me from living life.
Two weeks in, I drove out to Park City and then Denver. My friend Jon flew in and we roadtripped through Grand Teton, Yellowstone, and Glacier National Parks. It was exhilarating and tiring in the best way to Tetris our schedules around Zoom calls, Airbnb check-in times, and driving a couple hundred miles every day.
Fast forwarding through, I’ve spent the winters living in mountain towns, where everyday is a ski day by default and I’d only have a ‘down day’ when my legs were begging for it. Living in Hawaii taught me the value of community and what it feels to belong. So much so that I plan to visit at least once a year and eventually settle down in Oahu.
The initial L of getting laid off gave me the courage to intentionally put my career on the back-burner and shift everything else to the forefront. Isn’t it a bit ironic that losing my first job made me realize I should try less on my next one? Deep down inside, all the traveling, new relationships, and hobbies helped to distract me from the symptoms of not loving my job. After getting promoted in August 2021, I started to feel lost. I was on the fast-track in the career game by at least a year, yet nothing changed. I was expecting the promotion to stoke the fire within me, but instead I just let out a sigh of relief. I had the time to ski and surf in the world’s most beautiful places. Why did I still feel so lost and unfulfilled?
Feb 17th, 2022
Thankfully, last year I started journaling which is why I know the exact day I made the decision to quit my job without another one lined up. On February 17th, 2022, I was midway into The Pathless Path when I decided to quit my job and take a career break. (To this day, I’m still not sure whether to call it that or a career transition or funemployment or something else.) It was a late night at home, right before a ski trip, when I noted how I felt about deciding to quit:
… I should go pack for Aspen now that it’s already 11pm and I don’t want to keep Mom up too late. I’ll close with saying that this is the big move that I’ve been waiting to make. The last two years have shown me that the ceiling that I perceive for my own potential keeps being raised each time something happens to me or when I make a big move. A lot of people I know are living life waiting. Waiting for something - and not just anything, it’s got to be something positive and great. Something that’s just going to fall into their lap. I’ve realized that the greatest risk is not taking any risk. And therefore I’m taking the plunge. Now I need to pack - I’m stoked.
Choosing to take a career break felt heavier than deciding when to quit. Deciding to leave the corporate world, even if just temporarily, meant slicing off a part of my identity and approaching the abyss. When to quit could be tactically solved in a personal finance spreadsheet. Knowing my next step gave me an initial surge of relief as I was already several months into feeling lost.
The Journey To Quitting
In April 2022, I was surfing in Hawaii wondering why I was still feeling unfulfilled when I wasn’t overworking. I started to voraciously read anything that could help me navigate my relationship with work in the hopes of finding the perfect time to quit my job. That moment never came.
I met more Career Breakers who I would pepper with every possible question. I increasingly felt more disconnected to my job, title, and coworkers. I already knew my job wasn’t what I wanted to do over the long run, but now I felt like I was useless. As summer approached, I threw myself at a big distraction. I embarked on a six-week road trip that included summiting Mt. Shasta, through-hiking the Enchantments, and backpacking the Teton Crest Trail. It was an intensely beautiful time filled with solitude, stargazing and many nights not in a proper bed.
In the fall, I had begun collaborating with a friend on starting a climate tech startup. We spent a few months navigating the maze of trying to find the ‘right’ idea before having a cofounder break-up. I latched onto the startup founder path and had mentally come to terms with dedicating the next 5-10 years towards this singular pursuit. Even though we split on good terms, I was alone to pick up the broken pieces of my future plan and shape it into something new.
What happened next was eerie. The next day, I woke up feeling like a weight had been lifted off my shoulders. There was a renewed sense of creativity. Previous ideas came to the foreground of my mind. It was strange, yet refreshing to revisit my ideas with this new vibrant, HD lens. None of these projects were startup ideas with a clear shot to revenue generation, but they were inherently creative. I spent the next few weeks exploring some and pausing others. I consistently woke up energized to work on my projects simply because I cared. I experienced an initial taste of the cliché: find work that feels like play.
Why I Quit
Ultimately, I wasn’t proud of my work. As a world-class hoop jumper, I had to overcome the expectation to do well in everything. It felt foreign to intentionally not put my best effort into my job and instead channel that energy into other pursuits. What I didn’t anticipate was how stressful letting myself down would feel. At some point, I couldn’t live with myself barely trying. I wasn’t able to compartmentalize my lack of enthusiasm in my job with the rest of my life. Not trying at work bled into feeling like I wasn’t trying at life.
I wasn’t running out of time. I was running out of energy.
I knew I wasn’t burnt-out because I wasn’t working a ton. I finally had a proper diagnosis after reading Steve Schlafman write about burndown. Coming to terms with being ‘burnt-down’ was comforting at a time when I was hearing conflicting advice. My friend Ray who had taken a career break said the time to quit was when I started to run out of time. He was referring to all the outside-of-work time for personal projects, side hustles, and hobbies. To me, that felt like a hypothetical that would never materialize since I did have time. What I lacked was energy - which should’ve been an even stronger signal to quit. Eventually, it all came full circle because after deciding to quit, I regained my motivation and architected my projects in an ambitious way where I started running out of time every day. Ray turned out to be right; the advice just took a windy detour to arrive in my mind.
Understanding Fitness Landscapes
I started to familiarize myself with the concept of fitness landscapes through Tom Morgan’s writing. Every organism inhabits a landscape filled with local minimums and maximums and demonstrates fitness by advancing upwards:
Just how Steve Schlafman realized that venture capital was a local maxima for him, I accepted that remaining in my role as a big-tech-product-manager was also the wrong mountain to climb. I resonate with the peaks and valleys metaphor especially because in order to strive towards the global peak, we must first descend. Before we can advance uphill towards a new mountain (or in this case, a chapter of life), we must first tread downhill from the local peak which for me means walking away from a prestigious job title and stable, high income.
Our competitive modern economic structure means most of us don’t have the freedom, or “slack,” to follow our interests. The steep sacrifice required keeps us stuck at a local peak. My own personal obsession is the tragic loss of human potential from mid-career workers stagnating in their jobs. Midlife should be the period where we pivot our hard-earned skillsets towards individual creativity. When we turn our talents toward the benefit of the world. - Tom Morgan
I internalized the concept of buying time
“Time is money” is one of the most common aphorisms, yet isn’t practiced as much as it’s preached. We sacrifice years of later life via unhealthy habits and wait in those long ass lines for gas at Costco just to save a couple bucks. There are plenty of self-help gurus and successful businesspeople preaching that Time is the most valuable asset. We trade money for time when we take an Uber instead of public transit, pay someone else to mow the lawn, or Instacart our groceries. How come we don’t apply the same principles to such an important part of our life - What we do? As someone who recently turned 26, I feel solitary in taking a mini-retirement by sacrificing my semi-monthly paycheck for a year of creative freedom. I guess that’s part of the tax when you pay for more time.
Trusting the Process
What do Joel Embiid and ancient Chinese philosophers have in common? They both embrace the journey, rather than fixating on the destination. Embiid has his “Trust the Process” mantra and his nickname is literally “The Process”. Similarly, in the Tao Te Ching, Lao Tzu, Taoist philosopher taught about unfolding and wu wei, effortless action. I paired these two contrasting figures with my newfound appreciation for the concept of the Infinite Game, a type of game where the rules are unclear, the players constantly change, and the only purpose is to keep playing the game. Things became tangible from listening to David Senra present the theme that the greatest founders all pursued the Infinite Game in their respective craft. In concocting my own plan, I simultaneously juggled two truths that seemingly contradict: you can have high uncertainty in what is going to work while strongly believing that something will work.
Quitting my job comes with the ambiguity aversion of known losses and unknown gains. I knew what I was giving up, but it wasn’t clear what I would receive. Reading other people’s reflections on career changes gave me a sense of optimism as I approached the abyss.
In the past few months it’s dawned on me that the biggest impediment to my own success is my tendency to underestimate myself. It’s a fabulous coping mechanism: don’t set super high expectations, especially not in public, and you won’t have to deal with the sting of disappointment and embarrassment. I don’t even let myself imagine grand dreams of what’s possible for me, because once you’ve imagined it, supposedly, everything else will feel lame in comparison.
In his 2022 year in review, an inspiring climate tech writer (among other things) Tsung Xu reflects:
I have been surprised that by consistently doing the work, my results have exceed my expectations.
At times, it feels like my optimism towards my version of the pathless path is blind naïveté. But reading reflections like these makes me fired up to fight the Resistance and trust the process.
Returning to child-like curiosity
As kids, the word ‘play’ gets used abundantly. We go on playdates, we play games like tag, and even tucking in dolls to bed is playing house. Somewhere along the transition from kid to adult, precisely when our time becomes monetized, it no longer pays to play. In the Three Marriages, David Whyte quotes other poets to reinforce the idea that as adults we should return to the ethos of childhood.
Genius is nothing more than childhood recovered by will, a childhood now equipped for self-expression with capacities of an adult. - Baudelaire
If a child grew into adulthood according to early indications we should have nothing but geniuses. - Goethe
The secret of genius is to carry the spirit of childhood into adulthood. - Thomas Huxley
What does play look like as an adult? What’s the grown-up version of the sandbox? How can I get back to doing things just for fun? I realized that I wouldn’t find the answers while still employed and shackled to golden handcuffs.
Even with a year of contemplation, a plethora of reassurances, and a plan B for every permutation, I still felt anxious leading up to the day I put in my notice. Every hypothetical scenario entered my periphery. Like other Career Breakers, I thought that my coworkers would resent me for leaving them. I even thought about the possibility of my manager forcing me to leave the day I put my notice in, rather than a few weeks later.
The opposite happened. In our last 1:1, my manager and I bonded over our shared interest in climate. She even asked me if I knew of any resources on how to raise kids to be climate-conscious citizens. I’m completely unqualified to give any parenting advice, but I brought up the adjacent example of how the Japanese integrate chores into early childhood education which explains why the streets of Tokyo are spotless and why Japan fans cleaned the bleachers at the World Cup. While transitioning my projects to another PM, we talked about yoga, meditation and spirituality and afterwards he sent me some books.
The sad thing about corporate America today is that we view each other as total [co]workers. Since remote work is time-boxed by calendar events, there’s pressure to skip the small talk and cut to the chase. Not only do you never figure out how tall they are, you never get to truly know your colleagues.
The ‘How to Quit Your Job’ Guide
For over a year, I agonized over quitting my job and stepping away from a defined, decent path. Along the way, I collected artifacts in the form of books, newsletters, and articles that helped me navigate such a personal decision. Although it feels off to be sharing this during a time when layoffs are happening left and right, I know from my own journey how helpful other perspectives can be so I put together the How To Quit Your Job guide. Check it out here! Let me know what you think and feel free to forward it to a friend who could use a nudge.
I’m finally embarking on the career break that was first imprinted upon me over a year ago! I hope that by sharing my story, someone, even if it’s just one individual, will feel comforted as they chart their own path. I’m stoked for what’s to come and I’ll be sure to share some updates in the next post :) If you enjoyed this, feel free to share it with a friend!
big things coming in ‘23 - stay in the loop: