Last week I discovered something that made every single one of my achievements feel like elaborate self-deception.

The Question That Changed Everything

I was working from my Bali AirBnB in a corner when this thought experiment appeared:

“What would you do tomorrow if your parents were already dead?” (I know it sounds dark, but stay with me - this isn’t about loss, it’s about clarity)

Not “what if they died” (that’s about grief).
Not “what if they disappeared” (that’s about loss).

What if they’d been gone so long that seeking approval no longer made any sense?

I sat there dumbstruck. My mind felt like it had been shattered.

Because I realized: Every single decision I’d ever made - even quitting Google - was still predicated on their validation.

Why My Independence Was An Illusion

Let me paint you a picture of eight-year-old Jim.

My parents would promise we’d stay at family parties “just a short while.” Three hours later, I’d be standing in the corner while adults talked about mortgage rates and humble bragging their own children’s achievements in Mandarin.

I’d beg to stay home. They’d drag me anyway. I’d want to quit Chinese school. Had to go anyway. I’d want to play video games. Internet would get shut off.

To be clear: My parents wanted what every immigrant parent wants - security for their child.

But as a wee lad, the way I crystallized it in my mind was this: Your desires don’t matter.

So I developed a strategy. Say “no” to everything first. Create friction. Make them work for my compliance. At least then I’d feel like I had some control.

I never stopped doing what they wanted. I just made it messier.

Parent’s want: Stop playing video games and succeed in school
My rebellion: Became gaming addict for a decade... then proved I could still succeed despite it

Parent’s want: Stability above all
My rebellion: Leave a $350k job... after hitting $750k net worth

Parent’s want: Successful son with a stable, prestigious job
My rebellion: Quit Google... to chase more money my own way

No matter what I did, I ended up where they pointed. I just took the scenic route to feel autonomous.

The Uncomfortable Truth

I’d love to tell you I’ve figured this out. That after this realization, I immediately started living fully authentically.

But I’m writing this newsletter and still calculating how to “win” at quitting Google.

The difference is now I can see the pattern. And I feel blessed to have that awareness.

That’s why I wanted to share this newsletter with you today.

The Three-Filter Test for Authentic Desire

After wrestling with all this, I started looking for answers. What do I actually want?

I came up with three filters:

Filter 1: What would you do if you were guaranteed to succeed? (Removes fear of failure)

Filter 2: What would you do if you already had $100M? (Removes any fear of going broke)

Filter 3: What would you do if you were guaranteed to fail? (Removes ego)

Whatever survives all three filters might be your actual truth.

For me? Creating survived. Not “content creation” or “building an audience.” Just... making videos. Playing music. Writing stuff. And maybe even livestreaming. The same stuff I killed at 18 because it wasn’t “practical.”

The number one deathbed regret isn’t about money or success. It’s “I wish I’d had the courage to live a life true to myself.”

Not “true to society’s expectations.”
Not “true to proving them wrong.”
Just true.

So these coming weeks I’m trying all the things I mentioned.

Try the three-filter test yourself.

Don’t be surprised if at first, you find only silence. It happened to me. And it was the first honest moment I’ve had in a decade.

Because once you stop performing - even performing rebellion - you might discover who you actually are.

At least, that’s what I’m hoping.

See you next week,
Jim

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