The Daily Stoic – Episode Summary
"You’ve Gotta Make Them Work For It | The Presidential Biographies You Can’t Afford to Skip"
Host: Ryan Holiday
Date: February 20, 2026

Episode Overview

In this episode, Ryan Holiday intertwines two main themes: the enduring Stoic lesson of persistence and resistance in the face of adversity (“making them work for it”), and a lively, detailed rundown of his favorite presidential biographies—books he believes every history and leadership enthusiast should read. Holiday draws connections between the struggles faced by past leaders (and the lessons drawn from their lives) and the Stoic mindset required to confront today’s complex challenges.

Key Discussion Points & Insights

1. Making Them Work for It: Holding Out Against Tyranny, Fear, and Distraction

Timestamps: 00:00–01:56

• Modern Challenges and Stoic Virtues:
  Holiday opens with a reflection on the feelings of discouragement, distraction, and fear that permeate current events—be it political turmoil, groupthink, or cancel culture.
• The Stockdale Example:
  He recounts James Stockdale’s advice to fellow POWs at the Hanoi Hilton during the Vietnam War: resist until resistance is no longer possible; never surrender your agency preemptively.
• Stoic Relevance:
  The core Stoic message: don’t relinquish your power, focus, or freedom before you must.

  “They needed to resist up until that point. They should make their captors work for it, he said... They had to make the guards work for it.” (Ryan Holiday, 00:39)

• Contemporary Application:
  Don’t yield to fear or distractions before circumstances truly warrant; use the freedom and choice you still have.

2. Presidential Biographies: Recommendations & Reflections

Timestamps: 01:56–14:14

Truman

• Top Picks:
  • Plain Speaking by Merle Miller (Holiday’s favorite — an oral history)
  • Truman by David McCullough

  “Truman—underrated President. You wouldn't think you would want to read thousand plus pages, but this David McCullough biography is incredible.” (Ryan Holiday, 01:59)

Theodore Roosevelt (Teddy)

• Top Picks:
  • The Rise of Theodore Roosevelt by Edmund Morris (Holiday’s all-time favorite Teddy bio)
  • Mornings on Horseback by David McCullough

  “I actually bought [Rise of Theodore Roosevelt] on the same Amazon order as Meditations for the first time 20 years ago.” (Ryan Holiday, 02:19)

George Washington

• Top Pick:
  • Washington: A Life by Ron Chernow

  “The more you read about Washington, the more you like him…” (Ryan Holiday, 02:30)

John Adams

• Top Pick:
  • John Adams by David McCullough

  “The more you read about John Adams... you just find him kind of annoying... but still very good biography.” (Ryan Holiday, 03:08)

Abraham Lincoln

• Top Picks and Focus Areas:
  • Team of Rivals by Doris Kearns Goodwin (classic—Holiday interviewed Goodwin)
  • Lincoln at Gettysburg by Garry Wills
  • Lincoln’s Virtues and President Lincoln by William Lee Miller
  • Focus on Lincoln’s writing, moral character, and political savvy.

Ulysses S. Grant

• Top Picks:
  • Grant by Ron Chernow
  • Ulysses S. Grant: Triumph over Adversity by Brooks D. Simpson
  • Personal Memoirs of U.S. Grant (Holiday especially praises Grant’s own memoir)

  “Grant’s memoirs... is almost better than any biography you could read... so good that they thought that Mark Twain ghost wrote it.” (Ryan Holiday, 03:54)

William Tecumseh Sherman

• Memoirs: Not a president but highly recommended for insights into leadership and the famous “Shermanesque” refusal of the presidency.

Paul Jennings

• Book about Paul Jennings, a slave in the Madison White House (rescued the famous painting): A unique behind-the-scenes perspective.

Lyndon B. Johnson (LBJ)

• The Gold Standard:
  • Robert Caro’s multi-volume biography:
    • The Path to Power
    • Means of Ascent
    • Master of the Senate
    • The Passage of Power (final volume forthcoming)

  “…you don’t think you want to read... probably 4,000 pages... but you do... sweeping histories, not just of the man and how he uses power, but also the time and place that he is from.” (Ryan Holiday, 05:20) “Power doesn't corrupt. That's too simple. Caro says what power does is reveal.” (Ryan Holiday, 06:38)

• Key Themes:
  • LBJ’s complex legacy: champion of civil rights and social safety nets, but also embroiled in Vietnam.
  • These biographies as a master course in character study and the real use and cost of power.

Other Notables

• James Garfield:
  • Destiny of the Republic by Candice Millard—an unexpectedly gripping look at the Garfield presidency.
• Eisenhower:
  • Eisenhower in War and Peace by Jean Edward Smith.
• John F. Kennedy:
  • A Thousand Days by Arthur Schlesinger (major work on JFK)
  • Thirteen Days by Robert F. Kennedy (short, focused look at the Cuban Missile Crisis)
• Franklin D. Roosevelt:
  • The Lion and the Fox (political biography focused on FDR’s strategic effectiveness)
• Jimmy Carter:
  • An Hour Before Daylight by Carter himself (memoir praised by Holiday)
  • Biographies by Kai Bird and Jonathan Alter.
• Miscellaneous:
  • Biographies about “the women in Theodore Roosevelt’s life.”
  • Cincinnatus by Garry Wills—explores how Roman ideals influenced George Washington.

Reflections on Presidential Biography:

• Leadership vs. Politics:
  “Kennedy famously said that people want their kids to grow up to be president. They don't want them to be a politician. But to be a good president, you have to be an effective politician.” (Ryan Holiday, 13:20)
• The Value of Biography:
  Biography as a mix of history, psychology, character study, and cautionary tale.

Notable Quotes & Memorable Moments

• “You can't give up your work, your freedom of thought, your freedom of choice preemptively... You should not hand over your focus or your freedom until the tyrant actually made them.” (Ryan Holiday, 00:19)
• “There's nothing new in the world but the history you don't know.” (Harry Truman, quoted by Ryan Holiday, 02:09)
• “What good is sitting in the seat if you're not going to use that power to do good?” (Ryan Holiday recounting LBJ, 06:11)
• “Power doesn't corrupt. That's too simple. Caro says what power does is reveal.” (Holiday channeling Robert Caro, 06:38)

Key Timestamps for Important Segments

• 00:00–01:56: Stoic lessons on resistance and personal agency.
• 01:56–03:48: Presidential biography recommendations—Truman, Roosevelt, Washington, Adams, Lincoln.
• 03:49–07:12: Grant, Sherman, Paul Jennings, LBJ, the value and lens of biography, lessons from power.
• 07:13–10:35: Other favorites—Garfield, Roosevelt, Eisenhower, Kennedy, Carter, women in history.
• 10:35–14:14: Further notes and unique biography suggestions, closing reflections.

Episode Tone & Language

Ryan Holiday’s delivery is conversational, direct, and passionate—mixing bookish enthusiasm with practical wisdom. He peppers his recommendations with personal anecdotes, pithy historical quotes, and off-the-cuff asides, all in service to a key message: that learning from the lives and struggles of leaders (through Stoic principles and great biographies) arms us for our own moments of challenge.

Takeaways

• Don’t yield to fear, distraction, or mental tyranny before it’s necessary—make life “work for it.”
• Presidential biographies aren’t dry histories; they are stories of character, virtue, flaw, and the use (and abuse) of power—offering timeless lessons for anyone seeking to lead or simply understand the human experience.
• Make time for these in-depth reads; they’re “worth every page.”
• Understand that the study of another’s life is as much “history and psychology” as it is an adventure in personal growth.

If you’re looking to fortify your Stoic mindset and broaden your understanding of American leadership, consider Holiday’s well-curated list your next reading challenge.