#11 Ryan Holiday: The Stoic Whisperer
Shane Parrish interviews multiple bestselling author Ryan Holiday about his reading habits, Stoic philosophy, and managing unsolicited requests. They discuss his unique note card system, disciplined writing process, and strategies for valuing one's time and expertise.
Deep Dive Analysis
13 Topic Outline
Introduction to Ryan Holiday and Stoicism
Discovering Stoicism through Marcus Aurelius
Key Stoic Philosophers: Marcus Aurelius, Seneca, Epictetus
Seneca's Complex Life and Teachings
Decision to Drop Out of College at 19
Managing Multiple Projects and Learning to Say No
Apprenticeship with Robert Greene and Research Methods
Ryan Holiday's Physical Note Card System
Structuring and Writing a Non-Fiction Book
Daily Writing Routine and Energy Management
Strategies for Email Management
Implementing a Paid Strategy Session Model
The Importance of Valuing Your Time
3 Key Concepts
Stoicism
A practical philosophy, favored by statesmen and artists, that provides maxims and exercises for living a virtuous life by focusing exclusively on controlling one's thoughts and responses to the world, rather than external events.
Narrative Fallacy
The tendency to tell oneself a story about one's life or past events, making them appear more significant or coherent in retrospect than they actually were.
Turning the Obstacle Upside Down
A Stoic idea, discussed in Pierre Hadot's 'The Inner Citadel,' which involves taking a negative situation or challenge and transforming it into a positive opportunity or outcome.
7 Questions Answered
Stoicism is a practical philosophy focused on controlling one's thoughts and responses to external events, offering maxims and exercises for living a virtuous and excellent life.
Every generation needs its own translation because ancient texts, like Marcus Aurelius's 'Meditations,' were often written in colloquial language, and older translations (e.g., 17th-century) can misrepresent the original tone and meaning.
Seneca's life was indeed complicated, leading some contemporaries to call him a 'tyrant teacher' due to his immense wealth and influence while tutoring a pathological emperor. However, his writings, often produced during personal hardship like exile, demonstrate his practical application of philosophy, and his critics still valued his wisdom.
By compressing learning and experience through concurrent work, but also by recognizing a 'tipping point' where one must learn to say no, especially to opportunities that don't align with personal happiness or long-term goals, despite the allure of money.
Writing notes longhand on physical cards helps with memory and retention, as it forces the information through one's own processing. The physical nature allows for tangible manipulation and organization of ideas, making the vast amount of research for a book more manageable than a digital 'black hole.'
Break the book into discrete tasks or sections, research extensively to fill note cards organized by theme, then write individual chapters or parts in separate documents. Combine and edit the full manuscript only after these smaller sections are complete, and incorporate breaks like exercise to stimulate new ideas.
Prioritize urgent and important emails for quick responses, while saving less critical ones for dedicated catch-up times. For common questions, create articles or resources and direct people to them. For advice requests, consider implementing a paid strategy session model to qualify leads and ensure your time is valued.
23 Actionable Insights
1. Embrace Stoicism for Virtue
Learn and apply Stoic maxims and exercises to live a good, virtuous, and excellent life, as it is a practical philosophy favored by successful individuals.
2. Control Your Response, Not World
Focus exclusively on controlling your thoughts and responses to external events, as this is the only thing within your power and leads to contentment and fulfillment.
3. Define “Enough” for Happiness
Understand and define what constitutes “enough” for your baseline needs and happiness, then confidently decline opportunities that don’t align with this to avoid over-preparing and missing out on life.
4. Align Work with Happiness
Evaluate all opportunities based on what truly makes you happy and aligns with your desired lifestyle, as failing to make these decisions can lead you far from where you want to be.
5. Practice Saying No to Money
Develop the discipline to say no to opportunities, especially those that offer money, if they will lead to being overworked or overwhelmed, as this protects your time and focus.
6. Charge for Initial Strategy
Implement a paid initial strategy session for consulting, where you provide your best ideas and thinking, which qualifies leads, ensures fair compensation for your intellectual work, and can serve as a deposit for further engagement.
7. Don’t Give Time Away
Adopt the philosophy that your time is valuable and should not be given away for free unless you receive something worthwhile in return, as you sell your time for money.
8. Explain Why You Charge
When asked for free advice or work, clearly and politely explain that your expertise is your livelihood and that it would be unfair to your paying clients to provide services for free.
9. Value Time, Combine Tasks
Assign a high value to your time, understanding that informal meetings rarely compensate for it, and combine tasks like walking during calls to maximize efficiency and personal well-being.
10. Compress Experience Concurrently
To accelerate your learning and skill development, undertake multiple related tasks or apprenticeships concurrently, as this can significantly compress the time it takes to gain 10,000 hours of experience.
11. Break Writing into Discrete Tasks
Break large writing projects, like books, into small, discrete tasks such as individual chapters or sections, to make the process more manageable and combat the demoralizing feeling of slow progress.
12. Front-Load Demanding Work
Schedule your most demanding, high-focus work, such as writing, early in the morning when your energy is highest, then switch to less draining tasks for the remainder of the day once diminishing returns set in.
13. Aim for Writing Target
Avoid aimless writing; instead, define a specific target or aim for each writing session, as you cannot hit a target you haven’t aimed for.
14. Write Notes Longhand
Write down notes longhand instead of copying and pasting, as the physical act and ritual of writing enhances memory and makes you more likely to remember and use the information.
15. Implement Note Card System
Read books, mark important passages, and then transfer key knowledge, quotes, or stories onto physical note cards, organizing them by theme to build a database for writing projects.
16. Avoid Over-Optimizing Note Systems
Do not over-optimize your note-taking system for searchability or perfection; a simpler, tangible system can be highly effective for prolific output, as demonstrated by the author’s four books in four years.
17. Demystify by Asking Questions
When learning a complex skill like writing a book, ask seemingly basic or “dumb” questions about the process to demystify it and overcome intimidation, making the task feel more manageable.
18. Exercise for Creative Blocks
Use physical exercise, such as a mid-afternoon run, to help dislodge creative blocks and generate new ideas or solutions, as movement can free up your mind.
19. Prioritize Email by Urgency
Achieve “inbox zero” by responding immediately to urgent and important emails, while batching less critical correspondence for times when you are otherwise unproductive, such as during flights.
20. Turn FAQs into Content
Identify frequently asked questions from your emails and create content, such as articles, to address them, then direct future inquiries to this content, effectively creating a self-serve FAQ.
21. Add Friction to Requests
For unsolicited and burdensome requests, add friction by asking the sender to perform a more effortful task, such as printing and mailing a document, to filter out those not genuinely committed.
22. Choose Best Philosophy Translations
When reading philosophy, invest in the best, most modern translations, such as Gregory Hayes for Marcus Aurelius, to ensure you are accurately understanding the original author’s intent and colloquial language.
23. Draft Chunks, Then Combine
Write individual sections or chapters in separate documents, focusing on each piece recursively, and only combine them into a single manuscript for holistic editing once all parts are drafted.
6 Key Quotes
You don't control the world around you, you control your thoughts, you control how you respond to the world around you.
Ryan Holiday
Every generation needs its own translation because a book like Marcus Aurelius, he's writing to himself in colloquial personal language.
Ryan Holiday
Crimes often return upon their teacher.
Seneca (quoted by Ryan Holiday)
Be wary of any enterprise that requires new clothes.
Ryan Holiday
Writing is easy. It's just sitting down and writing, sitting down at a typewriter and opening a vein or something.
Ernest Hemingway (quoted by Ryan Holiday)
Let no man take a day of my life without, um, you know, giving me something worthwhile in return.
Seneca (quoted by Ryan Holiday)
3 Protocols
Robert Greene's Book Research and Writing System
Ryan Holiday (describing Robert Greene's system)- Read a book, taking notes and marking passages of interest.
- Transfer the marked knowledge onto physical note cards.
- Organize note cards to support specific laws or sections of the book.
- Use the organized note cards as reference when writing each section.
Ryan Holiday's Book Research and Writing Workflow
Ryan Holiday- Start with a book idea and begin extensive research.
- Write down quotes, words, and stories on physical 4x6 inch note cards.
- Organize note cards by theme, building a collection of thousands.
- Scan note cards periodically for digital backup to a service like Dropbox.
- Break the book into discrete sections (e.g., intro, part one chapter one).
- Write each section in a separate Google Doc.
- Combine all sections into a single Microsoft Word document for comprehensive editing.
- Maintain a consistent daily writing schedule, typically from 8 AM to 11/11:30 AM.
- Incorporate physical activity (like running or swimming) in the afternoon to stimulate new ideas and overcome creative blocks.
Ryan Holiday's Paid Strategy Session Model
Ryan Holiday- Qualify leads by requiring a paid strategy session upfront.
- Charge a flat hourly fee (e.g., $1500/hour) for the session.
- Conduct the session, providing comprehensive advice and giving away all best ideas.
- If the client proceeds to hire the company for execution, the initial fee counts as a deposit.
- Use the session time for personal activities like walking to maximize efficiency.