You know those “oh shit” moments where you realize you can never go back to how life once was?
On Christmas Eve in 2023, I had one of those moments.
Standing at the large dinner table with a plate of food in my hand from the potluck, I waited my turn as my family friend’s father made his way down the table to introduce everyone there.
“…we warmly welcome Andrew… from Michigan!”
“…and Channing… from Florida!”
Then he arrived on me.
“And we want to warmly welcome Jim… from Google!”
The room laughed as my friend joked with me, “You got a little shoutout.”
I was the only person introduced by their company name.
Underneath my own smile, I had a realization: I didn’t feel good about it. Not because I’m some shining beacon of humility. But because this moment was what I had always wanted since I was a kid.
That immigrant kid who used to eat family-sized bags of Lays while grinding League of Legends until 2am in the basement had somehow made it to the point where all the Asian parents in the room gave him their subtle nods of approval.
And inside that realization, I thought “oh shit”.
I climbed the exact mountain everyone told the twelve-year-old version of me to climb.
But it wasn’t the one I chose.
Sleepwalking
“I did fall asleep for a few years. I got caught up in the little life there. It wasn’t my dream, but it was dream adjacent. It was close. It put my ambitions to sleep for a little bit because I was happy enough.”
— Quentin Tarantino, on working at a video store before making films
I remember seeing the look on my parents’ faces as they toured the Google NYC office. They marveled at the office space. At the symbolism it held for immigrants who came here with nothing to their name:
The American Dream.
Maybe you know this feeling.
The feeling of guilt for living a life where you should feel grateful. You’re on track. Working a good job. Setting yourself up for marriage, a white picket fence, and maybe a kid or two.
Everything you should want.
And yet… a voice inside you can’t help but yearn for more.
For over a year after that Christmas Eve, I felt nothing but that yearning.
I couldn’t tell anyone - much less my parents who would think I’ve gone insane.
“You get free food! Remember?”
I watched endless YouTube videos, listened to podcasts, and read books about entrepreneurship.
All while feeling time slipping by like sand in an hourglass. Days became months became years. And I never felt more stuck.
Deep in my heart I knew this was the moment I'd been waiting for. AI was turning people into one-person companies. Social media was favoring new creators. And I was sitting on a decade-old dream of being a YouTuber and a five-year-long dream of building something of my own.
Ignore the distractions! Keep walking on the “right” path! It’ll get better after one more promo!
A full year of paralysis later, I finally jumped.
April 1, 2025
I remember sitting on my Jersey City apartment couch, mic in hand, fingers bone cold. My body was literally shaking while I stared at my iPhone lens on a $20 Amazon tripod. Underneath it all, thinking: “What the fuck am I doing with my life?”
Let me just wait another day… when I’m more qualified. When I’m feeling ‘ready’. Let me just wait like I… always do? Let me just wait another… five years?
I recorded an hour’s worth of retakes for that 1 minute video with a voice that shook and cracked. I edited the video while gritting my teeth and cringing at my own voice. I relived all the doubts and insecurities I ever had about myself.
And five hours later, against every logical objection in my head, I hit that blue “Share” button on Instagram.
The night before, I had written down in my journal while I was sitting in bed “COMMIT FIFTY DAYS”. Fifty days to make $1,000. Fifty posts to document the journey. No matter if one person or a thousand people saw it, I was going to show up every. single. day.
And from that first post, my entire life changed.
One of my videos went viral. The rest didn’t. I didn’t care. Because I was doing this for me.
I posted day 1. Then day 2. Then day 3. Every day I fought the cringe, and with each post the wall that towered over my psyche started to crumble away.
“Who am I to create?”
”What value do I possibly have to give?”
“My friends, family, and everyone I ever met is going to judge me.”
“I’m nuking my entire professional career.”
“I look and sound so cringe.”
“Tomorrow. Next week. Next year.”
All of those subtle, insidious beliefs that told my subconscious that I never believed in myself started to alchemize.
On Day 16—after putting up a pre-sale for a course on how I landed my five tech offers—came the first sale I ever made. A $29 Stripe notification:
In that moment, reading that email on my phone, I literally felt like I was on drugs. Someone… paid me. Someone paid… me? Someone paid me!
A shit-eating grin spread across my face. I couldn’t hold it back. I got up from my office chair and danced in my apartment bedroom like that Squidward scene from Spongebob.
Thankfully, this was never captured on video.
But that was the moment my world broke open.
I can do this.
Several exhausting weeks later on Day 50, I finished my first ever product launch. $1.3k in 24 hours.
I kept my promise. 50 days. 50 posts. $1,000.
What Happened Next
I flew to Japan to travel the world while making content and money.
That should have been the happy ending, right?
I ended up in a suburban Tokyo Airbnb with a trap injury so severe I couldn't lift my arm to put on a shirt. The mattress felt like concrete. My "desk" was a folding chair I bought for $20 from Don Quijote and a tiny round floor table elevating my laptop.
For 30 days, I guided people through the exact transformation I’d gone through with posting every day. I synthesized all my learnings into emails to over 3,000 people, managed a Discord community, ran group coaching on personal branding at a price I was terrified to sell, and fought through the pain of wondering if I’d just traded one kind of suffering for another.
There was one night in that apartment where I talked to my phone camera about how I’d avoided music my entire life - the thing I loved since I was twelve - because it didn’t seem “practical.”
The irony wasn't lost on me: I'd quit Google to follow my dreams, and I still couldn't stop running from them.
I didn’t post it. I made a promise to the people I was guiding through that 30-day challenge after all.
By the end of the 30 days, trap still throbbing, I crossed my first $20k month.
Two months later in Taiwan, I landed a $15k brand deal only to learn how difficult promotion is for me. I found myself putting off the promotional reels until the last minute.
And two more months later, to overcome that fear, I launched The Viral Playbook from my hotel in Bangkok and made $29.5k in the span of three weeks.
Through all these trials and tribulations and all the pain, the same guy who was doing $1 Instagram shoutouts on Day 20 of 50 Days to $1K and originally thought “I could never,” had figured something out.
Coming Home
A workaholic lifestyle and countless stories later, I finally came home from Asia.
I got to see old friends and feel like I re-entered society. They told me I “had become someone new”. I appreciated their compliments. But something felt a bit off.
It wasn’t until a month later, at my 28th birthday, that I understood why.
As I drove our 14-year-old Lexus around Atlantic City, my parents said the same thing. That I had changed.
Upon hearing that, my sister-in-law interjected, “No, I don’t think so.”
“I think Jim became more who he always was.”
Where I Am Now
If you're still on your 'perfect' path—LinkedIn looks great, parents are proud, bank account is fine, identity is validated—but that quiet voice won't shut up? I have to be honest with you.
By every one of those metrics, my life is worse.
I currently make less money than I did at Google. My would-be steady $350k+ total compensation is gone. And while I’ve made real revenue, it’s inconsistent. One month can be $30k+ if I successfully launch a product or run coaching. Or it can be near-zero if I fail to make a compelling offer or get too scared to sell. Stability is gone in exchange for true meritocracy.
I currently work more than I ever did as an employee. Not the performative "busy" of my previous corporate jobs. Creating content, writing newsletters, building products, responding to DMs, managing my own anxiety about whether this is all going to work with my face attached to everything I produce.
Not many people understand this path. Friends and family still don’t “get it” and probably never will. At Christmas Eve dinners, I went from “Jim from Google!” to “the guy who quit a $350k job to post on Instagram.”
And I wouldn’t trade it for anything.
The version of me at that Christmas Eve party was performing a role. He got good enough to fool everyone, including himself.
The version of me now is constantly learning who he actually is. It’s 10x messier. It’s 10x scarier.
And yet, it feels infinitely more alive.
In Closing
It’s been two months since I’ve last written one of these articles. I spent the holidays reconnecting with family and friends after my adventures abroad.
And after this time off and a bit of soul searching (as always), I realized something important: Quitting Google didn't change my life.
It was showing up and doing what I always wanted to do. Every day until I rewired my identity. For me, that was posting content.
And while it made for a great story, I now understand I didn’t need to implode everything in my life to do that.
So I'm working on something for the people who've been 'meaning to start' for months or years even. More on that later.
Appreciate you as always, and talk soon,
Jim
P.S. If this piece hit something in you, reply and tell me what you've been 'meaning to start' for months. I’ll be reading every single one.