Becoming a Rapper

Losing, Learning, Growing

Part of 2 of 3 in Arrivals
By Jason Chu
Illustrations by Maggie Chiang
Nov 01, 2016 | 10 min read
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Jason’s passion for rap was strong, but he still had no idea what art was and what success meant.

You know what freedom feels like? It feels like jerking awake with the gut-wrenching realization that I have no one to blame but myself.

It was the morning of June 13, 2012. I had been living in Los Angeles for all but 24 hours — and I was ready to leave.

Mission had prompted my move to LA: I wanted to speak hope and healing through hip-hop music. For two years in Beijing, as part of the underground Chinese rap scene, I'd seen the way music could voice unheard stories. It connected people — weed dealers, art gallery owners, missionaries — who would otherwise be strangers, and made them comrades. While working in China, I began to dream about using rap to tell my story, as a first-generation, Chinese American, Yale grad, self-harm survivor, and Christian, and the stories of my family, my friends, and our generation.

It was a dream that inspired me to change the course of my life, redirecting my path to land in Southern California, the epicenter of all that inspired me: the entertainment industry, the rising YouTube community, and the Asian American experience.

But now, lying miserably on a bare futon mattress, my inner voice jabbed at me — "What are you doing? You have no idea how to make music, and you definitely don't know how to do business. Everyone here in LA is cooler, more in touch, and more talented than you ever will be.

"Quit while you can. Run back to Beijing, to the church, back into college ministry. At least there, you knew what you were doing. There, you had friends. There, you were safe.

"You'll never be able to do this."

Losing, Learning, Growing

Have you ever felt the challenge of keeping your balance
As you walk down the line between naïve and callous?

My first month in LA was a feverish dream, painted against the dry heat and immigrant culture of Monterey Park. A Chinese/Vietnamese/Mexican suburban town just east of LA on the 10 Freeway, I'd never seen anything like it before: strips of massage parlors, dental practices, and convenience stores with signs in Chinese, Vietnamese, and occasional English. 

I was staying in a backhouse there, a patch of water-starved grass and cement, with two comedian/rapper friends in the beginning stages of their own YouTube stardom. My mentors and roommates, they introduced me to LA through their eyes. They showed me streams of Asian kids leaving the club en masse at 2 a.m. to continue the party at the all-night Hong Kong café. I followed them to the park down the street, and saw the local kids' eyes turn big when they saw my YouTube-famous friends. Through them, I was introduced to Mexican culture — baked into the land, from the elotes cart crawling down our street, to the 24-hour King Taco, to the Spanish street names.

I was a world away from Delaware's Italian/Dutch/Anglo culture, with its plentiful pizza places, pasta joints, and sandwich shops.

I drove around the city overwhelmed, soaking it all in — so dazed by the unfamiliar landscape, that I hadn't even yet realized the biggest challenges facing me .

From One Asian Rapper to Another 

By September 2012, I'd started coping with the fact that LA's lifestyle and culture were totally unfamiliar to me. But I began noticing a second way I was thoroughly unprepared for my self-proclaimed mission: I knew how to rap, but I had no idea how to be a rapper.

After arriving in LA, I'd recorded some songs, shot a video or two — and waited. As the weeks turned into months and no one came calling to book me for shows, sign me with a manager, or collaborate, the revelation came: I was going to have to change how I worked. I had to start doing business.

 Around the end of the summer, one Sunday morning at church, I met Tran. A slightly older, self-proclaimed salesperson, entrepreneur, videographer, and actor/ex-rapper/DJ, he seemed exactly like the kind of person who could guide me forward. 

Eager for help, I asked if he'd be interested in partnering. I laid out a blueprint for our collaboration: he'd handle business, infrastructure, and contracts/negotiations, and I'd provide content, artistry, and creative direction. He seemed cautiously open to the idea — which was a huge step ahead of anyone else I'd met.

We inaugurated our potential movement forward with a trip to perform out of town. While the show went well, I started noticing elements of our still-young friendship that seemed like red flags. He spoke about building infrastructure and managing other artists, but seemed uninterested in networking or playing the roles I'd imagined an artist manager would. For my part, I was trying to be an artist, but my songs, written during evenings and weekends in Beijing, were generic and mediocre. 

A few weeks after returning to LA, Tran and I met up to talk about shooting a music video — a meeting that didn't go well. I thought his pitch was clichéd and over-budgeted, and told him so; he stormed off, and later that night, shot off a string of frustrated texts, railing at me for my lack of authenticity, my lack of leadership, and how I'd used him.

"I don't believe you. You aren't hip-hop.

"You're not a rapper — you're just pretending."

My phone buzzed and shook as Tran's angry texts flooded in. I read them, half fuming at their disrespect — and half already dismissing him as small-minded and ignorant — anything to ignore the fact that he might be right.

With that relationship broken, I found myself back at square one: unprepared and overwhelmed, with little-to-no support network. Sitting in the office of the Reverend Ken Fong, one of my few mentors and allies in town, I griped: "I feel like I'm so behind, Pastor Ken. I'm 26, and I have no idea how to do business, how to lead people — shoot, even just how to take care of them. I want to be a rapper, but all I know how to do is talk about stuff — I have no idea how to make people feel what I'm saying."

As a 30-year ministry veteran, 20 of them as head pastor, Ken spread his hands and looked at me — "Jason, you're young. Don't worry about being something you're not yet — just keep growing."

I walked away comforted but still hearing that voice in my head, nudging me:

"You'll never be able to do this."

Losing, Learning, Growing

"Garden State" was my praise song, "500 Days", my drug
Every new crush, a new rush, a new first kiss — now I'm drunk

I met her at a weekly prayer meeting I'd started attending a couple of months before. She walked in chatting with a couple of girls I knew, friendly and animated. After prayer, a bunch of us headed to dinner at Myung Dong Kyoja, a noodle restaurant in Koreatown, where we started to dominate the conversation at our end of the table — rapid-firing questions and responses at each other. By 3 a.m., when the restaurant closed, we were high on conversational energy, and headed to the nearby 24-hour coffee shop, where we kept discovering mutual friends, passions, and convictions.

Four hours later, the bright LA sun lighting up the all-glass front of the shop, we parted — but first, I had to play her this track I'd told her about. I couldn't let her go without her hearing it.

I've always found it hard to let go. Ever since I was a kid, relationships had always slipped out of my grasp. Let me rephrase that: Healthy relationships had always eluded me.

Homeschooled until high school, when my rapid progression through our curriculum forced my mom to admit that I needed educational resources beyond her ability to provide, I'd never felt like part of the cool crowd.

I'd never felt like part of any crowd.

As a conservative Christian kid in the height of the "I Kissed Dating Goodbye" phase, I'd definitely never dated.

The best way to create an idol is to make it a taboo: Nothing is more simultaneously scary and desirable than uncharted territory. And just so, women had been a weakness for me: I'd fantasize, not about sex — well, about that too — but about love. And my deepest fears were tied to them too: that I would never experience affection, be forever alone and unattractive. 

So when I met her that night, and in the torrent of texts that followed the next day, and then as we started hanging out for 12 to 30 hours at a time, it was so easy to lose myself in "us". Elated by the rush of our chemistry, and especially in a city still new and lonely to me, I let go of discipline or motivation, and instead gave myself over to a new obsession. 

After binging on emotions for stretches of hours to days, we'd separate, and I'd find myself back where I'd been before, or even worse: guilty for wasting time, keenly aware of the months passing, and alone with the knowledge that I was failing to be a musician.

The voices kept on:

"You'll never be able to do this.

"You're not a rapper — you're just pretending." 

Tired of feeling weak — too tired to not repeat
Staring at the mirror, I fear what I see
— Live If I Breathe

You know what depression looks like? 

Depression looks like sleeping through the day, waking up to eat and watch TV for a few hours in the evening, and falling asleep again without ever seeing the sun.

I'd moved to California with two goals in mind: I was going to pursue a career in music while attending part-time classes at Fuller Theological Seminary toward a master's degree. It was a plan strategically calculated for maximum impact: I'd invest three to four years in seminary and music, and in return, build a sustainable musical following and earn academic credibility. By the time I hit 30, I'd be ready to change the world: a rapper/minister with a master's degree in intercultural studies, an established audience, and interdisciplinary credibility in academia, the arts, and ministry.

By the summer of 2013 — my one-year anniversary in Los Angeles — that neatly framed timeline was blown to bits, scattered across the brown grass clinging to life on my lawn.

I was living in Pasadena in a small house with a couple of other guys from Fuller and my church — and making no discernible headway on my music. Dismayed, I numbed and comforted my growing anxiety over this failure by losing myself in my relationship and in sleep, throwing away entire weekends or weeks staying up all night on our living room couch, binging on TV shows, cuddling with my girlfriend, or reading incessantly.

The truth was, while coming to faith had resolved the vast majority of my emotional and spiritual vacuum, I still had insecurities and needs that dug deep under what I'd imagined to be my well-manicured surface.

"All art is a response to trauma."
— Charles "Chucky" Kim

Looking back, my failure as an artist was no surprise; I was completely unprepared to be one. I had no idea what art is and what success means.

Ever since my youth, I'd been labeled a "gifted kid". In the 99th percentile on standardized tests, I was reading years above my grade level. My ability to perform won me praise and attention — from parents, Sunday school teachers, peers.

Everything I had — approval, friendships, relationships, success — had always come from my ability to measure up to someone else's standards. And so, naturally, I was constantly seeking validation. Affirmation. Pats on the back.

Even as I took the step to move to LA — ostensibly to pursue and value my music — I was looking for a ladder to climb. I needed an authority figure, whether that was YouTube's view counter or my Facebook "like" numbers, to affirm that my art was meaningful.

In depression, feelings run high but energy drops to an all-time low. This should have been a time when art — which thrives on emotional overflow — became a place of retreat, comfort, and processing. But instead, I found my creativity slowed, choked off by my inability to stop performing and actually start living.

As I hosted this WrestleMania between my heart and head through the first half of 2013, I came to realize that there was yet another blind spot obscuring the road ahead ...

Losing, Learning, Growing

And I know my numbers don't compare to you
'cause honestly? I never wanted to be near to you
— Sound & Fury

"Man, who cares about all that abstract crap! It's irrelevant ... nobody wants to hear that. It's all about making it easy for the audience to like you." 

Derek's words rang through my head for months after we'd fallen out. A fiery and opinionated YouTuber, whose year-old channel was already getting major views, he was a mentor and partner in my early days in LA.

Derek was everything I wasn't: clever at business, good at building up a team, and had strong vision for what artistic success would mean. He was a strong and natural leader — so natural, that I never bothered to check in with myself about whether or not I agreed with where he was leading to, or what he was making.

I'd already seen it happen often in our short time together. Derek would work with someone for a period, until they disappointed him. Then, he would label them "weak" and, sure enough, they would start to drift to the periphery, until they were no longer collaborators.

A periphery where I eventually found myself as well, exiled from the inner circle, observing from a distance as his numbers kept growing — hitting six figures, then seven. At the same time, my analytics dwindled: most videos barely getting a thousand views, my songs getting a few hundred. Show offers weren't coming, and I was making no headway in finding any place in the LA entertainment/artistic/cultural circles.

I was unquestionably a failure ... Or was I? 

We been a mess — but nothing's been amiss
You gotta break some eggs every time you make an omelette
— SPEAK (feat. Chance Calloway)

So there I was, by the summer of 2013: addicted to a relationship I wasn't ready for; incessantly distracting myself so that I could ignore my lack of ability to create the music I'd supposedly moved halfway around the world to make; fallen out with the very people I'd relied on to guide my art. The little progress I had was neither fast nor big enough to live up to my own expectations of perfection, and so I discarded budding explorations of growth before they could ever flower.

This was where I was when the message came through my Facebook page at 8:56 p.m. on May 5, 2013:

"Aloha Jason, enjoy your work. If you, or any young Asian American ministers are interested in spending time in Hawai'i, let me know. We have a visiting minister's program, and I would like to focus on getting the message out to our young adults. Aloha, N. C."

And so, on August 21, 2013, I flew 2,500 miles from Los Angeles International Airport to Hilo International Airport, on the extremely rural side of the Big Island of Hawai'i, to serve for five weeks as a visiting minister and artist-in-residence at the Church of the Holy Cross.

Long as Mauka we look and see the ageless peaks
Grave is no burden —
We tire, and we sleep, but we rise.
— Untitled, Sept. 29, 2013.

You know what freedom feels like?

Freedom feels like freestyling for a classroom of eighth graders more excited about my presence than my views, subscribers, or sales.

Freedom feels like a long, open afternoon spent writing songs in my living room, as the wet lawn stretches lush all the way down Lanikaula Street to the shimmering ocean.

Freedom doesn't lie in saying what I think people want to hear. It's not saying what people are willing to hear, or are ready to hear, and not even what they need to hear.

Freedom means saying what I need to say.

Freedom doesn't mean that the voices stop. But it does mean that they no longer matter.

I discovered freedom in Hawai'i.

And as I did, I began writing songs, and a project took shape — an album I'd come to call "MILLENNIAL". 

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Jason Chu

Jason Chu is a rapper on a mission to speak hope and healing in a broken world. He tells stories of a generation wrestling with fear and joy, greed and hope, hurt and healing. For more information, visit and

Maggie Chiang

Maggie Chiang was born to a Taiwanese family in the City of Angels and is a full-time artist and part-time dreamer. Inspired by places both real and fictitious, her illustrations evoke a longing for adventure and the pursuit of the unknown, exploring impossible landscapes and places unseen. You can find her online at

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