I didn't build this system. I asked for it.

 

I didn’t build this system. I asked for it.

I have wanted a world class group of advisors for every aspect of my life, and I was tired of waiting. 🧠🧭

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The Frustration 😤

It started like this: I was using ChatGPT regularly and getting a lot out of it — more than most people, probably. But over time, things got messy. Conversations would drift. Memory would fill up. I'd lose context, or worse, start preserving the wrong kind of context: fragments of specific details that clogged the system while the important, core parts of me — the way I think, the values that drive my decisions — got buried under domain names and test scores.

It wasn’t that ChatGPT was broken. It was doing exactly what I was asking — just not what I wanted.

So I stopped.

And I asked it a simple question:

"What if I want a team of world-class advisors who think like I do, but who each specialize in a different area of my life? What if I’m not the same person in every domain, and I want AI that reflects that?"

The Pivot 🔁

And that changed everything.

I didn’t design the system. I didn’t read a whitepaper or copy someone’s Substack.

I described the problem. I explained the tension: too much noise, too little structure, and the growing friction of trying to “manage memory” instead of building something that thinks with me.

ChatGPT gave me the blueprint. I gave it my personality. Together, we built something better.

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Enter: The Personal Cabinet 🧑‍⚖️🗂️

I now have a team of custom GPTs. Each one knows who I am — not just on paper, but through how I make decisions, how I respond to setbacks, what kind of advice I’ll ignore, and where I tend to thrive when things line up.

They all inherit my Core 'Wilbert' Identity Block — a distilled foundation of first principles, reasoning patterns, and preferences. But from there, they diverge. Each one is shaped into a specialist — because I’m not the same person in every context.

Here’s what I’ve built so far:

🧮 Math Project / Course GPT

For lesson design, curriculum flow, test construction, scaffolding, and pacing decisions.

🏫 Education GPT

Handles IEP blurbs, boundary-setting parent communication, and instructional strategy across co-taught, EL, and repeater classes.

🧒 Parenting / Family GPT

For raising four kids across a 16-year age span. Includes strategy, discipline, empathy calibration, and balancing boundaries.

🏖️ Retirement GPT

Focused on future lifestyle design, pension strategy, and what to build after I stop working. Travel, health, and habit architecture live here too.

📈 Investing GPT

Aggressive growth focus. IRA and 457 portfolio management. Sector speculation, conviction tracking, and risk calibration.

❤️ Health GPT

Late-start but essential. Now that I’ve hit 60, it’s a must. Sleep, longevity, bloodwork, gut health — minus the fluff.

🧠 Life Philosophy GPT

Not therapy. Not productivity porn. Just a place for clarity, ethics, meaning, and life design work.

🌱 Plant GPT

Lower priority, but tracks what I grow, what works in my environment, and what to experiment with next.

🌐 Domain GPT

Handles domain investing strategy, pricing decisions, negotiation scenarios, and portfolio pruning. My most used GPT.

📚 Stories GPT

Dedicated to fiction writing and creative work. Keeps the tone and genre consistent while helping me push through creative blocks.

🔨 Rehab/Home Projects GPT

Organizes everything from patching drywall to long-term renovation goals. Strategy, budgeting, and project planning.

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Why It Works ⚙️

I didn’t try to make one GPT do it all. I didn’t pretend I’m a single, consistent person across all domains. I'm not. I’m different as a teacher than I am as a domainer. I'm a different kind of dad than I am a retirement planner.

Each of these advisors is tuned to that slice of me. They don't contradict each other. They reflect the way I already live — and sharpen the way I want to live going forward.

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Final Word 🧾

This isn’t a system anyone handed me. I didn’t unlock it by being an expert. I asked for it. I got tired of waiting for AI to magically know what I needed. Instead, I started describing my problems honestly and letting the system co-design the solution with me.

It’s not perfect yet. But it’s close. And it’s mine.