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Deep Dive #20 Ryan Holiday on Writing, Measuring Success and Stoicism

Ryan Holiday is the bestselling author of The Obstacle Is the Way, Ego Is the Enemy, Conspiracy and other books on Stoicism, culture, marketing and the human condition.

Ali Abdaal
Ali Abdaal

Ryan Holiday is the bestselling author of The Obstacle Is the Way, Ego Is the Enemy, Conspiracy and other books on Stoicism, culture, marketing and the human condition. He has sold over 2 million books with his work translated into over 30 languages. In this conversation, we talk about his writing process, how we should measure success and Stoicism.

Here are some of the highlights from our discussion:

If you think of yourself as an author that implies some sort of focus on the results and writer implies more of a focus on the process. If you do identify more with the craft rather than the shiny side that the public see, then that's a better way to do it.

Structure is everything when it comes to writing a book. It’s not just important in terms of the finished product but it’s also a key part of the process. If you don’t have the structure you have no idea whether you have material, no idea if you actually did what you were setting out to do.

Making notecards from material that you are reading helps to reinforce key points and produce more connections. Just because you’ve read a book doesn’t mean it’s magically in your brain. It's the interactions and the chance encounters with the material which creates the connections and embeds the key messages.

To write effectively you do have to go to the actual source material. Many contemporary books fall down because they repeat the same studies that they’ve read in other books of the same genre. It becomes a refraction of a refraction of a refraction – readers need to be engaged and it’s fresh content or an innovative connection between disparate topics that will enable greater engagement.

Where we're going to spend our time should be the most important thing we should optimise. We know that our environment shapes many things, not just our happiness but the quality of the output of the work that we do and so to not optimise our living space for that means that we're leaving a lot on the table.

“Optimising for what you want your life to look like is really important. A lot of people optimise for their career and then you ask them what would you do if you made a million dollars? And they say, 'well I would leave' and you reply 'so you are living day to day in somewhere you don't like for the future hope that you can make a change to something you do like???' That's strange. The farm that I own now has a mortgage that is cheaper than the flat I had in New York city”.

Most people don’t live in the present. They live thinking about regrets towards the past or anxiety for the future. Many people are simply trapped on the hedonic treadmill, moving the goalposts all the time.

Metrics and numbers are a really easy way to outsource success but that’s not optimal. It's harder to sit with your thoughts and think about whether you did what you set out to do. The more you do or produce whatever it is that you are making, the more information or data you'll collect that allows you to de-couple statistical results from personal satisfaction and genuine quality.

"As a writer, if you are not also writing for yourself as an audience, you're probably performing more than you're actually putting anything valuable out there"

Journaling and Stoicism are inextricable concepts. In the way that Buddhism and meditating are the same, journaling and Stoicism are the same. It forces you to write, reflect and articulate your goals and principles into maxims and aphorisms that you hold yourself to.


Check out Ryan's latest book - Lives of the Stoics. He gave a short summary during our interview:

Lives of the Stoics is about what the Stoics did, who they were as people, what does the life of a philosopher look like and what we can learn from their actions and their struggles. It’s a biography of the Stoics and what we can learn from their most important moments as opposed to their most important words”
Deep Dive

Ali Abdaal

Junior doctor, YouTuber, web designer, aspiring musician. Trying out this blogging thing.