🎙 Deep Dive - Ali Abdaal x Ryan Holiday


Live Blog


On Lives of the Stoics

“My other books are about what the Stoics said, 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".

On Journalling

"I journal every morning and for me journaling and Stoicism are the same. For me journalling and Stoicism are inextricable concepts. In the way that Buddism and meditating are the same, journalling and Stoicism are the same. You have to write and reflect and articulate them into maxims and aphorisms that you hold yourself to".


"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"


On Walking

"The fact that it has no obvious value is the real value. Being on the move unlocks my mind which just sitting there isn't going to do. I try to see what's happening around me and I'm not smart enough to know why it works but I know it's had a very big impact on my quality of life"

On Alive Time vs Dead Time

"When things are outside of your control, like when you are waiting for something, how do you decide to use that time? Do you write it off as dead or do you decide to use it? And so I’m a big believer in using time. Not just using it for work, the point is we don’t know how much time we are going to get and so to write it off as dead is a profoundly arrogant and short-sighted things to do”

On Autonomy & Optionality

“I’m not so big on optionality but I am big on autonomy. By that I mean, I want to be in control of my own destiny as opposed to approval, green lights, acceptance etc. What frustrates me when I’m in engaged in things outside of writing is the bureaucracy that you have to put up with. Autonomy, for me, are you the captain of your own ship - that's what you want”.

On Measuring Success

"Doing a video it's hard to know whether it worked or not, whether it's good or not. The numbers are a really easy way to outsource that. It's harder to sit with your thoughts and think about did it do what I set out to do, am I getting better. The more you do whatever the thing you do is, the more information or data you'll collect that allows you to de-couple results from quality"

"If have a video that did 50,000 views comparing that to a video that had 5 million views is going to make you think that you didn't succeed but you have no way of evaluating whether a video that reached 50,000 people profoundly had more impact than a video that gave 5 million people a slight chuckle. You have to be really clear about what you are trying to do and the niche that you are trying to operate in".

“The book I’m proudest of isn’t the book that has sold the most copies. The book that has sold the most copies isn’t my best".

“With my new book there are three ways that you could choose to define success – success could be are you proud of the book, it could be did it reach the number of sales (partly in your control) and finally it could where did you land on a list (completely out of your control). Earlier in my career I had those things reversed – I was most concerned about the thing that other people decided, the next I cared about influence and finally I had my own sense of whether I did it or not. I do feel like I have reversed those".

“I don’t have any connections to the data – it usually gets filtered through other people. I don't have Instagram on my phone, I don’t see how the things are going. Part of it is creating a bubble and it’s also about asking yourself what are you trying to do – are you trying to beat the competition or are you trying to be the best at what you actually do”.

On Goals, Happiness & Life Measurement

“Most people don’t live in the present. They live thinking about regrets towards the past or anxiety for the future. Most people are just on the hedonic treadmill and they’re moving the goalposts all the time. I don’t think about goals as concrete bits of success but rather how I would like to live my life day-to-day”.

"There's no question that having money creates security which allows you to explore certain things BUT the favourite parts of my day are going for walks with my kids, time I spend writing, time I spend reading - the things that are actually really really cheap and accessible. We just tell ourselves that we have to have more and more...so I think really understanding what you actually want really costs".

“We struggle to understand just how accessible the things that we want actually are. We can learn these lessons early or we can learn them late but the earlier you can learn them, the better off you will be”.

On Optimising Environment

“Where you are going to spend your time should be more important - to me it’s the main deal. Early on in my career I was constrained by the opportunities that I was reliant upon but as I have been in more control of my destiny, I’ve tried to be very deliberate about where I live. 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 your living space for that seems like you'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're like '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".

On Reading

“I think it was Murakami who said 'if you only read the books that other people are reading you’ll only think the things that other people are thinking'. I do have a slight bias against popular contemporary books but when I do read a contemporary book, my test of whether it’s good or not is whether it introduces new concepts or whether it leads me to go and read other things. Many contemporary books fall down because they repeat the same studies and the writer never got them first hand, they just got them from other people so it's like a refraction of a refraction of a refraction. To write effectively you do have to go to the actual source material. I try to draw from a diversity of examples because I want people to hear about something for the first time”.


"The best time to plant a tree is twenty years ago, the second best time is now"


On Notecards & Note-taking

“I read physical books and mark all the stuff that I’m reading and then I transfer stuff onto notecards. I’ve done that for thousands of books and the real advantage of having it analogue rather than digital is that you are interacting physically with the material multiple times. You also want to be able to move the pieces around physically and you can see the whole book laid out”.

"The cards are to organise anything that I read that I find interesting. I've now got an archive that goes back 10 to 15 years and those cards are always there and I might come across a card that I'd written 15 years ago which reminds me of a specific book and the related ideas from that"

“Just because you’ve read a book doesn’t mean it’s magically in your brain. To me it's the interactions and the chance encounters with the material which creates the connections and embeds the key messages”.

On Writing A Book

“Structure is everything – it’s not just important in terms of the finished product but it’s also a key part of the process. A lot of writers mistakenly just write and try to figure it out as they go along...I don’t start a book until I’ve cracked the structure. 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. Structure is essential and figuring out the structure first is the only way to do it”.

On Being a Writer or Author

“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"

"Books come out of the back side of the writing process as opposed to the idea that I am consciously trying to make a certain amount of books. 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”

“I don’t know how much fun I was having on my first books. It was often a process that I wanted to finish just because it was hard. Then I realised that actually you only get so many cracks at this and so if you are not having fun, then what are you doing? Now I think about it in terms of did I enjoy myself (writing) on that day”.

Ryan Holiday

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. Ryan began his blog ten years ago and has since become known for his writing on Stoicism and how it applies to our societies and cultures today. In this conversation, we'll talk about Stoicism as well as what he has learnt from writing his books and how they have influenced a range of different people.

🌐 Website / 📸 Instagram / 🐤 Twitter / 📩 Newsletter


Ali

Ali is a doctor, YouTuber and podcaster. His day job used to involve saving lives, but as of this week he's making videos about productivity, tech, education and lifestyle stuff.

🎬 YouTube / 🎙 Podcast / 💻 Website / 🐤 Twitter / 📸 Instagram


Ryan's Books

Lives of the Stoics

The Obstacle is the Way

Ego is the Enemy

The Daily Stoic

Stillness is the Key

Timestamps

00:40 On Being a 'Writer' or an 'Author'

04:30 On Writing

08:40 On Notecards & Note-taking

20:10 On Reading Diversely

23:00 On Tyler Cowen

26:20 On Optimising Environment

33:10 On Goals, Happiness & Life Measurement

40:50 On Measuring Success

51:50 On Autonomy & Optionality

56:00 On Alive vs Dead Time

57:15 On the Value of Walking

58:00 On Journalling

01:00:20 On Lives of the Stoics