Previously, I wrote about How to Mentor Yourself.
LLMs have changed things.
Made things more convenient. I talked about how if you picked a mentor from history, you would need to do a lot of reading. Really dive deep into the context of their times.
And there’s a sense in which you still need to do that. But you can get started in an interactive way with AI.
Roleplay?
Getting Coached
Using Claude
Example Checks
Bonus Pantheon
READING TIME: 13 minutes
Roleplay?
I’ve been keeping up with all the over-the-counter options.
For the moment, Claude most readily takes on other personalities.
That is still somewhat fraught. For example, if you ask it to take on the personality of a skilled Native American or Australian Aboriginal tracker, it will usually refuse due to ethical concerns about representation and cultural appropriation. And so, ironically, the people who are marginalized will be harder for you to learn from. If you enjoy convincing Claude in every new chat, you may, but that’s quite a lot of time spent unless you’re picking people who would be uncontroversial to a Bay area intellectual.
A faster thing you can do is ask it about what your historical-figure-mentors might have been paying attention to when they were doing the thing that you admire them for doing.
Getting Coached
I’ve noticed, traveling all over the world and learning from different grappling coaches, that one of the most difficult things to get out of someone is what they’re actually paying attention to. Maybe because the skills for explanation are not necessarily tied to the skills for winning competitions and so on.
But you still get that picture, that the real thing you have to learn from a teacher is not their exact way of doing things.
It’s what they’re paying attention to.
I’m sure many people have heard about paying attention to the solar plexus of your opponent, when boxing. And using touch and vibrations to pay attention to their limbs. But your eyes, you know, you put that on the solar plexus.
But then we can even go beyond that to how you evaluate your training, how you tighten your feedback loops.
So, we might ask a coach something like: “How do you know when you’ve done it correctly?” And this is where some coaches will have trouble. It’ll just be like, “Oh it just feels good.”
I remember when I was in basic training. I was the runt of the pack, so to speak. I asked my buddy— one of the fittest guys there— “How do you run? How do you run effectively?”
He said, “You just put one foot in front of the other.”
There is a Zen quality to that. But also— what were you actually paying attention to, my dude?
Years of running long distance later, I can say that what I’m usually paying attention to is the horizon. Where you want to go.
And when I ran really well, it was beyond the horizon, right? Like the horizon— a single tiny point on the horizon— was where I was going physically. But simultaneously, I’d be paying attention to the future, what my vision for the future was. And I found that that’s when I did my best.
But when you talk to experts of various kinds, it’s often hard to get this out of them.
A lot of times, you have to have the skill of letting the coach open up to share with you what they pay attention to.
That’s a separate skill, actually, from whatever skill they might be teaching.
The skill of paying attention to your own attention. Not everyone has that skill. On top of that, the mentors we talked about in our last exploration of this are mostly not accessible.
Most of them are dead.
Regardless, this exercise should work.
It’ll help you figure out what your mentors might have been paying attention to.
Using Claude
AIs like to tell you like, “oh not everything we do is accurate, you have to check” and whatnot.
That’s actually true for everyone, right?
What we’re doing here is gathering information- just like you would from another person.
You have to check it against your own experience. Your own attempts, your own trials, and failures.
And so, I like anything else I would stay adjacent to a skill that you know well. Just so you can evaluate it more easily.
Example Checks
Here, I’ve focused on asking about figures I have read many sources to, including themselves. This gives me a feel for the distillation process.
Hackworth
Prompt:
Be as brief as you are inclined. What might David Hackworth have been paying attention to most, everyday? What was the unifying focus, the tiniest slice that he used to determine if he had got what he was trying to do or not, for every single moment? If it was a question, what might that question be?
Response:
“Are my people ready for their next fight?”
He was obsessed with realistic training, tactical competence, and unit readiness - evaluating every activity through the lens of whether it genuinely prepared his soldiers for combat. His autobiography “About Face” and his leadership style suggest he constantly asked himself if what he and his unit were doing right now would help them survive and win when it mattered.
–This one seems right on!–
Napoleon
Response:
“What time is it?”
Napoleon was obsessed with timing and tempo - in battle, in campaigns, in politics. He viewed time as the critical resource that, properly used, could multiply force. His famous quote that he “beat the Austrians because they did not know the value of five minutes” captures this. Many of his victories came from his ability to coordinate multiple elements to arrive at the decisive point at the precise moment needed.
This extended from tactical to strategic levels - he was known to keep exhaustive schedules and time tables, and to drill his subordinates on exact timing of movements.
–Checks out–
LBJ
Response:
“Who owes who?”
LBJ’s constant focus was on the web of obligations, favors, and leverage between people - who needed what from whom, who had done what for whom. He meticulously tracked these relationships and power dynamics, using them to maneuver legislation and policy through a complex human system. His ability to “trade” these debts and obligations, and to understand exactly who held real influence over whom, was central to his political effectiveness both as Senate Majority Leader and President.
–Checks out–
Rommel
Response:
“Where is the enemy weakest right now?”
Rommel was constantly seeking and probing for operational opportunity - looking for gaps, weaknesses, or moments of vulnerability that could be immediately exploited. While many generals focused on set-piece battles or predetermined plans, Rommel was uniquely focused on dynamic exploitation of momentary advantages. His success in both France and North Africa often came from his ability to spot and immediately act on temporary weaknesses in enemy dispositions or supply lines.
His nickname “The Desert Fox” came from this predatory instinct for finding and striking at vulnerable points, especially in fluid mobile warfare.
–Also probable–
Sir William Slim
Response:
“How does this benefit my soldier in the mud?”
Slim was uniquely focused on the welfare, morale, and effectiveness of his frontline troops - particularly infantry. From logistics to training to medical care, he evaluated decisions through the lens of how they would impact the common soldier’s ability to fight and survive. His leadership in Burma showed this - rebuilding a defeated army by focusing intensely on the basic needs and fighting capability of his infantry, from malaria prevention to ensuring they had the right boots for jungle warfare.
He was known for saying that leadership was fundamentally about raising and sustaining morale, and his perspective consistently centered on how strategic and operational decisions translated into tangible benefits for the soldiers doing the fighting.
–Spot on–
LKY
Response:
“What is the cold, hard reality - stripped of all wishful thinking - and how do we deal with it?”
Lee Kuan Yew was relentlessly pragmatic, focused on seeing situations exactly as they were rather than how he might wish them to be. Whether dealing with communal tensions, economic development, or geopolitical positioning, his approach was to ruthlessly strip away ideological preferences and pleasant illusions to deal with ground truth.
His success in building Singapore came largely from this uncompromising focus on reality and effectiveness over ideology or popular sentiment. He frequently spoke about the necessity of seeing things as they actually are, not as one wishes them to be, and making hard decisions based on that clear-eyed assessment.
–This seems fuzzier to me- I’m not sure about this one–
Oliver Sacks
Response:
“What is it like to be this person, in their own inner world?”
Sacks was uniquely focused on understanding and conveying the subjective experience of his patients - how neurological conditions affected not just their symptoms, but their lived reality and sense of self. Whether writing about music, memory, perception, or consciousness, he constantly worked to understand and communicate the phenomenology - the “what it is like” - of different neurological states.
His case histories stand out precisely because they weren’t just clinical descriptions but deep explorations of how his patients experienced and made sense of their conditions. He wanted to understand not just what was happening in their brains, but how it felt to be them, from the inside.
–seems like it matches–
Film Directors
Yasujiro Ozu
Prompt: What might Yasujiro Ozu have been paying attention to most, when making his films? What was the unifying focus, the tiniest slice that he used to determine if he had got what he was trying to communicate across or not?
Response:
I believe Ozu was most acutely focused on what he called “ma” - the spaces between actions and reactions, particularly in family relationships. If you watch faces in his films during conversations, it’s often not the speaking that he’s most interested in, but the tiny flickers of expression that come after someone has finished speaking, or just before they begin.
Think about when a parent tells their child something important - it’s not the words themselves that carry the weight, but that suspended moment afterward, when both parties are processing what was just said. Ozu would hold these moments just a fraction longer than feels natural, until they become almost unbearable with meaning.
In “Late Spring,” there’s a scene where a father and daughter are eating together, and she’s laughing at something. But Ozu holds on her face as the laugh fades, and in that transition - from social performance to private thought - he captures something profound about how we hide our true feelings from those we love most. He seems to have judged his scenes by whether he had captured these transformative micro-moments, these turns from one emotional state to another.
It’s as if he was always asking: “Have I shown not the feeling itself, but the moment when the feeling changes?”
Chad Stahelski
Response:
“Does this preserve momentum?”
Digic Pictures
Response:
Digic Pictures, as a high-end animation studio specializing in game cinematics and trailers, seems to evaluate their work through the lens of “Does this feel weighty?”
Their signature style, especially visible in work for games like Assassin’s Creed and The Witcher, shows an almost obsessive attention to the physics of movement and impact. They have a particular talent for making CGI feel physically present and consequential, rather than weightless and digital.
The single question they might be asking for each shot could be: “Can you feel the mass?” Whether it’s a character landing from a height, a sword connecting with armor, or a cape billowing in wind, they seem to judge their success by whether they’ve conveyed the proper sense of physical weight and material properties. You can see this especially in how they handle cloth simulation and character movement - there’s always a clear sense of gravity and inertia at work.
Jackie Chan
Response:
“Can the audience follow this?”
That seems to be Chan’s core question for every shot and edit. Not just physically follow it, but emotionally and comedically follow it. He’s famously willing to do multiple takes not for the perfect execution of the stunt itself, but for the perfect readability of what’s happening.
You can see this in how he often shows a prop or environmental element multiple times before it becomes important in a fight sequence - he’s setting up the spatial understanding. Or how he’ll frequently do a slight pause or reaction take after a particularly complex move, giving the audience a moment to process and appreciate what just happened.
His famous “multiple takes” philosophy isn’t about perfectionism - it’s about clarity. He’ll even sometimes sacrifice a more impressive version of a stunt for one that reads more clearly to the audience. In films like Police Story or Project A, you can see him actively managing the audience’s attention, making sure they never lose track of where everything and everyone is in space.
Unlike many action directors who might ask “Is this impressive enough?”, Chan seems to always be asking “Will they get it?” - with “it” meaning not just the physical action but the humor, the character moment, the story beat within the action.
Michael Mann
Response:
“Is this atmospheric distillation authentic?”
Jeremy Saulnier
Response:
“Is this as clumsy and desperate as it would really be?”
Robert Eggers
Response:
“Does this feel like a recovered artifact?”
Alex Garland
Response:
“Is this capturing the exact moment when comprehension breaks?”
Werner Herzog
Response:
“Is this touching the ecstatic truth?”
Nicolas Wending Refn
Response:
“Is this moment suspended enough to become myth?”
Bonus Pantheon
Lee “Flash” Young Ho
Response:
“What move seizes position in the most lasting way?”
n0tail
Response:
“What’s the actual state of the game right now, not what anyone thinks it is?”
Alexander the Great
Response:
“How much further can we go?”
Genghis Khan
Response:
“Are the people united or divided?”
Akbar the Great
Response:
“How can these differences serve unity?”
Cyrus the Great
Response:
“What would earn their loyalty?”
Shi Huang Di
Response:
“Is it uniform yet?”
Walt Disney
Response:
“Will this delight them?”
Lionel Messi
Response:
“Where’s the gap?”
Leonardo Da Vinci
Response:
“How does it flow?”
Abe Silverstein
Response:
“Can we control fire better?”
Ludwig Van Beethoven
Response:
“Did that move them?”