I’m Ryan Holiday, And This Is How I Work

I’m Ryan Holiday, And This Is How I Work

In the past week, Ryan Holiday read seven books, flew from Austin to Atlanta to Miami to Atlanta to LA to Maui, and juggled two demanding jobs: director of marketing at the controversial clothing retailer American Apparel, and partner at creative marketing company StoryArk. (Just writing that sentence made me tired.) Ryan is also a best-selling author. I caught up with the 26-year-old media whiz to find out how he juggles it all.

Location: Austin, TX (when I’m not on the road)
Current gig: Director of Marketing, American Apparel; Author of Trust Me I’m Lying,Growth Hacker Marketing and The Obstacle Is the Way; Partner at StoryArk
Current computers: 27-inch Mac desktop; MacBook Air
Current mobile device: iPhone 5 with a Mophie case; standard iPhone headphones almost always plugged in
One word that best describes how you work: Always

What apps/software/tools can’t you live without?

I’m Ryan Holiday, And This Is How I Work

Reference: My Commonplace Book (pictured above) is the first thing I’m taking out of my house in a fire. It’s several thousand 4×6 notecards — based on a system taught to by my mentor Robert Greene when I was his research assistant — that have ideas, notes on books I liked, quotes that caught my attention, research for projects or phrases I am kicking around.

Every book I read is also broken up and digested on these cards, which are all loosely themed. I don’t have a great exact memory but I know in broad strokes what I have on these cards and whenever I’m writing or speaking and need it, I pull it out and find it. I know a lot of people use Evernote for this but I think physical is better. You want to be able to move the stuff around.

Management: Basecamp is great for employee and task management — provided that you hire great people (of course that’s the best decision you’ll ever make, hiring good people) — especially now that they have an app. I also really like 15five, which has each employee spend 15 minutes a week writing a report that will take me (or their manager if they have one) just five minutes to read. I run my offices remotely so these are pretty crucial. I get visibility, they get freedom from feeling like someone is constantly looking over their shoulder. But they can always escalate problems and can work in public.

Reading: One of the hardest parts of my work life before I started working from home was the fact that I couldn’t get away with reading books in the middle of the day because to most people it didn’t look like work. Well it is. I try to read all the time. I’m a college drop-out, but I feel like books were a great equaliser for me — maybe even more than that, like a secret advantage.

I prefer books to articles, to blogs, to videos, to TED talks to basically anything (except first-hand experience, obviously). If I don’t have a book in my hands, I feel like I’m wasting time. If I’m not reading a physical book, I save pretty much every article I think I want to read to Instapaper and read it later on my phone away from the computer. I find most of them through my Feedly and through Flipboard.

What’s your workspace like?

I’m Ryan Holiday, And This Is How I Work

I just moved into a new house and got to build a new setup from scratch. It’s probably a good reflection of my priorities. Two full walls are floor to ceiling books (pictured below) and my desk is wedged into a closet (pictured above). I work from the road a lot too. I wrote my first book in the library rooms of the Los Angeles and New Orleans Athletic Clubs, where I spent a lot of time. I wrote my most recent one in the National Arts Club on Gramercy Park. If I’m not in my house, I really like being in something old and quiet. I never got the working on coffee shop thing. It seems like if you were trying to design the least productive and conducive working environment you could think of, it’d be hard to do worse than a coffee shop.

I’m Ryan Holiday, And This Is How I Work

What’s your best time-saving trick/life hack?

I think that my schedule is what allows me to do so many things all at the same time. In the morning, I wake up and write — before checking email if I’m being disciplined — but I don’t think just “general” writing time is that valuable. For me it needs to directed at a specific task, so an article, a chapter, editing a chunk of something. Writing without an end in sight can be really discouraging.

So I write in the morning for about an hour or two. Then I go out to breakfast with my girlfriend, (Kerby Lane in Austin, the Athletic Club in LA, or Barking Dog in New York) and work on email and my clients. I continue working when I get home, until the afternoon when I put it away and I go running or swimming. It’s in the pool or mid-run that I find that whatever intractable problem I was struggling with earlier — whether it’s writing or work-related, the solution magically comes to me.

I spend the last couple hours before dinner wrapping that up before starting it all again the next week. I can’t tell you how many times I’ve rushed home from a run and shouted, “Nobody talk to me, I have to write this down!” while I dripped sweat all over my computer or my note cards as frantically tried to get it down before I lost the thought.

Personally, I’ve found that doing more than one thing career-wise makes you not only more productive but better at what you do. Writing makes me a better marketing, marketing kicks up all sorts of ideas for stuff to write about. Working with clients helps me at American Apparel, the unique problems I’ve dealt with at American Apparel helped me with other jobs and projects I worked on. I’m somewhat amazed at people who can fully dedicate themselves to only one skill or field. I think I have too much energy or too little patience.

What’s your favourite to-do list manager?

I’m Ryan Holiday, And This Is How I Work

I use the same 4×6 index cards I use for my commonplace book to write down my daily tasks (pictured above) and only recently started using Google Calendar on my iPhone for appointments (ideally I try to have zero calls/meetings but it’s gotten to be unavoidable). I heard once that really successful CEO-types usually have a to-do list of about five big things to do every day. So I try keep mine at that. Every day I start sketching out my to-do list for the next day and put it down on the index card. The next morning, I get up, write a little in the morning and then start crossing stuff off.

Once the list it done, I play the rest of the day by ear with email, calls, and things that come up. But I always get the list done. The furthest I will ever go in advance in terms of planning an index card out is two days (like sometimes on Friday I’ll make a quick card for Saturday and one for Sunday). I take great pleasure in tearing the to-do list up into little pieces the second that last item has been crossed off. The rest of the day is mine when that happens.

Besides your phone and computer, what gadget can’t you live without and why?

Books. Physical books. It’s the perfect technology.

What everyday thing are you better at than everyone else?

I think I’m good at finding the angle on things. The way to play a particularly situation or scenario that will check off as many objectives as possible. It’s not just what you want to do but always the political and practical implications of any given decision. Also I plod along. I’m not the best or the smartest but I’m always moving forward.

What do you listen to while you work?

Oh man, I have the worst taste in music. I’m probably digging my own grave by showing this, but I’ve attached two recent screenshots of my iTunes most played lists on different computers (I’m sure they’re supposed to be synced but I have no idea how to do that. It was much worse on my older devices but thankfully these are both new.)

I’m Ryan Holiday, And This Is How I Work

You can see I find terrible — but catchy, melodic, usually radio-single-type songs and listen to them hundreds of times in a row. I find that this helps me write and read and think. The list you’re looking at probably doesn’t mean anything to anyone else, but to me I can tell you what article or what part of one of my books I wrote to that song on repeat. Or I can tell you what book I was reading.

I’m Ryan Holiday, And This Is How I Work

Though right now I’m working on writing a book with Birdman and Slim, the founders of Cash Money Records. So I’ve been listening to a lot of their stuff. I can do the same thing with good rap songs — especially the recent stuff — and play them until I get lost.

What are you currently reading?

In the last week:

Colonel Roosevelt by Edmund Morris, The Fat Lady Sang by Robert Evans, In the Heart of the Sea: The Tragedy of the Whaleship Essex by Nathaniel Philbrick (about the boat that Moby Dick was based on), Plutocrats: The Rise of the New Global Super-Rich and the Fall of Everyone Else by Chrystia Freeland, Why I Write by George Orwell, The Maltese Falcon by Dashiell Hammett, and Between Man and Beast by Monte Reel (about the guy who shot the first gorilla and brought it back to Victorian London).

I usually read a lot for my reading list email, where I recommend a collection of books each month. But I spent too much time on planes this week and if you resist the urge to buy wifi on planes, you can get so much reading done.

Are you more of an introvert or an extrovert?

Introvert for sure.

What’s your sleep routine like?

I like that quote from Schopenhauer: “Sleep is the interest we have to pay on the capital which is called in at death. The higher the interest rate and the more regularly it is paid, the further the date of redemption is postponed.” (I pulled that from my commonplace book, by the way.) I’m not saying I sleep all the time but I think it’s important to get at least 7-8 hours. I can count on one hand the times I pulled an all-nighter in my life. I think working really late is overrated and usually the result of poor planning. If I get up early, I try to match it by turning in sooner.

Fill in the blank: I’d love to see _________ answer these same questions.

Bo Jackson, Mark Cuban, James Franco, and Ta-Nehisi Coates.

What’s the best advice you’ve ever received?

“Be a good person, do what you love — those are the only rules for life.” I forget who said it, but I think about it all the time.

There are also two passages from the Stoics that I have posted above my desk. One is from Seneca, it’s short: “Some lack the fickleness to live as they wish and just live as they have begun. “The other one is from Marcus Aurelius — it’s longer and means less to me now as I am older, but when I was just getting started I think I used it to fuel myself past what Steven Pressfield calls the “Resistance.”

Is there anything else you’d like to add?

In terms of quotes or things that have made me think recently, I printed out this passage from Tyler Cowen recently and actually had it framed. I think it’s scary and motivating.

“In today’s global economy here is what is scarce:

1. Quality land and natural resources

2. Intellectual property, or good ideas about what should be produced.

3. Quality labour with unique skills

Here is what is not scarce these days:

1. Unskilled labour, as more countries join the global economy

2. Money in the bank or held in government securities, which you can think of as simple capital, not attached to any special ownership rights” — Tyler Cowen, Average is Over

We’ve asked a handful of heroes, experts and flat-out productive people to share their shortcuts, workspaces and routines. Every week we’ll feature a new guest and the gadgets, apps, tips and tricks that keep them going. Want to suggest someone we should feature or questions we should ask? Let us know.

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