In editions four and five of Good Work, I wrote about the importance of asking ourselves what we’re optimizing for. It’s painfully easy to stumble around in life without pausing to reflect on whether we’re pointed in the right direction, and there’s endless pressure to point ourselves off The Cliffs of Workaholism and The Pits of “Oh My God This is Not Where I Thought I’d Be By Now.” Tools for figuring out what we’re optimizing for and whether that’s what we want are about as abundant as tools for physical fitness, but this week I’d like to explore one close to my heart: journaling.
Journaling is my favorite tool for self-discovery. Journaling has helped me realize I need to get out of a toxic relationship and recognize the negative impact of poor life decisions like drinking too much or failing to exercise. Journaling is the reason why I’ve been able to repair relationship mistakes, both at work and away from the office. It’s what led me to leave my last company, Mattermark, and start Holloway.
To a lot of folks, journaling sounds great, but they give up quickly because well, it’s a lot of work. Instead of thinking of journaling as something you’ll do a few times and see the benefit, think of journaling like exercise. You’re going to have to do this for a while before you start seeing gains, and you’re going to have to do it regularly. You’re going to feel uncomfortable, and you’re going to feel like everyone else has it figured out. Remember, you’re new to this, and there are tools out there for making journaling easier (Day One, 750 Words, 200 words a day, and Jour are a few).
Beyond these tools, I recommend everyone buy Julia Cameron’s The Artist’s Way. You can take my word for it, or you can take the word of The New York Times: “Julia Cameron invented the way people renovate the creative soul.” Cameron prescribes several exercises in her book, but one of them is “morning pages,” which involves writing three pages, stream of consciousness, every single morning. Stream of consciousness means you don’t think about whether the writing is any good, you just open up your brain and put it on paper. I’ve done morning pages off and on for ten years now, and the first sentence is almost always silly. Here are a few real examples from my journal:
“I don’t need to be writing for anyone else. How are you doing, man? I know you’re struggling. You’re happy, but you’re struggling and that’s hard to reconcile. It’s been good to get back to work in San Francisco vs. running all over New York City and struggling to find internet.
“Calling this morning perfect is too much of an undeserved platitude. It’s downright cruel, in fact. My dear friend, Gary, is my hangover. On time and deserved, Gary reminded me the finer nuance of how Saturday mornings are indeed for sleeping in, but they are most certainly not for sleeping through.”
“I’ve got my goddam writing hat on tonight. There’s this hilarious aside to that statement and no one else is in on the joke but me, so I’ll do my best to cut you in on it.”
Morning pages don’t necessarily have to be done in the morning, but you’ll find they’re great for cleaning out your mental pipes so you can get to the office with a clear head. After you write Morning Pages for a month or two, you begin to notice patterns in your writing. You write about the same people, the same insecurities, the same dreams. I found the exercise immensely more valuable when I restarted Morning Pages when I moved to Silicon Valley at twenty-two.
The more I wrote, I began to pick up tricks. By twenty-six, I began Morning Pages with the prompt, “What are you avoiding writing about?” Another trick: “What’s everything making you anxious right now?” Once you see your thoughts on a screen or on paper, something strange happens. Your thoughts are no longer swimming with each other in your head, they’re somewhere else, somewhere for you to deal with them.
I left my last company, Mattermark, after continuously asking myself, “Why does something feel off about work?” It took me months of journaling to get to the bottom of this, but get to the bottom of it I did. I asked myself, “What do I want?” And then I wrote down everything I wanted. With it there on the screen, I could see that I wasn’t on the path to getting what I wanted. So I took a new path, one that journaling helped me find.