The Daily Stoic Podcast
Episode: Mark Manson: “I Didn’t Realize How Out of Control I Was.”
Host: Ryan Holiday
Guest: Mark Manson
Date: November 15, 2025

Overview

In this weekend edition of The Daily Stoic, Ryan Holiday sits down with best-selling author Mark Manson (The Subtle Art of Not Giving a Fck, Everything Is Fcked) for an honest discussion about the realities of success, the transition from chaos to balance, and the hard lessons about discipline and identity that come with age and achievement. Drawing on personal experiences in both their careers, Manson and Holiday reflect on the difficulty of integrating philosophical wisdom, the lure and trap of opportunity, managing volatility, and the pursuit of sustainable success in work and life.

Key Discussion Points & Insights

The Myth of “Balanced” Success

• Advice from Successful People Is Often Retrospective
  Manson cautions against taking lifestyle and balance advice from successful individuals, noting that the success often came from periods of intense imbalance.

  • Mark Manson (09:03): “A lot of positive lifestyle changes are a result of privilege… Once you do have the money to do a sauna every day or… a papaya creatine smoothie in the morning, like, that does feel like the most important thing… But… coming up… I ate Red Bulls and Reese’s cups every morning. I fell asleep with my laptop open on my chest and then would wake up in the middle of the night and continue working.”

• Early Career Volatility vs. Later Stability

  • Manson (11:27): “Early on, volatility works in your favor… But then once you’ve achieved escape velocity… you want to minimize volatility.”

• Hustle Culture & Who Benefits
  The “maniac” founder ethos benefits those investing or relying on others’ work ethic, not necessarily the individual.

The Difficulty of Saying “No” as Success Grows

• Shifting from Yes to No

  • Early in a career, success requires saying "yes" to everything; later, real progress comes from learning to say "no."
  • Manson (14:09): “Early in your career, you… need to say yes to everything because you don’t know what’s going to work… Once you’ve become successful or… achieved a certain amount of success. You need to say no to most things. But that inflection point… it’s very unclear where that inflection point is.”

• The “F*ck Yes or No” Principle

  • A rule for major decisions: if it isn’t a “f*ck yes,” it should be a “no.” But, as stakes rise, so does the complexity.
  • Manson (16:49): “The higher up the mountain you climb, the more difficult those nos become. And I didn’t anticipate that… subtle art blows up… Will Smith shows up… and I basically had to learn that lesson all over again.”

• The True Cost of “Yes”

  • Hard to gauge the opportunity cost of saying yes, especially regarding health, relationships, and sanity.
  • Holiday (19:11): “There’s no way to know what the individual toll of one thing is on a marriage… your health… burnout… That’s the trap of it.”

Outwitting Your Own Weaknesses and Creating Systems

• Don’t Rely on Willpower Alone

  • Manson describes forming strict rules to override his own tendency for justification, whether in work or health.
  • Manson (24:45): “There’s this cliché of like, trust yourself, you know best, whatever. That’s true in some cases. Right. But… in the case of accepting speaking gigs and… eating desserts or drinking alcohol, I can’t trust myself.”
  • Manson (25:26): “If you’re relying on willpower, you’ve lost… You shouldn’t even put yourself in the spot where you’re having to make a decision…”

• Iterating Rules with Accountability

  • Mark shifts gatekeeping of speaking gigs to his operations head (“only show me ones that fundamentally change my career”) to protect against his own impulsiveness.
  • Manson (21:12): “So now… I’ve told my head of operations to literally not show me any speaking opportunities unless she believes that they could fundamentally change my career.”

Habit Change, Aging, and Margin for Error

• Building Healthier Routines Requires Hard Stops, Then Eases

  • Early, Mark needed strict, “no exceptions” rules to break cycles and lose weight; now, he can operate on “more often than not.”
  • Manson (30:04): “I had to go through that period of hard rules and basically treating myself like an untrained dog… once the inner dog is trained, then you can let it loose and off the leash, but until it’s trained, you have to keep it.”

• Aging Means Less Margin for Error

  • What worked in youth (brute force, little sleep) is unsustainable; the body and mind demand better routines.
  • Manson (31:54): “When I think back to my 25-year-old self… I could go out, drink all night… sleep three hours and then wake up and bang out a whole day of work… Today I would be dead.”

Understanding Identity & Motivations in Work

• Re-examining Why We Do What We Do

  • Mark describes his realization that he loves building an audience and online media more than traditional publishing, leading to a shift away from book contracts.
  • Manson (38:10): “I burned myself out, and I struggled a lot mentally during that period. And so then I came back to kind of doing the online stuff… and I loved it. I’m a dog just chasing a car… I actually canceled a book deal…”

• Avoiding the Punishment of Success

  • Don’t let external measures of success strip you of what motivated you in the first place.
  • Holiday (40:32): “The decision for that is, like, I’m not going to rush it… The reward for succeeding at your thing should be that you get to not rush through it. But you have to know what that thing is. And then you need the discipline and confidence to go like, no, this is what I’m supposed to be doing, not what you think I’m supposed to be doing.”

• Team Building: Joy and Regret

  • Both Mark and Ryan found joy in building teams—something they were advised against.
  • Manson (43:31): “I fucking love having a team. I wish I did this 10 years ago.”

Notable Quotes & Memorable Moments

• On Volatility & Success
  Manson (11:27): “If you have nothing, you want as much volatility as possible… But once you’ve achieved escape velocity… you want to minimize volatility.”

• On Willpower & Self-Discipline
  Manson (25:26): “If you’re relying on willpower, you’ve lost.”

• On Aging & Margin for Error
  Manson (31:54): “I could go out, I could drink all night… today I would be dead.”

• On Opportunity Cost in Relationships & Health
  Holiday (19:11): “There’s no way to know what the individual toll of one thing is on a marriage, on your health, on your overall productivity, on the burnout that you are slowly… progressing towards. That’s the trap of it.”

• On Identity and the Danger of Success
  Holiday (40:32): “The reward for succeeding at your thing should be that you get to not rush through it… But you have to know what that thing is.”

Timestamps for Key Segments

• [09:03] – How privilege & success change your perception of health and balance
• [11:27] – Volatility: Asset in youth, liability after success; startup founding culture
• [14:09] – Transitioning from saying “yes” to “no” as career develops
• [16:49] – The “F*ck Yes or No” rule and why success complicates decision-making
• [19:11] – Calculating the unseen toll of saying yes; real opportunity costs
• [21:12] – Mark’s system for delegating decision-making on speaking gigs
• [24:45] – Admitting self-deception: “I can’t trust myself”
• [25:26] – Willpower as a losing strategy for discipline
• [29:49] – Progress: Moving from strict rules to “more often than not”
• [31:54] – Margin for error decreases with age
• [38:10] – Realizing true motivations: Mark’s shift from author identity to Internet media
• [40:32] – Holding on to what you love as you succeed
• [43:31] – Finding joy in building a team

Tone & Style

The conversation is frank, informal, and self-deprecating, with both participants sharing personal stories and occasional humor. Manson in particular reflects with candor on the illusions and realities of transformation, success, and self-control, while Holiday offers analogies and stories that make Stoic philosophy accessible and actionable.

Summary prepared for listeners interested in actionable wisdom on managing success, balancing ambition with discipline, and making life choices aligned with personal values and long-term fulfillment.