What AI Found in 9 Years of My Private Journals
Using nine years of journal entries in Google Docs, I exported them as TXT files, uploaded the files to ChatGPT, and asked AI:
“What do you make of these journal entries l I've kept since 2016? What are things I might not realize about myself, or goals that it seems like I want but aren't achieving?”
Some of the observations were gut checks!
I pasted the whole reply below, maintaining AI’s emoji formatting. My reaction is at the bottom.
Some stuff that felt too personal was censored with brackets, as in [you’ll never know what this one said] 😉
ChatGPT’s Initial Assessment
Thank you for sharing your journals. After reviewing entries from 2016 through 2025, I’ve pulled together key patterns and insights—some of which may be things you already know, but others you may not have explicitly noticed or connected.
🔍 1. You Have a Deep Desire for Alignment Between Mission, Work, and Spiritual Calling
Across nearly all the years:
You regularly express discontent with work that feels misaligned or mediocre (e.g., [Company Name], [Military Position]).
You crave “your own thing” and a sense of mission. In 2025, that centers around Christian leadership and a personal brand. In 2019, it was eBay/Amazon listings, sales, or real estate.
You often write things like:
"How can I be so blessed and feel so lost?"
"I don’t feel like I’m entirely aligned with the correct mission."
🟨 What you may not fully realize:
You’ve already defined your mission multiple times—what’s missing is consistent long-term commitment to seeing it through.
You write with clarity about wanting to lead, teach, and build—yet return to conventional work out of necessity or lack of traction. There’s an unresolved tension between calling and comfort.
🧱 2. You Are Consistently Building, But Often Shift Tracks
From eBay and car sales in 2019 to the 4x4 Recall brand in 2024–2025, you constantly generate ideas and execute with discipline:
“Day 100 of publishing short-form content”
“Sold seven cars this month”
“Paid off both cars, planning rental investment, publishing daily”
🟨 But:
You often hit the "slog" phase—when initial excitement fades—and either pivot or stall.
You write extensively about the middle of the marathon, yet still sound surprised when the feelings of funk or stagnation arrive (e.g., July 2025).
❤️ 3. You Are Highly Motivated by Relationships and Legacy
You repeatedly express:
A desire to be a better father to [Daughter’s Name]—even noticing when she doesn’t appear on your practical goal lists
Passion and tension around romantic relationships (e.g., [Woman’s Name]) with deep emotional and practical consideration
Gratitude for your wife, kids, and the life you’ve built
🟨 Yet:
You sometimes feel guilty or uncertain about how much to sacrifice your personal mission in the name of those relationships—and vice versa. That creates ambivalence and cycles of burnout.
📉 4. Your Health and Energy Correlate with Clarity and Execution
When you feel in shape, you write about clarity, optimism, and drive. When you fall off track:
You write things like “I found the bottom” or note feeling “tired, groggy, overweight”
You admit using food or drink as escapism
There are moments of re-commitment to diet and discipline, but they tend to be short bursts
🟨 This means:
Your body is a feedback system for your mental and emotional state—and discipline here affects every area of your life.
🎯 5. Your True Goals Are Crystal Clear—and Still Unfulfilled
Across the journals, you repeatedly name the same vision:
Run your own mission-driven business
Serve a real community (specifically, men and leaders)
Generate income through value and wisdom
Lead from Christian principles
Achieve financial independence with time and space for family and purpose
🟨 What you might not realize:
You’re already capable of the future you want. The challenge isn’t clarity, talent, or insight—it’s persistent execution through the woods, not around them. You crave freedom, but freedom only comes after prolonged captivity to your mission.
🚩 Potential Blind Spots
You often chase structure (school, [military], corporate) when you feel unclear—but structure may be the very thing suffocating your deeper drive.
You want mentorship and brotherhood, but rarely talk about specific efforts to find it beyond journaling.
You delay revenue creation in your own brand, even when traffic and consistency are improving—this blocks your breakout from corporate dependence.
🧭 Summary: Who You Seem to Be
You’re a deeply intentional man with sharp intellect, emotional range, and spiritual awareness. You have lived many lives—and often try to live them simultaneously. You’re seeking integration of fatherhood, faith, calling, and financial freedom. You’ve made enormous progress—and still often feel like you’re behind.
Would you like a structured plan to align your brand, calling, income, and health over the next 12 months based on these insights?
My Response
First off, heck yeah I asked to see what that 12-month Structured Plan looked like! 😉
After I saw its plan, I asked it to create the outline and first draft of the 12-point Lead Magnet it mentioned in that plan.
And then I asked it to outline and draft a book for me based on these nine years of entries, because why not? 🤷♂️
Main Take-Aways
Overall, I spent about two hours with ChatGPT on 7-23-2025. The output was this full assessment, a 12-month action plan, an outline and sample drafts of a book idea, and instructions on how to continue on the book work.
It’s almost too easy to just say that: “I spent two hours.” That’s really mind-blowing when you consider it. That is almost six months of deliverables by any standard. I’ve done similar work with companies, teams, and other men looking for perspective…this kind of output does not come in TWO hours.
In hindsight, many of the observations are obvious. I often look back on my entries over the years, and I too can see the trends and patterns. In fact, that in itself is my number one reason for journaling (besides the immediate clarity effects).
The real power here is that AI did it in 30 seconds. I mean literally. It took all four files, thousands of rows of text, 9 years of driveling, and pulled out concise trends and actionable items to work on.
It comes in HIGH volumes of output.
Even as a guy that considers himself “high-performance,” it’s a lot. It’s easy to see it all and then just want to drink a Diet Coke and take a nap.
My advice here is to pause. Stop work at a certain point. The computer can keep going, but YOU need to digest it and let it assimilate. Go pick two key action items from it all and put them in place!
Follow-Ups
Yesterday, I had already build the new landing page from its prompts, and settled on the new direction of the Personal Brand.
AI delivers a huge amount of output. Pick two and got them done.
Today’s main output focuses:
Document, draft all these outputs as posts that I can video from [that’s already done, so this action item is sort of a gimme].
Organize the Book Folders per ChatGPTs instructions, and get the outline in place. Type the first 250 words of that.
Clarify the Lead Magnet delivery and get that in place. Right now, I’m pretty sure it’s just going to be a blog post, and then I’ll let people opt-in if they want to see the polished version I ended up with from all that work.
Conclusion
This is useful and high-powered. It’s leverage.
I recently listened to Dr. Roman Yampolskiy on The Joe Rogan Experience talk through his view of Super Intelligence / AI destroying humanity within 2-5 years. Honestly, he’s got some STRONG points. I’ve been in technology for 20 years. What we built here, we don’t fully fathom.
Still, AI is extremely useful. I tell my employees now it’s like a tractor. If you told me you plowed your 20 acre field by hand, I would not be impressed. We have tractors.
While we still live, breathe, and make our own decisions. I’m still using this.
For a more optimistic view on the doomsday idea, see Dr. Roman Yampolskiy on Lex Friedman’s podcast. That conversation was much more productive, in my opinion.
Overall, this exercise was useful and I got the clarity that would have previously come from reviewing a few fiscal years with a full board of advisors. I’ll continue to lean into this.
