An Overthinker's Almanac
An Overthinker's Almanac OTA
My Intellectual Mount Rushmore
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My Intellectual Mount Rushmore

A Journey of Self-Discovery with Aurelius, Franklin, and Munger

Ben Franklin, Charlie Munger, and Marcus Aurelius walk into a bar. Not a joke, more a dream Saturday night with me as the bartender, as this unlikely trio has become my personal Mount Rushmore of intellectual role models. By dissecting their lives and philosophies, I hope to gain clarity on my path and perhaps inspire you to reflect on yours.

This essay is a bit of self-discovery. I've spent the last few years rethinking my path, and I keep returning to this unlikely trio of a Roman emperor-philosopher, a Founding Father polymath, and Warren Buffett's sarcastic sidekick.

What do they have in common?

Why am I so drawn to them?

And what does that say about me?

As I overthink this analysis, I'll unpack what attracted me to each of these wildly different men, what they pursued, and what I can learn from their motivations, virtues, and contradictions.

A Well-Worn Library Card

If we start with raw intellectual breadth and horsepower, Ben Franklin has long been my north star. The guy basically invented the American generalist ideal that I've aspired to. 1 Ben epitomized range as a printer, diplomat, scientist, inventor, philosopher, and even a self-help guru.

Charlie Munger drew me in for a different reason: quiet candor, insightful leadership, and a healthy passion for irreverence. While less obviously diverse than Franklin, Munger's career was far from linear, as he pivoted from law into investing, became one of the most respected minds in business, and built a legacy beyond wealth, emphasizing a style that silently screamed clarity and calm.

Marcus Aurelius is harder to pin down. His LinkedIn profile from 170 CE reads: Roman emperor, military commander, and Stoic philosopher. That's impressive, though more constrained by his era. Still, for his time, that's about as polymathic as they come.

They each embody intellectual range in their own way, but that alone isn't what I care about. I didn't want just to analyze what they did. Let's overthink this with a quest to understand why they did it.

The Why Behind Learning

"An investment in knowledge always pays the best interest."

– Ben Franklin, The Way to Wealth

Let's start with Marcus. His pursuit of knowledge was grounded in the Stoic desire for inner virtue and peace:

"The impediment to action advances action. What stands in the way becomes the way."

Meditations, Book 5

In modern (or Ryan Holiday's) terms, the obstacle is the way. Growth isn't about avoiding detours or being perfect from the start. We learn and evolve when we reroute with purpose. In my journey, leaving a steady career to return to school, I've accepted a near constant cue from my mental GPS yelling, "Recalculating." Channeling my inner Marcus, I'm realizing that the real fun (and growth) begins when your path leads to a "Well, this sucks," moment. It's then applying your knowledge that helps you turn to the right.

Ben, by contrast, chased knowledge for self-improvement and social mobility. His learning was less inward-facing and more of a ladder for betterment and influence.

Charlie's why is a bit of a paradox. He often frames learning as an end in itself. It's a daily practice of becoming better at decision-making, not being complacent and reliant on natural gifts, but carpe-ing the diem.

"I constantly see people rise in life who are not the smartest, sometimes not even the most diligent, but they are learning machines."

— Charlie Munger, Poor Charlie's Almanack

One of his most famous lines drives the point home:

"In my whole life, I have known no wise people who didn't read all the time — none. Zero."

— Charlie Munger

Though I agree with Charlie's sentiment that pure intelligence is less critical than passion for learning, I likely fall somewhere on the Marcus/Ben side of things. I value the journey for inner growth and virtue, while seeking social utility with a Franklinian desire to contribute.

Connecting Ben and Charlie, I could definitely see Munger saying Franklin's exact quote from the start of this section. They just had different endgames.

Leaving A Legacy

"Waste no more time arguing what a good man should be. Be one."

– Marcus Aurelius, Meditations, Book 10

That leads to a second dimension, the desire for legacy. Early in my corporate days, I learned that impact was truly the magic word. It doesn't matter how hard you work or how much you try. What matters are results. Hard work is only a virtue in its ability to develop skills and make a difference.

Marcus understood this in the most existential way. As Rome's "last good emperor," his legacy has persisted for nearly two millennia. While his military and political success offer value, his writing provides his most enduring presence, continuing to help people navigate the chaos of their lives. Recently, I've been using an audio version of Meditations and a Bluetooth headband to go to sleep each night.

Franklin left fingerprints on everything from electricity to governance to fire insurance, and even the US postal service. He was obsessed with practical virtue. Learning was cool, but only if it could light a lamp or launch a republic.

Munger, by contrast, played a quieter hand. While his financial legacy is still to be felt posthumously, his intellectual contributions through speeches, books, and Berkshire Hathaway meeting quotes feel more like a reflective gift than intentional legacy-building. He never seemed to actively chase fame or status but created a ripple effect through his clarity, partnerships, and principles.

Personally, I'm still writing my story. Work like this essay and my increasingly unwieldy Google Drive feel like my en media res Meditations, on a much less "running an empire" scale. I'll give myself a pass for now, but at least these gentlemen feel like some reasonable north stars to emulate.

Like the Stoics, I've come to believe that intellect for its own sake is vanity and that knowledge must lead to service.

To paraphrase Seneca in Letter 88, a man is not wise just because he knows many things. Knowledge is only impactful when it is useful to oneself or others.

That's the kind of legacy I want to leave. Offering my pursuit of knowledge and wisdom to help society. Wish me luck!

Motivations and Ego

"If you would not be forgotten, as soon as you are dead and rotten, either write things worth reading, or do things worth writing."

– Ben Franklin, Poor Richard's Almanack

Let's shift to another why question, understanding the motivation around fame and legacy. In Stoicism, such aspirations are a distraction. Or, as Marcus puts it bluntly:

"People who are excited by posthumous fame forget that those who remember them will soon die too." – Meditations, Book 6

Marcus clearly wrestled with this. Fame came with the throne, yet unlike many who achieve such recognition, it seemed to be something Aurelius endured rather than coveted. I get the sense that if he'd seen Pixar's Coco, he would've nodded thoughtfully and mumbled something about ephemerality as I passed him a tissue.

On the other hand, Ben made no such effort to hide his ego. Recognition and notoriety became a calling card he leveraged to open doors in America and Europe. Franklin understood the power of legacy branding and would have absolutely owned revolutionary-era LinkedIn self-promotion.

Then there's Charlie, who, in some ways, feels like an accidental Stoic. Always the wingman to Buffett's public persona, Charlie said far less and, by all accounts, was happy about it. Turning this into a fictional interview, Charlie, what do you have to say about that?

"I have nothing to add."

Charlie Munger (frequently)

Yet despite (or because of) that minimalism, Munger built a near-mythical status, not by seeking followers, but by saying just enough, only when it mattered, and making each word count.

Personally, I feel most aligned with Marcus, with a desire to be more Charlie, and a wish that I had Ben's penchant for authentic self-promotion. I don't crave the spotlight, and I'm trying to overcome my reptilian brain's desire for external validation-fueled dopamine rushes.2 I want to be useful. To make things better. To understand, and to contribute.

I've discovered, particularly through my startup work, that I thrive with a complementary partner. I can think, create, strategize, and advise, but I need someone who fills in the gaps and supports with sustaining energy. I need to find the Kirk to my Spock/McCoy persona. In that way, I find myself drawn to Munger's dynamic with Buffett. Charlie was a force in his own right, but his most significant impact came through partnership with the right counterpart. Munger and Buffett epitomize the 1+1=3 mentality. When you get that kind of impact, combined with a partnership lasting more than half a century, shareholder value wasn't the only thing exponentially compounding.

That's my desire.3 Recognition earned through contribution, amplified through collaboration. (Collaborators wanted)

Equanimity as an Attribute

Stoicism introduced me to the concept of equanimity, a state of calm emotional balance in the face of chaos. I didn't realize there was a word for this, as this was just naturally who I am. Early in my career, my team praised me for being relaxed, focused, and confident in a crisis. From my reality, this was normal. I've always lived a "next play" mentality, focusing on the next move and not stressing how I arrived at my current predicament. If WoTC created a Dungeons & Dragons: Office Space edition, my character would get max points in equanimity.

Reflecting on this trait, I realize how essential it is to embrace detachment from the moment. To be our best, we must remove the natural tendency to seek blame and look backward. Nothing can change the past. The only path is forward, so allow that to be your focus.


This is the perfect moment to plug that next week, we start a five-part deep dive into the philosophy of one of the most equanimous video game heroes of all time, Mario. Don't miss it!


Looking at our three protagonists, Charlie is probably my closest buddy in this category. His public persona was one of deep emotional neutrality, expressed as only Munger could.

"Spend each day trying to be a little wiser than you were when you woke up. Discharge your duties faithfully. Don't whine. Don't envy. Don't be a damn fool."

– Charlie Munger

Marcus, by contrast, worked hard to earn his equanimity. He wrote daily reminders to himself to manage anger, ego, and the frustrating humans around him:

"When you wake up in the morning, tell yourself: The people I deal with today will be meddling, ungrateful, arrogant…" — Meditations, Book 2

(Heard, Emperor.)

Given the pressure of war, empire, and legacy, his need for Stoic balance was existential. I get the sense this might be one of the few Stoic principles where I actually have a natural edge on Marcus. I mean, I never had to rule a continent, but I'm a pretty cool customer in a leadership team meeting that goes off the rails.

Ben, for all his genius, seemed a bit more excitable. Franklin even seemed to lean into his moments of external admiration. His reflections on vanity read like a man trying to rationalize his own likability:

"Most people dislike vanity in others, whatever share they have of it themselves; but I give it fair quarter... being persuaded that it is often productive of good."

— Ben Franklin

He's not wrong. Performative virtue with a healthy appreciation for being your own hype man, if done well, still helps people. But I'll give Charlie the emotional composure badge on this one, with Marcus earning an honorable mention for effort under much more challenging circumstances.

Self-Discipline (+ Wine)

Self-discipline is one of those traits people like to praise, especially when you're calm, measured, and not diving into a bag of HEB tortilla chips at 9 pm on a Tuesday. In Stoicism, though, it's deeper than delayed gratification. It's essential for tranquility, recognizing the stillness of mind that allows reason to guide action. For me, discipline often shows up as deliberateness, with a slow, reflective consideration before reacting. 4

Ben Franklin was never shy about his virtues, publishing his own moral scorecard. Furthering his status as ahead of his time, he developed a system of 13 self-improvement values he tracked in a daily log. I'll spare you my own report card, but let's just say I'm pretty good in most of Ben's categories… except temperance.5 That one gets a "needs improvement/work in progress."

"All things in moderation — including moderation."

— often attributed to Franklin, and frequently repeated by my grad school advisor

Marcus, ever the struggler, used Meditations to wrestle with self-mastery. His reflections suggest that discipline wasn't easy for him.

"You have power over your mind — not outside events. Realize this, and you will find strength."

Meditations, Book 12

Remember that he was writing Meditations to remind himself of that truth, not to lecture others. Reading with this lens makes it that much more powerful.6

Conversely, Charlie seems to have skipped the struggle entirely, or at least replaced it with pure rationality. He simply outthought his appetites. There was no inner turmoil, just, "That's dumb. Don't do it."

Despite them being Ben's own 13-virtue system, I anticipate Franklin experienced some of my struggles, particularly regarding food and beverage, if nothing else, from seeing Ben's physical outcome and health impact that inspires me to spend time on my rowing machine. We'll give Charlie the win in this category, with Ben being more of my faulty inspiration.

Looking Up at My Mount Rushmore

If I had to sum them up:

Marcus was a Stoic icon who always saw himself as a work in progress. Meditations offers a glimpse of his struggles to achieve what he felt was the ideal. His position of power provided a constant battle not to be consumed by the power it offered, with writing providing an outlet for self-discovery and processing his emotions through grief, war, and duty. It serves as an amazing template of self-awareness and honesty in journaling, and as a model of why I hope this work is valuable to you, the reader.

To me, Ben is the quintessential American practical philosopher. Delving into countless areas of societal impact, some of my favorites of his contributions are his thoughts on pursuing virtue and self-improvement. Like me, Ben takes a more optimistic tone at odds with some Stoic negative visualization principles. Ben better mirrors my "Before Stoicism" or my BS stage.7 Ben emphasized optimization more than achieving a more harmonious life, devoid of external validation needs. Much like my desire for external validation,8 Ben seemed to like to be liked.

Charlie is trickier. More modern, more private, and in some ways the most Stoic of them all, seemingly accidentally by his natural disposition. Where Marcus struggled and Ben sought praise, Charlie simply chose wisely and kept quiet. He's a stronger embodiment of my aspiration to be a philosophical Statler and Waldorf, willing to blend dry wit, ruthless clarity, and emotional detachment, replacing philosophical aspects with wisdom shared at Berkshire Hathaway annual meetings.

Like any honest self-evaluation, I see reflections of each of these men in myself, gaining an appreciation for their strengths, blind spots, and struggles. From Marcus, I seek peace through reflection and detachment. From Franklin, I embrace curiosity, communication, and a little performative virtue. From Munger, I borrow clarity, restraint, and the occasional urge to heckle humanity from the balcony.

As any Mount Rushmore should, I seek to be inspired, to be my best self, to learn from them, and to apply an honest lens on who I am today and how I can continue to grow. Maybe through this aspiration to learn from three unique individuals, I can live a little better, a little wiser, and be a bit more impactful.

But practicing Stoicism, I know all I can control is sharing this with the world.

Thanks for reading.

Who is on your Mount Rushmore?

So who would make your personal Mount Rushmore?

What virtues do they represent, and how are you trying to live them?

I hope this gave you something helpful to reflect on. I'd love to hear what's shaped your journey, and as always, I welcome you to walk a bit further with me on mine.

Cheers!

1

At least intellectually. I've yet to solve the modern employability dilemma.

2

Hey, "like and subscribe"

3

Sharing like this is a bit more Aurelius and Munger, less Franklin.

4

Humble brag? Sure. But also accurate. Inquire for references.

5

Food and wine are delicious.

6

It also shows the power of journaling, which I highly recommend.

7

Though if you're reading, you're likely confident I'm squarely in some personal BS phase.

8

Nudge – like and subscribe!

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