You’ve Gotta Make Them Work For It | The Presidential Biographies You Can’t Afford to Skip

Summary

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

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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.

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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.

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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.

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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)

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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.

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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.

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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.

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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.

Transcript

[Ryan Holiday]

Welcome to the Daily Stoic podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom, into the real world. You gotta make them work for it. It's depressing, it's discouraging, it's distracting. All this stuff that's happening in the world, all that's wrong in the world. Maybe you're worried about authoritarians destroying institutions we once trusted. Maybe you're worried about groupthink and cancel culture and chilling effect. Maybe this is making it harder for you to focus. Maybe this is making you afraid. But you know what you can't do? You can't give up your work, your freedom of thought, your freedom of choice preemptively. It may well be that the social media mob or the goons with guns come for you at some point and you'll be forced to reckon with that use of force. But this is not that point. So why are you giving up your power voluntarily, in advance? In the Hanoi Hilton, James Stockdale counseled his fellow prisoners of war that they would inevitably be tortured and almost certainly break under the torture. But he told them, and this was the key, they needed to resist up until that point. They should make their captors work for it, he said. They should go as far as they could. They should not surrender until they had to. They had to make the guards work for it. The Stoics knew about tyranny. They knew about exile and torture and duress. But they also understood that for the time being, that is to say right now, they possessed a freedom of choice and they had to use it. They had to hold out. They should not give up out of fear or anticipation prematurely. They should not hand over their focus or their freedom until the tyrant actually made them. And this advice applies as much today as it did then.

Favorite presidential biographies. I haven't read a biography of every president, but I've read most, and I'm gonna give you some of my favorites. Okay, Truman, underrated President. You wouldn't think you would want to read thousand plus pages, but this David McCullough biography is incredible. It's not my favorite. My favorite Truman biography is Plain Speaking by Merle Miller, which I have upstairs in my office. It's out of print, but it's sort of an oral history of Truman's presidential administration. And absolutely incredible. As Truman said, there's nothing new in the world but the history you don't know. McCullough's biography of Theodore Roosevelt is really good. Mornings on horseback. But again, not my favorite. My favorite Roosevelt biography. This is Teddy Roosevelt is the Rise of Theodore Roosevelt by Edmund Morris, which I actually bought on the same Amazon order as Meditations for the first time 20 years ago. Love this book. Very good. They say about Washington, the more you read about Washington, the more you like him. And we should have Chernow's biography of Washington here somewhere, which I'm not seeing it, but Chernow's biography of Washington is very good. The more you read about Washington, the more you like him.

John Adams.

The more you read about John Adams, it's not the less you like if you just find him kind of annoying and you understand why some of his colleagues thought the same. But still very good biography. As far as Lincoln goes, this is Doris Kearns Goodwin's Team of Rivals, which is a classic for a very good reason. I just interviewed her on stage a couple weeks ago. But I have a couple other Lincoln biographies that I like. Here's Lincoln Biography of As a Writer, which is a look at Lincoln as a writer. This is Gary Wills's Lincoln at Gettysburg, which is all about the Gettysburg Address. And then these two books by William Lee Miller, Lincoln's Virtues and President Lincoln, which are biographies of him as a politician and then as a man of moral character. Very, very good.

Love those.

As I said, Chernow's Washington quite good. Chernow's Grant is quite good. Although I would say that Grant's memoirs, which is over there, is almost better than any biography you could read. It's so good that they thought that Mark Twain ghost wrote it. That's how good it is. So I would definitely read that. Not a presidential biography, but that's by choice. Sherman, the Sherman esque statement where he refuses the presidency is Sherman's. One of my favorites. His memoirs, equally good as Grant's, not exactly a presidential biography, but this book about Paul Jennings, he's a slave in the Madison White House. He's the one that saves the famous painting. Very, very good. I have that next to Barack Obama's memoir. Okay. And then of course, the gold standard of presidential biographies. He is probably the goat. He is the goat. And he is rushing to finish the fifth and hopefully final installment in the Lyndon Johnson series. I'm of course talking about Robert Caro. Path to Power, means of Ascent, Master of the Senate, passage of Power, the four amazing epic Lyndon Johnson books. Again, you don't think you want to read. What is it? It's probably 4,000 pages, close to 4,000 pages about Lyndon Johnson. But you do. They are as readable as any novel. And what they are sweeping histories, not just of the man and how he uses power, but also the time and place that he is from. So the path to power is fascinating because it gives you like a whole. Like it starts like before people have even come to Texas. He does this big sweeping history of each moment in time. So these are all Pulitzer Prize winners, number one bestsellers, classics for a reason. If you say, hey, I'm going to read this whole series from start to finish and it's going to take me three years, that would be a good three years of reading and be well worth it. These are just incredible, amazing books, worth every page. And I would say Robert Caro earns every page. Why should you care about Lyndon Johnson, first off? Because you could argue that that was the last time the Senate worked, when he was master of the Senate. As the third book is all about when they actually passed real legislation. And then when he was president, he's the one that gets the civil rights legislation passed. His whole life had been about power, his whole life had about his own ambition. And then he'd been your standard southern racist politicians. And yet the second he gets the presidency, he goes and he says, I want to pass Kennedy's civil rights bill. And his advisors are like, I think you should wait till later in the term or the next term. And he says, oh man, what the hell is the presidency for? As. As in to say, what good is sitting in the seat if you're not going to use that power to do good? And that's what Johnson did. But the tragedy, of course, of Johnson is that the same guy that creates the Great Society, the idea of the social safety net also gets us into Vietnam. And so it's not hero worshiping by any means. He's looking at what makes this person tick, what happened to him as a kid, what's broken in him, what's good in him. So it's just a masterful diagnosis and character study and then also, I think, some real lessons in Cautionary Tale. One of the famous lines in this book is he says, you know, power doesn't corrupt. That's too simple. Kara says what power does is reveal. And what it reveals in Lyndon Johnson is both much better than people think and in other ways much worse than people think. And so is this is what biography

is meant to do.

It's history and psychology and character study psychology and all this other stuff. These are, these are worth every page. Okay, river of Doubt, another good Roosevelt biography, really good. But then she has another book, Destiny of the Republic, which is about the assassination of President Garfield you wouldn't think Garfield president James Garfield would be an interesting president you would want to read about, but you would be wrong. Very good.

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Also, there's a little bit of a Wilson biography here in Dead Wake, Rapisinga and Wilson, another president. The more you read about, the less you like. Do you have a favorite presidential biography? Okay, Okay. You want some quick presidential trivia? Okay. This is a letter from like a week after Roosevelt became president. Dear George, I'm very much obliged to you old fellow, for your letter on the 16th. I shall do my best to bear myself. Well, Executive Mansion. That's incredible. And then that over there is a ticket from Grant's funeral. Here's the first edition of his memoirs, as I said. Very, very good. Okay, Other presidential biographies that I like. I think my favorite Grant biography is Brooks D. Simpson's Ulysses S. Grant, Triumph over Adversity. That's about as early years. Very, very good. Eisenhower in War and Peace by Jean Edward Smith. Very, very good. A Thousand Days. This is a Schlesinger bio of Kennedy. Very good. I prefer as a shorter Kennedy biography, the thirteen Days which is written by his brother. As I said. Here's river of Doubt. Love that one. Here's my original copy of Rise of Theodore Roosevelt, now 20 plus years old. Get a great Washington biography. This is Cincinnatus, the myth of Cincinnatus, the great Roman general who becomes his name dictator and then resigns his powers after he saves Rome. Is. This is a great Gary Wills biography about what that myth and that idea means to Washington as far as Lincoln goes. Team of rivals, as I said. David Reynolds and David Donald. Two big epic bios of Lincoln. Very, very good. Oh, this one was good. This is about the women in Theodore Roosevelt's life. Oh, Jimmy Carter, underrated, great president. Loved these two books. This is Kai Bird's biography. And then this is Jonathan Alter's biography. However, it's hard to beat Carter in his own words. This is an Hour Before Daylight, which is about his boyhood. Loved this. Oh, here's plain speaking. My favorite Truman bio. Okay, biography of the other Roosevelt. This is fdr. This is called the lion and the Fox. It's a political biography. It's again a biography. 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. How did Roosevelt manage to change the country for the better? How did he actually operate effectively as a politician? That's not a thing people know enough about. That's what this biography is. Robert Greene recommended this to me. It's a great book. Here is Washington from Chernow. Hey, it's Ryan. Thank you for listening to the Daily Stoic podcast. I just wanted to say we so appreciate it. We love serving you. It's amazing to us that over 30 million people have downloaded these episodes in the couple years we've been doing it. It's an honor. Please spread the word, tell people about it. And this isn't to sell anything. I just wanted to say thank. You.

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