I’m turning 28 in just under three months.
This realization hit me differently than I expected.
I held some dreams in my heart since I was a kid. Buy my family a big house. Become a YouTuber. Be as fit as a superhero.
Back then, it felt like I was brimming full of potential.
With my life almost one-thirds over, I have come to terms with the fact that I have spent a lot of my life in the waiting room.
Growing Pains
A brief 10-year recap:
At 17, I told myself “once I get to college, I’ll finally start taking life seriously.” Instead, I spent four years playing endless video games, skipping all my classes, watching hundreds of anime, and joining a fraternity out of desperation to fit in.
At 22, I told myself “once I get the high-paying job, I’ll be ready.” I landed American Express and learned I hated corporate. Escaped with ten hours of World of Warcraft daily and ballooned up to nearly 200 pounds.
At 24, I started working at Google and felt like I was finally turning things around. Cut down the weight and video games. Got a girlfriend. But I started living on autopilot.
When I turned 27, I was fit and making more money than ever. And I was depressed.
Because I finally saw the facts: I had played small for my entire life.
In April of 2025, I started playing to win.
And I learned just how costly my last decade had been.
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The Viral Playbook limited launch pricing ends October 25.
If you have interests, skills, or expertise you want to share with the world and actually get seen, consider enrolling here.
The Turning Point
From April 2025 to September 2025 (6 months), I went from 0 to 300,000+ followers and made $36,180.
All while in the midst of a third-life crisis, navigating rapid identity shifts, and jumping from country to country.
When I posted my first viral video about quitting Google, it was a storm of dopamine. But underneath it all was a growing sense of unease.
“Did I have it in me all along?”
I thought that first viral video was a complete fluke. I’m no content creator. I gave up that YouTuber dream when I was twelve years old.
But something had lit up inside me.
I studied content obsessively and posted daily -sometimes twice a day- for 50 days.
I managed to go viral a second time. A third time. A fourth time. Launched a full-suite tech offer course that helped people land interviews at Google and Apple and got me my first internet dollar (the first dollar feels better than the next ten-thousand).
Four months in, I hit a $20k month while in Tokyo despite having a massive trapezius injury and perhaps the worst ergonomic setup known to man.
All while guiding students to overcome their fear and making their first posts.
Some even used the email lessons I wrote to grow tens of thousands of followers from zero in just thirty days.
Both Wingo and Sukrita grew to these results after 30 days of daily posting:
And they ended up having similar realizations as I did.
While every win felt good, the unease grew stronger:
I am capable of figuring my own sh*t out.
I did have it in me all along.
That’s when I realized the true cost of all my years of inaction.
I decided to quantify it.
The Cost of Five Years of Inaction
If I gave myself 5 years with conservative math, no viral story, and no skills:
Year 1: Learning - 5k followers, make $1k MRR while learning the game
Year 2: Progress - 20k followers, $5k MRR with basic monetization
Year 3: Build - 50k followers, $15k MRR with first real offer
Year 4: Momentum - 100k followers, $25k MRR in a groove
Year 5: Scale - 200k followers, $40k MRR (beats my Google pay)
That’s $1M dollars over 5 years with a conservative estimate.
But I never looked at year 5. I always looked at year 1 and thought “not worth it”.
The Costs I Didn’t See
The money is obviously painful.
But I also want to talk about something deeper: the cost of living half a life.
From 22 to 27, I was:
Living life “right” but secretly miserable
Saving obsessively for early retirement
Never questioning the script
Waiting to “eventually” create
I told myself I was being practical. Strategic. Smart.
The content creators and entrepreneurs who I saw posting their stories online? Idiots. Can’t they see how embarrassing they are?
Gut check: those “embarrassing” content creators are making more money in college doing their own thing than I did at my first “real job”.
A month ago, I met Sebastian, a 15-year old follower of mine in Bali. He asked me if he should consider skipping high school. Why? Because he was about to out-earn his father’s salary through content creation.
The creator economy is insane. But I’m still conservative enough to say stay in school :)
Looking back, I realize that I was envious. Content from others was a constant reminder that I was still playing scared.
Here’s the irony.
Smart People Stay Small
Psychology shows us a brutal fact:
Loss aversion is 2x more powerful than potential gain.
When I thought about creating content, my brain calculated:
Potential loss: Credibility, respect, “looking stupid,” wasting time, failure
Potential gain: Maybe followers? Maybe fulfillment? Maybe money someday?
The losses felt astronomical and idiotic on paper. And the gains were so abstract.
If you’re smart, you take the logical path and you get really good at ignoring your pain. And the sad thing is... you’re rational for doing so.
On paper. But not in spirit.
The Two Games
90% of people play game 1 and aren’t even aware of game 2.
Game 1: The Salary Game (the “rational” play)
Trade time for money
Build skills for someone else’s business
Optimize for job “security” and 5% raises
Hope the company doesn’t lay you off
Retire early with a modest lifestyle if you’re lucky
Game 2: The Sovereignty Game (the spiritual play)
Work hard, but build owned assets (audience, products, systems)
Develop skills that layoffs and “bad job markets” can’t take from you
Capture value you create directly
Retire never (you’re perpetually moving towards fulfillment, not just tolerating pain)
I spent 5 years optimizing Game 1. I did it well.
Reverse-engineered happiness from the societal formula itself.
Except I wasn’t happy. Because it wasn’t my formula.
And after my friend got terminated in the first wave of Google layoffs in 2022, I realized something uncomfortable: I was absolutely terrified of being let go.
I’d lose this paycheck that I didn’t know if I could ever get again. I’d lose my entire identity around my title. The job market was terrible. I was on constant defense.
No audience. No distribution. No owned assets.
No agency.
For over ten years, I played game 1 and dismissed game 2 as sheer, delusional fantasy. I didn’t even try.
If I could go ten years back in time, I’d shake seventeen-year-old Jim by the shoulders and scream at him to wake the hell up.
“You’re not crazy for wanting more. You can figure it out. You can do so much more than you even realize.”
Action
If you’re reading this and thinking “I should have started years ago,” or “Maybe it is possible,” you’re feeling what I felt.
That pain is your brain telling you something’s wrong.
I’m not saying quit your job tomorrow. I’d be a hypocrite. I had an abundant safety net and even I was terrified.
But I am saying this: Start building your owned assets now. Start developing independent skills now. While you still have the safety net.
Become so damn independent that a job title can’t define you.
So autonomous that when layoffs come, you hope for severance pay while your coworkers gossip in a panic.
Every day you delay starting:
Fear grows bigger
Identity solidifies
Regret gets heavier
Compounding goes both ways.
Five years from now, future you is going to be somewhere.
Would they be shaking you by the shoulders and screaming at you to wake up?
If the answer right now is yes, ask yourself this:
What action can I take today such that 5-year future me would pat me on the back?
Then go do it!
See you next week,
Jim
P.S. If you want to start posting content but struggle with:
Self-doubt
Thinking it’s all luck
Having no concrete plan
The Viral Playbook gives you the step-by-step systems I used to go from 0 to 300K followers from scratch in six months.
Limited launch pricing ends on October 25. You can enroll here.