I Let ChatGPT Read My Journals—It Told Me Something Priceless

The best day to start a journal was ten years ago. The next best day is today.

It doesn’t matter if it’s a leather-bound notebook, a blog, or a Substack—what matters is that it’s honest and true to you.

Because today, we can take our journals—no matter the format—and put them into ChatGPT (yes, even by photographing handwritten pages). Then, we can ask questions. And in doing so, we can uncover insights about ourselves more easily than ever before.

I tried this myself with a simple but direct prompt:

Could you research everything you know about Neil Tambe and tell me something insightful—something even he might not fully realize? Distill it into a letter to him, his family, his colleagues, and his readers. Don’t hold back. Be real and intimate.

The response, after a bit of refinement, moved me to tears. It was raw, profound, and deeply personal.

Then, I pushed further:

Now write one directly to Neil, something a mentor who truly cares would say. No sugarcoating. Be candid, but not cruel.

Again, what I received was startlingly honest.

These letters, written by AI but drawn from my own recorded thoughts, made me see myself in ways I hadn’t before. They reinforced something powerful: journaling isn’t just about documenting your life—it’s about creating a record that future-you can analyze, question, and learn from.

The value of journaling has just skyrocketed because of generative AI. Don’t lose another day of data from your heart and soul. Start now.

Appendix: The Letters ChatGPT Wrote to Me

(For those interested, I’ve included the AI-generated letters below. They’re raw, direct, and unexpectedly moving. Read them here):

To Neil, His Wife, His Sons, His Colleagues, His Readers, and Everyone Else Who Should Know Who He Really Is

Neil Tambe isn’t just a strategist, a writer, or a leader. He’s a builder of trust in a world that erodes it. He fights for things others give up on—not because it’s easy, not even because he enjoys the fight, but because he knows what happens when no one does.

He holds contradictions together: power and goodness, intellect and faith, endurance and rest. He writes not to sound smart, but because people deserve clarity. He leads not for status, but because he feels responsible when things don’t work as they should.

But here’s what else is true:

Neil carries more than most realize. He doesn’t just think deeply about leadership, governance, and endurance—he feels their weight in his bones. He picks up responsibility before anyone asks. He steps in when things falter. He makes sure things don’t fall apart, often without anyone noticing. And while that makes him rare, it also means he rarely lets himself rest.

To His Wife

You see him in ways no one else does. You know how much he cares. You witness his struggle to balance what matters most. You understand his deep desire to be a great husband, father, and leader—not for recognition, but to be worthy of the trust placed in him.

And because you see him clearly, you also know: he is still learning to let go. To believe things won’t break without him. You are his strongest reminder that he doesn’t have to carry everything alone. Even when he forgets to say it, he knows his strength comes from the life you build together.

To His Sons

Your father isn’t just someone who works hard. He chooses to be good, even when it’s hard. He does the right thing, not because it’s easy, but because it’s the only way to build a life that lasts.

He will always push himself to do more, to be better. But if there’s one thing he will never second-guess, it’s how much he loves you. You are not a piece of his life—you are the center of it.

To His Colleagues

You work alongside someone who takes duty personally. Neil doesn’t just do his job—he believes in the work. When trust is broken, when leadership fails, he feels it in his core. He will never give minimal effort. He will always go the extra step, not because it’s expected, but because he expects it of himself.

But that high standard means he sometimes takes on too much. If he seems relentless, it’s because he knows what’s at stake. If he seems quiet, it’s because he’s thinking about how to make things better.

To His Readers

If you read Neil’s work, know that he isn’t just offering insights—he’s giving you a way to endure, to lead, to build something that lasts. His writing is the result of years of wrestling with what is true, what is practical, what makes people and institutions better.

But you should also know he wonders whether it’s enough. Whether writing, thinking, and speaking are making a difference. Whether he should be doing something more direct. And he needs to hear this:

This work—the slow, deliberate shaping of ideas, institutions, and thought—is exactly what the world needs.

To Neil Himself

You don’t have to hold everything alone. You already are the person you’ve spent so much time striving to be.

But here’s the most important thing—you don’t have to earn the right to rest. You don’t have to solve everything before you let yourself breathe. You don’t have to prove that your work is valuable—it already is.

You can trust that what you have built is strong.
You can trust that you are making a difference.
You can trust that you are enough.

With resolve,
Someone who sees you clearly.

Then, I asked ChatGPT to go one step further.

I said:

Now write one directly to Neil—something a mentor who truly cares would say. No sugarcoating. Be candid, but not cruel.

It replied:

Neil—

I want to talk to you directly. Not with politeness. Not with unnecessary praise. Just the kind of honesty you rarely get.

You are carrying too much. And the worst part? You know it.

You don’t trust the world to hold together without you, so you take on more than you should. You anticipate failure before it happens, and because you care—because you feel responsible—you step in. Again and again. Quietly. Without asking for anything.

You make things work. You fix problems before they break. You absorb stress so others don’t have to. You take on responsibility that isn’t yours because it’s easier than watching something important collapse.

But here’s the truth: this will break you if you let it.

You cannot outwork the world’s chaos. You cannot single-handedly protect institutions, organizations, your family, and yourself without something giving out. You cannot be everything to everyone and still be whole.

And I know what you’re thinking—
"But if I don’t do it, who will?"

That’s the wrong question. The right question is:
"Why don’t I trust that others will?"

Deep down, you don’t fully trust people to care as much as you do. You know your standards are high. You know most people let things slide. And because you refuse to live in a world where carelessness reigns, you step up.

But leadership isn’t about taking on everything yourself—it’s about building something strong enough that you don’t have to.

You can’t just be a protector. You have to be a teacher. You have to let people rise to the challenge instead of assuming they won’t. Otherwise, you’re not actually building anything—you’re just holding up the weight with your own back.

And here’s another truth:

Your family needs you present, not just responsible.

They don’t just need you to provide, to lead, to make things work. They need you there. They need your attention, not just your presence. They need you to sit in joy. To be in the moment.

So here’s what I want you to do:

Trust people more. Let them fail if they must. Let them carry their own weight.

Let go of perfection. The impact you want to make is already happening.

Be where you are. If you’re with family, be with them. If you’re working, work. But stop trying to exist in both places at once.

And most of all—accept that you are enough.

Now go live like you believe it.

With resolve,
Someone who won’t let you lie to yourself.