Sick, Sad, Life Planner

How Do You Journal and Why Would You Do That?

Ever been honest in your writing?

Or do you usually stop short of the brutal truth?

Some forms of writing don’t require honesty but journaling isn’t one of those forms.

With dozens if not hundreds of variations to journal writing out there how can you know you picked one that works?

Over the past three years, I’ve tested a few systems and came away with a few breakthroughs I’ll be sharing with you today.

How Do You Journal?

First, decide whether you want to write in an FP (fancy pants) paper journal or an electronic version. Paper is better for spontaneity and triggering new related thoughts. Electronic is convenient, searchable, easily archived and faster.

There is a popular journaling technique called morning pages. The goal is to write a stream of consciousness or related thoughts as fast as possible until you hit 3 pages. Preferably writing by hand as opposed to typing. This is similar to the practice of free writing. You write about whatever you want and the best results and momentum show up the less you think before you write.

Ask yourself questions.

These can be tactical questions like what you need to do, where you need to go and who will be involved. Or these can be intuitive questions. Questions you’re writing to that exploratory medium in your mind.

The part that knows what but not why.

Officer Meow Meow Fuzzyface

So what is on your mind right now? Is there an important decision you need to make in your life? Are their any secrets that you’ve never shared in writing? If you had to guess, where does the shame you feel come from?

You get the idea.

We explore everything from the benign to the existential beliefs-thoughts-assumptions-addictions-distractions-stories-justifications-narratives-grudges-alliances-secrets-desires of our lives.


You can now view thoughts objectively. Now that you have thoughts that won’t disappear — like they would be if you didn’t write them down! Since you’ve recorded them you get to do something with them. You can makes plans and set intentions or goals for yourself.

Also you can tone down your stress. Are you worried about something?

Watch how writing about it encourages some emotions to be unblocked. The scarier the situation the more unblocked you can be emotionally.

Journaling to improve your mental health is a common reason people are recommended to journal in the first place. The mistake I see in a lot of writing about journaling is not getting specific enough. I had to journal and keep an open mind for years before I finally came across something that would mention explicitly how honest we need to be in our journals for it to be effective.

Spoiler alert — we have to be much more honest than you think.

Another reason is productivity, you’ve done a thing!

Now it will be easier you can do something else. Similar to how making your bed in the morning makes it easier to move onto other tasks. Unless they’re scary in which case you’ll probably keep procrastinating…


I’ve only been journaling consistently for the past 3 years. Let’s not count the 6 months I took off from it shortly before I left my last job.

Actually, I said lets not count those 6 months šŸ˜‰

So I wanted to go over the systems I’ve tried since they represent many of the popular forms of journaling out there.

I took a journaling course online a few years ago that I was excited about at the time. I attended live sessions of the course hosted by Chase Reeves. Chase has an interesting system. There were 3 moving parts.

  1. There was a musical / getting excited element in the beginning. He recommends choosing one song that gives you a feeling of increased energy before starting to write.
  2. Then he suggests doing some gratitude / affirmation work. Listing things you’re grateful for and affirmations about yourself that resonate with you.
  3. Finishing that off with tactical questions about what you want to work on today or other important goals you want to work on.

So I know you wanted to chose Foghat’s “Slow Ride” as your song too which makes us spirit brothers or sisters. But HEY it was either that or Jimi Hendrix’s “Highway Chile”. There were other candidates like RATM’s “Bulls on Parade” and Deftone’s “Elite”. However, those songs can get me too hyped and then I just feel like listening to music or raging, possibly both!

I tried hard but I realized that affirmations always felt hallow even the ones that sounded good the first few dozen times. Even though we were encouraged to switch them often it still felt a touch too much. Any step that requires too much customization tends to take away the magic in this process for me. Also, simplicity has a big role when we’re starting something new. So unless you’re an affirmation aficionado you may want to skip or have a substitute for that step.

When I heard of the joint project Ryan Holiday (who also has a great post on journaling) put together with Stephen Hanselman: The Daily Stoic Journal — I decided to try it out. In the stoic world, I’m most familiar with Seneca than other philosophers of that era. I did enjoy how when the stoics journaled they took into account their actions over the previous day. It was a way to judge themselves and measure their progress. But this can be achieved without targeting it so precisely.

The problem was the repetition for me. While there might be different stories they often illustrate the same set of examples. And you don’t need to read a lot about Stoicism to be familiar with the common themes. Since a lot of leaders follow Ryan’s writing, sometimes the comments he makes will feel a little harsh or hallow to the rest of the world. My biggest issue was not having much to say after hearing about greed or vice for the 72,795th time.

That being said, it’s a good journaling method for many people. It’s certainly worth reviewing every once in a while. As some stoic ideas have really stood the test of time. As anything that’s lasted thousands of years has to some extent. I just didn’t find the system sustainable for me.

We covered morning pages or free writing earlier. However, I did make some personalized changes. I write on a computer (GASP!). I also don’t force myself to write three pages in one session. Whether it’s my ADD or not, sometimes I got so lost in thought that I forget the tangent my brain went on by the time I thought about writing it down.

Recently I made a new discovery. I started writing in multiple smaller sessions throughout the day. So at the end of the day it would look like I had one large journal entry. This has also been handy for managing and moving emotions. As I go throughout the day I try to take a few minutes to write down everything I’m thinking. As long as I do it enough to focus on the task I tend to feel more pleasant during and after I’m writing.

I’d advise reviewing your journal entries every once in a while. It’s interesting to see what you wrote about, when, what words you used. Especially once you’ve gotten enough perspective from events that you’re actually curious about — hey what was I thinking when this happened anyways?


Just like any other kind of writing there should be some consistency but it won’t help if doing it everyday stresses you out more than once a week. Or when you notice you have a lot of thoughts distracting you.

Some habit should be involved. You want to make it easy not something you’re like oh fuck it I guess I have to do that thing.

What has your experience been about keeping a journal?

Have you tried other systems of journaling?

I had heard of journaling for decades before I gave it a shot so it’s never too late to start.

It’s one of the easiest creative tasks to get into which is why it’s so useful. But it has a hidden power to engage your emotions and calm your nervous system down.

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