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.

Beyond Efficiency: Strategically Deploying Gen AI in Enterprises

The concept that velocity is different from speed is one of the core ideas I draw upon when thinking about strategy, leadership, and organizational management. Lately, I've been using this concept to think about how to deploy emerging tech, like Generative AI, within enterprises.

The difference between speed and velocity is crucial. Speed is about how fast we're moving, for example, 55 miles per hour. Velocity, however, describes moving at 55 mph towards a specific direction, like heading East. This distinction has helped me see some nuance when discussing generative AI with colleagues and peers. For example, a computer software engineer can debug code faster using a large language model as a coding partner. While generative AI certainly helps with speed, merely focusing on productivity through speed probably misses the larger opportunity generative AI provides to managers of teams and enterprises.

In this example, improving speed might actually reduce overall productivity and impact, if the software being improved isn't solving a valuable problem in the first place. Here, generative AI would be more useful in helping the software engineer determine which feature would be most relevant and impact for the user. Going faster is only helpful if you're going in the right direction, the most valuable direction, to begin with. Using generative AI to increase speed in the wrong direction would be a missed opportunity.

It might be tempting to think of generative AI as a tool to "make our employees more efficient." However, it would probably be more transformative to use generative AI as a tool to "help our colleagues spend their time on the most valuable problems." This logic doesn't just apply to IT departments. For example, generative AI can help marketing teams draft copy faster, but it's probably more valuable to ensure they're targeting the best possible consumer segment. For operations teams, Gen AI might help to spot and improve manufacturing inefficiencies, but it might be more useful to help spot which product lines aren’t worth producing in the first place.

As an enterprise leader scrambling to deploy Gen AI, it’s easy to assume that the job to be done is to make everyone else more efficient. While this is partly true, business and technology leaders, especially those deploying powerful, emerging, tech like AI, should also contemplate use cases that improve the quality of leadership and strategy in enterprises - even though doing so might indicate that those leaders had it wrong in the first place.

Employing generative AI in a self-aware manner will require a significant degree of humility. But I believe it's worth it. After all, what's the point of heading east faster if we should be going northwest to begin with?

Consider the lesson learned from my own experience at work, which vividly underscores the crucial difference between speed and velocity in the application of generative AI. As a product owner for data, I've seen my engineering colleagues leverage tools like ChatGPT to streamline coding SQL queries, boosting our operational speed. However, a pivotal moment came when I discovered that a dataset we had meticulously prepared and delivered was left untouched by our business customer for months. Which, by the way, indicated that I had made a poor decision on what was worth spending time on.

Despite our efficiency in producing the dataset, it lacked the essential element of value to the customer. This incident revealed a stark truth: our focus on making engineering tasks faster, though beneficial, paled in comparison to the importance of selecting the right targets from the outset. There have been instances where the right datasets, aligned with clear and compelling use cases, saved our customers millions of dollars. The real win, therefore, isn't just in enhancing our engineers' efficiency but in ensuring that our efforts are directed towards creating datasets so valuable and relevant that our customers are eager to utilize them for significant impact from the moment of delivery.

To truly leverage the potential of generative AI within our enterprises, we must go beyond the pursuit of efficiency. The most obvious path is often the least disruptive—enhancing what already exists. However, the opportunity to create significant, long-lasting value lies in our willingness to question the fundamentals of our strategies and leadership approaches. It's about asking ourselves:

• Where are we merely maintaining the status quo when we could be exceeding it?

• In what areas are we failing as leaders and strategists to anticipate and shape the future?

• How can we redefine our objectives to not just improve but transform our enterprise?

This journey requires a substantial dose of humility and a willingness to embrace change, characteristics not often associated with leadership but absolutely critical in this context. Challenging our 'sacred cows' and reevaluating our core assumptions about what our enterprises do can reveal the most impactful opportunities for applying emerging technologies. Let's commit to this introspective and transformative approach, aiming not just to enhance but to innovate and redefine our enterprises for the better.

Leadership in the Era of AI

Just as the invention of the wheel revolutionized transportation and societies thousands of years ago, we might actually stand on the brink of a new era. One where generative AI, like ChatGPT, could transform our way of life and our economy. The potential impact of AI on human societies remains uncharted, yet it could prove to be as significant as the wheel, if not more so.

Let's delve into this analogy. If you were tasked to move dirt from one place to another, initially, you would use a shovel, moving one shovelful at a time. Then, the wheel gets invented. This innovation gives birth to the wheelbarrow—a simple bucket placed atop a wheel—enabling you to carry 10 or 15 shovelfuls at once, and even transport dirt beyond your yard.

But, as we know, the wheel didn't stop at wheelbarrows. It set the stage for a myriad of transportation advancements from horse-drawn buggies, automobiles, semi-trucks, to trains. Now, we can move dirt by the millions of shovelfuls across thousands of miles. This monumental shift took thousands of years, but the exponential impact of the wheel on humanity is undeniable.

Like the wheel, generative AI could be a foundational invention. Already, people are starting to build wheelbarrow-like applications on top of generative AI, with small but impactful use cases emerging seemingly every day: like in computer programming, songwriting, or medical diagnosis.

This is only the beginning, much like the initial advent of the wheelbarrow. Just as the wheelbarrow was a precursor to larger transportation modes, these initial applications of generative AI mark the start of much more profound implications in various domains.

One area in particular where I'm excited to see this potential unfold is leadership. As we stand on the brink of this new era, we find ourselves transitioning from a leadership style that can only influence what we touch, constrained by our own time. Many of us live "meeting to meeting", unable to manage a team of more than 7-10 people directly. Even good systems can only help so much in exceeding linear growth in team performance.

However, with the advent of generative AI, we're embarking on a new journey, akin to moving from the shovel to the wheelbarrow. Tools like ChatGPT can serve as our new 'wheel', helping us leverage our leadership abilities. In my own experiments, I've seen some promising beginnings:

A project manager can use ChatGPT to create a project charter that scopes out a new project outside their primary domain of expertise. This can be done at a higher quality and in one quarter or one tenth of the usual time.

A product manager can transcribe a meeting and use ChatGPT to create user stories for an agile backlog. They could also quickly develop or refine a product vision, roadmap, and OKRs for annual planning—achieving higher quality in a fraction of the time.

A people leader can use ChatGPT as a coach to improve their ability to lead a team, relying on the tool as an executive coach to boost their people leadership skills faster and more cost-effectively than was possible before.

These are merely the wheelbarrow-phase applications of generative AI applied to leadership. Now, let's imagine the potential for '18-wheeler' level impact. Given the pace of AI development, it's plausible that this kind of 100x or 1000x impact on leadership could be realized in mere decades, or possibly even years:

Imagine a project manager using AI to manage hundreds of geographically distributed teams across the globe, all working on life-saving interventions like installing mosquito nets or sanitation systems. If an AI assistant could automatically communicate with teams by monitoring their communications, asking for updates, and creating risk-alleviating recommendations for a human to review, a project manager could focus on solving only the most complex problems, instead of 'herding cats.'

Consider a product manager who could ingest data on product usage and customer feedback. The AI could not only assist with administrative work like drafting user stories, but also identify the highest-value problems to solve for customers, brainstorm technical solutions leading to breakthrough features, create low-fidelity digital prototypes for user testing, and even actively participate in a sprint retrospective with ideas on how to improve team velocity.

Envision a people leader who could help their teams set up their own personal AI coaches. These AI coaches could observe team members and provide them with direct, unbiased feedback on their performance in real time. If all performance data were anonymized and aggregated, a company could identify strategies for improving the enterprise’s management systems and match every person people to the projects and tasks they can thrive, and are best suited for, and actually enjoy.

Nobody has invented this future, yet. But the potential is there. What if we could increase the return on investment in leadership not by 2x or 5x, but by 50x or 100x? What if the quality of leadership, across all sectors, was 50 to 100 times better than it is today?

We should be dreaming big. It's uncertain whether generative AI will be as impactful as the wheel, but imagining the possibilities is the first step towards making them a reality.

Generative AI holds the potential to revolutionize not only computer programming but also leadership. Such a revolutionary improvement in leadership could lead to a drastically improved world.

When it comes to the impact of Generative AI on leadership, the sky's the limit. Let's dream BIG.

Photo by Ēriks Irmejs on Unsplash