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The Simple Steps to Fuel Your Creativity – Ryan Holiday
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Sign Up for "Writing Examples" and Learn From The Best Writing of All Time: https://www.writingexamples.com Ryan Holiday is one of the world’s most prolific writers. He’s published sixteen books, written a daily email newsletter every day for the past eight years, has 1.7 million YouTube subscribers, and runs his own creative agency. (Reciting that list is difficult enough to remember, let alone accomplishing all of those things.) This conversation will get you off your butt as a writer. It’s 78-minutes of learning how to generate creative inertia for yourself — because that’s where Ryan thrives. He’s a no-BS writer. And by “no BS,” I mean: no coddling or making excuses for himself. He’s exceptional at just doing the work. Generating that kind of momentum is exactly what fires me up, and exactly what I teach at Write of Passage. If you’re feeling called to write, you should join one of our programs. I’m telling you: Write of Passage will light a fire inside of you. I recently heard a story about Ryan that sums him up in a nutshell. His editor called to congratulate him on hitting the #3 spot on the New York Times Bestseller list. His book had only been out for a week. I don’t know about you, but I would be camped out by the phone, biting my nails while I waited for that call. But Ryan? Ryan was heads-down writing, halfway done with his next book. And today, you’ll learn exactly how he generates that level of momentum. WRITE OF PASSAGE: Want to learn more about the next class of Write of Passage? https://writeofpassage.com TIMESTAMPS: 00:00:00 Introduction 00:06:00 Book launches 00:08:55 Quantity vs Quality 00:11:35 Process of writing a book 00:15:00 Ryan's note card system 00:18:20 How Ryan's writing has evolved 00:21:40 How Ryan's writing has improved 00:23:55 Editing 00:26:45 Great introductions 00:30:55 Your next big piece 00:32:40 Breaking down Marcus Aurelius 00:38:40 Writing Examples 00:39:17 How music helps you write 00:41:15 Best advice about reading 00:45:10 Research for your writing 00:47:10 Schedule and productivity 00:50:10 Reading for style vs content 00:51:10 What will be Ryan's next book? 00:51:50 Biographies 00:54:10 Criticism 00:55:20 Feedback (like Seinfeld and Curb Your Enthusiasm) 01:00:30 When are you ready to start writing a book 01:01:45 Fear of failure 01:05:30 Momentum 01:05:50 Storytelling 01:12:30 Top lessons from Ryan 01:12:50 Getting more practice (reps) PODCAST LINKS: Website: https://writeofpassage.com/how-i-write Apple: https://podcasts.apple.com/us/podcast/how-i-write/id1700171470 Spotify: https://open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv ABOUT THE HOST: I’m David Perell and I’m a writer, teacher, and podcaster. I believe writing online is one of the biggest opportunities in the world today. For the first time in human history, everybody can freely share their ideas with a global audience. I seek to help as many people publish their writing online as possible. How I Write is a podcast by Write of Passage // Production by Adam Soccolich
Segments Timeline
Facing the Blank Page
Ryan Holiday discusses the fear of the blank page and how it can block creativity. He emphasizes that everyone experiences fear of judgment and failure, which can hinder productivity. He believes in writing to think and maintaining momentum, rather than waiting for the perfect moment to start.
"well the blank page is scary because what's on the page is Never As Good As what's in your head yeah we're all scared of judgment we're all scared of failure the fact that we're all scared is blocking..."
Ryan's Creative Output
In this segment, the host highlights Ryan Holiday's prolific writing career, mentioning his sixteen published books, daily newsletter, and creative agency. The conversation sets the stage for exploring how Ryan generates creative momentum and inertia, encouraging listeners to take action in their writing.
"working on the book I have like a biography project I'm going to do I know what I'm going to do and I know who it's going to be about [Music] and Ryan holiday one of the world's most prolific writers ..."
The Call That Changed Everything
Ryan shares a story about receiving a congratulatory call from his editor after hitting the #3 spot on the New York Times Bestseller list. Despite this achievement, Ryan was already halfway through writing his next book, illustrating his relentless work ethic and focus on creating rather than celebrating.
"conversation all about well I think it's going to get you off your butt as a writer I'll tell you that I think it's going to give you a much clearer sense of what you can do to generate momentum and c..."
The Antidote to Disappointment
Ryan discusses how working on the next project can insulate a writer from the highs and lows of book launches. He reflects on his experience with 'The Obstacle Is the Way' and how focusing on the next book helped him avoid disappointment and maintain momentum in his writing career.
"next book and that is Ryan funa nutshell he is a beast of a Creator and this episode is all about how he generates momentum hey Steve you made it I made which one advice to number three no way you mad..."
Defining Success on Your Terms
In this segment, Ryan talks about the importance of defining success based on personal satisfaction rather than external validation. He emphasizes that the majority of fulfillment should come from the creative process itself, rather than the reception of the work, and shares insights on how to measure success in a way that aligns with personal values.
"a news as you would like it to be and I just found like the antidote or the insulation from that disappointment is just to be working like I found so I got I had a weird experience so when the obstacl..."
The Balance of Quantity and Quality
Ryan explains his philosophy on balancing quantity and quality in writing. He believes that producing more work can lead to better quality over time, and shares his thoughts on the challenges of maintaining momentum between projects. He encourages writers to keep creating to stay in shape creatively.
"and so I try to always start the next project and be not just be in the next project but I like usually the sales results come in like the Tuesday or the Wednesday subsequent to the launch and so I'm ..."
Learning from Experience
Ryan reflects on how his understanding of success and self-worth has evolved over the years. He discusses the importance of earning confidence through experience and how familiarity with the creative process can help writers navigate challenges more effectively.
"creative projects are only for you you like you made choices from putting a cover on it to writing marketing copy and doing interviews you are like by definition you said you want it to resonate and R..."
Trusting the Process
In this segment, Ryan emphasizes the importance of trusting the creative process, especially after experiencing the ups and downs of writing multiple books. He shares how past experiences have equipped him with the confidence to tackle new projects, knowing he can navigate through challenges.
"things that are up to you so like is it the best thing that you wrote did you leave it all you know in the pages versus whatever um was it creatively fulfilling did you like I I've even tried to measu..."
The Shift in Author Culture
Ryan discusses the changing landscape of authorship and the challenges of being a prolific writer in today's market. He contrasts his approach to writing with that of traditional authors, highlighting the need for adaptability in a rapidly evolving industry.
"couple things F first off I would say the economics or the uh possibility of being a Robert Caro may or may not exist like I think Robert Green is one of the last sort of big authors especially in non..."
The Importance of Staying in Shape
Ryan shares his belief that staying consistently productive is crucial for writers. He likens writing to physical fitness, suggesting that maintaining a regular writing schedule helps prevent the difficulties that come with starting new projects after a break.
"people uh there's a there's an expression in football that if you uh don't get out of shape you don't have to get into shape you know like it's it's easier to stay in shape and and like I think the pa..."
Navigating Creative Challenges
Ryan discusses the challenges of comparing new projects to past successes and how experience helps mitigate these feelings. He emphasizes the importance of being comfortable in the creative process and trusting one's ability to produce quality work.
"way to get confidence and that's to earn it right I think any any kind of confidence that's not earned is is probably better defined as ego and so um one of the things you you get from having done it ..."
The Power of Momentum in Writing
In this segment, Ryan shares his personal experience with writing and the importance of momentum. He reflects on how confidence in his writing ability allows him to push through uncertainty and create a publishable book. This discussion highlights the significance of maintaining a steady pace and trusting in one's creative process.
"there is a level of chill that I didn't have before because you don't know yeah a cool example of this watching one of your Vlogs before is you're working on discipline as Destiny and early on you wan..."
Trusting the Process: A Note to Future Self
Ryan recounts a pivotal moment while working on his book 'Discipline is Destiny,' where he wrote a note to himself as a reminder to trust the writing process. He emphasizes the importance of perseverance and how revisiting research can lead to unexpected connections and insights. This segment illustrates the value of patience and faith in one's creative journey.
"project starts and so I'd be like these are all the note cards let's see what the book is right and so you have years of research but you don't know what it's going to look like the order things are g..."
Finding Connections in Research
In this segment, Ryan discusses the process of sifting through research and how seemingly unrelated observations can coalesce into a coherent theme or chapter. He shares his experience of reading extensively about Queen Elizabeth and how that research ultimately shaped his writing. This highlights the importance of thorough research and the unexpected connections that can arise from it.
"much faster than I thought and ultimately the book was different but better than I thought and and so better than I thought but what I loved about that was like it was like how did I time travel that ..."
The Evolution of Writing Through Children's Books
Ryan reflects on how writing children's books during the pandemic influenced his writing style. He describes the iterative process of storytelling for his son and how it taught him to be concise and engaging. This segment emphasizes the importance of audience feedback and the lessons learned from simplifying complex ideas.
"than chronology how do you feel like your writing is different now in the stoic virtue series on the far side of having written the children's books like I was just playing around with them in the in ..."
Balancing Precision and Nuance
In this segment, Ryan discusses the challenge of maintaining precision in writing while avoiding long-windedness. He reflects on his growth as a writer and the importance of being concise without sacrificing depth. This highlights the ongoing struggle writers face in balancing clarity with complexity.
"only like 500 Words or8 words or something which is a lot for a kids book but not a lot for a fable um but uh but I what I found doing it was like the the process of doing it over and over and over ag..."
The Cringe Factor: Reflecting on Past Work
Ryan shares his thoughts on revisiting his older works and the discomfort that comes with it. He explains how certainty in writing can age poorly and how his perspective has evolved over time. This segment underscores the importance of growth and the natural progression of a writer's voice.
"between getting more precise and more uh nuanced but also not becoming like a windbag and so that's a great question you know so so like I noticed each one of my books was and then I stacked them all ..."
The Art of Cutting and Combining
Ryan discusses his editing process for his upcoming book, focusing on the importance of cutting unnecessary content and combining chapters for clarity. He shares insights on how to refine writing to make it leaner and more impactful. This segment emphasizes the discipline required in the editing phase of writing.
"like I had a stack of note cards of things about how obstacles are the way that I wished I'd known in 2013 when I was writing the book so there was stuff I wanted to put in and then there were other e..."
Crafting Effective Introductions
In this segment, Ryan elaborates on the significance of introductions in writing, particularly in essays and books. He explains how a strong introduction sets the tone and outlines the central themes of the work. This highlights the foundational role of introductions in shaping the reader's understanding.
"up a little bit uh it's just a lot like I I mean I wouldn't even read this many books from one person right and so so I was like let's take an extra year and so which actually I I in discipline I I re..."
Crafting Powerful Introductions
In this segment, Ryan explores the significance of introductions in writing, particularly in essays and books. He explains how a strong introduction sets the tone and outlines the central metaphor of the work. By analyzing examples from literature and music, he illustrates how impactful beginnings can captivate an audience and establish the shape of the narrative.
"ago called how to write a great essay and you have this idea of create that the introduction is the creator of the shape yeah the introduction is is the creator of the shape tell me about that well I ..."
Finding Beauty in the Mundane
Ryan delves into a passage from Marcus Aurelius, reflecting on how even nature's inadvertence can possess charm and beauty. He discusses the vivid imagery in Aurelius's writing and how it reveals a philosopher's eye for detail. This segment emphasizes the power of observation in writing and the ability to find beauty in unexpected places.
"and and realizing first off most people uh are not going to make it all the way to the end so the beginning has to be very powerful it's got to sort of grab you by the throat and and make a statement ..."
The Intersection of Preparation and Opportunity
Ryan shares his thoughts on the idea that every writer should aspire to create their best work in the future. He reflects on the notion that past experiences and preparation can lead to significant creative breakthroughs. This segment encourages writers to view their journey as a series of preparations for future projects that may not yet be clear.
"going and then come back to it h do you feel like you're working towards something like Steinbeck always said east of was like his late life Masterpiece do you feel like you're working towards somethi..."
The Universality of Specificity
In this segment, Ryan discusses how the most specific art can resonate universally. He reflects on the timeless relevance of Marcus Aurelius's 'Meditations' and how personal reflections can connect with a wide audience. This highlights the importance of authenticity in writing and the ability to convey universal truths through personal experiences.
"going I want to walk through a specific sentence with you so right here at the top and you've spoken about why you like this sentence from Marcus aelia so I want to basically break it down with you uh..."
The Impact of Translation on Writing
Ryan shares a personal anecdote about the translation of 'Meditations' that influenced his writing style. He discusses the nuances of translation and how the choice of words can significantly affect the interpretation of a text. This segment emphasizes the importance of language in conveying ideas and the impact of literary choices on a writer's voice.
"to Europe so he's looking at this imported lion from Africa and he's just he's just got this sense he's looking at things um I like that and then I actually as I've come to think of this passage speci..."
Music as a Creative Catalyst
Ryan talks about his writing process and how music plays a crucial role in enhancing his creativity. He explains how listening to specific songs repeatedly can create a trance-like state that fosters emotional engagement. This segment highlights the relationship between music and writing, illustrating how sound can influence mood and productivity.
"me the stylistically how has it sort of bled into your words so you take the the first the the famous first passage not not the the debts and lessons but the the first famous passage he says when you ..."
Introducing Writing Examples
In this segment, Ryan introduces his project 'Writing Examples,' where he deconstructs great writing throughout history. He explains how he analyzes various forms of writing to uncover what makes them effective and how others can apply these lessons to improve their own writing.
"go to the top of the page and your email address and I'll send it to you whenever it goes live all right back to the episode why do you have I Dreamed a Dream on here because you listen to that a thou..."
Music as a Writing Tool
Ryan discusses the role of music in his writing process, sharing how he often listens to the same songs repeatedly to create a trance-like state. He explains how this practice helps him achieve a heightened emotional state conducive to writing, stabilizing his mood and enhancing creativity.
"kind of just lost in the in the hook of it um and you can it gets you to some sort of heightened emotional state I find to be very conducive to writing and then also there's not any bad songs right li..."
Memorization and Understanding
In this segment, Ryan explores the concept of memorization in relation to writing and understanding. He shares his thoughts on how repeated exposure to texts can lead to a deeper internalization of ideas, emphasizing the importance of truly knowing a subject beyond mere memorization.
"uh the the lyrics kind of get burned into your head in the same way that like reading a book hundreds of times gets burned into your head and then there's kind of a a recall that can come from that ar..."
Reading to Lead
Ryan shares a pivotal piece of advice he received about reading: to read not just for knowledge but to lead. He discusses the importance of learning from the experiences of others through literature, especially for those in leadership roles, and how this can prevent costly mistakes.
"some some level you have to get it more than just knowing it of course let's talk about reading so there was a conversation that you had many years ago here's what you say the best piece of advice I'v..."
The Cost of Ignorance
Ryan reflects on the high stakes of leadership and the necessity of reading extensively to avoid costly errors. He cites General Mattis's perspective on the importance of learning from books to prevent dire consequences in decision-making, emphasizing the responsibility leaders have to be well-informed.
"always taken is that you you you have to read the things that challenge you and you have to read about sort of big moments in history and you also have to have a a deep experience um you you have to b..."
The Depth of Research
In this segment, Ryan discusses the importance of thorough research in writing. He emphasizes the need to explore multiple perspectives and gather comprehensive knowledge on a topic to create meaningful and impactful content, rather than relying on superficial examples.
"know very costly for someone how's that for a turn a phrase by the way it's crazy body bags like yeah it you could say it's costly or you could say body bag yeah the phrase well so and but the phrase ..."
The Writing Process
Ryan outlines his writing process, detailing how he organizes his notes and integrates them into his manuscripts. He explains the steps he takes to ensure that his writing is well-informed and reflective of a deep understanding of the subject matter.
"confirmed at like the real testing point of You Know The Human Experience or the laboratory and so it can be easy as a writer to to just like find an example that confirms what you want and to just us..."
Tracing Ideas Back to Their Core
Ryan discusses the importance of tracing ideas back to their origins to gain a deeper understanding of contemporary issues. He shares his approach to researching historical contexts and foundational texts to enrich his writing and provide a more comprehensive perspective.
"is all that I had right there were a few things I noticed from the way that you read that I'm instantly going to apply and the two that stand out was the first one is and this probably applies more to..."
The Value of Classical Knowledge
In this segment, Ryan reflects on how a solid foundation in classical literature enhances his understanding of modern works. He explains how recognizing the roots of contemporary ideas can inform and deepen his writing, allowing him to connect historical insights with current narratives.
"you've read uh you know most of the sort of core Western Canon um you start to see it in other things and I kind of I got there the other direction which is I would read modern stuff and then I'd go w..."
Daily Writing and Productivity
Ryan shares insights into his daily routine and how he manages his time to maintain productivity. He discusses the balance between family responsibilities and writing, emphasizing the importance of making consistent progress in his work despite life's challenges.
"all the things that you've done it's not just the books but it's brass check it is the daily dad the daily stoic the podcast I mean it's crazy what is your schedule like this week like really just to ..."
Integrating Notes into Manuscripts
In this segment, Ryan explains how he organizes and integrates his notes into his writing projects. He describes his method of filtering through notes to determine what is valuable for his current work, ensuring that his writing is informed and cohesive.
"are like to explain that so it's there's three steps so you read the book you have the stickies then you take a few weeks away then you only transfer the stuff that's really worthy yes and then now wh..."
Contributions to Writing
Ryan discusses his philosophy on making daily contributions to his writing. He reflects on the importance of feeling accomplished with each writing session, regardless of the amount of time spent, and how this mindset fosters a productive writing habit.
"don't know what it's for um but but hopefully it's for something so that's kind of the that's kind of the process so like today isn't going to be a super productive day cuz I'm still you know putting ..."
Reading for Style vs. Content
Ryan contrasts reading for style with reading for content, sharing his approach to learning from other authors. He discusses how he seeks to understand the techniques and rhythms of writing rather than just the narrative, highlighting the importance of style in effective communication.
"today how much are you reading for style as opposed to content what does that mean like for example I've spoken to a lot of authors who as speaking for myself I would like to get better describing thi..."
Exploring Biographical Writing
Ryan shares his thoughts on writing biographies and the different styles he might adopt for his upcoming projects. He reflects on the balance between narrative depth and stylistic choices, considering how to best convey the life stories of influential figures.
"differences well if you ever read Rich Cohen I haven't read he wrote like uh tough Jews he wrote um he did that book you'll know I'm when I'm when I stop talking you'll know I'm dead and then but his ..."
Balancing Vision and Criticism
Ryan shares his thoughts on navigating feedback and criticism in the writing process. He explains the challenge of staying true to one's vision while also being open to constructive criticism. This segment emphasizes the need for writers to articulate their goals clearly to editors and to seek feedback that aligns with their creative intentions.
"them and so I'm I I tend to find that older biographies were very rarely do I read a new biography and I go this is worthy of being up there with those other ones and I I think it's because the the th..."
Creative Freedom vs. Self-Indulgence
Ryan discusses the tension between creative freedom and the risk of self-indulgence in writing. He uses examples from shows like 'Curb Your Enthusiasm' and 'Seinfeld' to illustrate the balance between discipline and spontaneity in creative work. This segment highlights the importance of knowing when to embrace freedom and when to adhere to structure.
"doesn't mean that much to me or you know what random people say doesn't mean that much to me in an environment where you could arrange it so everything is rubber stamped how do you not allow that for ..."
The Fear of Starting
In this segment, Ryan addresses the common fear of starting new writing projects. He shares a personal story about a dream that motivated him to begin working on a book, illustrating how fear can paralyze creativity. This discussion resonates with writers who struggle with the daunting blank page and the pressure of perfectionism.
"which I would say is probably earlier in the creative process like you ever watch get back the Beatles documentary so when they're playing or when any musician is going you're not like what is the aud..."
Overcoming Procrastination
Ryan elaborates on the procrastination that often accompanies the writing process. He discusses how writers can create excuses to delay starting their work and the importance of recognizing these patterns. This segment encourages writers to confront their fears and take action, emphasizing that the journey begins with the decision to start.
"things that are not that type and but but then you get these just general notes or you realize you you see this in advice too right people are giving you advice for what they would do in your situatio..."
The Ugliness of Creation
Ryan uses the metaphor of Michelangelo's unfinished sculptures to illustrate the messy and often uncomfortable process of creating. He emphasizes that every great work requires navigating through the 'ugliness' of early drafts and ideas. This segment serves as a reminder that the path to a polished piece is fraught with challenges that must be embraced.
"and we'd all got around the circle and I was just like you know what the problem is everyone's just scared everyone is scared we're all scared of judgment we're all scared of failure the fact that we'..."
The Pressure of Perfection
In this closing segment, Ryan reflects on the pressure to achieve perfection in writing and how it can lead to paralysis. He shares insights on how to combat this mindset by focusing on the process rather than the end result. This discussion encourages writers to embrace imperfection as part of their creative journey.
"other side the risk is when you start because you could it up and and I you could imagine coming up with endless delays and reasons for not doing it because you want to get it right there's this senic..."
Crafting Compelling Stories
Ryan shares his approach to storytelling, emphasizing the importance of presenting familiar figures in surprising ways. He discusses how effective stories often involve well-known characters and themes, allowing for deeper insights and connections. This segment highlights the significance of research and thematic consistency in storytelling.
"oh I think a couple things I'm looking for in a story ideally something that someone hasn't heard before or something surprising but it's often about someone that they have heard about before Oh inter..."
Pacing and Structure in Writing
Ryan explains his unique writing process, where he creates individual drafts for each chapter instead of a complete manuscript. This method helps him maintain pacing and momentum, ensuring that each section is engaging and self-contained. He draws on the example of Raymond Chandler to illustrate the importance of keeping the reader's interest throughout the narrative.
"existence so I'm I'm I'm just kind of looking for for those things often um how do you judge the pacing like when you're editing how are you judging the Cadence of what's going on um there's a story a..."
Researching for Depth in Storytelling
In this segment, Ryan discusses the critical role of research in enhancing storytelling. He shares his experience of diving deep into the lives of historical figures to create richer narratives. This emphasis on thorough research allows him to present well-rounded characters and compelling contrasts, ultimately leading to more impactful stories.
"point where like I'm I'm I'm about 2/3 of the way through the wisdom book um so but but maybe a maybe two months from now there'll be a process where all those come together and then I'll See For the ..."
Balancing Strengths and Weaknesses in Characters
Ryan reflects on his growth as a storyteller, particularly in how he portrays characters with both strengths and weaknesses. He uses the example of John F. Kennedy to illustrate how understanding a person's complexities can lead to more nuanced storytelling. This segment emphasizes the importance of depth and contrast in character development.
"read eight and and then I read obituaries and articles and you know ESPN pieces I just read a ton about him and and um it I think it's largely the I I would say it's the vast majority of it is the mat..."
The Importance of Momentum in Writing
Ryan concludes with key lessons on maintaining momentum in writing. He stresses that many writers lose their drive after completing their first book and highlights the necessity of trusting the process. This segment encourages writers to seek out opportunities for practice and to find ways to keep their creative energy flowing.
"yeah I think that was that was maybe why that worked let's close with this I want to just take this conversation and just throw out some lessons that I think I want to bring to my own writing that rea..."