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#11 Ryan Holiday: The Stoic Whisperer

May 16, 2016 47m 4s 23 insights
In this episode, I talk with multiple best selling author Ryan Holiday about how he reads, what it means to be a stoic, and how to gracefully deal with freeloaders. *** Go Premium: Members get early access, ad-free episodes, hand-edited transcripts, searchable transcripts, member-only episodes, and more. Sign up at: https://fs.blog/membership/   Every Sunday our newsletter shares timeless insights and ideas that you can use at work and home. Add it to your inbox: https://fs.blog/newsletter/   Follow Shane on Twitter at: https://twitter.com/ShaneAParrish
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.