Ryan Holiday has worked with some big names in the non-fiction book world, including Tim Ferriss and Tucker Max, and I'm thrilled to bring you this interview with him around his own latest book, “The Obstacle is the Way: The Ancient Art of Turning Adversity to Advantage.”
In the introduction, I mention the latest Author Earnings report, plus how our indie panel went at Bristol CrimeFest and why you should read ‘Opening up to Indie Authors‘ if you want to get into literary festivals as well as bookstores, libraries etc.
This podcast is sponsored by Kobo Writing Life, which helps authors self-publish and reach readers in global markets through the Kobo eco-system. You can also subscribe to the Kobo Writing Life podcast for interviews with successful indie authors.
Ryan Holiday is a media strategist for corporate brands and best-selling authors like Tim Ferriss and Tucker Max, as well as the Wall Street Journal best-selling author of “Trust Me I’m Lying: Confessions of a media manipulator,” and today we’re talking about his new book, “The Obstacle is the Way: The Ancient Art of Turning Adversity to Advantage.”
- What is Stoicism anyway and how Ryan integrates that into his life
- How to find an emotionally even keel as an author in this crazy up and down life
- Crafting stories and how to use that in non-fiction books
- Creating a body of work and what really matters over the longer term
- Definitions of success
- How reading is changing and how it impacts authors
- How Ryan researches his non-fiction books and how he tracks quotes using index cards
- The importance of figuring out what you want to say, and why a proposal can help with that
- The best ways to market a non-fiction book right now, and some of the biggest time wasters
- Thoughts on the future of publishing
Transcription of Ryan Holiday Interview
Joanna: Hi, everyone, I’m Joanna Penn from thecreativepenn.com, and today I’m here with Ryan Holiday. Hi, Ryan!
Ryan: Hi, it’s good to be here.
Joanna: Great to have you on the show. So, just as a little introduction, Ryan is a media strategist for corporate brands and best-selling authors like Tim Ferriss and Tucker Max, as well as the Wall Street Journal best-selling author of “Trust Me I’m Lying,” and today we’re talking about his new book, “The Obstacle is the Way: The Ancient Art of Turning Adversity to Advantage,” and I’ve got my copy here. So, brilliant book, Ryan, thank you so much for that.
Joanna: I wanted to get straight into asking you about branding, because you have this book, “Trust Me I’m Lying,” and then you’ve got this sort of very intelligent, philosophical, self-help book, “The Obstacle is the Way.”
Joanna: So, how are you living stoicism in your very mixed branded life?
Ryan: I actually don’t see them as being sort of in conflict at all. Stoicism is about making the best out of less than ideal situations, and my first book is about a media environment that I think is very corrupt and conflicted and confusing for people, and so my approach, when I was younger, was one of sort of, “OK, let’s be very realistic about what it is, let’s be very honest about what it is, and let’s just try to make the best out of it, given the job that we’ve been tasked with doing.” So stoicism has sort of been within my personal system for dealing with problems or undesirably situations, and then this book is obviously a little bit broader, but it’s not as much about marketing, it’s about sort of how you live your life, and that’s where I would see the two working together.
Joanna: It’s interesting, because some people might see stoicism as a kind of dead philosophers’ ancient classical situation.
Maybe you could just give a broad overview of why people should care about stoicism today.
Ryan: It’s not so much why they should care, it’s why they should join all the other people that are practicing it. Stoicism is huge in the armed forces, it’s huge, obviously, in academia, it’s huge in the entrepreneurial community, it’s always been huge with writers and creative types. Although it’s obviously quite old, it’s thousands of years old, it’s always existed through history, and, I sort of followed them through history, everyone from George Washington to Ambrose Bierce to James Stockdale, there’s been all sorts of explicit practitioners of stoicism, and then people who were living stoicism, whether they knew it or not.
Stoicism is not like a religion, where you have to accept certain tenets, it’s much more about how you actually exist and function in life. So there’s plenty of people who I would consider to be stoics who maybe have no idea.
Joanna: It was interesting, because a lot of your writing, you do a lot of strategy and war stuff, and the book is obviously full of very famous men, but you do have a woman in the book, don’t you.
Ryan: There’s a bunch, it’s more than one!
Joanna: There is, but there is a lot of masculinity, I guess, in your examples.
Joanna: Perhaps you could just tell us about them, I like the Amelia Earhart example.
Ryan: What I liked about Amelia Earhart is her first offer for a transatlantic flight was one that I think most people would rightfully consider to be pretty insulting: “You’re going to have chaperones, you are going to not be paid, they’re going to be paid, by the way, you’re not even our first choice, we already went to someone else before you who turned it down.” And it’s like, what did she say to that? She said, “OK, that’s fine, I’ll make it work.” And so she starts off the action section of the book, which is how do you get started, how do you start moving? I think so many people, they suffer problems–even if it’s just in writing—they don’t know how to start their project.
And there is no magical way, other than just doing it. You sit your ass in the chair and you get to work. I like that she was willing to do that, and she also knew that, it didn’t matter what the opportunity was, if someone gave her even the smallest one, she would be able to parlay that into something bigger. And I think that’s something that my generation of people has trouble with. And I think creative types have trouble with it too, they want their first story to be published in the New Yorker, or they need a major publisher to tell them that they’re good enough, rather than just going out there and getting an audience.
Joanna: I agree. And it’s interesting, the book talks about having an emotional even keel, and not being affected by massive highs and lows. So, how do authors, in particular, balance this, given what you’re saying, the vagaries of best-seller lists, and lots of money this month and rejection and self-doubt.
How do authors get that emotionally even keel?
Ryan: It’s interesting, I’m going through that right now. I sold for the first three days, more than enough copies to hit New York Times, and more than enough to hit Wall Street Journal, and I didn’t make either list, which I think, two years ago would have been crushing, because I hit the list with my first book, but having been familiar with how those lists work, I was very much prepared for that to happen. And I knew that it does happen all the time.
And obviously I wanted to sell as many copies as possible, but I see so many authors take their eye off the ball in terms of building an audience or building a sort of sustainable marketing machine for their book, to chase these sort of arbitrary status symbols that are being a best-selling author. And so, with this book I said, “I’m going to do everything I can, but I’m not trying to make the best-seller lists.” Like, it’ll be nice if it happens, but I’m not trying for it. And then I had to test that in the real word when I sold enough copies and didn’t hit it.
I think it’s about understanding why you want something, whether that’s something that matters or not, and what the stoics do is they make a distinction between things that are in our control and things that are outside our control. I control how many copies I sell, I don’t control what does or doesn’t make the list, and I have to make that distinction, and I can’t place my expectations or my happiness on an external, or I’m setting myself up to be disappointed, possibly.
Joanna: Absolutely. And in case people don’t realize, because you obviously have an insight into media manipulation, and the lists are a crazy thing in general, can you explain why you didn’t hit the lists, then?
Ryan: The thing, is, you don’t necessarily know, because it’s sort of a black box, but you know certain factors influence the list, and you also have to just understand that these are not reflections of actual sales; they are a reflection of sales plus a bunch of editorial criteria that is often selectively applied. And it’s like a lot of life: you can put yourself in a position to succeed, but sometimes the success, the actual markers of success are a little bit outside of you. You can deserve a promotion, that doesn’t mean you’re going to get it, and the world is not always right and it’s not always fair, and I think if you can be prepared for that, it’s not going to wreck you when it sometimes doesn’t go your way.
Joanna: It’s interesting, because I read your “Confessions” book as well, which I thought was great, and because you do so much marketing work. How do you stop yourself getting very cynical about all of this stuff?
Ryan: You can’t stop yourself entirely, and I don’t think cynicism is necessarily unhealthy, I think sometimes it can be sort of protective and illustrative. So it’s not something that I necessarily try to avoid. But I understand that the process has to be enough. Like, making a book, getting in front of readers, that’s why you have to be doing it. If you are in the writing or art business to be loved by critics, or to be recognized by these various institutions, you’re essentially putting your happiness in somebody else’s hands, and you don’t know how they’re going to treat it.
Joanna: Fair enough. Now, I was really interested with the book, because a lot of my listeners write fiction, and I was fascinated by the nature of conflict, overcoming obstacles:
What are some of the things from the book that can help authors craft fictional stories?
Ryan: It was a stretch for me, because although I write non-fiction, I’m usually talking about my own thoughts or opinions. So it was a stretch for me to write, this book is mostly stories, so I had to learn myself, how do you sort of write and tell a story, and at first I was very overwhelmed by the prospect, it was like, “Oh, I can’t believe I just sold a proposal, now I’m going to have to tell these fifty stories, which I have no experience doing, I’m screwed.” And it’s something, how do you get good at telling stories? By telling a lot of them. And so if there’s fifty in this book, I wrote many more than that, I rewrote these many times: it’s like sometimes the only way to accomplish a skill is to sort of throw yourself in the deep end and really struggle at it.
I guess one of the things that I realized with the book, and this is sort of a metaphor, obviously, I talked about a lot of times we face an obstacle and our reaction is to sort of attack it head on, when really that’s sort of the worst way to, that gives up so many strategic benefits, whether it’s surprise or what have you. So I talked about the indirect approach, and I think that’s something that authors and creative types can think more about. You know, am I attacking this head-on, or does sometimes going around or illustrating something by omission or obliquely, is that not more powerful?
I just read an interesting work of fiction, yesterday, called, “I Pity the Poor Immigrant,” which is about Meyer Lansky, and his attempt to emigrate to Israel, near the end of his life. And it’s this very powerful book, but when you read it, it’s like nothing happens in this book. Like, basically, nothing happens, but he’s sort of so constantly alluding to things, and the figures that he picks have such interesting backgrounds and stories, that it kind of all adds up to something being very powerful, but he didn’t sit down to write like an ominous gangster novel, but he still harnesses all that power. So I think that indirect approach can be really interesting.
Joanna: Absolutely. And of course just the general overcoming conflicts is kind of generally in fiction, it’s what you have to do: throw bad stuff at your characters so they overcome it.
Joanna: I was interested as well, because you mentioned on other podcasts that you want this book to stand alongside “The War of Art,” by Steven Pressfield, why do you feel that that book is so important, and how had that impacted your own creative process?
Ryan: I think even that book is probably a good example of the indirect approach. It’s about art, but he’s sort of telling stories and illustrating them in a way that feels much less preachy than most books. Like, most books about writing and art are really bad. They’re just not good at all. And, you know, Steven’s is obviously different, and I think it’s clearly been vindicated by the market.
That book was very influential to me, I think it’s a very quick, simple read that a lot of people have gotten a lot of value out of, so I wanted to write a book that is going to help a lot of people over a long period of time. I could have put myself in the book, because that was actually something that the publisher wanted. I didn’t want it to be all in the first person, I didn’t want it to have like a lot of current examples, because you don’t know how they’re going to pan out.
I don’t want to talk about what Google is doing right now, or YouTube is doing, or something, because it might not, who knows how that’s going to play out? And so I wanted it to be very timeless and it wanted it to sort of talk about timeless themes, and obviously I hope I succeeded in that.
Joanna: It’s interesting, you talk about timeless themes, and you also in the book talked about meditating on mortality, which I do a lot: I write a lot of dark fiction. A lot of death! But you obviously work with people who have fame and money, and the things that most people think that they want.
What are your thoughts around what will last and what are you aiming for in a body of work?
Ryan: It’s interesting, it’s like, OK, you try to write a book that is timeless and will last for a long time, but then you also have to remember that Proust doesn’t care that we’re still reading his book, and neither does Mark Twain, because they’re dead, and they don’t know. And so I think a lot of people, writers especially, can be very caught up with their legacy, or lasting for ever, or all that, and it’s very tempting and seductive, but you have to remember that your work may outlive you, but you have no idea, and so you should write something that you’re happy with now, that you can get out now, that doesn’t wreck your or ruin your life, also.
So, the timelessness is important to me, but it was also I cared about the timelessness because I wanted a book that would last, but it was more like I just didn’t want to write a book that I wasn’t proud of, that I felt didn’t stand up next to the books that I really admired and thought were good. So, I talk about meditating on your own mortality, and I think the darkness that you were talking about is important. A lot of people are too skittish to think about the fact that life is short, that life is brief, that things like fame, or money, they don’t last, and that you’ve got to remember that, and that realism is, is honest and authentic and important.
Joanna: Knowing that, and knowing the people that you do,
What is your definition of success?
Ryan: I think it’s hard, because I think obviously we have our own definitions of it, but to me, it’s being able to get up and write about something that I care about, that I feel is important, and having an audience who can receive and benefit from it. I’m not interested in writing from obscurity for 40 years and then hoping that I’ll be appreciated after my death or something, maybe that works for some people, but that’s not the game that I want to play!
Joanna: Fair enough, I get that. It’s interesting, because you are a huge reader, and what I like about your website is, you have a sign-up for your email list, which is your reading list, basically, which is, which is awesome. What do you think about the changing way that people read, and how do you think that’s going to affect- Like you have a very nice hardback book here, it’s also available on Kindle, and all the e-books, but
What do you think about the way that reading is changing, and how will that affect authors and your clients, basically?
Ryan: It’s weird. You can see in the background, it’s all physical books, that’s all I read. I really appreciate physical books, I think it’s important for my reading and learning process, but I’m not one of these people that’s in love with independent bookstores, and loves the smell of books. I think part of the problem with publishing is people have forgotten that books are just a vehicle for ideas. And, it doesn’t really matter if the vehicle changes, provided that it still can deliver interesting or important ideas. So, my last book started as a Kindle Single, and then based on sales, we decided to turn it into a paperback, so, I definitely advise experimenting, I read a lot online.
I think that if there’s one sort of technology that I would push back on, it’s this new thing, have you seen it? It’s where it’s supposed to be so you can speed-read really quickly, it just flashes like one word in front of your face? Not only is that sort of missing the point of reading, it’s not supposed to be a race, but, the struggle of reading and the time that it takes our minds to understand and comprehend words is part of the cognition process, from the research that I’ve read, and part of what helps us remember and make connections on what we read.
So I think if the technology’s about making reading, reading more accessible and cheaper, and empowering new authors to reach audiences, I think it’s fantastic, and I don’t have any problem with it. When it’s about stripping some of the benefits intrinsic in the written word, that’s where I start to have some problems with it.
Joanna: Sbsolutely. And of course, part of your reading is research for for the books.
You have this incredible research process. Could you talk a bit about that?
Ryan: Yeah, it’s funny where people go, “Oh, how do you read so much?” It’s like, “Well, it’s my job!” So I’m not expecting you to read as much as I do, I’m reading for work, and block out time in my day to read, so it’s a little bit differen. I learned this from Robert Green, who was my mentor, I read a book, I usually have a pen or I fold and I mark the things that I think were important, and then, a couple of weeks later, I go back through the book, I take notes, I transfer those to notecards, so here’s a bunch of them with writing on them. So I transfer them to notecards, and then those notecards are organized by theme in boxes, and each book is normally its own box, and that’s sort of my personal system. Right now, I am probably 40 books behind in terms of transferring them to notecards, because I’ve been so busy, but that’s the system that I try to observe.
Joanna: And then, how do you synthesize those? Many of us use Scrivener. Do you use Scrivener, or how do you synthesize that into a book?
Ryan: No, no, just the notecards, and then the notecards are in themes, and let’s say an item, say, is three parts, and an intro and a conclusion, so there are five sections, and then notecards go in each little section, and then each, Part 1, 2, and 3, are say, fifteen individual chapters, then they’re broken up into fifteen smaller sub-sections. So each section is a stack of notecards with little, like a file folder, and then let’s say I have to write Part 2, Chapter 6, and I’m traveling, I just take those cards with me and I write until I’m done, and then they go back in the box.
Joanna: Wow, that’s so analog!
Ryan: Yeah! And then I actually, up above my desk I have a box of articles and papers that I’m reading that are materials for the book that are not notecards, so if there’s a really good New York Times piece that I read, I’ll take notes, and then it goes in the box until I transfer it to notecards later.
Joanna: Wow, that’s amazing.
I also heard you say on one interview that people shouldn’t write non-fiction books if they haven’t sorted out what they’re going to say first!
Ryan: Well, I try to crack the code of the book first. So, I find it to be very dangerous, and maybe it’s a little different for fiction, I don’t know, but when people just sit down and they’re like “Chapter One,” and they just take it wherever it leads them, in non-fiction, that leads to a very meandering, pointless, unclear thesis. I think you should be able to distil every non-fiction book down to a single sentence, and every sentence should be a meditation or a callback to that theme, over and over again, and you should know where the examples fit. And so I’m a big proponent of structure and organization, and I just see so many authors just kill themselves by writing all this material that they ultimately end up cutting because it has no part of what they’re trying to say.
I’m a big fan of Robert Caro, who wrote “The Power Broker,” he wrote a bunch of biographies of Lyndon Johnson. I heard they had to cut like 250,000 words from one of his books, and to me that just seems like, obviously he’s a great person, I’m not criticizing him at all, but that just seems like the saddest thing in the entire world to me. Can you imagine cutting that many words?
Joanna: There are lots of fiction authors who are listening who have had to cut that many words!
Ryan: Oh, I can’t even wrap my head around it!
Joanna: No, I know what you mean. I’m a sparse writer myself. Now, I’m interested just to switch into marketing. You say in the book, “Action is commonplace, right action is not,” and I think that applies to book marketing as much as anything else.
Joanna: So, I wonder, what do you see right now, obviously you’re going through it, as the best things to do for a non-fiction book launch.
Ryan: Obviously I think podcasts are big. I probably spent the single most amount of time doing podcasts for this. I think content marketing is very big. A lot of people, they write the book and then, you know, publishers are very concerned about excerpts. I think you should give away as much of the book as you conceivably can. No one ever goes, “Oh, I was going to buy that book, but I read too many great articles from it, now I’m not going to.” You know what I mean? It’s much more like, “Why should I spend $30 on this, I don’t know if it’s any good or not.”
I think giving away as much as possible in interesting, compelling ways. I think if you’re not building a list, or an audience, you are putting yourself at the mercy of Amazon or book publishers or someone else to sell your book, and they never do a good job. So, to go to your question, I think it’s like a lot of people work very hard marketing their books, and don’t sell a lot of copies, because they haven’t planned it out and they haven’t really questioned what the ROI on each action is.
Joanna: Obviously I think it’s brilliant you’re doing podcasts, because you’re on mine.
Why do you think podcasts have become so popular, and why focus on it so much?
Ryan: I think podcasts have really exploded because of Smart phones. It’s so easy to download them and to listen to them. I think that’s why audiobooks are doing really well right well. But you’ve got to realize that the vehicles to find out about new books have basically disappeared. Newspapers don’t publish book reviews, radio doesn’t have time for a lot of authors, there’s not that many smart mediums left.
People who listen to podcasts buy books, because most people don’t listen to podcasts. You know what I mean, what are smart people doing? They’re listening to podcasts, they’re reading blogs, and they’re reading books. So, that’s where you can find potential people for your audience.
Joanna: Fantastic. And do you think that people are craving the author’s voice in some way? I wanted to hear your physical voice, as well as just the written word. Do you think people do want that?
Ryan: You know what I think, I think that’s part of it. I think now we expect more than just a good book. We want to know about how it was created, and who made it, and what they were thinking, and so I think that’s definitely part of it. Like, I’ve done two of my three audiobooks, and I’ve definitely seen a much greater response when I did the audiobook myself, than when I didn’t. I don’t know if you know who Austin Kleon is, but he wrote “Steal Like An Artist,” he taught, it’s like show your work, show the strings, show what’s behind the process and you don’t need to do it all in private, sort of hidden in the writer’s den or something, expose part of yourself, and it makes your work more accessible.
Joanna: Absolutely, that’s very cool. And then, in terms of I guess things on marketing that are really bad.
What are the biggest time-wasters for book marketing?
Ryan: Do you know what, I’m not going to say there’s any huge time-wasters, because most of those things have sort of gone away, I think the biggest mistake that I see authors making, this is what I do with my clients most often, is they make decisions that they think are creative decisions, that actually have marketing implications, they pick a bad title, they pick a bad cover, they write about something that there isn’t a big audience for, and then they expect marketing can dig them out of those holes, and it can’t.
Joanna: OK, so really being strategic.
Ryan: It’s like the best marketing decision you could make, look, the best marketing decision you could make is to write a really good book, and to write a really good book for an audience that you know is hungry for a book about this thing. And it’s not, like, hey go wait for inspiration to randomly strike: you know, write this book and then two years later, put it on Amazon and hope that it’s magically going to be successful be you were on NPR. That’s not a great model for success.
Joanna: And do you think that your blogging has played a big part, because you write a lot on blogs, thought catalog and other places, do you think that that changed, that continues to be part of that, why people want to hear from you?
Ryan: Sure, I mean, look, I’ve built up a huge list, my list is, I don’t know, 20,000 people now, for, for my reading recommendations. I ‘ve built up media contacts at places that will publish stuff that I’ve written, I acquire, every day, even for articles that I wrote two or three years ago, someone new will read them and become a fan of my work, and that sort of sucks them into my universe. And then, that’s something that I’ve thought about a lot, I wrote an article about why you should drop out of college, and that brings in young kids who like what I have to say and then read one of my books, and I think a lot of authors, they go, “Oh, I’m just a book writer, so I can’t do any of that stuff,” but to me, it matters and it works.”
Joanna: And just one more question on the writing non-fiction, do you think that that, getting the right point, getting it organized, is why you should do a proposal or a pitch, even if you’re self-publishing?
Ryan: Sure. I tell people when they’re thinking about it, you might as well try a proposal, because, who knows, you might sell it for a lot of money, which would be nice, and it’s never going to hurt that you organized and synthesized your idea down into a very clear and compelling explanation and outline.
I hate proposals. No, look, I hate proposals, they’re really hard. It’s really hard for me, I’m working on my fourth proposal right now. It’s really hard just to write a proposal for something—I don’t know what the book is going to be, that’s the whole point, that’s what I’ve got to go spend two years thinking about, you know? But I do think it’s really important and you can tell when someone hasn’t done it.
Joanna: And, and then just on publishing, you know a lot of different authors who are publishing in different ways.
What do you see as the way publishing is going, and what are your kind of predictions for that in the next couple of years?
Ryan: I think it’s becoming increasingly hard for people who don’t have an audience or don’t have an idea that has an audience. Like I was saying, I think audiobooks are sort of seeing a resurgence, so I think that’s interesting. I think you’re seeing books be a little shorter, a little more straightforward, the idea of like taking seven years to go write a book or something, I think is very hard to do, not to say that’s necessarily a positive trend, you understand. I think you’re seeing smaller, more concise books, with more of a clear purpose and call to action.
So I think those are some trends, obviously there’s a lot more. I think you’re seeing that even authors that publish with traditional publishers are having to become more entrepreneurial and take on more of the project, like, you’re the CEO, your publisher is just your investor. I think that’s the way to think about it.
Joanna: OK. So, just as a round-up, just talk a bit more about “The Obstacle is the Way,” and who is going to find this useful amongst the audience listening?
Ryan: The book is based on stoicism. It’s this idea that look, we don’t control the world around us, we control how we respond to it. So, it’s a meditation on this single line from Marcus Aurelius, where he says, “The impediment to action advances action: what stands in the way becomes the way,” and then I unpack that idea through stories: Amelia Earhart, John D. Rockefeller, Ulysses S. Grant, Eisenhower, Margaret Thatcher, Churchill, Abraham Lincoln. I tell these stories that illustrate the the ideas and the approach required towards tackling really difficult situations and scenarios, and not just surviving them, but ideally thriving because of them: that’s the idea.
It’s a book I’ve wanted to write for a really, really long time, and now it’s here, it’s got a great response, so I’m really excited about it.
Joanna: Fantastic. And where can people find you and the book online?
Ryan: The book’s available obviously Amazon, bookstores everywhere. My website is www.ryanholiday.net, that’s where you can sign up for the reading newsletter, and I’m just @ryanholiday on Twitter.
Joanna: Fantastic. Thanks so much for your time, Ryan, that was great.
Ryan: Thanks for having me, this was awesome.