Answering a friend’s questions on my experience writing daily journals for five years. 

It started in 2015. This practice of talking to myself every day. From answering a few questions every morning and night to writing essays to my past, present, and future self. 

Naturally, when you are among the few people in a circle of friends that does something most people don’t do for a long enough time, one or two friends genuinely get curious. 

Not the kind of curious where they try to detract you from what you do so they can feel better for their own lifestyle choices of not doing things (i.e. exercise, sleeping better, eating better). 

Most questions come in similar fashions and the one on journaling came as “What do you think is the best way to journal?” 

Given how loaded the question is, a simple “it depends” deters away the conversation-making questions and the ones where the person already knows “why” they want to journal asks about the ‘how’ and ‘what’. 

I think I’d break this down to two sub questions.

1. What do I think is the best way to start journaling?

2. What have I found to be the best way to journal?

I break it down with the “I” because these are opinions based on a single sample size’s worth of empirical evidence. Sure, I could unconsciously incorporating the various psychology frameworks I learned about but the result is formed from empirical testing. 

How I think one should start journaling.

The most first requirement would be to actually want to start the practice. Not trying it out because a friend tells you to or because you feel some kind of obligation towards it. 

I think only a true desire to start a new practice. One that sees journaling as an actual change you want to make to yourself will amount to it being sustainable. 

It seems to be one of those fundamental rules of building a habit (i.e. practice). It needs to be driven by an intrinsic desire. I mean, what’s the point of starting something like this without an intention to make it into a habit? It’ snot something where there is a clear ’ending result’. 

From my experience, no matter how many times I tell people to read certain books to learn investing, study tactics to sleep better, learn about strength training etc… no body adopts it. They just want to “lose fat in a specific body part, the one stock to put all their money in for guaranteed wealth, and some supplements so sleep isn’t needed.” A waste of time. 

That’s how I started journaling. Plenty of individuals I read about and are fans of have some kind of journaling practice. But it was only when I decided I wanted to incorporate some kind of practice for myself that I started seriously looking for options. 

The benefit of digitally surrounding myself with people that journaled is that it created a passive environment where I could be influenced by my environment without feeling like I was being forced to do anything. It’s like how schools beat the joy out of children by forcing them to read. Anything someone tells you to do, you will end up hating as a form of psychological rebellion. It just is so. 

The first hump is actually wanting to do it. The second is to control that desire and ambitious energy and do as little as possible. 

My problem is that I try to overdo anything I get excited about because of the sheer excitement and desire to build momentum. It may seem ironic but once you are super excited to start this practice of writing daily journals, I think the best way to start is to find the easiest one. 

For me that was the Five Minute Journal. The only reason I picked that over the many others out there in book stores is because back when I started, it wasn’t as popular so there weren’t many options and Tim Ferriss said he used it. 

It was also advertised as just 5 minutes a day. I whiffed through it and found there were guided questions. I’m sure there were apps out there but I like to lean towards the analog options so a physical journal made more sense. It may also be related to how I like physical books vs. Audio/ebooks. 

Regardless, it was about picking the one that would fit the easiest and preferred parameters for me. Not what worked for others with their pros/cons lists. 

I found the barrier to be just low enough that I would get out of bed at 2am to write my answers to the few night journal questions. Purely out of the guilty feeling I had in the back of my mind. Knowing that it’s such an easy thing. It was just about doing it. This was the same way I started the practice of training in the gym 4-7x a week for the 10+ years. It started with 20 minute runs every day. The length of one TV show. 

What have I found to be the best way to journal?

Once again, a short answer: There isn’t one. It depends. 

I believe in individualization of everything. I do not believe we are all equally created beings. We do share some psychological dispositions and biological structures that are similar but I believe every one operates a little differently from others. 

Hence there cannot be an absolute answer for the ‘best way’. I consider life to be closer to being 50 shades of grey than black/white. Some may disagree and that’s fine. I don’t care. 

This means that I believe every one will find their own ‘best’ way through practice. It’s through such an introspective practice that you may gain insight into who you are, how you operate and what purpose journaling serves for you. But all these will only be formulated from the practice. 

Just like how my reading practice has evolved over time and how my strength training programs have evolved over time, so has my journaling. 

It started with the 5 Minute Journal. But I found it too restricting and I had other thoughts I wanted to vomit on to the page. After 6-8 months, I felt I had graduated and bought a Moleskine notebook.

With my own notebook, I wrote out questions for myself and proceeded to write things down daily. This continued for some time but given the stage I was in my life, I wanted to write down more than the small diary-sized notebook would allow. I also wanted to draw diagrams and pictures as well. 

So I upgraded to a bigger notebook. One that resembled a stack of A4 papers with rings. That gave me plenty of room to write and draw everything from the day. A few years in, I realized I wanted to review my entries and it was daunting to dig through hundreds of entries. I even had a hard time reading what I wrote down for some as well. 

I decided to go digital and started writing on Evernote. But within a few months, I felt it didn’t ignite the same inspiration of writing my thoughts down. So I moved back to writing in a Moleskine notebook because I wanted the portability to write things down throughout the day and not just the morning. 

Eventually, I decided that the ability to parse through my information and search through my entries would be valuable in future review processes so I switched back to writing on my Evernote. I also found it painful to write out my daily questions every day by hand and then writing my thoughts. By going digital, I started creating journal templates with set questions, prompts, and a system of activities I could incorporate into a full morning practice. 

As of this essay, it’s been two years since I moved over to Evernote. The process now takes about 30 minutes every morning to read through everything from my intentions, my goals, my vision, my focus to writing out 500 words daily and focusing on what I need to do every day. There is a separate night time practice as well. But this is probably closer to being version 20 since I migrated to digital.

Now my average journal page will be about 1500 words whereas my first entries were about 150 words. Like that, my practice has had to evolve to meet the needs of me of the present and future. 

I consider what I’m doing now to be the best way of journaling for me of now. If it wasn’t, then I wouldn’t be doing it. But if I were to think about what would be the best.. most effective.. way to journal for someone.. it would be one that keeps them from quitting the practice. 

After all, I think it’s always about doing things that move you forward. No matter how small the step. 

Talking to Myself Every Day.

Like any practice, there are days when you don’t want to do it. There are days when you wonder whether there is value in doing any of this. There are also days where it’s awesome and you can’t imagine not having this practice in your life. 

For me, this practice of taking to myself is the small pilgrimage I take every morning. These are what I’ve realized from my experience.