I was one bad day away from deleting everything.
Five months into content creation.
$21k total revenue and 200k followers.
Hundreds of people transforming themselves in my Personal Brand Challenge.
And I wanted to burn it all down.
I was holed up in a suburban Tokyo Airbnb with a trapezius injury so bad I couldn't put a shirt on. The mattress felt like concrete. I'd been writing 1000-word emails daily, running coaching calls, and creating content for 30 straight days on a folding chair.
I hadn't exercised nor talked to a person not through a screen for over a month.
My brain kept whispering: "Is this really what you escaped Google for?"
When David Park, who built Jenni AI to over $8M ARR, invited me to Seoul, I fought my lone-wolf instincts and said screw it. Maybe getting out of Tokyo isolation would help me see straight.
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The Magic of a Whiteboard
Three days into Seoul, David asked what was next for me.
"I don't know man. I have Creator OS to finish, Personal Brand Challenge 2.0 to plan, and coaching on the table. It feels like I have to double down on this business model or else I’m throwing away everything."
"When I need to make a decision," he said, "I literally write all the options on a whiteboard."
So we wheeled the big office whiteboard over. I grabbed markers and brain-dumped every possible way I could make money. Without filter. Without judgment.
SaaS. Investing. Coaching. Courses. Newsletter. Music. Speaking. Podcast. Affiliates. Physical products. OnlyFans (look, the exercise works better when you don't censor - more on this in a bit).
Getting everything out on a whiteboard isn’t just some woo-woo trick. Psychologists call this externalization — when you unload your brain onto paper, you actually reduce cognitive load and see options more clearly.
I ended up with a whopping 30 options.
Then we ranked them. Not by what I "should" do. By what criteria on things that actually mattered to ME:
Enjoyment.
Lowest operational load.
What I want to be known for.
Speed to cash. (missing from photo)
Once it’s out of your head, patterns appear. Rank by what matters to you and you’ve built a decision matrix.
This exercise forced me to take a step back. It made me realize that I’d trapped myself into a false binary of continue doing things the same way or burn everything down. I’d been too zoomed in to think rationally.
Psychologists have a term for this called cognitive defusion: creating distance from one's thoughts, rather than trying to change them, to reduce their influence and increase one's power over them. That’s what the whiteboard exercise did for me.
The Second Revelation
A week later, I stumble on this Taki Moore video (guy who has coached Hormozi). His client says "I love coaching but hate sales calls."
Taki's response? "So don't take them. Sell in DMs."
The client did. It worked.
Wait. You can just... not follow the "rules"?
I thought back to times when I had broken so-called rules:
“You MUST be a technical genius to pass Google software engineering interviews” — I wasn’t. I leaned into being collaborative and personable.
“The ONLY way to make money is with a job” — I made money as a creator with <15k followers.
“You MUST take sales calls to sell high-ticket” — I sold coaching with a sales page + email.
“You MUST be an elite writer to monetize” — this newsletter just got its first sponsorship; I’m not a pro writer.
Then, I started deconstructing my own recent burnout:
Daily emails burning me out? Try pre-writing them.
Discord management exhausting? Cut the complexity.
Coaching tangential to the challenge too much? Just don't offer it.
This two-step process began to neutralize my crisis.
The Brainstorming Exercise (When You Feel Trapped)
When you feel trapped - whether it's wanting to quit your job, burn down your business, or even picking where you want to eat:
Write EVERYTHING down Every possible option. Even the stupid ones. Especially the stupid ones.
Rank by YOUR criteria (you can use these for inspiration)
Energy (gives or drains?)
Finances
Values alignment
Regret factor
Question the "rules" For each option you’ve been stuck on, ask: "What rule am I following that might not exist?"
Hate meetings? Just don’t accept them
Hate being a manager? Stay solo
Hate your industry's standard model? Create your own
Follow your heart. Once everything is out of your brain, no amount of strategy or rumination will help. Flip your whiteboard (like David did for me) or the piece of paper. All that’s left is to follow your intuition.
I started writing this newsletter again because of that exercise. It’s why I’ve been sending them weekly for the past three weeks. The irony is that as soon as I started writing again, I landed my first newsletter sponsorship (that I actually wanted to do and was financially worth it). Life’s a funny thing.
Now I can’t say this is some sort of overnight panacea and that you’ll never doubt again. But it helps you to zoom out and gain perspective. My whiteboard has haunted me for weeks now and keeps me hoest. Once you see what you really want, you can’t hide from it anymore.
So try it out! I’d love to hear how it goes.
See you next Thursday,
Jim
P.S. I’ve started posting my newsletters on my Substack. If you want to read past newsletters like “How I Gained 45K Followers and Made my First $1K Online”, subscribe over there.