1. P1: Now I’m speaking with Ryan Holiday who is the author of “The Obstacle Is The Way”, among
many other things. So first of all, Ryan, thanks for talking to me.
Ryan Holiday: Yes, it’s good to be here!
P1: So, I want to talk about a bunch of things and I guess maybe we’ll work sort of backwards. Let’s
start with the book. So “The Obstacle Is The Way” is in a lot of ways about stoicism and overcoming
challenges. What was sort of the genesis for the book?
Ryan: Yeah, so the genesis is a single passage inside “The meditations of Marcus Aurelius” which I
think is this totally really unique historical document. You have the most powerful man in the world
sitting down every night writing these notes to himself about how to deal with the responsibilities
and burdens of his position. And that struck me very early on in my life; I think I was 18-19 years old
when I first read it. And then as I’ve been successful in life and as I’ve read and experienced things, I
sort of kept coming back to this idea about how the problems we face that are not inside our control
our responses very much is and sort of developed a framework around that concept.
P1: Okay, so first of all, can you tell me a situation where you had difficulty applying stoicism?
Ryan: I mean, I think everyone has trouble applying stoicism every second of every day. That’s sort of
why it is a philosophy. If it was easy and natural, I don’t think it would require being written down.
But you know, one of the stories I tell in my book is this story of Thomas Edison. His factory burns
down and he responds by enjoying the scene and tells his son to go get his wife ‘cause they’re never
going to see a fire like this ever again. And again, in our lives, you know, my computer crashes or I
lose something I’m working on I get so angry I want to throw things or I kick a trash can. You know,
that’s not how we respond. It’s a very sort of unnatural response. It’s the right response but it’s
something that requires a lot of training and practice. So stoicism is something that, it’s a set of
reminders or exercises that still those muscles that allow you to respond properly in difficult, trying
P1: Okay, so obviously one of the things I wanted to talk about is you reading habits and obviously
you have all the books behind you and we’ll get back to that. But for the first time in my life ever, I’m
reading “Around the royal mighty gaze”[?], and then keep thinking about stoicism because Phillis
Pharg[?], you know, bad things keep happening and the waves keep coming up and he doesn’t react
ever, and just sort of moves through it. It’s kind of a really interesting embodiment of it.
Ryan: Yeah, I think you see stoicism very, like in the Golden age or Victorian age when the book was
written. Stoicism was going through a major resurgence at that time, and I think it was a result of it
being a very exciting but still unpredictable and difficult world. As a lot of inventions that were
happening around that time have been refined and perfected, we’ve started to confuse those
institutions with certainty and with reliability. You saw the generation in that book existed in a world
where those things were luxury, right? But they understood that the alternative was like, riding
round on a horse. So they were much less entitled and I think you’re starting to see stoicism resurge
again as income inequality widens, as people become more and more responsible for themselves.
Stoicism is sort of a formula for an unpredictable world, as we’ve always lived in but it can ebb and
flow as well.
2. P1: I like that; it’s a formula for an unpredictable world. Obviously, and you said this already, if it was
easy everybody would be doing it. But how can you train yourself to be more stoic without walking
what I think is a fine line of apathy, in some cases? Cause you can sort of just “check out”, you know.
Ryan: Yeah, so the stoics have a word “apathea” which is “apathy” comes from but apathy [?] does
not mean not caring, it means not ruled by you passions. It means you’re sort of even keeled and
centered. You’re not getting delusionally happy and suicidally depressed over the things that happen
to you. You care, you’re just also able to practice a kind of indifference to how things shake up. If
things go terribly, you’re fine with that ‘cause you’re going to make the most of it. If things go
amazingly, you’re fine with it but you don’t need it to live. It’s sort of practicing that centeredness,
and that ability to adapt to any event. Sort of like a hedge fund, right? A hedge fund trainer has to
make money whether the market goes up or down, and that’s a much better way of looking at the
world than needing the market to go up to be happy, right?
P1: Sure, the external factor versus the internal.
Ryan: Yeah, the stoics sort of say indifference to all external events. Marcus Aurelius - emperor,
Sentacus [?] - one of the richest men in Rome. They didn’t not succeed, or not care about success. It
was just that success and failure were sort of external events and they were able to exist and thrive
wherever they happened to be and that was satisfactory. ‘Cause we’re always in this state of flux.
Sometime things are going amazing. Sometimes things are going bad. Sometimes things are just
even. But you’ve got to be able to be the same in all of those circumstances. Otherwise you’re just
being jerked to and fro.
P1: Right, and how do you feel like that guides the goals and the way you proceed in general?
Because you know, sometimes those events are supposed to happen and suppose to make you
change course and you’re supposed to… I’m sort of referring to my own story actually about
overcoming Crohns because I wouldn’t do it any way differently and I wouldn’t be where I was now if
I hadn’t had this sort of traumatic experience in my life. I feel like I kind of had to go into a deep dark
place in order to be able to come out a better person.
Ryan: Sure, I don’t think it’s about… It’s about dealing with this situation in front of you pragmatically
and honestly, which means you’re not throwing yourself up against an impossible brick wall. But
you’re also not giving yourself in because things are not perfect. Marcus Aurelius was the emperor of
Rome. He had a job that he had to show up and do every day, and it’s probably not a fun job. You
look at Obama and you see how great he got from day one to 6 years into his presidency. Now
imagine that 2000 years ago. That would be quite a trying difficult job. But it’s about understanding
that this is the responsibility that I’ve gotten, this is what I’m doing, this is what I owe the people, and
responding with hard work, dedication, with justice, with generosity –the stoic virtues, right? And I
think we can all apply that to whatever it is we’re doing. I’m waking up and working on a book, and
you know those working on a book; it’s not fun! Writing can be a long hard slog but you made a
commitment, you’re working on a project. How can you understand that one day it’s going to come
easy and feel awesome, the next day it’s going to suck and then it might suck for a week, and then
you’re going to get your rhythm back, and being able to sort of persevere through that rather than
letting your understanding of the project and dedication to it be dependent on how it happens to be
going in an individual moment?
3. P1: Right. I feel like every parent should understand stoicism. And actually I’m making a joke and
being serious too because last week everyone in my house was basically sick and we had 103 fever
and such. And we actually had to fire our nanny because she wasn’t really helping very much and
when I was firing our nanny I said to her, ‘cause one of the issues was that she didn’t like to be
around the children when they were sick, and I was like “As a parent, I don’t get to be sick. Yes, I have
103 fever. It doesn’t matter. There are people who’s lives depend on me, my wife and I not getting
sick basically, or not slowing down at all.” So it’s particularly relevant, I feel like in this case, it’s like
you have a job to do. It doesn’t matter what happens. It doesn’t matter if someone hurts themselves
or if you have a good day or a bad day. You have sort of a baseline.
Ryan: Totally! I think that idea of “Look, I’m responsible for this. It’s mine and I own this and I have to
do the job and there’s no one else to sort of come save me. “ is both an empowering and somewhat
intimidating idea, and people have to come to terms with that. I think once you learn it, it’s great. But
I think it makes a lot of people weary because they rather someone else do everything for them.
P1: Sure! So shifting a little bit, how do you feel like this plays into your productivity? Because you
are clearly a very productive person, you know you’ve had a marketing firm for American Apparel,
you’re writing a pretty varied kind of writing. I mean, “Trust Me, I’m Lying” is a completely different
book obviously than the “The Obstacle Is The Way”. You’re writing for media. I mean, you’ve put out
very different kinds of pieces. How does this play in to your productivity?
Ryan: Yeah, stoicism is a great operating system because it says like “Look, things aren’t going to be
perfect but I’ve got this job to do and I’m going to do it and I’m not going to be distracted by things
and I’m going to do things for the right reasons, right?” So for me stoicism… Like when I look at other
people who are not as productive as me, and I’ve gone through periods when I’m very productive
and not very productive, I’ve seen this a lot with people I hire and work with; people think genius is
like having an idea and it’s really not. You have a great idea, the difficulties arise and you have to go
through those difficulties. Part of the reason I wrote this book is I see in the millennial generation, in
my generation, people run into problem and then they just stop. They don’t do anything past that.
They’re like “Hey, I tried it and then it was difficult so I’m going to wait for it to not be difficult
anymore.” And that doesn’t really happen. That’s not how it works. I try to… and this is written in the
book, “How can those difficulties help you in some way?” So if I’m working on something and
something happens, how can I learn from that experience? How can I write about that experience?
How can I use this as a way to connect with other people that will help me down the road? Like, how
can you use everything that happens into some benefit? So for me it’s like, the way I’ve kind of set up
my life is all the different things I do feed into each other and make me more successful, and I can
channel those energies that allow me to do more than one thing.
P1: Sure, that makes total sense. So you do write a lot. So what is your daily routine or writing
routine I guess?
Ryan: So I wake up early at the morning like 7:30, 8 o’clock and I try to write for the first like hour or
two hours of the day. And then start taking a break from writing which is sort of what I’m doing now.
P1: Why? What brings that about?
4. Ryan: I’m just like a little exhausted and I feel like if you force writing when you don’t have something
to say, you know, that can be problematic. I’ve been writing a lot and when I say I’m not writing it’s
like I’m writing an article every other week, so it’s not like I’ve quit altogether. And I’ve been
travelling a lot. I’m just sort of getting back to my routine. But I usually write in the mornings. Then in
the middle of the day I do emails, phone calls, stuff like that. I do like heavy exercise in the afternoon
and then I go back to work evening then I dinner and then I just hang out with my fiancé for the rest
of the day.
P1: Okay. So you’re more of a start-of-the-day kind of person.
Ryan: Yeah, I think a lot of the research shows that you’re most productive in the morning because
you’ve just started and there’s usually fewer interruptions in the morning. Obviously you can work
late at night but I find that working at the end of the day means that you’re exhausted in some way.
So I like to sort of start fresh, then get it over and out. That way the rest of the day… Let’s say I’m
working on something writing-wise and I’m having trouble with it, if I’m working out later I have
some sort of creative breakthrough now that I’ve put the problem that I was facing aside. It sort of
let’s you marinate on stuff the rest of the day. That’s how I try to do it.
P1: Sure. And how does the American Apparel stuff fit it?
Ryan: Sort of there in the middle; my phone calls, interview, emails… I work remotely for American
Apparel, so sort of as long as I handle the stuff it doesn’t really matter.
P1: Okay. So how did you get to American Apparel? Again, it’s like everything that you do seems to
be completely different from everything else. In some way, I’m sure there’s some theme tying them
together for you.
Ryan: Yeah, so I got to work at that while I was at American Apparel. But Robert is on the board on
American Apparel so I got introduced to Doug, the founder, and I came on as a marketing consultant
and I ended up seeing a niche for myself. I built the marketing department there, hired a team,
trained them, created the strategies. So then when I left for my book I was sort of able to hand the
most of the day-to-day stuff off to someone else and then I’m just there as this supervisory, advisory
P1: Okay, gotcha. Okay, so let’s talk about books because it’s something that’s been a very, very big
struggle for me for a long time and I sort of finally figured out a system. But you read about 250
books a year, right?
Ryan: A lot, yeah. I don’t really count but I try to read a lot of books. I try to always be reading. If go
to the doctor I try to get there 15 minutes early and I read. I carry a book with me if I go out to read. I
have a book with me to the car. When I travel I read a lot. People think I… and I am always reading,
but normally what happens is I’ll read a book a week but then I travel and… I was in Australia last
week and I think I read 4 books so like I tend to read in spurts. So I see myself now more as like a
binge reader than anything else – which averages out to a lot of books, rather than like reading a
book per day.
P1: I’m guessing based on behind you that you like physical books.
5. Ryan: Yeah, that’s not even all. If you go this way.
[Ryan moves web camera to his right to show more bookshelves]
P1: Yeah, I’ve seen pictures. It’s very cool.
Ryan: So yeah, physical books for me because the way I learned to research from Robert is I use note
cards that I sort of write everything down on. So I have boxes of note cards that I keep this stuff. And
so I take the physical books, I transfer to note cards and organize it. And the I use the notecards to go
back to the books when I need to reference them. So having eBooks is one) less tactile and physical
for me and two) I find that reading digitally while it can be easier in a lot of ways just highlighting
something in a Kindle does not create that sort of place in your mind where you remember it deeply
and it’s there.
P1: So that actually what I wanted to ask you about. So first of all, it’s actually really fascinating to me
that you’re… well you’re only five years younger than me, but I’m very big into technology. It’s
interesting to me that you do so much with paper and with notebook and stuff like that. But I’ve also
heard other interviews with you and it seems that you have incredible recall for the books that
you’ve read and information from those books.
Ryan: It’s sort of a mix of how like you don’t have to memorize something if you know where it is, but
then through creating a place for it as a process allows you to… like when there’s a quote I like read
it, I marked it down, then I wrote it down on a card, then I put that card in a place and then I might
have referred back to that card on one or more occasions. So I’m like bumping into that card several
times, rather than just making some digital bookmark and then moving on.
P1: The other thing too, for me is, everything I heard about an interesting book or something, I would
get it the Kindle route or on my Iphone app and I’d think “Great!” but it’s not like it’s on my shelf.
You know, you never go and look and like… cruising for the book you want to read. It’s totally
different. It’s a weird… For me it’s a place where technology really is a deficit… or detriment rather.
Ryan: It’s weird. For one I don’t think people see book as a piece of technology but they actually are.
Most people don’t pick up a physical book and say “Ah, this is so broken and inefficient”. The only
problem with books as a technology is it’s a problem to have a lot of them at the same time, right?
And so the Kindle definitely solves that but unlike say an Ipod or something, I don’t think we
necessarily need to have lots of books with us at one time the way it is much more convenient to
have lots of music with you at one time. And then two, usually I have like an Amazon wish list that I
just buy next book I want to read whenever I’m ready. By the end of the year I was like get to write
books off my taxes, I’m just going to buy all the books that I’ve wanted for a long time, that I’ve had
on this wish list. And so I bought them and there’s a shelf in my garage where I have all the books,
and I actually found that I’ve been reading less since I did that because there’s like less excitement
over what the next book is cause I just have this endless stack in the garage. And I also realized that a
big reason that these books were on my wish list was that I wasn’t actually interested in them. So it’s
like I had this big shelf of B-side books that I don’t really care about in the garage that I paid for that I
can’t drag myself to read. So I think being on this shelf matters, but I also think like, getting the next
thing and having that visible sign of progress is motivational for me.
P1: First of all, do you know DailyLit?
6. Ryan: No.
P1: Okay, so DailyLit is the one piece of technology that I use to help me with this. So for non-fiction,
I’m good. I can read non-fiction really well and get through it. Your book was really easy to read
actually and I kind of flew through it. Fiction which I think is important to read mentally but I just
could not do it. So DailyLit, basically they have… I think they have 80,000 books on there, and most of
them are public domain and stuff but that’s how I’m reading around “Around the World in Eighty
Days”, send you an email everyday with between two and five pages, essentially your choice, and it’s
amazing basically. So I’ve gone 64 days, every day reading a very small passage of the book, and I’m
almost done. And it’s amazing. It’s really amazing because first of all I’m never going to be able to
justify to myself the ten minutes to read that one email and I just won’t delete it from my inbox. And
I have bin bag zero. I will not delete that email until I’ve read it.
Ryan: Interesting! By the way, speaking of “Around the World in Eighty Days” I read this book
recently and it may have been called and it might have been called “Around the World in Eighty
Days” but it’s a about Nellie Bly who was the first person to actually go around the world in 80 days
and she did it in the early nineteen hundreds, I think. She met Jules Verne on the trip, but it’s really
interesting. She was a really famous news correspondent. She was the one who… she pretended she
was insane and she got committed to the terrible mental institution in New York City. It’s really,
really interesting. And actually two female journalists at the same time attempted to beat the record.
One of them did it in 83 days and one of them did it in 79 days or something like that. It’s really
P1: How do you choose what you want to read and what is that sort of mixture of fiction, non-
Ryan: So I have an Amazon wish list that I check out. Obviously I have this stupid shelf in my garage.
But I usually try to read a book… I try to connect the books like sort of read one thing and then try to
read something related to that thing but it all depends. Obviously when I was researching this
stoicism book I was reading books more or less around the same sort of themes. Like things that I
thought would fill holes in the project that I was working on. But also understanding that when you
read random stuff it… you know, I open “Trust Me, I’m Lying” with a quote from “Ender’s Game”
which I have never read so I was probably 80% done with “Trust Me, I’m Lying” and I read this quote
and I was like “Oh wow, this is perfect! This exactly what I’m talking about, how can I put this in the
book?” So I sort of see it as, you have this framework or this thing you are studying, and how can you
introduce serendipity into that system by pursuing random, unrelated things that you’re interested
in? And the when you’re really zeroed in on an idea you can see connections to that idea in just
P1: Yeah, it’s really fascinating to me how often I see a connection to something I’ve recently read to
what that I end up writing, or even to the podcast. Just like “Around the World in Eighty Days”; that’s
totally irrelevant to what we’re talking about. So when you’re reading is there like a mode you get
into? Do you have like a cup of tea? How do you get into that mode?
Ryan: No, not really. ‘Cause I try to do it anywhere. When I’m in my car or when I’m on a plane or
whatever. I like to listen to music but I usually listen to like a playlist of like one song or like five
songs, just over and over again. I like to have silence but like noise-cancelling headphones don’t just
7. work as silence so if I can turn on music that becomes background noise really quickly that tends to
be really effective for me.
P1: And are you a pretty fast reader?
Ryan: Not super fast. I think I’m probably faster than normal. Most people tend to think I’m some
kind of speed reader but I’m really not; I just read a lot.
P1: Okay. Now I’m not going to be mundane and ask you what your favorite book is because there’s
so many. I’m sure you are familiar with the Ben and Frank [?], right? Okay, so is there a special book
that you have that is your pride and joy?
Ryan: There wouldn’t be one book that I have. So my thing is that I don’t loan books out to people. I
borrow book and then keep them but I don’t loan books out to people. I have… Someone gave me a
signed copy of “What Makes Sammy Run” which is one of my favorite books. It’s like a first signed
edition. Then I have a couple of really old copies of “the meditations”. Like, I have one copy from the
eighteen fifties and maybe one that’s older than that, that’s like really old. But other than that, like, I
tend to treat book really poorly. I read “Count Belasarius” about the Byzantine-Roman general, and
I’m reading this book, and I bought it on Amazon for like a dollar or whatever, and taking notes and
I’m folding the pages and I get about half-way though and this page falls out. And it turns out I’ve
been given this pristine 1933 review edition of the book and it’d never been opened. I don’t know if
it was worth anything but it was weird. Like, here’s this book that is pre-World War II that had been
sent to newspaper reports to review it prepublication and like I’ve already ruined it. But to me the
book is more valuable to have notes in it than it is in perfect pristine condition.
P1: I guess that’s a little bit the journey of it too. So does the note cards, that sort of extends to
everything obviously, it’s not just notes and quotes. But I mean, I’ve seen a couple of pictures about
like the light pattern, but like how do you actually organize it? I know you have the boxes, but?
Ryan: Yeah, you want me to grab one of the boxes?
P1: Yes, please! Give people more reason to watch the video!
Ryan: Yeah, so this is the one is for the “The Obstacle Is The Way” so it says “The Obstacle Is The
Way” on it, and then… so this is actually a thing that’s supposed to hold like photos but basically the
book is an intro, a conclusion and 3 parts. So each of the parts has 2 sections, but basically like…
these are the note cards for part 1. Here is all the different chapters that are in chapter one. And
each of these parts has a file folder, like part 2. And you can see on there, this one says “Persistence”.
This one says “Pragmatism”. Each of the tabs is all the cards that I would need for that specific
section. So I have a section on ”In the wheel cart on the heart of renaissance”[?]. It’s all these note
cards as you can see. So when I was writing that section I just took these cards with me, where I was
writing or if I was writing at home obviously I just took them out. But I would just travel around with
those cards and take them out. It has all the pieces that I need to write those chapters.
P1: See, this is amazing to me. And actually, it illustrates something that is important to me and my
audience in general. I have methodologies that I teach people and frameworks that I like people to
use to do this stuff. And personally I could never do it that way, because it just wouldn’t work for me.
But what I’m always telling people is that if you have a system that works, no matter how archaic or
8. different it may seem, please stick with that system. And this system is clearly working really, really
well for you because the information that put out is very well researched and organized. I would be
afraid of losing stuff.
Ryan: Yeah, so I learned this from Robert Greene and this is sort of my version of that system. It’s
very similar. Like, if you look at his note cards, they are like covered in text. Mine tend to be just a
couple of words. So mine is more reference oriented while his is more totally self-sufficient. But
yeah, I’m petrified of losing it so I bought this scanner and I’m going to scan the cards and have like a
digital archive of them. Right now I keep them in a fireproof safe in my garage when I’m not at home.
P1: You should use the Livescribe pen. Have you seen that?
P1: So Livescribe, it connects with Evernote and a whole bunch of things but basically it’s a normal
pen. It’s a little thicker but you write with it as normal and it records whatever you’re writing
digitally. So you can kill two birds with one stone that way. Livescribe.
Ryan: Interesting! I’m writing this down. And I’m putting it on a note card.
P1: Thank you. Okay, so last question here. I know you’ve been asked before, but what are your top 3
personal tips for being more effective?
Ryan: I think commitments are very effective. Like if you make public commitments in some way. If
you’re like “Oh, I’m doing this!” that’s very different than… or even just talking about doing it then
like… Part of the reason that I work with traditional publishers, it’s not the major part but it’s a big
part, is that when you sign a contract for a book you have to deliver a book by that date, you know?
And you’ve already taken the money for it. So what I see with self-published authors all the time is
like, the release date is always getting pushed back because they have that luxury. So I think that’s
important. I think physical exercise is very important. Like strenuous physical exercise because it’s a
metaphor for hard work and success and it can also be a way to sort of create a momentum that you
put back in your work. I don’t know what the last one would be. I think sleep is important and
underrated. Yeah, so maybe I would say exercise, sleep, unalterable commitments to deadlines.
P1: I think that’s really good. I like all of those. I have to push a little bit more on the sleep one.
Obviously sleep is important, but what is you kind of sleep philosophy?
Ryan: It’s not like some science or whatever. I don’t use any of those devices. I just actually sleep like
7 to 8 hours a night. And I’ve like never pulled an all-nighter in my whole life because I plan I just
don’t let that happen. I think people tend to see sleep as this reserve that they can draw from.
People are like “Hey, now I have procrastinated and I have to stay up late and work on this project”. I
don’t do that. Like, sleep is a thing that I do every day and it’s not negotiable. So that’s sort of my
approach to it.
P1: Well that’s great. Those are really great tips. And Ryan, you know we’re going to have links in the
show notes and everything, but what is the best way for people to find out more about you and the
book and everything?
9. Ryan: Yeah, so the book is “The Obstacle Is The Way” and I think it’s for sale everywhere. I think it’s
like 3.99 on Amazon right now, which is cool. My website is ryanholiday.net and I’m ryanholiday on
P1: Okay, well great. Thank you so much. It was really great talking to you.
Ryan: Yeah, awesome. This was fun.
10. Ryan: Yeah, so the book is “The Obstacle Is The Way” and I think it’s for sale everywhere. I think it’s
like 3.99 on Amazon right now, which is cool. My website is ryanholiday.net and I’m ryanholiday on
P1: Okay, well great. Thank you so much. It was really great talking to you.
Ryan: Yeah, awesome. This was fun.