BigDeal Podcast #111 - How To Build Self-Discipline (5 Step Routine) | Ryan Holiday
Date: December 31, 2025
Host: Codie Sanchez
Guest: Ryan Holiday (bestselling author and modern authority on Stoicism)
Episode Overview
In this in-depth, candid conversation, Codie Sanchez sits down with Ryan Holiday to break down the practical art of self-discipline, pulling wisdom from ancient Stoic philosophy and modern personal experience. Ryan shares actionable frameworks on building discipline, overcoming procrastination, handling criticism, structuring focused work, and living meaningfully—both now and for the long term. Expect clear, no-BS advice on how to cultivate habits, make sharper decisions under pressure, and achieve freedom through structure. The episode is packed with direct lessons, memorable quotes, and personal stories that will resonate with ambitious listeners seeking more agency and resilience in their lives.
Key Discussion Points & Insights
1. The Nature of Discipline: Identity vs. Practice
Timestamps: [00:32], [08:22]
- Discipline is not an innate trait but a habit you build.
- “The problem is, we tend to think of these ideas as like, things you are or aren’t... Aristotle specifically says, no, no, that’s totally wrong… If you want to be more courageous, you gotta do stuff on a consistent basis that scares you. That’s how you have courage. That’s what discipline is. It’s a habit or a practice that you build, not a thing that you are or aren’t.” — Ryan Holiday [00:37]
- Make discipline accessible and atomic.
- Rather than framing discipline as a monumental identity goal, pick one clear, actionable habit—like bedtime, or “no sugar”—and build from there. Identity forms through repeated action.
2. Panic Rules & Handling Crisis
Timestamps: [01:43], [01:57]
- Stoicism is practical for crisis:
- “When you're sort of in the shit, all [complexity] goes out the window. That’s what I feel like Stoicism as a philosophy is… For the ancients, it was this kind of thing that you practiced…So that in big moments...what do you do then?” — Ryan Holiday [01:57]
- Panic Rules:
- Focus on what you control.
- Do the right thing.
- Don’t let emotions cloud judgement.
- Simple doesn’t mean easy—return to fundamentals under pressure. [01:57]
3. Delayed Gratification: “Labor Passes, Rewards Last”
Timestamps: [03:23], [03:50]
- The Stoic View: Hard effort leads to lasting satisfaction; shortcuts yield only fleeting pleasure.
- “When you do something in pursuit of pleasure, the benefit passes quickly, but the shame or the consequence of it lasts. Conversely, when you do something hard, the labor passes quickly, but the good from that remains.” — Ryan Holiday [03:50]
- Discipline = Present constraint, future freedom.
- “At some point you do get that gratification and it’s a more sustainable, enduring and stronger reward than whatever you would like to get in this moment.” — Ryan Holiday [03:50]
4. Freedom Within Constraints
Timestamps: [05:18], [05:57]
- Rules as channels for creativity and cooperation:
- “If you question everything…what you live in is chaos and dysfunction…discipline is freedom from chaos and dysfunction. It’s allowing you to channel your energy.” — Ryan Holiday [05:57]
- Balancing independent thinking and structure:
- The best teams (military, business, creative) balance rule-following with independent thought when rules fall short.
5. Atomic Habits & The Power of Preemptive Moves
Timestamps: [10:30], [10:55]
- Identify “gateway” habits that snowball into larger success:
- “What is that preemptive move you could do that’s 10x easier but leads to a higher likelihood of you doing the next step?” — Codie Sanchez [10:30]
- For example: Laying out workout clothes → gym attendance. Deleting social apps → less screen time.
- Remove temptation and make good choices easier.
- “I don’t have any social media apps on my phone…” — Ryan Holiday [11:05]
6. Focus & Deep Work
Timestamps: [12:31], [12:42], [14:49]
- Uninterrupted time is key:
- “The secret to success in almost all fields is large, uninterrupted blocks of focused time.” — Ryan Holiday [12:42]
- Systems to protect focus:
- Ruthlessly keep things out of your calendar. Schedule your best concentration zones (often mornings) for your most important work.
- Example: Toni Morrison wrote before sunrise for best focus.
7. Procrastination as Entitlement & The Reality of Mortality
Timestamps: [16:26], [16:48], [18:59]
- Procrastination is arrogant:
- “To procrastinate is to be entitled. It assumes there will be a later. It assumes you’ll have the discipline to get it later despite not having the discipline now.” — Codie Sanchez quoting Ryan Holiday [16:26]
- Memento Mori:
- Stoics meditate on mortality not to be morbid, but to urge action now—because “I'll do it later” is an assumption you may not get to test.
- “Not only do you not have forever… the person or the thing you’re taking for granted could go away at any moment…in light of it, [procrastination] becomes extremely entitled and in some cases, very reckless.” — Ryan Holiday [16:48]
8. Enjoying the Journey & Not Just the Reward
Timestamps: [20:26], [23:20]
- Don’t mortgage happiness for results alone:
- “The idea that the shit now is worth enduring because it will be amazing later is a dangerous thing to fool with…You can do everything right in life and get fucked.” — Ryan Holiday [20:26]
- Love the work itself:
- “You’re entitled to the work, not the rewards of the work.” — Ryan Holiday [23:20]
- Don’t be “miserable fuck day to day so that in the future I feel good for two weeks when it comes out, and then I start the whole thing again. That seems like a bad trade…” — Ryan Holiday [23:20]
9. Negative Visualization & Planning For the Worst
Timestamps: [29:16], [31:52]
- Stoics practice negative visualization:
- “The unexpected blow lands heaviest...the job of a leader is to be like, okay, we planned for this. Here’s what we’re gonna do.” — Ryan Holiday [29:16]
- Anticipate adversity so you’re not caught off guard.
- Napoleon: “His generals should say...‘What would I do if the enemy appeared on my left? On my right? Behind me?’” — Ryan Holiday [31:52]
10. Knowledge Crafting: Ryan's Method for Deep Learning
Timestamps: [33:47], [34:15]
- Analog note-taking:
- “When I find information that is interesting to me, I write it and organize it and return to it enough times that I develop a feel for it...I read with a pen and I take notes and then I transfer those notes by hand.” — Ryan Holiday [34:09]
- The slowness is the point:
- It’s about scratching information into memory—“Some things are supposed to be hard.” [34:15]
11. Favorite & Most-Influential Books
Timestamps: [40:05]
- Marcus Aurelius, Meditations
- Robert Greene, Mastery, 48 Laws of Power, Laws of Human Nature
- Emerson & Thoreau, Self-Reliance, Civil Disobedience
- Tolstoy, Calendar of Wisdom
- (Recommended as a daily reader)
- All of the Stoics: Seneca, Epictetus
12. Teaching Wisdom to Children
Timestamps: [42:34], [44:46]
- Use stories and fables to seed wisdom.
- Familiarity with great stories (e.g., Odyssey, myths) builds long-term moral frameworks.
13. Self-Knowledge as the Ultimate Asset
Timestamps: [45:13], [45:34]
- Know thyself: “So much knowledge is lost to us because we are ourselves lost and lost unto ourselves.”
- Self-awareness beats “smarts” in crucial moments—know what triggers your patterns.
14. Ego: When Confidence Becomes a Liability
Timestamps: [48:07], [50:16]
- Ego prevents growth by blocking feedback and objective self-evaluation.
- “The idea that you don’t have an ego is like the definition of ego.”
- Most obstacles are internal, not external.
- Don’t let achievements trap you in a fixed identity or fear of failure.
15. Practices to Check Ego and Accept Critique
Timestamps: [53:21]
- Watch for signs: defensiveness, “How dare you?” “Who do they think they are?”
- Delay your reaction to criticism.
- Your first reaction is usually ego; engage with feedback after a cooling period.
16. Opinions: The Power to Abstain
Timestamps: [55:06], [55:22]
- You always have the power to have no opinion—don’t waste energy on unhelpful arguments.
- Save strong opinions for things that truly matter to your life or values.
17. Social Media & Haters: The Stoic Perspective
Timestamps: [61:58], [62:10], [64:05], [66:52], [67:33], [68:40]
- Negative reactions are inevitable; the more success, the more raw numbers of critics.
- “I take to mean there are millions of people who don’t like me, not just millions who do.” — Ryan Holiday [64:05]
- Criticism is a mathematical certainty: accept it, don’t personalize.
- Marcus Aurelius: We care more about others’ opinions than our own, which is irrational.
- “If they truly knew you, they’d probably say something worse.” — Epictetus via Ryan Holiday [66:52]
- “Don’t let them drag you down to their level...we’re all made to work with each other.” — Ryan Holiday [67:35]
- Compassion for haters; their negativity is their lot, not yours.
18. Bonus: Donkeys, Parenting, and Marketing Stunts
Timestamps: [68:43], [70:08], [71:05]
- Ryan is a fan of donkeys—protective, loving, clever animals, useful for his ranch and family.
- His early career explored the limits of marketing, sometimes via provocative or unconventional stunts (Trust Me, I’m Lying).
- Eventually pivoted to focus on work that reflected his values, informed by lessons on integrity and selfhood.
Notable Quotes
- On Discipline:
- “It’s a habit or a practice that you build, not a thing that you are or aren’t." — Ryan Holiday [00:37]
- On Procrastination:
- “To procrastinate is to be entitled. It assumes there will be a later…" — Codie Sanchez [16:26]
- On Work and Reward:
- “You’re entitled to the work, not the rewards of the work.” — Ryan Holiday [23:20]
- On Critics:
- “This person was statistically guaranteed to exist. There’s no escaping it.” — Ryan Holiday [64:05]
- On Ego:
- “The idea that you don’t have an ego is like the definition of ego.” — Ryan Holiday [48:07]
- On Deep Work:
- “The secret to success in almost all fields is large, uninterrupted blocks of focused time.” — Ryan Holiday [12:42]
- On Self-Awareness:
- “So much knowledge is lost to us because we are ourselves lost and lost unto ourselves.” — Codie Sanchez [45:13]
Memorable Moments
- Ryan talks through his “no social media apps on phone” rule and the power of environment design. [11:05]
- The story of the editorial feedback loop and using delay to override immediate ego reactions. [53:21]
- A frank discussion on the futility of chasing universal approval or legacy—and why it doesn’t matter. [64:05]
- Parenting wisdom: using myths, stories, and history to impart enduring lessons to children. [44:46]
Suggested Action Steps
- Choose one “discipline gateway” habit to start, with a clear boundary (e.g., bedtime, dietary rule).
- Schedule a blank block on your calendar for deep work.
- Practice negative visualization: plan for what could go wrong so you’re less rattled by setbacks.
- Set up your environment to make good behaviors easier: remove digital temptations, etc.
- Cultivate self-knowledge: reflect, journal, and seek objective feedback.
- Accept that criticism and haters are a mathematical inevitability—not a personal referendum.
- Remember: “You’re entitled to the work, not the rewards of the work.”
- Re-read formative books, not just once, but again as you grow.
For further reading:
Ryan Holiday’s books (The Obstacle is the Way, Ego is the Enemy, The Daily Stoic, Wisdom at Work, Trust Me, I’m Lying) and recommended classical texts: Meditations, Emerson, Thoreau, Robert Greene, Tolstoy’s Calendar of Wisdom.