23 Lessons About Life, Writing and Doing Work That Matters by Reading Ryan Holiday

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If Tim Ferriss is the “Oprah of Audio,” that means that Ryan Holiday has to be on the short-list for being named the “Pharrell of Marketing and Book Writing.”

Rarely on the cover, but if you dig a little deeper you will find his fingerprints everywhere. From some of the worlds most influential and innovative people and companies, to the locker rooms of some of the most successful sports teams, to even the clothes on your back, his name is in the conversation.

Recently, Ryan sat down and wrote “Thank You Letters” to his friend, Tim Ferriss, and his mentor, Robert Greene, addressing 23 things he has learned by being fortunate enough to work and play with them.

While reading these articles it dawned on me that people do not do this enough, sit down and write out what their friends and mentors mean to them.

After reading his articles I sat down and wrote out “thank you letters” to my wife and parents and realized that I should give credit, to where credit is due, by taking the time to thank Ryan for not only positively impacting my work, but more importantly, my life.

A few years back I told my dad about a book I really liked, thinking it would start a conversation. Instead he replied “Good, now go read the counter-argument.” End of conversation.

Ryan and my dad would get along just fine. His work shows that after reading a biography on Grant, he picks up Lee next. By hearing both sides of the story, he has found a way to write his own, and in the process by sharing his thoughts and book recommendations, he has helped thousands of others to write theirs.


I used to treat reading as a hobby, reserved for rainy days and the occasional bathroom break. It was not until I came across Ryan´s article on “How To Read More — A lot More” did I make the switch from reading for fun to reading for necessity.

Ryan has said numerous times that the reasons he reads so much (hundreds of books a year) is because, “Someone, somewhere, at some point in time, experienced the exact same problem you are facing now and they took the time to write about it, what took them years to figure out on their own, we get to learn in a matter of hours.”

Is there a better reason to read?

Even if you have absolutely zero aspirations to be a writer, there is no better way to clear your head and organize your ideas than putting pencil to paper.

Much of Ryan´s marketing success has come down to the idea, and execution of, “Picking one of the our sacred cows and then slaughtering it.”

Although, he may do this to get clicks, from what I have gathered, he also lives his life this way.

Instead of being seduced by the lifestyles of LA and NYC he decided that a small farm in Austin, Texas was the best place to be able to do the work that mattered most to him and anything that could potential lure him back he thoroughly analyses to make sure it is not throwing him off track of what “he” really wants to do.

If you create an environment, instead of allowing the environment to create you, you might just find that the very people you once chased, come knocking.

Ryan’s post, “3 Questions You Need To Answer Before You Have The Life You Want,” shaped my thinking and my business more than any other. It could have just come down to good timing. However, prior to reading this article I had a tendency to jump into things without answering the personal side of business questions, which ultimately led to my demise.

Define your “why” and get clear on “how you want to live.”

Answer the question, “What do you need money for?”

Take the time to audit what you really want to accomplish, not only in your career, but in your life.

For a long time I skipped this part and I paid for it.

Like Yogi Berra said, “If you do not know where you are going, you will end up somewhere else.”

Successful people are successful for a reason, they have meticulously determined how, and with who, to best spend their time.

However, a “no” does not always mean a “no.” It just means that you did not do your homework well enough and did not identify what tools in your own skill set can provide them real value.

Ryan taught me to take my time with this, and to make sure when I do make contact, it serves “them” more than it does “me.”

Take the morning and knock out the things that matter to you first. If a few hours into the day you have already done your most important work, and filled the “you” void, playing a more reactive role going forward becomes a lot more tolerable.

Give your work the respect it deserves and block out all potential distractions for a certain amount of time each day. No phones, no emails, just what Cal Newport calls “Deep Work.”

Block out three hours today to get your work done. You might be surprised at how productive you can be. Most of the time, emergencies are not emergencies an hour later. Things can wait.

A great deal of Ryan´s work involves the ancient Greek philosophy of Stoicism. In the works of Marcus Aurelius, Seneca, Cato, Epictetus, Ryan has found his own way to navigate through the things that he cannot control.

Problems are a lot less scary if they are identified before they happen.

No matter how intelligent you are, if you cannot communicate your ideas in a way that is simple to digest and easy to understand you, will never make the mark you set out to make.

Ryan has taken the works of some of histories greatest teachers and packaged them in a way that is relevant to modern times. In doing so his work has impacted thousands of people who would have otherwise written off anything with the word “philosophy” in it. See his presentation tips here.

Learn new skills, network like crazy, have new experiences as much as you can, right up until you know exactly what you want to do, then protect that privilege of finding work that matters like crazy by saying “no” often.

And for those of you that lead emails to strangers with “can we grab a coffee” and “steal just a little bit of your time” click here.

The body and mind connection is real.

Ryan is an avid note-taker. If he reads something that hits home, he writes it down by hand on a note-card and then categories it to use at a later date or to spur ideas when he is in a rut (a habit he learned from Robert Greene).

How often do you get stuck frantically searching for a thought or quote that could properly fill a hole? Often? Me too. When you come across something of value, take the time to catorgize it in a way that allows your dots to connect more efficiently.

My first article for Thought Catalog was a direct rip-off of an article Ryan had written on his wedding day.

Jim Rohn famously coined the expression, “You are the average of the five people you spend the most time with.”

A big part of me agrees with this statement. However, what Mr. Rohn failed to mention was to be very careful about who takes the top spot, as that person may actually equate to more than 50% of your time.

The perfect spouse will give you the confidence to do the things you dream of doing and also some of the things you never dreamed you were capable of in the first place.

Ryan is a master of taking the ideas of others and putting his own twist on them. If you think about it, that is all innovation is today. Simply a different take on an existing idea or product.

I used to think that in order for me to publish something I needed to come up with something truly original. I regret that, and Ryan helped me to move away from that thinking, and recognizing that adding to the conversation can be just as powerful as trying to create a new one.

At an early age Ryan was fortunate enough to apprentice under some extremely successful people. And from the looks of it, he has not slowed down in the least from doing this.

Seek out people you admire. Figure out a way to help them. Then rinse and repeat. As Ryan said, “The best way to clear your own path, is to help others to clear theirs.”

Shortly after Ryan send out a Facebook message with the words, “Define Irony,” above an image of his book, “Ego Is The Enemy,” shown on the big screen in Time Square, he released another book, “The Daily Stoic.

What got you where you are, very rarely is going to keep you there.

As soon as you hit send on the work you are doing, or hang up the phone after making a sale, get back to work.

I grew up with a speech impediment. The one constant in my career has been trying to overcome my embarrassment by becoming a good communicator and strong salesmen. I love that Ryan went against the grain of “stick with your strengths” for us underdogs when writing “The Obstacle Is The Way.”

I cannot count the number of interviews with authors, entrepreneurs, or successful people in general, where Ryan´s name was brought up as a quick side note. By doing good work, day in and day out, Ryan does not have to rely on his marketing skills to sell books. His reputation takes care of that.

After having a light-bulb moment it is difficult to not get ahead of ourselves and build castles in the sky.

However, Ryan has trained himself to do the opposite and also plan out worst-case scenarios. This is not a gloomy way to look at things. It is a very pragmatic one. Planning for when things go south, because they always will in some form or another, alleviates some of the inevitable stress because you already have thought through the worst case scenarios and have a plan in place to keep moving forward.

Every successful person can vividly recall the moments in their lives that shaped their stars, and more often than not it involved making a hard left instead of an easy right, despite the pushback.

What I admire most about Ryan is the fact that instead of taking low-risk, high-profile jobs, he consistently follows his intuition by choosing personal projects that “may work out.”

Kind of a gimme since the inspiration for me writing this was Ryan thanking both Tim Ferriss and Robert Greene for all that they have done for him. But I would imagine a young guy like Ryan did not get to where he is today by not thanking people every chance he gets.

The more I think about Ryan´s influence the more I could easily keep going. But I am going to stop at 22 (See Law #1).

I am not sure how my wife is going to feel about me writing out 23 lessons I have learned from a guy who I have never met, especially one who lives on a farm in Texas surrounded by goats, when I only wrote out five for her.

But like Tim Ferriss taught Ryan, “You have to keep somethings for yourself,” and heeding their advice, I am going to keep the other 197 lessons my wife has taught me just for us.

Big THANK YOU Ryan Holiday for all that you do.

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Co-creator of 2 boys with my dream girl • Career coach • Featured in Business Insider, Fast Co, MSN, & Forbes • Join 40K+ others by following along.

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