Ask Ryan Holiday: Why journaling & self-reflection help us stay consistent when building a new practice

Q: Ryan, your book The Obstacle is The Way teaches about how to use Stoicism practically in our day-to-day lives. My question is: When you’re just starting the practice of Stoicism and have a natural inclination to follow your old habits, what technique have you found most effective to stay consistent? – hiitide member

A: Every morning, I spend a few minutes journaling. Prompting myself, chewing on ideas and having an ongoing discussion about those ideas. I know that doesn’t seem like that much of an earth shattering concept but if you look at Meditations, it’s Marcus Aurelius doing exactly that. 

In book eight he’s reminding himself not to be overheard complaining. He says, “you know, you can hold your breath until you turn blue, but they’ll still go on doing it.” There’s an entry at the beginning of book five where he talks to himself about struggling to get out of bed because it’s so warm under the covers. You can imagine him writing this as it’s happening, exactly as it was difficult for you to get out of bed in the morning. 

The idea is this is an ongoing dialogue, an “interview with yourself.”

“All the prompts you’re doing here at hiitide are great.” Stoics went to philosophy classes and had dinner where they debated ideas. But it’s primarily an interior voyage that you’re having. One where you explore yourself on an ongoing basis, checking yourself against your ideas, where you are making progress, where you’re falling short, what you’re struggling with and what you’re worried about. “This is a huge part of it for me.” 

One of the journals I use is called the “one line a day journal.” It has five lines on each page. You write a sentence about what you’re thinking that day. I’m in my fifth year, so I’m filling out the fifth spot. 

For instance, “it was incredible for me,” recently, as I filled this out, I was starting my next book. When I looked back, that day a year earlier I started my last book and the year before that I had started a book on the same day.  

I like this sort of exercise. It gives me a chance to ask a variety of questions like: “Where was I? What was I doing, struggling with, excited about, worried about on this day, one year ago?” It gives me an opportunity to realize that a lot of the things that were going well, don’t really matter to me anymore. I was so excited that this one thing happened and it receded into the distance. That’s equally true about the bad things and the things I was worried about. They faded into the distance and don’t really matter anymore. 

The purpose of “reflection” is to remind yourself that most of the things that you’re thinking about, that you think are very important right now are not important at all. Often it’s the case that “most of the things you should be doing something about, you’re not thinking about at all.”

In fact, putting yourself up for review is something I cannot speak highly enough of as an active practice.