Ryan Holiday has led the popular revival of stoicism since 2014, with his acclaimed bestsellers The Obstacle is the Way, Ego is the Enemy, and - in partnership with Stephen Hanselman - The Daily Stoic. Now Holiday and Hanselman are back with The Daily Stoic Journal, an interactive guide to integrating this ancient philosophy into our 21st century lives.

Readers will find weekly explanations and quotations to inspire deeper reflection on Stoic practices, as well as daily prompts and a helpful introduction explaining the various Stoic tools of self-management. The beautifully designed hardback features space for morning and evening notes, along with advice to encourage ongoing writing and insights, day by day through the year.

Now Ryan Holiday has written his top tips for starting - and continuing - to journal, and the benefits it can have. And you can follow Ryan on Twitter here.


1. Set a Time

The Stoics believed that the two best times for reflection were in the morning and evening: Prepare for the day ahead; Review the day that just passed. Marcus Aurelius likely wrote his famous Meditations in the morning, while Seneca seems to have preferred the evening. As he put it, “When the light has been removed and my wife has fallen silent…I examine my entire day and go back over what I’ve done and said, hiding nothing from myself, passing nothing by.” The lesson there is not that one or the other is better but that you need to set a time and make a practice of it. If you just do it whenever you feel like it, too often you will find that you don’t feel like it and it will not become a habit.

2. Make Time

Tony Robbins once said, describing his morning routine, that there was no excuse for him not to find ten minutes each morning to meditate and prepare himself for the day ahead. “If you don’t have 10 minutes, you don’t have a life,” was how he put it. The issue is not whether you have time or not to journal, it’s whether you are willing to make time for journaling. Is there anything more important than taking time each day to clearly define what you want to accomplish, how you want to act, clear your mind and prepare yourself for the day ahead? Maybe you don’t have 10 minutes today. But surely you have five. Or one minute. Can you start with journaling for one minute tomorrow morning?

3. No Pressure. Just Write.

The great General George C. Marshall refused to keep a diary during World War II despite the requests of historians and friends. He worried that it would turn his quiet, reflective time into a sort of performance and self-deception. That he might second-guess difficult decisions out of concern for his reputation and future readers and warp his thinking based on how they would look. This was admirable, but most of us are not George Marshall. Don’t put the burden of history on yourself—safely assume that nobody will ever read what you are writing. Not even you. It’s about getting your thoughts on pages. As Tim Ferriss has described it, journaling is really about trapping your worries and fears on a page so you can get on with your day. To see things clearly and so that your worries don’t “bounce around all day like a bullet ricocheting inside your skull.”

4. Have Easy Things You Put In Each Entry

Another way to make journaling more fun is to jot down little things each day which are easy to do. I would write down each morning how far I walked, how far I swam or ran, one thing I am grateful for as well as how many hours of deep work I have done the previous day. There are like little throat clearers. It helps get me started. I never look at the blank page and think, “What should I say?” because I have a bunch of go-tos that I start almost without thinking. For instance, writer James Clear records his pushups and reading habits, Nobel Prize winner Danny Kahneman suggests keeping track of the decisions you’ve made in your journal, and the Quantified Self community uses all sorts of gizmos and gadgets to keep track of different metrics in their everyday life.

5. Keep a Logbook

Bestselling author and artist Austin Kleon has talked about keeping a logbook—writing down each day a simple list of things that have occured. Who did he meet, what did he do, etc. Why? For the same reason many of us struggle with keeping a journal: “For one thing, I’m lazy. It’s easier to just list the events of the day than to craft them into a prose narrative. Any time I’ve tried to keep a journal, I ran out of steam pretty quick.” But this still has the effect of recording what he has done and paint a portrait of each day that he can flip back years later and see what his days were like. It’s easy enough to combine this strategy with the one above. If you’re having trouble starting a journal, don’t. Start with a logbook

6. Start Your Private Idea Book

Thomas Edison would keep a notebook titled “Private Idea Book” in which he kept different ideas that popped into his head, such as ‘artificial silk’ or ‘ink for the blind.’ This is similar to what bestselling author James Altucher does to exercise his “idea muscle.” He carries with him a waiter’s pad and forces himself to come up with at least ten ideas per day. Personally, I keep a separate journal I call a “commonplace book” that is a collection of quotes, ideas, stories and facts that I want to keep for later. I’m not the only one who does this. You can even look at the commonplace books of people like Lewis Carroll, Walt Whitman, and Thomas Jefferson.

7. Don’t Break The Chain

“I’ve tried journaling before but after a couple days I just stopped doing it.” The comedian Jerry Seinfeld once gave a young comic named Brad Isaac some advice about how to write and create material. Keep a calendar, he told him, and each day that you write jokes, put an X. Soon enough, you get a chain going— and then your job is to simply not break the chain. Success becomes a matter of momentum. Once you get a little, it’s easier to keep it going. Start journaling every day, build a chain and then work not to break it. Don’t ruin your streak.

8. Be Grateful—For The Good and The Bad

One common journaling practice is to write down the things you are grateful for. And the candidates are usually pretty obvious: We should be grateful for our families, for our health, that we live in a time of peace. But what I’ve come to do is that now in the mornings, when I journal, I try to find ways to express gratitude not for the things that are easy to be grateful for, but for what is hard. The Stoics saw gratitude as a kind of medicine, that saying “Thank you” for every experience was the key to mental health. “Convince yourself that everything is the gift of the gods,” Marcus Aurelius said, “that things are good and always will be.” No matter how poorly a situation went, or how a person treated you, find the good within them and what you can be grateful for.

9. Develop a Shorthand

One trick that I’ve come to adopt is using little acronyms that only I know what they mean and that makes the practice more fun and efficient. For example, I’d write TAF (tired as fuck) when I am running myself ragged. This is something I saw bestselling author Robert Greene do—whenever he would encounter in a book an example that illustrates the Stoic concept of amor fati, he would write AF in the margins. I’ve come to use this both in my notecard system and now in my journaling practice. It helps speed the process up. Depending on how elaborate your shorthand becomes, you might accidentally end up like author Charles Wesley whose diary took nine years to be cracked by scholars because of its elaborate shorthand script.

10. Unleash Your Creativity With Morning Pages

Back to the timing thing: Author Julia Cameron has become known in creative circles for her practice of Morning Pages. That is, writing three longhand stream-of-consciousness A4 pages early in the morning. Writer and producer Brian Koppelman (Billions, Rounders) has been one of the most vocal proponents of this practice and swears by it, saying he does it each morning, to get himself going creatively, “priming the pump, …getting the creative juices flowing in a very free way.” Other proponents include bestselling authors Oliver Burkeman and Tim Ferriss.

11. Give Your Thoughts Room to Marinate

But evening pages work just as good. For instance, the founder of Linkedin, Reid Hoffman, jots down in his notebook things that he likes his mind to work on overnight. Similarly, chess prodigy and martial arts phenom Josh Waitzkin, has a similar process: “My journaling system is based around studying complexity. Reducing the complexity down to what is the most important question. Sleeping on it, and then waking up in the morning first thing and pre-input brainstorming on it. So I’m feeding my unconscious material to work on, releasing it completely, and then opening my mind and riffing on it.” By journaling questions and problems during the day, you can let your unconscious do the work and then you revisit first thing in the morning.

12. Practice The Art of The Unsent Angry Letter

Whenever Abraham Lincoln felt a pang of anger towards someone, he would write them a letter…which he would then never send. He would “put it aside until his emotions cooled down,” as one historian explained. Your journal can similarly become an outlet for your emotions and feelings towards someone so you can then approach them in person in a calm and rational manner. Say the things, process the things that you would love to be able to say out loud but can’t or won’t. You’ll feel better—and you’ll always have something to say.

13. Ask Yourself the Tough Questions

Journaling isn’t just about patting yourself on the back and listing all your accomplishments. I also think it’s important to wrestle with big questions and to hold yourself to account. When we created The Daily Stoic Journal, we added for each day a helpful prompt to provide guidance for the day’s reflection. These can sometimes be the tough but necessary questions you need to reflect and meditate upon. Some helpful examples: Where am I standing in my own way? What’s the smallest step I can take toward a big thing today? What blessings can I count right now? Why do I care so much about impressing people? What is the harder choice I’m avoiding? Do I rule my fears, or do they rule me? How will today’s difficulties show my character? 


You can buy Ryan Holiday and Stephen Hanselman's The Daily Stoic Journal here.