I’m turning 28 in under three months.

This realization hit me harder 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.

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.

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 their pages by tens of thousands of followers from zero in just thirty days.

With each win, the unease grew stronger:

That’s when I realized the true cost of all my years of inaction.

I decided to quantify it.

If I had started at 22 instead of 27 with conservative math and without a viral story:

Year 1 (Age 22-23): Learning - 10k followers, make $1k MRR while learning the game

Year 2 (Age 23-24): Progress - 50k followers, $5k MRR with basic monetization

Year 3 (Age 24-25): Build - 100k followers, $15k MRR with first real offer

Year 4 (Age 25-26): Momentum - 200k followers, $25k MRR in a groove

Year 5 (Age 26-27): Breakthrough & scale - 300k followers, $40k MRR (beats my Google pay)

That’s $1M dollars over 5 years with an extremely conservative estimate as a creator.

All with the skills I already had in me. Making money from work I chose.

All while optimizing for 5% annual raises and early retirement calculators. Instead of dreaming of escape from my job, I could have been compounding real leverage.

For five years, I looked at year 1 and thought “not worth it” without considering the long-tail effects of compounding.

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:

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 what they enjoy than I did at my first “real job”.

I realized that I was envious. Creators (authentic ones) were the bane of my existence because they were a reminder that I wasn’t playing the game I wanted to play. Still playing scared. All while my own 8-year old dreams collected dust.

Here’s the irony.

Psychology shows us a brutal fact:

Loss aversion is 2x more powerful than potential gain.

When I thought about creating content, my brain calculated:

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.

90% of people play game 1 and aren’t even aware of game 2.

Game 1: The Salary Game (the “rational” play)

Game 2: The Sovereignty Game (the spiritual play)

I spent 5 years optimizing Game 1.

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. Telling myself I’d do it after I retired.

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 figure anything out.”

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:

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:

See you next week,

Jim

P.S. If you want to start posting content but struggle with:

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