The Personal Board of AI Advisors You Didn’t Know You Needed

How I built a Personal Board of AI Advisors and how it’s working suspiciously well.

I'm a future optimist.

If you read my inaugural post, you know I'm using AI to build a personal brand and a life I never want to retire from. This field note is about how that's actually working.

I wanted to understand what prompt engineering really means. Not just getting ChatGPT to spit out better responses. Real engineering.

So I created a personal board of advisors.

I already had a personal operating system.

I've been building it for two decades. It's how I operate, love, make choices, navigate joy and grief, move through stress, and grow my agency over my thoughts, feelings, and the life I get to live.

So I basically digitized the whole thing.

I trained my board of advisors on my values. The statements about my life I want to be increasingly true. The dreams I have. The yearly goals I set to make those dream outcomes inevitable.

My monthly reviews where I align my time with my goals, recalibrate thought patterns and time investments.

My weekly check-ins where I see how the week went, what bottlenecks or resistance I hit, and think about how I can resolve, move around, apologize, listen better, unsubscribe... whatever it takes to realign with my highest aim of the life I'm building.

Over time.

I fed it my boundary statements and mindset statements that feel true for me.

And I gave it a framework for asking me questions.

Yes, it's a lot. But I've built this over the past two decades. It's how I operate.

(I'm actually working on templatizing this whole system so other people can use it. Planning to launch The Personal OS in July 2025 if you're curious about what it would look like to digitize your own operating system. But that's a whole other field note.)

I trained my personal board of advisors on all of these pieces.

The result of my first board meeting honestly blew me away.

I closed my laptop feeling like …

If you're AI curious - and I know you are because you're down here reading the 22nd paragraph of a post with AI in the title - it turns out, this Board of Advisors is a great place to start.

Why?

Because you’re actually the expert on you.

That means you can train the LLM with higher accuracy and make it that much more helpful to you.

How to Build Your First AI Advisory Board (Without Getting Overwhelmed)

Okay, let’s get into it.

This isn’t expert advice. I’m literally just a week ahead of you, and this is what’s actually working.

If you’re curious about using AI as more than a novelty, this is exactly how I built my own Personal Board of AI Advisors:

Step-by-step (the way I did it):

• 1. Choose 1–3 types of guidance you wish you had
  Think about the areas in your life or work where you second-guess yourself, stall out, or just want another smart brain in the room. Then give each one a title.

Examples:
The Priorities Advisor – helps you sort what actually matters this week
The Perspective Advisor – helps you reframe problems when you’re stuck
The Communication Advisor – helps you say what you mean clearly and calmly

• 2. Describe what each advisor is for
  Just a few sentences. What should this advisor help you notice, challenge, or decide?

“My Priorities Advisor helps me step back and choose one meaningful focus instead of spinning in urgency.”
“My Perspective Advisor helps me zoom out when I’m caught in mental loops.”

• 3. Introduce yourself like you would to a new collaborator
  Instead of jumping straight to a question, give the AI context:

  • What you care about

  • What you’re working on

  • What kind of support would actually help this week
    Keep it short but honest.

“I’m trying to make better use of my time without burning out. I want help choosing what’s worth doing now and what can wait.”

• 4. Ask something real
  Don’t brainstorm in the abstract. Bring a real decision, a real frustration, or a real goal.

“I keep putting this off even though it matters. Can you help me figure out why and what to try next?”

• 5. Make it a back-and-forth, not a one-shot question
  Treat it like a conversation. Push back when it misses. Add detail when it helps. Tell it what worked. The clarity builds over time.

• 6. Save what shifts your thinking
  When something clicks—a prompt, a question, a way of framing—save it. I keep mine in a notes app. That’s how you start building your own internal advisory bench.

• 7. Keep adding layers of you
  Over time, I added things like my personal values, goals, weekly check-ins, and reflections. It doesn’t need to be perfect. Just add what helps the advisor get to know how you operate.

---

I didn’t set out to “engineer prompts.” (Okay, okay, maybe I did) I really just wanted to experiment with saved memory in ChatGPT. I am so over having to start from scratch every time I open a blank chat.

I’m building a full version of this AI Personal Board of Advisors where all these pieces live in one place, and it’s launching July 2025 so you too can unlock the next level:

“Hard to say, let me run it by my board.”

“Can’t. Currently onboarding a new advisor.”

“Can you let the dog out? I’m presenting Q1 regrets to the board.”

It’s working.