Journaling: Tips, Tricks, and Hacks To Make It Work For You

Last week, I was out of sorts. I was just a bit off on a lot of things that I do normally, things that come naturally and are routine were harder than they should have been. But, it was week seven in quarantine, so I didn’t dig too deep on it. Everything is weird, it was just another thing that was weird. 

But then I did want to dig deep on it and needed to work through a couple of other things that were happening. And that’s when I realized there was a backlog of issues to be expressed and ideas to be processed. I was full of thoughts but they weren’t arranged in any particular order or with a sense of priority or urgency, they just were all mashed together.

This moment was when I got really mad at Amazon for not having delivered my new notebook. I had seen I was coming to the end of my current one and had ordered my soft-back lined Moleskine a full week before I thought I would need it. It showed it was delivered, but it wasn’t. So I ordered another one, but this time, the wait was going to be 10 days. (How fragile our supply change - a blog post for another time.) I started writing on some scratch paper and in another notebook, but that was very much a stop gap. 

I went for a walk to clear my heard, a secondary tactic that used to be a little more helpful than it is now as a walk outside reminds me in stark detail the dystopian I Am Legend feel of my surroundings. But walk I did and to my great delight, a small bodega near NYU was still open and in the very back, had a couple of my Moleskins for sale. I came home like a proud child having discovered a great treasure in the back yard and showed off my discovery. 

What I learned about myself quite a while ago (I have notebooks and journals going back to 1997) is that for me a thought isn’t real or something that I have to address until I externalize it. If I play with the thought in my head, it bumps into too many other thoughts and doesn’t stand on its own. But when I get that thought out of my head, either through speaking it out loud to someone or through writing it down, it becomes something I can deal with, process, and build on. In my pursuit to be a life time learner, this has been one of the most important discoveries for me. 

My notebook is a mishmash of journal entries and notes from meetings, personal and professional. It is with me in just about every meeting and is always in my bag. I’ll frequently just carry my notebook with me into a bar or restaurant when I have a hunch of an idea and see if it comes to me over a coffee, lunch, or a beer. In meetings, most people at the table have their laptops out, I have my notebook. 

I have had a lot of folks ask me about my journaling and expressed a desire to have their own practice. I’ve never thought too much about it, but I wanted to share a couple of the things that I do that have made it such a sticky and valuable habit for me in hopes that they might give you some jumping off points for your next journal entry and creating the routine that works best for you. 

STARTING

There is nothing as intimidating as the first blank page of a book full of blank pages. I have created a bit of a ceremony around my first page. I write the most important quote or lyric or Bible verse in my life right now on the inside of the cover of the notebook. In looking back over my past 15 notebooks, it is interesting to simply see what that quote was in my mind as I began. Then on the first page, I don’t write much of anything concrete, it is mostly just setting my intentions for this notebook and what I think will be the theme or the story arch over the next few months that are captured there (I average about seven months per Moleskine - but this last one was just over three months) These opening page intentions are really fun to reread also. The one I wrote on January 15th of this year at the beginning of my last notebook was almost comical given how much changed in the ensuing 100+ days. 

The second scariest page is the next page. Always. But this is where the relationship begins. What you write on these next pages will never be seen by anyone else. These pages just became your least judgmental friend and can show the most truest reflection of you. This is your new home for what you actually really think. These can be for your full range of emotions and can be the first place you share hopeful moments and rage fueled expletive rants. It’s just for you to really say what you mean and write down what you feel, or at least what you think you feel. I often find that when I make that feeling concrete, ink to paper, it is often more extreme or not extreme enough. “Is that really what I think? No, I’m even angrier than those words convey!” Or “Is that what I really think? No, I’m whining, it is not that bad. But at least I got it out.” 

HABITS

First things first, you don’t have to journal. Ever. But if you have a thought, if you have a memory, if you have an internal struggle, having a journal available to capture it is a beautiful thing. There is nothing too small to be memorialized in a journal. There is nothing to extreme that you can’t share. It is just for you. But, like most relationships, there is a comfort in the familiarity. If you haven’t written in a long time and you come back with a doozie of a intention or moment to share, you may find the first few pen strokes to feel foreign or like an intrusion on a friend who doesn’t have the rest of the context. But if you are frequently using your notebook for a whole range of different topics, to have a sounding board sitting next to you on your desk or as your treasure chest of ideas and themes and even notes from meetings and classes and online content, you’ll see more and patterns appear of what you choose to write down and what is important. 

It may feel strange at first to write anything and everything down, but like most things, it is better to start broad and then work your way through the process to narrow it down to your own scope and your own niche of journaling. My journals have everything, profession, personal, spiritual, educational, financial, and artist (so many doodles next to notes.) But that is just because I know what it does for me and I have built up an appreciation for each of those aspects. It is my written train of thought some days. And it is exactly what I needed it to be, unedited and raw. I don’t ever go back and cross anything out or tear out a page, I write the next page and add more context, often even draw arrows back to the sentence in question. 

FUNCTIONALITY

Because my notebook contains journal entries in between meeting notes in between quotes and doodles, I have created a functional way to make sure I call out the things that need to be addressed or remembered. Every Sunday night or first thing Monday morning, I go back through the past week or entries and pages. I look for the symbols and short hand notes that I have created to pull forward everything that I need to remember or to do for the week ahead. 

Box: When in meetings, if there is a to do list item that I am responsible for or that I am responsible for helping someone get done, I make a check box next to it. As soon as I complete that task, I check the box. If the box is still unchecked at the beginning of the next week, it goes on the to-do list for the week.

Dash: If there is something that is more memorable than others in a conversation, in a meeting, or in my journaling, I will put a big dash mark out to the side of the page in the margin. When rereading my journals, I sometimes just read the dash marks as they usually are the lessons learned or the ideas that I want to come back to. 

Stars: A lot of times, when I am writing, I realized I really would love to hear what other people think about the thought or entry I am contemplating and that I need to find a way to share it out with a larger audience. As a result, some of my best blogs, quotes, or social media quips started off in my notebook and then I found a way to sanitize the thought for public consumption or to summarize the essence of what my question is and offer it up to a my network for their input and feedback.

Cheat Sheet: If I am an in person meeting (back when that was a thing), I draw the table and then as people go around and say their names for introductions, I write them down (including people dial-in.) This helps me during meetings to always refer to people by name and then after meetings remember who said what and make sure in all follow up communications I am including everyone that was in that meeting .

MINDSET

Journaling should never feel like a chore or a have to, but it will take some time to find your practice and the value that you derive from it.  John D. Rockefeller kept incredible journals until his death. When the biography TITAN came out, it set the record straight on all other books and historical entries about him because the Rockefeller family gave the biographer unlimited access to his journals for the first time ever. That is the way that I think about these notebooks, I am doing my future biographer a favor and letting them know exactly what I was thinking and what were the circumstances that shaped me and how I thought about the world. 

The past few years have been absolutely wild for me, personally, professionally, and spiritually. There has been a lot of loss and a lot of growth. There has been very little comfort and very little consistency. And all of it has been captured, the good and the bad, in my notebooks. These stories, these lessons, these roller coasters of experience are just for me right now, but they are captured and codified in a way that one day, when the time is right, I hope to be able to reread them and glean even more wisdom and insight from - for me and perhaps in the future for others.