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Should You Keep A Journal?

A reflection on my time journaling, and whether or not others should follow in my path.

Jonah Woolley
7 min readAug 28, 2019

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For a lot of people looking for self improvement, journals seem like an attractive thing to start. It’s seen as a good way to build a habit and have a place to reflect, and therefore many people have considered doing it themselves.

I started journaling myself last September. I found a blank notebook hiding on a shelf in my bedroom, and since I wanted a way to fill it, I decided to start writing down my thoughts. It’s been 332 days since I wrote my first entry, and I’ve filled 6 and a half notebooks. I’ve written in the journal nearly every day, and it’s followed me throughout the highs and lows of the previous year.

However, it hasn’t always been the rosy experience some people think it is. Today, I’m here to give you the pros and cons of my time journaling, so if you’re thinking about it, you’ll know what you’re getting into.

The Pros of Journaling

1. Journaling helped with self reflection

Journaling turned me into a more reflective person. Having to write what happened in my life and what I thought about it made me able to examine what I was doing from a more objective light, and therefore be able to better judge my actions.

In the past, I would always look at a situation from my perspective. It would always be emotionally charged and tinted to make me feel like I was in the right, and that made it a lot harder for me to notice what I was doing wrong and improve.

Once I had to sit down and write what happened, I would feel what I did wrong in a way doing it mentally couldn’t.

Having that objectivity also helped me make better decisions. While I used to make major decisions about my life quickly, or by weighing facts from a subjective lense, writing everything down allowed for me to be more honest about everything and make a better decision.

The result was that I made major decisions that had better outcomes overall, and when I made a poor decision, I was able to evaluate why and take that into account to improve in the future.

2. I was able to commit to self improvement

People make promises to themselves all the time, whether it’s saying they’ll eat healthier or write every day, but when you make these promises, there’s usually not a good way to hold yourself to it. All you have is your own willpower.

The journal changes that, however. With the journal, I would make a promise to myself and write it down, and while it’s small, writing the promise down made it a lot more concrete. Even if it was just a notebook, I now had some form of accountability to follow through, and if I didn’t, I would have to come back to that same notebook I made the promise to and say I chickened out.

It was surprising how quickly I started following through with things. I was able to start working out more and get more serious with schoolwork and creative work, and while it wasn’t a foolproof system, it was better than me having to hold myself accountable completely on my own.

3. There were many emotional benefits

Writing my thoughts in a notebook gave me a place to express my emotions completely freely. Paper doesn’t judge, unlike people, meaning I didn’t have to worry about sounding good or putting up a nice image.

It felt nice to be able to be honest, to write down what I was thinking, the good and the bad, and that helped to ground me during some extreme points in my life.

For example, back in early July, I wrote an article called “Should You Wake Up At 5:30 AM?”, and I posted it one night without thinking much of it. When I woke up the next morning, however, it had blown up, getting 1.5K views in a single day and being featured by one of Medium’s largest publications, The Startup.

Now, for many full time productivity writers on Medium, that likely isn’t a lot of attention, but it blew my previous record, which was 200 views, out of the water.

In the face of that, it was hard to hold it together. It felt to me like I was starting to get a break, and it all kind of went to my head. While I’d started writing on Medium for fun and to share my thoughts with others, now I had gotten thousands of views, and it felt like I could possibly go beyond that.

The journal served as a reality check on those thoughts.

Once I wrote it all out, I was able to realize that it wasn’t as big as I was making it out to be. Sure, that article had gotten some solid attention, but it was just that article, and it probably wouldn’t continue.

And, I told myself, even if it did, it wouldn’t matter. I would still have to be true to myself and write what I enjoyed, and the attention shouldn’t eclipse any of that.

I was able to maintain a level head in that situation, and surely enough, my views went right back down after that article. Had I started focusing too much on popularity, it’s possible that would have devastated me or even pushed me away from writing altogether, but I was able to remind myself that that wasn’t important. What was important is writing what I enjoyed and what mattered.

The Cons of Journaling

1. Journaling cemented some problems, rather than improving them

Throughout the fall and early winter, I was going through a period of creative doubt. For me, I always need to be working on something to feel like I have a purpose, and during that time, I couldn’t decide what I wanted to do.

I’d just lost an interest in music, as I realized it wasn’t for me, and I now had to figure out where to go from there. I tried to find a new pursuit, but nothing interested me.

During that time, I recorded my thoughts and doubt in my journal, and while I expected that to help, it just kind of perpetuated things. The doubt that I felt just carried over and got recorded, and have that all written down felt like I was truly stuck in that state.

Thanks to that, I just got more and more frustrated with myself, and there wasn’t really any way out. I eventually found a new interest in writing for Medium, but that came after months of going back and forth that was only emphasized by the fact that I had to write it down.

While journaling was usually a way to reflect on and solve problems, in cases like that one it only served to make them worse.

2. Journaling became a chore

While at first I journaled because I was interested, I started losing interest after a while but told myself to keep doing it. I thought I couldn’t stop, as I’d finally gotten a journal going after so many previously failed attempts, and it would be evidence I was falling off if I stopped journaling.

So, every night, I continued to write in my journal. I would often do it when I was exhausted, so I was just trying to get through the entry so I could go to bed. That meant a lot of entries lacked any real substance, and were basically just “I had a good day. I went to school. Goodnight.”

While there were times when I was able to use the journal to write down an interesting idea or really ponder something, a lot of the time I was just tiredly recounting the details of my day without anything real there, which made journaling a pointless exercise at times.

3. The journal became a place to complain

While the journal can be a tool for improvement, it can also just be a place to whine.

As I said earlier, I cemented problems I was having by writing them down, and there were many times when I didn’t use the journal to improve my situation. I would just use it to complain about my situation.

That’s not to say it was all bad — your journal doesn’t have to be a constant self improvement machine to be useful — but there was far more complaining than actual reflection and improvement of my life, and it felt like my journal was just a place to fester negativity.

Final Thoughts

For people considering journaling, I would tell them to go for it. While there were pros and cons, and time when my journal was more annoying than anything, overall journaling has been a positive experience and I will continue doing it.

You don’t have to do it daily like I did, or do it as long as I did, but I would suggest you give it a try for a few weeks or months and see how you like it. Maybe it will be great and improve your life a lot, or maybe it will be boring and you’ll get nothing out of it. Either way, it’s good to at least know what it’s like, and if it works out, you’ll have a great mechanism for relieving stress and improving yourself in the future.

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Jonah Woolley
Jonah Woolley

Written by Jonah Woolley

Angry opinions from an angry writer on an inconsistent basis.

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