My Decade in Review — Jeff Li Chronicles

Reading Length: 22 minutes (this is long!)

Shoutout to Andy Tran for giving me this idea!

2012 (19/20 Years Old)

The stiff smell of booze swarmed my nostrils as I knelt down to take another shot. Gulp. Gag. Burp. Another one. Gulp. Gag. Burp. If 2012 were a broken tape record, that sequence replayed every weekend. Gulp. Gag. Burp.

In high school, I was anti-drinking and smoking. I judged “those” kids who drank alcohol. I intentionally coughed when someone smoked cigarettes. I’d lightly punch my friend on the shoulder whenever he said a swear word. Its as if I got D.A.R.E tattooed on my pubescent, high school brain. If I met this kid, I’d probably take the back of my hand and slap him in the face. That ain’t cool.

Then during senior prom, I had my first lick of alcohol. I wasn’t drunk. I probably had like 5 shots. But like most people who drink, alcohol allowed me to be someone else. F*ck DARE, alcohol allowed me to be cool.

Me being drunk

In high school, getting into college is like climbing Mt. Everest. Everything you do is to reach the summit of “that acceptance letter.” SAT Prep classes. Extracurricular activities. AP classes. Cheating on tests. So once I climbed that mountain, I thought “I finally made it, fuck yeah, I’m done.”

Combine my new, anti-DARE mindset with climbing Mt. High School, I had one thing on my mind: I want ot be cool. Let’s party.

College is the only time of your life where being an alcoholic gives you more status. Turning down a shot? Don’t be a b*tch. Shotgun three beers? Ohhhhh shietttt!!! *in a frat boy voice*.

I wanted to be cool. So I lived the normal alcoholic college lifestyle. I pounded spicy shots of fireball while playing beer pong at a frat house. I danced the night away to the euphoric edm sounds. I passed out next to a toilet in a random person's apartment, vomiting my organs out. Girls invited me over to “hangout” and I actually thought they truly wanted to just hangout (lolz).

At USC, white frat stars were the “cool” ones. They got the girls. They were confident, good looking and buff. I girls, so I copied them. I wore bro tanks, only worked out my upper body, drank a lot, played a lot of beer pong. I wanted to be “white.”

Tailgating, an excuse to wake up at 9am to drink

It’s an interesting paradox. When you don’t care about being cool, that makes you cooler. When you desperately want to be cool, it makes you uncool. You compare yourself to others. You care about what others think of you. You become a Yes-Man just to please others.

Actually a better term is “Yes boy”. I wasn’t a man. I thought that saying yes could buy “coolness”. If someone offered me a shot, I’d say yes. If someone asked me to go to a party, I’d say yes. If someone asked me to do anything, I’d say yes. I was known as the guy who was “always down.”

But the yes’ came at the cost of my own identity. I was a mish-mash of all the people around me. Cliche’s tell you to “be yourself” but no one knows what the f*ck that means. My name was Jeff but I wasn’t “myself.”

My friends took this useless video game QA class, so I took it. My friends studied business, so I studied business. My friends got into consulting, banking, accounting, so I did. My friends went to raves/parties, so I did. My friends joined a business fraternity, so I did. Hell, I even went to USC because a friend wanted to go (he didn’t get in). Rene Girard would be proud (See Mimetic Desire).

A 7-year old knows what he wants. He knows what he’s passionate about, what he hates and isn’t afraid to voice it. As we grow up, society, people, parents silence this voice. If you imagine your voice at the center of the onion, these societal, parental and communal influences wrap onion layers around that voice, muffling that inner, 7-year old voice that desperately wants to be heard. We spend our adult-lives trying to peel those layers, to let that voice shout into the abyss.

Those onion layers were thicc. 7-year old Jeff’s voice was smushed. I couldn’t hear it. My singular goal as a 19 year old was to party and be the cool kid that I wasn’t in high school.

2013 (20/21 Years Old)

If inebriation was the flame of my 20 year old self, turning 21 is like pouring gasoline on the fire. And what do people do when they turn 21? Vegas, baby.

Within the first three months of turning 21, I went to Vegas four times. I don’t remember a single thing from these trips, partially because I was inebriated, but partially because they weren’t memorable. I went to Vegas because I saw other people going.

I don’t want to oversell this. I was drinking more than the average human being. However, I was not drinking that much more than the average college kid. I was not drinking alone. There are people I’ve known who’ve gone to dark places with alcohol. That wasn’t me. There’s a line and I don’t think I crossed it. I drank to be accepted by everyone around me. I didn’t drink to escape from life. I partied to be cool. I even had a moniker at the time “Jeff can’t hang.” I couldn’t hang, because I kept going past my comfortable limit to try to prove to others I could take the most. I wanted to be cool.

I was obsessed with BP. We trolled this dude.

As my junior year of college trudged along, I continued this college lifestyle of partying and skipping class’. My #1 focus was fun. Then, near the end of the semester, I’d pull insane, stressful all-nighters mixed with adderall, to pass my finals, only to decompress through post finals partying.

Like most college students, I had no clue what to do with my life. The bumbling quarter-life anxiety started to bubble to the surface. I was not on top of my shit for my career. So my solution was to take a step back from my life, re-examine my relationship with alcohol & partying and set myself in a new direction. Jk, I drowned out that anxiety with more partying.

I scrambled to find myself an internship, only to be “nicely let go” from it after they realized I wasn’t adding value. I vividly remember my manager being in pain “letting me go” when I literally did not give a f*ck.

More time for fun! At least I can put it on my resume now and make up some bullshit stories about it.

As my junior year closed out, while many of my friends had full time job offers lined up, I had no full-time job prospects in sight. I scrambled to find an internship and managed to get an internship doing financial valuation. I wasn’t thinking about what I wanted. I just needed something to do.

To celebrate the end of the year, a few friends and I planned a one night camping trip out in the Southern California desert, which changed everything.

2014 (21/22 Years Old)

Out in the desert, stars filled the night sky like freckles on an 8 year old farm boy. Camping mixed with “vegetables” created a tiny, ever so small, opening, that allowed my inner voice to poke through. The voice swam through the thicc fog and whispered. It was him. It was the voice.

7 year old Jeff knew what he wanted, but I could never hear him. That’s why I always “did what everyone else did.” It’s why I studied business, but deep down, I wanted to study statistics. It’s why I wanted to be in analytics, but went into consulting. It’s why I wanted to start my own business but I never started. I wanted to go to Duke for college, but I never applied.

As the voice poked its head through, I heard the faint whisper: go study abroad. I didn’t know shit about the world. My view of the world was California. I didn’t know what was out there. That camping trip taught me that I didn’t know what I didn’t know. I needed to study abroad.

I mentioned this to my Dad and he wasn’t pleased. I didn’t have job prospects lined up and I was asking him to pay for this adventure. We had a heated argument and I said “if you don’t wanna pay for it, that’s fine. I’ll just work for a semester or take out a loan to go study abroad.” It was the first time I had 100% conviction this was going to happen. I was going to study abroad no matter what. He sensed it and relented. It was the first time I felt this strong of a conviction to do something.

So for my final year of college, with no job prospects lined up, I moved to Rotterdam, Netherlands.

Near the beginning of study abroad, I went on a trip with a few study abroad classmates. I remember being miserable. They wanted to go to one restaurant whereas I wanted to go explore the city. They wanted to party but I remember a nagging thought in my head saying “you didn’t study abroad to just party.” We just weren’t on the same page. But It was the first time I actually knew “hey I don’t wanna do this shit.” Before, I would’ve just said yes and gone along with it. I started to hear my voice, but I didn’t know how to express it. I needed to learn how to express it. I had to travel solo.

I made beautiful memories traveling solo. I slept homeless in Maastricht and recorded a shuffling video across the city. I accidentally rented a stick shift car in Santorini and ended up asking a stranger to teach me. I met a Hungarian singer and fell into “infatuation” (love at the time) with her. I got scammed by a mustache-man at a Turkish strip club. I talked for 4 hours with a former french drug lord in the Swiss Alps. I woke up without my phone, wallet and keys, in Dutch jail. But most importantly, traveling solo forced my inner voice to take the steering wheel.

Me walking around Maastricht, shuffling in random spots:

Study Abroad Crew! We biked 60 miles that day.

I made mistakes, broke out of my shell, met people I never thought I’d meet. Traveling solo opened up that inner voice. What did I actually like doing? I remember going to the Louvre museum in Paris and I was bored out of my mind. I was standing in front of world-famous paintings and I could barely keep my eyelids open. Museums, not for me. I still don’t like museums. I remember going to the Arc De Triomphe and was unimpressed. I didn’t give a f*ck about the things people said I should do.

But on top of traveling solo, I made incredible memories with my study abroad classmates. We all skipped classes (and stressed the fuck out when we had finals), partied every Tuesday night at BED, lots of “veggies”, hung out at the beautiful park in Rotterdam:

All of us chillin at the park on a few classmates' last day.

I also hated writing growing up. But studying abroad inspired me to start writing about my adventures. In school, I wrote because I had to and it sucked ass. It’s been 10 years and I still love to write.

While it seems like I became enlightened studying abroad, I didn’t shed my old ways. I still wanted to be cool. I still wanted to party. If anything, I partied more than ever. I went to a rave almost every few weeks. We went to deep house festivals in Amsterdam, saw Armin Van Buren went to a Kings Day music festivals and got lit almost every weekend.

At the time, I had the habit of walking to a bar, and asking for the strongest drink they had. We went out on a standard Tuesday clubbing night (its normal to club on tuesdays there) and I ended up making this request during happy hour. 2 shots for 1 baby. They gave me two shots of this black licorice, poison shots of death. I downed both shots immediately. Next thing I remember, I wake up in a jail cell, no phone, keys or wallet. Apparently, a police officer found me passed out on the street, in 30 degree weather.

Club BED, the place I blacked out.

Near the end of my trip, I was walking near the subway line in Rotterdam. I walked awfully close to the edge of the subway line and a subway car flew right past me. The wind of the car ruffled my hair and I felt a cool wave of wind pass through the crevices of my clothes. The subway was about a foot away from me. I had this odd thought that, “I was one foot away from death.” I intellectually knew life was fragile, but this was the first time I felt how fragile life was. And nothing peels away the layers of the onion, like seeing death on our doorstep.

The thought was foreboding. Jordan Basl was one of my closest friends from study abroad. He was the only dude on study abroad who was willing to freestyle rap with me at a moment's notice. He got us all together for our weekly, Tuesday clubbing nights at BED (some club in Rotterdam) where he always hosted the pregame. He started our study abroad group’s group chat too:

But he was his own bully. I remember one night, Jordan and I were at a deep house club. We were drunk so I didn’t remember what he exactly said but something like: “I’m so fucking stupid. I’m an idiot. Fuck me. I don’t deserve this shit. I just need to die.” He was Mike Tyson, piecing himself up with upper cuts, jabs and right hooks.

I remember pulling him to the side and we talked for over an hour. I remember telling him, “It’s not that you’re just amazing but my study abroad experience wouldn’t have been the same without you. Your apartment is literally the centerpiece for everything, pregames, travel, freestyle rap session, parties. You connected everyone. You got everyone together. We would not have had the sick crew we had had it not been for you. Nobody else was willing to do what you were willing to do. You literally made our study abroad experience man, and I’ll never forget it.” Jordan then told me, “Not do I appreciate this, but you have a superpower for this man. I don’t know if this is a teacher, therapist or a life coach but you have a talent for this man.” This was the first time someone told me I had a talent for mentorship.

Myself, Luis and Jordan chillin in Amsterdam. Jordan’s the one in glasses.

A year after study abroad, I started seeing facebook posts on Jordan’s timeline saying RIP. I thought it was a joke, so I called our friend Kevin. He told me he hung himself in his apartment in South Carolina. This was 7 years ago. RIP Jordan, still freestyle rapping in your honor.

Death is the ultimate key to allowing our inner voices to shine. It’s why it’s called “deathbed clarity.” And as I peeled off layers off the onion, like a caged baby, that voice got louder and louder. But since that voice had been trapped so long, it was unrestrained. I hadn’t fully shed my old, supplicative self.

So my two selves clashed.

2015 (22/23 Years Old)

After studying abroad, I stopped doing things “because everyone else was.” I started thinking for myself. But this version of Jeff didn’t know how to act in public.

I’d say what’s on my mind, regardless of whether it was rude or not. I remember bumping into this girl I knew 6 years ago at a bar and rudely said “why are you here??” She was appalled and I don’t think she ever wants to talk to me again. I went to a friend’s party, only to leave 30 minutes in because I got bored and wanted to go check out this Tiki bar. I started writing ridiculous facebook posts. Half of the people thought they were hilarious. Half thought they were rude.

My old “yes boy” self clashed with this new, unrestrained inner voice. Let’s call this new Jeff, “Jeff 2.0”. I felt like I had two versions of myself inside me. And they caused a ton of friction. The “yes boy” Jeff, people pleasing, supplicative Jeff, who picked consulting as a career, said yes to everything. Jeff 2.0 hated consulting. Since study abroad had been so lifechanging, Jeff 2.0 wanted to travel. The battle between “yes boy” Jeff and Jeff 2.0 begun.

The friction made me angry at the world. My attitude was “fuck everyone, everyones a sheep.” I started hating the old Jeff. I hated my job. My old self picked this job, just copying what my friends did.

I developed a superiority complex. I thought I was better than others because I was “enlightened” now. I read all these “digital nomad” blog posts telling me to “reject the system” and “unchain myself from the shackles of the office job.” Seeing an office job as a metaphor for jail made me hate my job (and my life) even more.

And this friction, sent me to a dark place. This was the least happy I have ever been. I’d wake up, dreading the day. It was like a low hum of sickness that hummed in the background of my life, grinding away at my soul, taking bites of my happiness.

This is me at the top of my company office. I was so bored, I’d regularly come up here to do hand stands.

I couldn’t live like this. I had to escape.

2016 (23/24 Years Old)

Most college kids these days feel this anxiety: the quarter-life crisis. From the age of 1 to age 22, someone else draws the map for us. We go from elementary school to middle school. We go from middle school to high school. We sign up for AP class’, extra-curriculars, study for the SAT’s, with the goal of going to a great college. We don’t draw our own map. When we finish college, we have to start drawing the map ourselves. It’s uncomfortable. We don’t know what we’re doing. We don’t know if we’re going to make the wrong decision.

And throughout my life, I rarely drew my own map. I never really made my own decisions. Somebody else unconsciously made that decision for me. I played tennis in high school because my friends and parents chose it for me. I went to USC because my friend was also applying. I joined a Business Fraternity because a bunch of my friends were in it. I went into consulting because all my business fraternity members did it.

The “yes boy” Jeff wanted to copy someone else’s map. But study abroad was the first time I drew my own map. But like any skill, I wasn’t good at making my own decisions. And this caused a ton of anxiety at the time.

Since I loved studying abroad so much, I saw becoming a digital nomad as an escape from this anxiety.

So in 2016, my plan was to become a digital nomad. I figured the way to do this was 1) develop a valuable skill, like copywriting then 2) hustling to find freelance clients then 3) once I earned at least $2 to $3k a month, I could live in a cheap cost of living country like Thailand indefinitely.

At the same time, I read the book So Good They Can’t Ignore You. This book changed my perspective on careers. The core thesis: forget finding your passion. Find something you’re willing to get good at. Once you’re good at something, you can use your skills to attain more autonomy, creativity in your work-life. This leads people to feel more “passion” for their work.

After reading So Good They Can’t Ignore You and mapping out a path to escape, I didn’t know what skill I wanted to target to become a digital nomad. So I figured I could get better at the skill of “learning.” Then, I could apply it to any skill I wanted. I started researching different strategies & techniques to learn skills faster. I learned speed reading, memorization techniques, and mind-mapping.

Once I felt like I grasped these concepts, I needed to test these ideas on a skill. In high school, my friends and I would drive around our hometown and freestyle rap. I was bad. My rap always devolved into vulgar, crass topics. I was probably the worst out of my friends, but I had fun with it. After a few years of rapping, I still wasn’t good. Let’s test these meta-learning ideas on freestyle rapping.

I committed myself to practicing rapping for two hours a day, for 30 days straight. It felt like a slog. I had never disciplined myself to do anything for 30 days straight. But I felt called to do this. I learned random songs by Eminem and Outkast to develop my flow. I’d do random word drills to get the improvisation down. After 30 days, I was highkey spitting fire. I went from middle of the pack to best rapper within my friend group. I realized If I just committed to improving my skills everyday for a measly 30 days, I’d well surpass most of the population in anything. This was the birth of my framework for learning anything. Jeff 2.0 taking over the steering wheel of my life.

With my newfound framework, I wanted to keep testing these ideas. The next skill I wanted to test this on were social skills, specifically dating. I went out everyday, for 30 days and just cold approached attractive women. I’ll detail this more in a later section.

Now with my framework solidifying, I decided to apply my framework towards a skill that would allow me to escape my job, I decided on copywriting. I enjoyed writing, might as well monetize it. I’d find the best copywriting letters and copy them by hand. I’d write every day for 2 hours. My writing improved significantly and I ended up writing copy for a small, language-learning business. But I realized that learning the skill was one thing, learning how to monetize was a different skill. I didn’t want to hustle for a year to monetize it enough to earn $2k to $3k per month. I lacked patience. Perhaps I didn’t want digital nomad-ing as much as I thought.

My impatience drove me to find other money making opportunities faster. A friend of mine made over $300k from playing poker. He told me that I could probably make $2k to $3k per month within 3 to 6 months if I worked hard. So rather than drink & go out, I’d spend my friday and saturday nights at the casino. At this point, I was barely drinking alcohol. I failed to achieve $2 to $3k per month. In total, I was probably around break even in earnings. Although I failed to achieve my goal, poker taught me a ton about life. Choosing the right table is just as important as playing well. You can play everything correctly and still lose. That’s life.

So I went back to the drawing board. I asked myself three questions 1) what am I good at? 2) what is the market paying for 3) what’s a growing industry? 4) what am I willing to get good at?

In high school, I crushed math class’ and always got A’s. I was initially a Math major in college. During my freshman year of college, I got a B in Calculus. With the old Jeff driving the ship at the time, the B destroyed any strand of confidence I had in myself.

From playing poker, I liked the statistics behind it. I was also good at statistics in high school and college. So I decided, Data Science it is.

I needed to escape my current job. A smart person would’ve tested this career choice before committing. I was not a smart person. I pushed all my chips into the middle and went all in on data science. I figured that at the worst, this career choice would be wayyyy better than what I’m currently doing. I applied my meta-learning techniques to rapidly learning to program in Python. Then, I signed up for Galvanize bootcamp.

The New Jeff was getting better at drawing his own map. Goodbye Los Angeles. Hello San Francisco.

Note: I didn’t take many pictures in 2016, because I was just unhappy.

2017 (24/25 Years Old)

I quit my job. Moved out of Los Angeles and back home in the Bay Area. Everybody was moving to the Bay at the time. I wasn’t sure if this was the right path, but I finally had some direction. At some point, it’s better to pick something, execute and learn from it, than wallow over whether it was the right decision or not.

Meditation Retreat

Right before I attended my bootcamp, I took a detour to go on a 10-Day silent vipassana retreat. I drove from SF to Portland, Oregon to meditate for 10 hours a day for 10 days. No writing. No sex. No exercise. No talking. No eye contact. Just me and my mind. I wrote a more in-depth post here.

I didnt take photos because we weren’t allowed to, but this is what the room looked like.

I sat in a room with about sixty people, cross-legged, inhaling & exhaling through my nostrils as I sunk deeper and deeper into my subconscious mind. My subconscious mind was like a maze full of dark alleyways, doorways, demons scurrying the crevices of the hallway. I’d take a step onto a doorstep and decide, do I want to go there? I felt ready to open some doors and didn’t feel ready to open others.

As I’d crawl the labyrinth of my subconscious, painful memories would pop up. As a kid, I’d sit at the dinner table, with a thunderstorm of tension between my parents, raining on our dinner table every night. I didn’t notice when I was a kid but I carried the weight of that tension for my whole life. It became my model for what a “relationship” looked like.

Another memory surfaced, I was a 7 year old sitting in piano class. My teacher would tell me my head was like “glue” and that I was too stupid to play it right. Being told you suck every week, especially as a kid, destroyed my confidence and sparked my hatred toward piano. Every week, I dreaded going to piano. After each lesson, I’d feel a huge sense of relief since I didn’t have piano for another week.

I remember trying to learn how to swim but I was too scared to get into the water. So my grandfather started scolding me for being “weak” for being afraid.

Getting ridiculed for having head like “glue” or being stupid, destroyed confidence in myself and my choices, which is why I lived my life up to 22, really having never made any of my own decisions. If I expressed my opinion, I was afraid I’d get crushed.

With all these memories, what the retreat teaches you is not to suppress them. Let them surface, become aware of them, forgive and let go. Whenever they’d surface, I’d start crying. But after I stopped crying and the meditation session ended, I’d walk outside, to the fluffy snow of the Oregon wilderness, feeling lighter, calmer and feeling true peace.

Another moment stood out to me. Within the retreat, you have about 60 minutes of meditation followed by a 5 minute break, then another 60 minutes. I decided to just meditate through the break. So I’d be meditating for a total of 2 hours straight. As I sat there, my legs gradually started to burn. It was as if someone was gradually turning on an oven. As it magnified, I felt like I was sitting on a hot stove. Then, in a split second, I started laughing. I was a third person, watching this human object named Jeff, sit there. I experienced true detachment from pain.

Experiences like my piano teacher or feeling the burn on my legs may be “bad.” But experiences aren’t good or bad. Our minds assign judgment to them. The only path forward is to accept them, be aware of them, even appreciate them. And like butterflies in a garden, let them float away. Because when I finally accepted my experiences or the pain, I didn’t feel happy or sad, I felt true peace.

I left the retreat feeling lighter, calmer and stronger than ever. I packed the newfound peace & serenity and dove into data science.

Data Science Bootcamp

Jeff 2.0 started drawing his own path. His path was clear: Learn data science and get a job in the field. I had 100% conviction this was going to happen.

In the last few years, I worked on seemingly random learning projects: copywriting, social skills, poker, freestyle rapping, programming. I used every single one of those to get my first data science job.

Copywriting trained me to write killer cold emails. A recruiter said I wrote the best email she’s ever read. My social skills training made me unafraid of approaching people. I introduced myself to the founder of an edtech startup who ended up extending me an offer. I freestyle rapped for the head of department and got the job. You can’t connect the dots looking forward. You can only connect the dots looking backward.

I wasn’t the best student, probably middle of the pack. I worked hard but others had years of experience in math & statistics. Others had years of CS experience. I only worked as a technology consultant for two years. However, with these random skills, I landed my first data science job in 1.5 months.

A key element of the growth mindset is that you don’t attribute your success to “being smart.” You attribute success to “working hard.” I developed this self-narrative, I’m decently smart, but I achieve my success through hard work. But most importantly, I developed the belief that everything is figure-outable.

This was the first time I had 100% conviction that I’d find a job. It was going to happen. I’d do whatever it takes. I’ll need to reignite this feeling for my goals going into my 30’s.

I ended up receiving two job offers. I accepted an offer to go to Booking.com in Amsterdam. After accepting my offer, I had a few months to kill. So I decided to attend a data science event in San Francisco.

By then, I had been writing for a few years and developed a deep interest in skill development & learning. At the event, I met the founders of an edtech startup called dataquest.io. My interest in learning & writing on my blog made me the perfect fit for the role. They read my github project brief and then offered me a job. This was the first time I viscerally experienced the idea of positive serendipity: put yourself in places where you’re exposed to bulk, positive random luck. Attending events with interesting people, writing online are activities that cultivate positive serendipity. Do this more and good things happen.

I took the offer. So in August 2017, I started my first role in data science.

2018 (25/26 Years Old)

In 2015/2016, I learned five different skills: copywriting, poker, social skills, programming and freestyle rap. I became fascinated with the end-to-end process of skill development.

In the movie The Matrix, Neo hooks his body up to a machine, jiggling for a bit, opening his eyes, then saying: I know Kung Fu. He spars with Morpheus, flinging around kicks and strikes with the confidence of a seasoned veteran. I wanted to be like Neo. I wanted to be able to download skills into my brain with the click of a button.

Of course, instantaneously gaining years of experience isn’t realistic. But in November 2017, after a night out, I remember sitting in a San Francisco coffee shop, with a giant hangover, just browsing Youtube videos. After mindlessly scrolling through random content, I discovered a person named Max Deutsch. He was a brown-haired, blue-eyed tech kid who looked like both a bro and a nerd, built into one person. He came up with a project called “Month to Master.” The idea was to “master” one skill per month.

I started crying when I read through his challenge. 7-year old Jeff was locked in a closet for years, finally breaking open the door, getting on his knees and begging 25 year old Jeff to do it. I had to do it.

I spent a month developing the plan and got started. Here’s a link to the whole project.

I first worked on my social skills where I went out everyday, high-fiving strangers, going out by myself, approaching pretty girls. Then, I worked on completing 40 pull-ups in a row, but ended up only hitting 27. I learned deep learning by using neural networks to automate dating apps. I memorized a deck of cards in 3 minutes 14 seconds. I traveled to Medellin, Colombia and became conversational in Spanish. I played finger style guitar. I completed the “World Cup of Cooking.” I traveled to Costa Rica to learn how to surf. I learned how to pop and lock. I built an iPhone application. I learned how to draw portraits and finished the challenge of starting a mini-business.

A few videos/photos from the challenge. Here’s me doing 500 pull-ups because I only hit 27/40:

Final conversation of my spanish in a month challenge:

Me after a month of popping:

Link to all the challenges here.

2018 was the happiest and most meaningful year to date. I learned that I derive happiness from grinding on a skill. I tweeted at Kevin Systrom (founder of Instagram) and asked him how he taught himself how to code:

Skills are like video games and everything you learn unlocks the next level of the game. I want to be playing the game of skill development for the rest of my life. And having a larger goal made me live everyday with purpose. I made decisions and used my free time intentionally. It was easy not to drink because I had a goal.

On top of Month to Master, I nearly doubled my salary by switching to a machine learning role at DoorDash. I started feeling like I was hitting my stride. My identity was coming into place.

2019 (26/27 Years Old)

In 2019, I felt purposeless without Month to Master. I felt scattered. To others, Month to Master looked like hard work and supreme self discipline. To me, it was play. I kept trying to jumpstart multiple projects but they’d flame out. I wasn’t emotionally invested in them. I tried to get into crypto, do a 100 dates experiment, and take these random courses. None of them stuck.

At this point, I wasn’t drinking alcohol much at all. In 2018, I could count on one hand the number of times I got drunk. I learned that the key to stop drinking (or to regulate any inhibition), isn’t just to develop iron-clad self-discipline to stop me from drinking. It’s to have a goal or mission that gives me a good enough reason not to drink. During Month to Master, it was easy for me to say no to alcohol. I had goals to focus on. And when my friends would peer pressure me, I’d tell them I had an important goal to accomplish.

In 2019, I felt a bit lost. I lost purpose. Then, I discovered David Goggins.

For the unfamiliar, David Goggins is an ex-Navy Seal. He went through three hell weeks on broken legs. He ran 100 miles without training. He qualified for the Boston Marathon on fractured fibulas. He broke the world record for most pull-ups in 24 hours. He was a superhero. He did the impossible.

There was a term for these types of activities: Misogi. A misogi is a Japanese purification ritual. The western interpretation of it is to do something where you have less than a 50% chance of success. The goal isn’t necessarily to achieve it, but to expand what you believe is possible.

Inspired by David Goggins and this concept of the Misogi, a random idea popped in my idea: let’s bike from San Francisco to Los Angeles. 500 miles. I found my purpose for 2019. I won’t write about it here since I wrote about the entire trip here.

After making it to Santa Monica — We made it from SF to LA!

Relationships

When I was 16, I remember sitting on a rooftop, at 2am with two of my really good high school friends. They were in relationships so we started talking about sex, girlfriends and I literally had nothing to contribute. All my friends were in relationships and I wasn’t. Was there something wrong with me? Was I not valuable? Was I not wanted?

I remember liking this one girl for two damn years. She obviously didn’t like me back, but my mushy, high school brain deluded myself into thinking, “one day, I’ll get her.” I had no model of what to do with women, so I resorted to Disney Channel love. I’d pay for everything. I’d buy gifts. I’d try to do “sweet” things. Never worked. I had no model of what to do.

Part of being “cool” was getting girls. I wasn’t getting it. So combine that with hearing the sex stories of my friends, this planted a seed of insecurity. I didn’t feel worthy. And I covered this seed with a thick layer of false bravado. I made fun of people. I teased people. I put down others. I tried to make myself feel worthy by diminishing the worth of others. It was terrible.

Somehow, I managed to get a girlfriend in the beginning of college, out of desperation. One thing I remember her telling me, which stood out was “I don’t think I really know you.” I responded saying “I have no idea what you’re talking about.” But it was “yes boy Jeff.” The boy who just did what everyone else did, never anything decided by himself. She didn’t know him because he didn’t know himself.

After we broke up, I thought I could just start fresh and just immediately be “cool.” I could be the person I wasn’t in high school. I thought I could get girls, no problem. But really, I had no clue what to do. I remember in college, a woman I had a crush on invited me over to her place to “watch movies.” I legitimately believed she wanted to watch movies and we just watched movies. I was too afraid to make a move (unless I was drunk).

At USC, the prototypical tall, white, muscular male got all the girls. Since I equated getting girls with being cool, I rejected my asian identity and wanted to become the “tall, white, muscular frat bro.” I wore boat shoes. I worked out and got buff. I played a lot of beer pong. This is what I had to do.

A lot of Asian American men feel this way. They feel envy toward the tall, white guys who get girls effortlessly so they feel a need to reject being asian to get what they want.

That was, until I started seeing videos of “Simple Pickup.” Simple Pickup was a Youtube Channel that would do ridiculous things to get a girl's phone number, like picking up girls wearing a costume, smearing food on their face and getting their number. The two guys running the channel were both asian. And they were getting girls’ phone numbers from all races! My mind was blown.

Simple Pickup taught me you don’t need to be a tall, handsome, white male to get girls. So I started copying Simple Pickup. I’d go outside everyday and try to talk to at least one girl. Sometimes, I’d walk around for hours, just being stuck in my head, before I built up the courage to go talk to one. I remember one instance, a friend and I were at a Japanese restaurant. There was a cute waitress and I tried to get the waitress’ phone number. With zero swag, I fumbled over my words, croaking out a weak “whats your number?” Not sure why but she gave it to me. It’s interesting because years later, she popped up on my “recommended IG feed” and is now a decently successful Hollywood actor.

The topic of asian identity deserves its own post. But similar to me seeing David Goggins run 100 miles, or Simple Pickup getting girls’ phone numbers, I needed to see examples of people doing things I thought were impossible. More specifically, with dating, I needed to see other asian men breaking these hidden stereotypes. These stereotypes like “asian men are weak” or “asian men are nerdy” etc. Every race has these. And the best way to crush limiting racial stereotypes, whether you’re asian, black, white, mexican etc, is to find people to contradict that belief. That’s how we move all races forward and destroy cultural baggage. Every race needs this, I can be that role model for asian men.

As I went out everyday talking to women, I naturally got better and better. I wasn’t looking for serious relationships at the time, but I went on a ton of dates, had flings, and small relationships and gradually built my confidence. But the value wasn’t in getting dates, it forced me to do things outside my comfort zone. I never felt bad after getting rejected. I always felt bad if I didn’t try. This exercise always trained me to take a step forward when I felt a lava of fear in front of me.

I had to get over my fear without alcohol. Fear of making a move. Fear of going for the kiss. So over a three year period, from 2015 to 2018, I challenged myself to get over this fear through comfort challenges. I didn’t limit myself to getting girls’ phone #’s. I’d do a bunch of random things that scared the shit out of me. I signed up for Improv and performed in front of an audience. I did stand up comedy. I’d wear a costume on a random day. I’d introduce myself to strangers. I’d attend events where I didn’t know anyone. I performed a rap in front of 400 people. These years were transformative in developing my confidence.

One of my challenges, was to take a photo with a stranger. This is the stranger.

So going into 2019, with my newfound confidence, dating experience and career moving in the right direction, I had a renewed focus on “dating & relationships.” I went on over 40 dates over the whole year. I felt like I started to figure out dating. I made mistakes. I got catfished. I went on great dates. I learned how to manage my emotions. I started painting a picture of what I liked and disliked. I was a charmander that evolved into a Charizard.

2020 (27/28 Years Old)

I wanted a relationship. I didn’t find it. Rather than take responsibility, I blamed San Francisco. I justified this by thinking that San Francisco had a poor guy to girl ratio. This type of thinking is bullshit. Every city I’ve lived in, people have blamed the place for not finding a relationship. In Hawaii, people said there weren’t enough ambitious people. In NY, people said “its too casual, focused on hook ups.” In Los Angeles, there were “too many flakes”. As Richard Feynman would say “The first principle is that you must not fool yourself and you are the easiest person to fool.” It wasn’t the city, it was me.

My distaste of San Francisco grew like a slow-growing mold. I expected San Francisco to give me what I wanted. I never invested myself into the city. I didn’t try making new friends, I leaned on the friends I already had. I never took advantage of what’s unique about the city (tech scene, hiking, surfing), but I expected things to land on my lap. To top it off, the homelessness was getting worse in the city.

Pair that with stress at work, it was like a two-pronged spear, taking multiple stabs on my happiness. I needed a reset.

In February 2020, I took a 14 hour flight to Sri Lanka. If India and the Greek Islands made babies, the baby would be Sri Lanka. It had the beautiful beaches of an island, but the rustling busy-ness of India. I literally didn’t know anything about the country. My friend and I were there to surf.

If I were a chef and had to craft the perfect meal of camaraderie, friendship, fun, the Surfer Sri Lanka Surf Camp was the perfect omakase meal. The communal areas felt like freshman year of college, everyday, running into a new face, with the common bond of surfing. The sounds of crumbling waves knocked on our doorstep everyday, inviting us into their home. And at the end of the day, someone pelted the sky with oranges, flipping on the perfect orange-juiced sunset wallpaper, while we caught waves.

People from all over the world littered this surfing paradise, people from Austria, Germany, Australia, Sweden etc. They’d have parties every Wednesday and Saturday. We’d surf twice a day, once in the morning, once at night. We’d have communal dinners, eating meaty and mushy Sri Lankan dishes.

It was the most fulfilled I’d felt in a while. I didn’t know it at the time, but I knew now: surfing and community.

This was the missing piece in San Francisco. This was the missing piece in Los Angeles. When I was 21, I needed to allow my inner voice to speak. I needed to go solo. That was what I needed.

But now that I’ve brought my inner voice out, with Jeff 2.0 taking over, that’s no longer what I needed. The most memorable moments of my life were never done solo. They were done with others. This Sri Lanka trip planted the seed of community.

Back when I was a beginner, still figuring out how to surf in Sri Lanka

When I got back from Sri Lanka, work started to pickup. The late nights, the stress, my manager being on my ass, was taking a toll on my mental health, combine that with not seeing a path to promotion, it didn’t feel worth it. With covid exploding, the timing fucking sucked, but I had to find a new role. I stopped dating, I moved out of my apartment in San Francisco and moved back home. My singular focus was to find a new job.

Finding a job during the covid job market was the most difficult thing I have ever done. Every morning, I woke up at 630am, studied from 7 to 10am, then worked from 10am to 6pm. I felt stressed, frustrated, angry. It was my “most difficult” because the outcome was out of my control. My success with Month to Master and biking to LA was 100% in my control. The hiring manager decides job offers, not me.

But what I learned when playing poker, was that you can have a great hand, but still lose. There will be bad beats. There will be moments where the odds are in your favor but still lose. But as long as you play correctly, with a large enough sample size, you’ll have an edge.

After grinding for two months, I ended up receiving 7 job offers and ended up joining Spotify as a Senior Data Scientist.

With covid still running rampant, there was one place I had to go: Hawaii.

2021 (28/29 Years Old)

As the plane touched down on the runway, luscious, green, plant-riched mountains filled the peripherals of my plane window. Silky smooth waves gently crumbled on the soft, white sand beaches. Aloha Hawaii.

People go to Hawaii to escape from their normal lives. During covid, people went to Hawaii to escape to a normal life. A lifestyle centered around hiking & surfing was the perfect environment for a socially distanced world.

Hawaii was my second home growing up. Since my grandparents lived there, I spent summers frolicking across Ala Moana Beach Park, building sand castles at Hawaii Hilton Village and eating at the same damn Chinese restaurant everytime I go. Hawaii was an integral part of my childhood. So on top of the socially distanced hangouts, Hawaii made a lot of sense for me for family.

I didn’t buy a return ticket but I only booked a month on AirBnB. That month turned into six months. Recurring reasons: surfing and community.

Community

When I was 21, my focus was solo-traveling. My mindset was to meet as many people, try as many things, and experience as much as I can. I went to 15+ countries, met tons of people, and experienced many, many things. I loved it. But now at 28, this “exploration” mindset felt empty. My mindset switched from “exploration” to “depth.”

I still wanted to meet people, but my intention was to go deeper with the people that I vibe with. This mindset planted some seeds for a special Hawaii community that I’ll never forget. It started when an old high school friend and I reconnected in Hawaii. We decided to host a BBQ, which lit the fire. There were many tech folks working remotely in Hawaii but in the same boat as me, we had some friends scattered on the island but we didn’t know too many people. But like freshman year, everyone was looking for friends. Combine that with a year of being bottled up “quarantining,” everyone thirsted for social gatherings. This BBQ solved that. Hawaii became “adult study abroad” or “adult summer camp.”

We held more BBQ’s, drove up to North Shore to surf 10 foot waves (with me getting barreled for the first time), late night parties at the amazing Aukai mansion, freediving at Electric Beach, post-work Waikiki surf sessions, full moon surfing, catamaran parties, partying on a sandbar in the middle of an ocean (Kaneohe sandbar). A lifetime of memories tattooed into our souls.

On top of that, I got to meet Youtuber Ken Jee, an amazing person who I call a close friend:

When I reflect on the most cherished memories of my life, study abroad, Hawaii, it was never the place that made the memory. It was the people that made the memory. The things that really matter in life are not the things we buy, places we go or money we make, it's the relationships we have and the people we help. That’s it.

Surfing

When I was a kid, if I had to pick a “passion”, it was sports. I especially loved football. I’d fly through my homework early so I could go play football at the park. I had a damn near encyclopedic knowledge of every football player statistic. I’d devote my entire Saturday & Sundays watching every game. In elementary school, I’d voluntarily wake up at 5am to go to the gym to workout because that's what athletes did. I wanted to get injured. Injuries were a badge of honor (luckily I didn’t). My dream was to become a pro football quarterback.

7 year old Jeff dreamed of becoming a pro football quarterback. As a 5’9, 150 lb asian male, pro football quarterback wasn’t gonna happen. I didn’t have to be a pro athlete, but I could train like one. So 28 year old Jeff found a compromise with 7 year old Jeff: surfing.

If I was feeling anxious about something, I had surfing. If I was dreading a difficult conversation, I had surfing. If I lost all my money, I had surfing (beaches are free :) ). If anything terrible was going to happen, I had surfing.

Surfing became a damn near spiritual experience. Everyday after work, depending on the wave size, I’d take out my board to catch waves:

I didn’t care if it was crowded or if the waves were small, I always had fun. There’s never been a session where I didn’t have fun.

And within surfing, I was able to spread my love for it to others. In 2020/2021, I taught four friends how to surf. The only thing better than surfing, is making someone else’s life better through surfing. Whenever we tackle a new skill, 99% of the time, we’re terrible. For the teacher, explaining the concepts isn’t the most important part of their job. It’s to breathe confidence into the student and get them excited about the skill. Because with excitement and confidence, the student will push themselves to figure things out on their own.

Therapy

I learned that I catastrophize. This means I start believing the absolute worst case scenario is going to happen in a relationship. As I reflect, catastrophizing caused me a ton of anxiety, sleepless nights in relationships. I never realized I had these thoughts, but these thoughts would control my behavior. So I started seeing a therapist to work through some of these emotional bugs.

Moving to NYC

As covid wound down, I left Hawaii to move to NYC. My goal was to make it to NYC eventually. As life began opening up, NYC came back to life. I spent my first 3 months in NYC going out everyday. Like Jordan coming out of retirement, I came out of retirement, partied, drank, went to raves, but this time, from a place of fulfillment rather than need.

When I was 21, I wrestled between two versions of myself. 2021 was when I felt like I fully shed the old, supplicative, people-pleasing version of myself. I felt like all areas of my life were the most aligned it had ever been, my career was growing in the right direction, I fell in love with surfing, I built an amazing community and was dating some super cool people.

2022 (29/30 Years Old)

So in 2022, the mountains in Salt Lake talked to 7 year-old Jeff, attached a rope to my heart and tugged me away from New York City, into the snow capped mountains of Salt Lake City. If it makes you happy, it doesn’t have to make sense to anyone else.

So my friends and I spent a month in Utah, with a singular focus on snowboarding. We watched youtube tutorials grinding to improve our skills, boarding in frigid 8 F/-15C temperature, “sending it” in the terrain park and carving through the snow caps of Brighton, Snowbird and Solitude. It scratched both my itch for athletics and my itch for skill development.

After Salt Lake City, I booked a trip to Denver to board the famous Copper Mountain. On the second run of the day, I tried to do a 360 butter. A 360 butter is spin move on a flat, snowy surface:

My board caught an edge and landed on my right shoulder. I stood up, something didn’t feel right. I wasn’t in pain but it wasn’t a feeling I’d felt before. I couldn’t lift my right arm up.

I boarded down the mountain and bolted for the ER. Yup, clavicle fracture:

I’d been extremely active all my life. Surprisingly, I’ve only had one injury, a concussion from a snowboarding accident in high school. Never a broken bone.

A part of my mind started catastrophizing about the injury. Another part of me was my higher self that kept saying “this is going to make me better than ever.” The reality is usually in the middle. Sports were my main outlet. I ended up replacing it with unhealthy habits like eating junk food, eating “special gummies.” However, I was never down or depressed. Injuries are the price I’m willing to pay for an active lifestyle. Next time, I’ll need to do a better job of preventing them.

Today, I have this scar from my surgery:

It brings me back to that 7-year old Jeff. The 7-year old Jeff who worshiped these superheroes (athletes). I’m 100% today, but the 30-year old Jeff wears the scar like a badge of honor. He wears it like a badge that hopefully 7-year old Jeff would be proud of.

Final Reflection

Reflecting on the last 10 years, key experiences and recurring themes created my set of values:

Disliking my consulting job, month to master led me to become interested in self-education and constant skill development.
Living in Hawaii & Sri Lanka taught me the importance of building community.
Being afraid of talking to girls led me to always seeking discomfort.
Falling in love with surfing, snowboarding and Brazilian Jiu Jitsu reignited my childhood passion for becoming an athlete.
Writing, data science and Building an AI that automated Tinder developed a hacker/builder mentality.
My long talk with Jordan, diving into the science of surfing and teaching my friends to surf reinforced my love for teaching and mentoring.

As long as my life contains these six values, I’ll be happy.