The Daily Stoic – "The Question That Haunts the World’s Most Successful People" | Andrew Ross Sorkin (Pt. 2)

Date: December 6, 2025
Host: Ryan Holiday
Guest: Andrew Ross Sorkin

Overview

In this engaging and thoughtful weekend episode, Ryan Holiday sits down with celebrated financial journalist and author Andrew Ross Sorkin for a wide-ranging conversation that delves into ambition, the meaning of "enough," creativity, and the psychological complexities of success. Building on their previous discussion (Part 1), the two address what drives high performers, how to remain grounded amidst “success mania,” and what lessons can be drawn from history’s titans—from Mark Twain to Elon Musk. The episode is laced with candid stories, memorable quotes, and a deep dive into why even the most accomplished find themselves haunted by the question, "Is it ever enough?"

Key Discussion Points & Insights

1. Defining Stoicism and Personal Practice

Timestamps:
[05:25] – [06:56]

• Ryan Holiday's Take: Stoicism is not about controlling events, but about controlling one's response, using the virtues of courage, discipline, justice, and wisdom.
  • "My working definition is a stoic doesn’t control what happens, but they focus on how they respond to what happens... and the idea is the virtues of stoicism are courage, discipline, justice, and wisdom." —Ryan Holiday [05:28]
• Andrew’s Reflection: Even as a writer of stoicism, Ryan admits he's not mastered it—writing is as much to remind himself as to teach others.
  • "I’m writing about them first and foremost to myself, because I need reminders as much as anyone else." —Ryan Holiday [06:19]

2. The Real Challenges Behind High Performance

Timestamps:
[07:18] – [08:14]

• Elite performers (athletes, CEOs, generals) are all grappling with the mental side of things—the need to bounce back from setbacks, manage stress, and find inner stillness.
  • "At the elite level, it comes down to the mental side of things… that’s where the philosophy side of things really comes in." —Ryan Holiday [07:35]

3. The Writing Process: Procrastination, Output, and Health

Timestamps:
[10:04] – [15:18]

• On Procrastination: Sorkin recasts his own procrastination as mental space for ideation; Ryan values small daily contributions over strict word counts.
  • "Even when you’re tooling around the Internet looking at other things… it may be a way of like creating a little bit of space in your brain to then figure out the other thing." —Andrew Ross Sorkin [10:13]
  • "Did I do something that moved the ball forward today?... It might be that you had two hours and you wasted an hour and 58 minutes, but in the last two minutes, you’re like, 'oh, you know what? This would be a good opening sentence for chapter 16.'" —Ryan Holiday [10:25]
• Writing Rituals: Sorkin's early book processes were unhealthy—night writing powered by Diet Coke and beer, with little sleep.
  • "I used to get Tostitos and a six pack of Diet Coke and oftentimes a six pack of Corona Beer… I would write from like 10 o'clock at night till 5 in the morning." —Andrew Ross Sorkin [12:35]
  • "Did you just feel disgusting all the time?" —Ryan Holiday [13:21]
  • "So disgusting. I felt so disgusting. I gained… Everything was bad about it." —Andrew Ross Sorkin [13:23]

4. Financial Mania and the Allure of More

Timestamps:
[15:21] – [18:43]

• Vivid examples from history—such as Winston Churchill and Mark Twain—who, despite intelligence and fame, fell victim to speculative bubbles and the drive for more.
  • "Churchill being a great example of a rube who's like sucked into the market and... he gets like hit by a cab in New York City." —Ryan Holiday [15:45]
  • "He starts trading like crazy… then of course, he loses it all like everybody else. But interestingly… his reaction was America’s sort of optimism… was actually something that should be adopted more in the UK." —Andrew Ross Sorkin [15:59]
• On Mark Twain: Twain got caught up in "the mania of his time," unable to restrain himself, making and losing multiple fortunes.
  • "It’s never enough. And he can’t restrain himself and he makes and loses several fortunes as an investor." —Ryan Holiday [18:02]

5. The Eternal Question: “Is it Ever Enough?”

Timestamps:
[18:43] – [22:08]

• Alluding to Jim Carrey, Wall Street, and literary anecdotes, both discuss the insecurity driving success and the rare skill of feeling satisfied.
  • "Isn’t that ultimately the lesson of all of us? … We all want more. I mean, some people call that greed." —Andrew Ross Sorkin [18:43]
  • "How do you keep your eyes on your own paper? ... Like, how do you go, I’m doing my thing. We’re running different races." —Ryan Holiday [19:32]
  • "Can you ever be enough, have enough? Is it enough?" —Andrew Ross Sorkin [20:16]
  • "I have something this guy doesn’t have… I have enough." —Ryan Holiday re: Joseph Heller [22:02]

6. Ambition, Satisfaction, and the Joy of the Work Itself

Timestamps:
[26:42] – [32:10]

• Both reflect on the emotional aftermath of publishing a book. Relief, not triumph, is the common feeling. Ryan fixates on the “journey” of writing, less on accolades or external validation.
  • "I have come to realize that my job is to write… The euphoria is in the journey." —Ryan Holiday [27:17; 27:20]
  • "I thought I was going to feel a sense of euphoria… and the truth is, I just felt a sense of relief." —Andrew Ross Sorkin [28:58]
  • "The Marcus Aurelius line is, we all love ourselves more than other people, but for some reason, we care about their opinions more than our own." —Ryan Holiday [32:10]

7. Transferable Success, Domain Expertise, and the Midas Paradox

Timestamps:
[34:32] – [43:21]

• Grant, Mark Twain, and Ray Dalio exemplify how prowess in one field tempts people to overreach into others—with disastrous results.
  • "The hubris of being like, hey, I’m good at… I should also be a great financier... That’s where you get yourself in trouble." —Ryan Holiday [35:19]
  • "People have success in one thing... and then they think, I can do this, this, this and this, as well… of course, most of the time they’re not." —Andrew Ross Sorkin [35:59]
• On Elon Musk and Big Bets: The perils of winning big, often, is the inability to recognize real risk or hear “no.”
  • "If you were writing a book about Elon Musk, it would be titled The Man Who Knows Nothing About Risk. Because he just takes—he goes all in all the time and then doesn’t die." —Ryan Holiday [44:05]

8. The Dangers of Success: Isolation, Distortion, and Self-Delusion

Timestamps:
[44:27] – [47:56]

• Success breeds a lack of honest feedback, creating "reality distortion fields."
  • "There’s no longer any intellectual give and take. It’s just we’re listening to the genius or to the guru… suddenly subjected to market forces in the way that in their life, it no longer is." —Ryan Holiday [45:22]
  • "Some of your ideas have no inherent significance or genius. They are just reflecting the glitter of your 70 millions." —Mark Twain’s letter, paraphrased [46:44]

9. Wealth, "Enough," and the Social Contract

Timestamps:
[48:08] – [51:48]

• Discussion of the material ceiling of wealth—how, past a certain point, money no longer changes quality of life, yet the desire for “more” remains.
  • "Once you get to about 5 or $600 million, there’s nothing that makes me different than the guy who’s got $20 billion or $100 billion." —Anonymous billionaire via Andrew Ross Sorkin [49:08]
  • "For almost everybody the number changes." —Andrew Ross Sorkin [50:17]
  • "It’s that ceaseless desire for more… that propels humans from where we were even 30 years ago… but if you don’t figure out some way to turn that off or turn it down, you end up in ruin." —Ryan Holiday [51:48]

10. Social Friction, Systemic Opportunity, and Disillusionment

Timestamps:
[51:48] – [52:32]

• Recognition that ambition and opportunity are not universal—many feel shut out of the system, fueling social and political tensions.

Notable Quotes & Memorable Moments

"Can you ever be enough, have enough? Is it enough?... That’s a question that everybody asks themselves all the time."
—Andrew Ross Sorkin [20:16]

"I have something this guy doesn’t have… I have enough."
—Ryan Holiday, recounting Joseph Heller’s remark [22:02]

"My job is to write… the euphoria is in the journey."
—Ryan Holiday [27:17–27:20]

"There’s no longer any intellectual give and take. It’s just—listening to the genius or to the guru. And then sometimes they’ll say the things that they’ve been pontificating about in public and people are like, 'what the fuck are you talking about?'"
—Ryan Holiday [45:22]

"We all love ourselves more than other people, but for some reason, we care about their opinions more than our own."
—Ryan Holiday [32:10]

"People have success in one thing... they think... I can do this and this... and of course, most of the time they’re not."
—Andrew Ross Sorkin [35:59]

Highlighted Timestamp Index

| Segment / Topic | Start | Key Quote / Moment | |:---------------------------------------------------------|----------:|:------------------------------| | Stoicism for modern life | 05:28 | "A stoic doesn’t control..." | | The elusive “enough” question | 20:16 | "Can you ever be enough..." | | The Heller/Vonnegut anecdote | 22:02 | "I have enough." | | Actual satisfaction: writing as a joy, not just output | 27:17 | "The euphoria is in the journey." | | The dangers of celebrity self-delusion | 45:22 | "No longer any intellectual give and take..." | | Money’s real limits | 49:08 | "Once you get to about 5 or $600 million..." |

Final Thoughts

This conversation is an honest deep-dive into the strivings, insecurities, and philosophical questions faced by even the world’s most accomplished. Both Ryan and Andrew peel back the layers of status envy, creative drive, and existential doubt—to reveal that all the acclaim, wealth, and success in the world can’t answer the question alone: “Do you have enough?” Through stories of past greats and their own confessions, the episode offers not just caution, but comfort: the real fulfillment lies in the work, in recognizing your own race, and occasionally, in stepping back to say, "enough."