PAIN, POWER, PURPOSE: The Emotional Struggles of Alexander Hamilton and Mark Twain (Ron Chernow)

Here are the top 10 key takeaways from Ron Chernow's conversation with Ryan Holiday about how Washington conquered his temper, Hamilton's past destroyed him, Grant transformed failure into greatness, and Twain evolved from racist to revolutionary.

1. Self-mastery precedes all other victories

The conversation reveals a profound truth about George Washington through Gouverneur Morris's observation: Washington's first contest was with himself, and his first victory was over himself. This wasn't a man naturally blessed with equanimity. Jefferson noted that Washington's temper was "naturally high-toned" but that reflection and resolution had gained ascendancy over it. When his temper broke its bonds, witnesses described his wrath as "terrible."

This transformation from a man of tumultuous passions to the embodiment of stoic leadership wasn't effortless. Washington recognized that to command others, he first had to acquire command over himself. The theatrical play "Cato" served as his philosophical guide, performed even at Valley Forge to inspire his troops. He aspired to see things through "the calm light of mild philosophy."

The lesson extends beyond Washington. Ron Chernow notes that self-control and self-restraint were big parts of success for most of the figures he's written about. This battle between our lower and higher selves determines whether we'll win other battles in life. Without self-mastery, external achievements remain fragile and incomplete.

2. Denying your past creates dangerous instability

Alexander Hamilton's tragic flaw illuminates the perils of shutting the door on one's history. As an orphan who lost his mother at eleven and was abandoned by his father, Hamilton chose complete reinvention. He never spoke of his childhood, never took his children to see his birthplace, and built an enormous superstructure of accomplishment on a fragile emotional foundation.

Byron Wien's advice about orphans proved prophetic: "You reinvent yourself and never look back." While this strategy helped Hamilton rise from Caribbean poverty to become America's first Treasury Secretary, it left him vulnerable. The suppressed past eventually surfaced through the Maria Reynolds affair, where a woman who claimed abandonment triggered his own unresolved trauma. His inability to break away from this destructive relationship nearly destroyed everything he'd built.

Chernow observes that our foundational emotions stem from childhood. When you slam the door on that past and create a new personality with no connection to it, the result is inherently unstable. Hamilton's brilliance couldn't compensate for this emotional void. His need to be wanted, rooted in childhood abandonment, made him easy prey for manipulation.

3. True growth means abandoning cherished prejudices

Mark Twain's moral evolution stands as one of history's most dramatic transformations. Born into a slave-owning family in Missouri, his teenage letters contained crude racist jokes. The church taught him slavery was sacred and "a peculiar pet of the deity." Yet by life's end, he declared that American liberty began not in 1776 but in 1865 with slavery's abolition.

This change began with curiosity and genuine human connection. When Twain presumed his cook Mary Ann Cord had never experienced trouble, she revealed how slavery had torn away her husband and seven children. This story became Twain's first piece in The Atlantic Monthly. He later paid for the education of Black law students, calling it his form of reparations. He held himself personally responsible for the harm white people had done to Black Americans.

His growth extended beyond race to anti-imperialism and anti-colonialism. Initially supporting the Spanish-American War, he later condemned American soldiers in the Philippines as marching with "disgraced muskets under a polluted flag." This evolution required tremendous courage. He lost friends but gained moral clarity. His capacity for growth, shared by all of Chernow's subjects, allowed him to become someone far greater than he could have imagined.

4. Objectivity conquers circumstances

Ulysses S. Grant's story defies conventional success narratives. By his late thirties, he was selling firewood on street corners to survive. He worked in his father's leather goods store, junior to his younger brothers. When asked about his situation, he simply said he was "solving the problem of poverty." This wasn't false bravado; it reflected genuine objectivity about his circumstances.

Grant's strength lay in refusing to accept others' assessments of disaster. At Shiloh, after Union forces were badly beaten, Sherman found Grant standing under a tree in the rain. When Sherman commented on the terrible day they'd had, Grant responded: "Lick 'em tomorrow." This wasn't blind optimism. Grant understood the fundamental mathematics of the Civil War: the Union had more men and materials. If they didn't quit, they would win.

His superstition about never turning back manifested throughout his life. When other generals retreated after facing Lee, Grant's troops marched south toward Richmond instead of north to safety. Soldiers cheered, recognizing a leader who "don't scare a damn." Grant's objectivity allowed him to see past immediate setbacks to ultimate victory. He evaluated situations based on facts, not emotions or social judgments.

5. Financial discipline enables moral choices

The conversation reveals how financial irresponsibility constrains moral action. Washington could free his slaves because his financial discipline gave him that option. Jefferson's spending habits made such idealism impossible. Mark Twain's speculative itch and baronial lifestyle cost him years of exile and creative energy. He invested millions in failed inventions while living in a 25-room house with six servants.

Twain's tragedy is particularly poignant. Despite making fortunes from books and lectures, he couldn't resist get-rich-quick schemes. He admitted being "always the easy prey of the cheap adventurer." His investment in the Paige typesetter and failed publishing company forced him into bankruptcy. Even in supposed poverty, he lived in 30-room villas and palatial hotel suites. His wife wrote they were "poor as church mice" while employing teams of servants.

These self-inflicted wounds had broader consequences. Twain's financial pressures meant chasing money rather than writing the books only he could write. His need for income limited his ability to speak freely on political issues until late in life. Grant similarly fell prey to Wall Street schemes, wanting to compete with financiers who would have given fortunes to win one of his battles. The inability to be satisfied with what they had led both men into unnecessary suffering.

6. Reading enables conversation across centuries

The discussion illuminates how books transcend time's limitations. Stoicism's founder, Zeno, received advice from the Oracle at Delphi to have conversations with the dead. Years later, hearing a bookseller read stories of Socrates, he understood: reading allows us to converse with those long gone. Philosophy becomes the "Great Conversation" spanning millennia.

Chernow embodies this principle, having "inhabited multiple centuries" through his biographies. He discovered Seneca's insight that we can "annex past ages" and "harvest the store of riches from the past." This isn't mere academic exercise. Living with Grant, Washington, Hamilton, or Twain for years while writing their stories creates genuine relationship and understanding.

Ryan Holiday calculates he's read 4,200 pages of Chernow's work, effectively expanding his life experience by centuries. The past may be a foreign country, but human nature remains constant. The struggles Washington faced with self-control or Hamilton faced with childhood trauma resonate today. Books allow us to learn from their victories and mistakes without paying their prices.

7. Difficult childhoods forge exceptional adults

A striking pattern emerges from Chernow's subjects: every single one had a difficult, domineering, distant, or absent parent. Washington lost his father young and battled a difficult mother. Hamilton was orphaned. Grant struggled under his father's shadow. These early challenges taught emotional self-governance through dealing with unpredictable, difficult relationships you couldn't escape.

This commonality suggests that greatness often emerges from adversity. Early struggles with parental relationships forced these figures to develop exceptional self-control and determination. They learned to manage their emotions when dealing with someone they couldn't simply walk away from. These skills later served them in managing nations, armies, and business empires.

However, the scars remained. Hamilton's complete rejection of his past created instability. Grant's relationship with failure perhaps stemmed from early experiences of paternal disappointment. Washington's tremendous self-control might have developed as armor against maternal criticism. Understanding these connections helps explain both their strengths and their vulnerabilities.

8. Appreciating your gifts prevents destructive envy

Mark Twain possessed a once-in-a-generation comic gift, yet felt contempt for it as "a trade of a low nature." After brilliant lectures, he'd complain he'd merely entertained people who'd forget everything by morning. He wanted to be a mogul, not just America's funniest man. This dissatisfaction drove him into ruinous financial speculation.

Grant similarly failed to appreciate his military genius. Sherman observed that Wall Street financiers would have given all their wealth to win one of Grant's battles. Yet Grant felt compelled to compete in their arena, where he was hopelessly outmatched. Both men possessed gifts others would trade anything to have, yet couldn't see their own value.

Chernow notes how wealthy people he's met often fantasize about writing books. They've achieved financial success but crave creative fulfillment. Meanwhile, creative people often destroy themselves chasing wealth. The inability to want what you have while wanting what others have leads to tragedy. Twain's financial obsessions cost him years of productive writing. Grant's Wall Street adventures led to humiliation. Both would have been happier accepting their extraordinary gifts.

9. Achieved stoicism surpasses natural temperament

The conversation distinguishes between natural and achieved stoicism. If someone is naturally calm, their equanimity isn't self-discipline but inherited temperament. Washington's stoicism was earned through struggle, making it more impressive and instructive. He wasn't born with marble composure; he forged it through years of self-conquest.

This distinction offers hope to those who see themselves as naturally emotional or passionate. Washington's tumultuous passions didn't disqualify him from stoic leadership. Instead, they made his achievement more remarkable. Every moment of composure represented a victory over his nature. Others could feel the passionate force beneath his control, which kept them slightly off-balance and respectful.

The lesson extends beyond historical figures. Those who think "I could never do that" because of their emotional nature miss the point. Stoicism isn't about lacking feelings but processing them constructively. Washington felt anger but learned to reflect before reacting. This is achievable for anyone willing to do the work, regardless of natural temperament.

10. Curiosity and empathy catalyze transformation

Twain's moral evolution began with simple curiosity about people. Despite his prejudices, he spent time in slave quarters as a child, drawn to their storytelling. Later, his willingness to listen to Mary Ann Cord's story opened his eyes to slavery's horrors. This curiosity about human experience gradually dissolved his inherited biases.

The pattern repeats throughout these biographies. Good leaders read people well, as Washington did at dinner parties, opening up to those he trusted while remaining guarded around others. Grant's ability to see his firewood-selling as "solving the problem of poverty" showed curious reframing rather than shame. Hamilton's tragedy partly stemmed from incuriosity about his own past and its effects.

Chernow himself exemplifies this principle. His curiosity about these historical figures, sustained over years of research, allows him to bring their humanity to modern readers. He learns from each subject, carrying their lessons forward. This openness to learning from others, living or dead, enables the continuous growth that marks a life well-lived. Without curiosity, we remain trapped in our first beliefs and limitations.