How Journaling helped Ryan Holiday succeed immensely in his career

Ryan Holiday strikes a rare balance between reality and motivation in all his works.

He said, “The difference between a great work and an idea for great work is all the sweat, time, effort, and agony that go into engaging that idea and turning it into something real. That difference is not trivial. If great work were easy to produce, a lot more people would do it.”

He believes in the need to give your top-notch work commitment. His philosophy emphasizes the need for thorough research, having a plan for whatever you want to achieve, and utilizing everything you do as a drive to make something more substantial. He believes you need to work with people more exceptional than you to learn more. He also believes a lot in stoicism.

He shared his opinion, “I can’t say I know too many people whose success was built by spending one-fifth of their time creating and four-fifths loudly hawking the work they’ve just thrown together.”

He also said, “An audience isn’t a target that you happen to bump into; instead, it must be explicitly scoped and sighted in. It must be chosen. For any project, you must know what you are doing — and what you are not doing. You must also know who you are doing it for — and who you are not doing it for — being able to say: THIS and for THESE PEOPLE.”

Summary of Ryan holiday’s success

Ryan Holiday (born June 16, 1987) commenced his professional career when he dropped out of college at a young age of 19. Previously, He was studying political science and creative writing at the University of California. He worked alongside great and influential authors like Tucker Max and Robert Greene on their bestseller books. After this, he became the Director of Marketing for American Apparel. However, he left the company in October 2014. Holiday has written for several organizations like The Guardian, Thought Catalog,, The Huffington Post, and Forbes. Some of his bestseller books include Trust Me, I’m Lying: Confessions of a Media Manipulator, Growth Hacker Marketing, The Obstacle Is the Way, Ego Is the Enemy, The Daily Stoic and Stillness Is the Key.

He believes that if you want to achieve anything from life, you have to work hard and not give up. As he said, “It’s okay to be discouraged. It’s not okay to quit.”

How he journals?

Ryan Holiday believes in setting time aside to journal. His philosophy in life sees Journaling as a way of keeping all your fears and worrisome thoughts on the page of a book so that you can get on with the day. He maintains a private idea book where he writes stories, quotes, and facts he would need later. He also keeps a logbook to write down his daily experiences to build self-reflection.

He said, “In the diary, you find proof that in situations which today would seem unbearable, you lived, looked around and wrote down observations, that this right hand moved then as it does today, when we may be wiser because we are able to look back upon our former condition, and for that very reason have got to admit the courage of our earlier striving in which we persisted even in sheer ignorance.”

He stated in an interview that he loves writing early in the morning, around 8 a.m. He loves writing with pen and paper as well as typing his ideas on a computer.

How long has he been doing it?

Ryan Holiday has been journaling ever since. He launched his writing blog in 2006. In 2011, he had his first book deal.

Source: Ryan Holiday[@ryanholiday]. (2019, July 11) [Ryan Holiday giving a speech at the Navy Yard]. Retrieved from

How self-reflection has helped him to achieve their success?

Ryan Holiday believes you should always aspire to achieve bigger and better goals. He emphasizes the need to keep pushing and not give up when dealing with internal resistance and failure. Meditation, as a virtue, is highly valued by him. He believes that it is a crucial ingredient for success.

In his book “Ego is the enemy,” he wrote, “The ability to evaluate one’s own ability is the most important skill of all. Without it, improvement is impossible. And certainly, ego makes it difficult every step of the way.”  

He also upholds the fact that humility should always follow any accomplishment of success.

“Success is intoxicating, yet to sustain it requires sobriety.”

The quote emphasizes the need not to give room for too much ego when we achieve success. Instead, it’s time to focus on getting better and better. The journey to success is a never-ending one. We need to avoid the impulsive pleasure that comes with short term success. The ability to achieve this lies in self-reflection.

Ryan Holiday has touched many lives with his books.

What challenges has he faced?

He dropped out of college very early. Facing uncertainty on what he wanted to become in life, he still persevered and continued writing. While working at American Apparel, he encountered difficulties, which made him learn how to survive trying times.

He narrated, “Against almost every instinct, I listened. I passed. The intervening years are a blur of events—some good and some pretty bad. I would rise pretty rapidly in business. Around that time, I became the Director of Marketing at American Apparel. The chaos and the conflict in that company—to say nothing of the temptations and responsibilities—would shape me as a person. I learned how to manage people. I learned how to maneuver and accomplish things. Mostly, I learned how to survive—crisis after crisis after crisis. The stuff that Ben Horowitz calls the hard things…”

What does the future hold for him?

Through the power of self-reflection, he has proved that it is possible to overcome any challenge. He is mentally mature and stable. More breakthroughs still await him. He is one of the bestselling authors around. What he has achieved signifies that the future is glowing.

How can you get started with self-reflection?

Like Ryan said,

Self-reflection is the key to unlocking the abilities in you.

“I will keep constant watch over myself and—most usefully—will put each day up for review. For this is what makes us evil—that none of us looks back upon our own lives. We reflect upon only that which we are about to do. And yet, our plans for the future descend from the past.”


Interested in other self reflection and gratitude practices?