32 Lessons From “Millennial Philosopher King” — Ryan Holiday

Ryan Holiday was the Director of Marketing at American Apparel in his early twenties. He apprenticed under the great Robert Greene. At 31 years old, he is the author of 6 Bestsellers. His most recent book, Conspiracy, is sheer brilliance.

If you aren’t familiar with his work, you should be.

What’s most compelling about Ryan (for me anyway) is that he came of age during a time when blogging was cool. You know “the golden age” of writing online that present bloggers dream of.

The difference between Ryan and many other bloggers of “the golden age”?He had dreams of taking it offline — of being an author, not just making a quick buck.

And he put that dream into practice — by working incessantly on his craft. Working with and for accomplished authors. Learning the ins-and-outs of the media industry. Positioning and marketing his and others’ work. And writing… writing on his personal blog, refining a message, and opening his contrarian thoughts to public feedback.

Ryan is a great case study on how Millennials and Gen-Xers should think about operating in the working world. Not because of the accolades or financial success. But because he has been strategic in his approach, followed his curiosity, built a world-class network, and inspired a few million people to think a bit differently.

He also provides comprehensive analyses of ancient philosophy, specifically Stoicism — showing us how to pick and choose the right tenets and use them as a “personal operating system.” In other words, he challenges each of us to find ways to live better.

Ryan’s work is not without critics. He is a white male chasing perennial status. Attempting to be one of the greatest writers to ever do the craft. Not to mention, his entire career and the transgressions therein, have been documented online.

So while I make no claims that he is perfect, nor would I think he’d make those claims, I believe that it is because of his commitment to learning and growing — to tackling his imperfections — that there’s so much to learn from him.

In taking his work as a gestalt, in studying it as the progression of a person, you very well may find the keys to a map for success and fulfillment as a creator.

It takes guts to document your “becoming” online. But for the aspiring authors out there, like me, it has been invaluable. Thank you, Ryan.

And so with that, here are just a few of the many lessons I’ve learned from him over the years — through interviews, articles, and books:

On Writing…

  1. You have to be part of the audience, but you can’t BE the audience. As Ryan said on the Love Your Work podcast, “If an author doesn’t at least consider themselves part of the audience, then you’re just lecturing.” On the other hand, if you are only thinking about yourself — no one will connect with your work and it will fail to achieve its purpose: to serve or solve something.
  2. Focus on what’s timeless about timely events. If you are going to make something that you want to stand for a long time, it’s best to look pay attention to what hasn’t changed (and likely will not in the future). An example he uses is that Amazon (especially Jeff Bezos) knows that people will always want things fast and cheap. The modalities for delivering those things may change, but that fact won’t. Ryan has followed this advice deciding book topics — he knows people will always deal with ego, face obstacles, want to create lasting work, etc.
  3. Research, outline, then write. In some senses, it can be powerful to sit down and write to “figure it out.” But that’s usually just called journaling. It may be the first step in the process, but it’s not usually the way to a well-crafted, clear, and persuasive piece of prose. To get an idea across in the most powerful way possible, you have to go back to the process you were taught in school. Ryan details this exhausting process for book writing HERE.
  4. Build a list (even if you don’t need one, yet). If you are planning on maybe at some point eventually launching a project or writing a book, you’ll need an engaged audience that trusts you. The best way to build that relationship is through email — because social media platforms (including this one) are volatile. They’re useful and amazing, but if you want certainty and stability — email is where to start.
  5. “A book should be an article before it’s a book, and a dinner conversation before it’s an article.” There is this commonly held ideal of the successful artist. He must sit tortured — alone in a locked room in the dark. He must expend every ounce of energy to create one life masterpiece. Ryan dismantles this with this one phrase. Ideas are not meant to be incubated in private. The purpose of any idea is to share it. And therefore, it is best not to hide it, but to refine it in public and see if it resonates before committing yourself to the torturous process of writing a book.
  6. Write what you can write. There is a fine line between sharing what you want to and what you can. I’ve certainly fallen in this trap many times — approaching a topic I know very little about with such bravado. Basically just repurposing others ideas. This is the worst thing you can do — not only because it isn’t as useful for the reader, but also because it makes you feel like an imposter. On the other hand, the best thing you can do is write about what you know, what you’ve experienced, what you’ve read, and what you’ve seen. There’s something there that will be way more valuable in there to readers than writing about crypto or morning routines because you heard they were all the rage.
  7. Do other things. On the same note, creators have to live before they can create anything of meaning. Sitting at home all day just writing isn’t the equation for powerful insights. Going for hikes. Hanging out with friends. Exploring. Running. Reading. These things are what powerful stories are made of. It’s as Roosevelt famously said:

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.

On Learning…

  1. Always be researching. He’s not the only person to say you should keep learning, but he is the only person (I’ve come across anyway) that openly says you should be always be researching. Researching is the process — not just of consuming information — but organizing it, synthesizing it, and finding connections between ideas. I find that the more I do this — sit down and really think through what I’ve just read or listened to — the clearer I am, the better I write, and the better I show up in the world.
  2. Read books that other people aren’t reading. If you read all the books on the Barnes ‘N Noble’s sale shelf, you will be better off than most people. But to jump ahead by leaps and bounds in terms of your perspective, you have to do what others aren’t doing. To do what others aren’t doing, you must think how others aren’t thinking. To think how others aren’t thinking, you must expose yourself to different ideas. And so, the way to get ahead, according to Ryan is to seek out old or ancient ideas that still hold today. It is through that practice that he has brought Stoicism to the frontlines.
  3. Treat learning as part of your job. Ryan earned a senior position at a major publicly-traded company at a young age. How did he manage that? He read — every extra minute he had — to learn everything he could about power, strategy, productivity, business, marketing, etc. He knew that his big task was not to put out this fire, but to understand the marketplace and power dynamics at play. He treated learning (reading, especially) as a core part of his job.
  4. Learning is an infinitely long process (and that’s a good thing). Robert Greene and Malcolm Gladwell’s theories of mastery are meant to serve as a benchmark — a researcher’s attempt to understand what mastery might theoretically and practically entail. But to use that as the “end all” is to live in a world with a ceiling, or worse…to live with happiness, success, or mastery always on the horizon, never in this place. Ryan writes “Is it ten thousand hours or twenty thousand hours to mastery? The answer is that it doesn’t matter. There is no end zone. To think of a number is to live in a conditional future.”
  5. Follow your curiosity. Ryan reads books that interest him. He embraces the “wormhole” you can go into on certain topics like The Civil War. He becomes a near expert at understanding certain ideas, people, and places. Not because he knows they will lead to some profound breakthrough or book idea. Maybe they will; maybe they won’t. He just sees the inherent value in learning more about what you naturally gravitate towards.

On Work…

  1. The end of a successful creative project is not when the work is finished, but when word of mouth has taken over. Success is the result of people sharing your work for you. They love it so much or it’s helped them so much that they can’t help but suggest it to the people around them.
  2. You can’t walk two mutually exclusive paths. My experience deeply reinforced this. I tried to write and stay on a high-powered exec track. They were both coming at the cost of another. Ryan writes, “Nothing has sunk more creators and caused more unhappiness than this: our inherently human tendency to pursue a strategy aimed at accomplishing one goal while simultaneously expecting to achieve other goals entirely unrelated.” Try doing things that overlap or are loosely related. This may make you better at all of them.
  3. Have a grand strategy. You don’t have to have a precise plan, necessarily. You just have to have a deep understanding of the direction you want to head in. The difference between this and having a goal is subtle — a grand strategy incorporates a unique sense of flexibility. You aren’t tied to the outcome so much as you’re tied to the process. Ryan wanted to make a life writing books — so he lined up the dominos to build all the tangential skills, acquire the knowledge, and have the experience necessary to do just that.
  4. There is a middle path for creatives. He writes in Perennial Seller, “Either we have dreams of utter dominance and stardom, or we retain a sort of hipster disdain for popularity.” But this is a false dichotomy. You can be good at doing your work and get attention for it. This is called creating value. Striving solely for popularity is empty; striving solely for “purist art” is destroying the meaning behind creation in the first place: to tap into something uniquely human and share it.
  5. Give “it” away. Your writing. Your best ideas. Don’t have such a big ego that you think others will steal your idea.
  6. Employ “The Canvas Strategy.” This is maybe the idea that’s helped me most in my work and in my life. Our role is often not to develop the best new feature or to give someone all the answers, it’s to create space for others to do those things. In other words, we shouldn’t be finding ways to assert our own creative dominance, but to search for blank canvases for others to paint on.
  7. Forget credit and free yourself. Ryan writes, “You can forget credit. You can forget it so hard that you’re glad when others get it instead of you — that was your aim, after all. Let the others take their credit on credit, while you defer and earn interest on the principal.” In the long run, everything will play out in your favor if you have the right intentions. It is only someone who is consumed by short-term rewards and accolades that cares about credit or accolades.
  8. His test for taking on projects: Is this going to be work I’m proud of doing or is it going to give me something I need (i.e. money, relationships) to do something I will be proud of?
  9. Jump on the opportunities that present themselves. The reason that The Obstacle Is The Way became a sensation in the professional sports world is because Ryan was approached by one NFL coach. He rode the wave and started providing free copies of the books to other coaches and players. He was able to apprentice under Tucker Max because he wrote an article for his school newspaper about him. He became “Director of Marketing” at American Apparel was because he met Tucker, who knew Robert Greene, who was on the board of AA. He wrote his first book about media manipulation which led to the creation of his creative marketing firm Brass Check. In all senses, he has a clear strategy and takes each and every opportunity that fits in it (at all).
  10. Place personal growth over work. Ryan writes, “Perfecting the personal regularly leads to success as a professional, but rarely the other way around.”

On Life…

  1. “What am I missing right now that a more humble person might see?” This is one of the best questions I have found for grounding myself back into reality.
  2. Amor Fati. Or “The Love of Fate.” He introduced me to a phrasing for this idea, although it’s something I’d been pondering for a while. It’s this idea that we must love everything that happens to us — not just the people and experiences have that we claim are “good.” We must see the benefit in every struggle, see the lesson in every fall. This is a life philosophy
  3. Keep it simple (stupid). He lives on a farm. He does what he likes for a living. He runs every day. He lives modestly (it would seem). He writes. He goes at the pace that’s right for him.
  4. “All of us waste precious life doing things we don’t like, to prove ourselves to people we don’t respect, and to get things we don’t want.” Fuck.
  5. Drop out of things that others wouldn’t. Not as to say “I’m better than you” or anything, but because there is a better opportunity — one that’s more aligned with your grand strategy. Line up the right safety net and take the risk.
  6. You don’t have to be perfect. This is so dumb to say that he’s evidence of this. But I think the more we fear judgement, the less we can learn about the world and about ourselves. I’ve read a lot of the archives of Ryan’s work. There’s some dark stuff down there — stuff he probably isn’t arrogant enough to still believe. That’s okay. Through the process of putting his ideas and work into the world, he’s been able to acquire valuable feedback, not only to increase the value of his work but to become a better human being.
  7. “Narrative is when you look back at an improbable or unlikely path to your success and say: I knew it all along. Instead of: I hoped. I worked. I got some good breaks. Or even: I thought this could happen. Of course you didn’t really know all along — or if you did, it was more faith than knowledge.” The narrative pro
  8. Share in the process. Gary Vaynerchuk talks a lot about this idea “document, don’t create.” That’s hard to do when you’re an artist, writer, or musician of some sort. But Ryan has managed to do it artfully — by showing younger up-and-comers how the book writing process actually works, releasing the veil that publishers have long relied on. He shows just how hard these things are. He documents and creates.The progression of who Ryan is — as a man, marketer, and writer — is available on the internet. That is invaluable to someone who would like to vaguely emulate his path.
  9. “It’s human being, not human doing.” Ryan says, “You can end up doing action for the sake of doing action.” And really, what’s the use in that?
  10. Build strategic relationships. Focus on what you can give and what you can learn. “Networking is not going to networking events and handing out business cards — that’s flyering.”

If you haven’t read any of Ryan’s books, I sincerely suggest that you check them out HERE. I am not doing his work enough justice in this article to even scratch the surface here.

If this article at all interested you — go to the source. I promise you won’t be disappointed.

Tips on where to dive in:

  • Start with The Obstacle Is The Way if you’re struggling at all in life.
  • Start with The Ego Is The Enemy if you think you are inhibiting your own successes or creating your own failures (hint: you are).
  • Start with The Daily Stoic if you are interested in adding the review of a new, empowering idea to your daily rituals.
  • Start with Conspiracy if you are more into narrative non-fiction. This one is a page turner — about the details of the fall of Gawker at the hands of billionaire, Peter Thiel, and his Trojan Horse, Hulk Hogan.
  • Start with Perennial Seller if you are a creator (of businesses, videos, books, music, whatever) seeking greatness.
  • Start with Trust Me I’m Lying if you are interested in the current state of the media or media manipulation in general.

Or at the very least sign-up for his reading list here. It’s brilliant and one of the very few emails I look forward to receiving this month.

Thinking deeply about how to make myself and the world a little better. & writing about creators mostly | email: kate@onedayent.com

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