A Journaling Journey: My Top 3 Regrets

Wed, Mar 13, 2024

In my opinion, journaling is one of the top 5 most important habits a person can cultivate. 

I’ve been journaling consistently since my late teens when I started listening to Tony Robbins CDs (#old).

I looked through my old journals yesterday and wished I had done things differently.

First, I wish I had given myself more context. 

The further back I go in my journals, the less likely I am to remember what was going on. What was I doing? Where was I in business? Who was I spending time with? Where did I live? What car was I driving? What were my biggest struggles?

I wish I had provided a quick and basic outline of my “general everything” once a quarter or so. That way, when I reviewed my journals, I could start with one of the quarterly updates and better understand where I was. I feel like that would make the entries more valuable.

When we journal, we write to ourselves, assuming no additional context is necessary. The problem is time. We forget, move on, grow, etc. And we leave the context behind us. That context can be critical to understanding the importance of the things we’re writing about.


Second, I wish I had been more honest. 

Especially with my earliest entries, I didn’t allow myself to get as vulnerable as I would have liked. I read some old entries and felt like they were written for someone else, as though I was posturing for an unseen audience. It makes them feel fake. 

For journaling to be of maximum value, we need to drop our guard, even with ourselves, especially with ourselves. As a young man, I refused to admit to certain feelings, like fear or loneliness. I would say them in different ways to help salvage my ego. 

The problem with this approach is that it instantly dilutes our ability to write about what’s truly happening with us. We can’t speak to how what we’re feeling is impacting us unless we can admit to the feeling fully and entirely in the first place.

Lastly, I wish I would have celebrated my wins. 

I feel like I’ve done a lot in my life that I could choose to be proud of if I allowed myself to. You wouldn’t know it from reading my journals. I obsess over a problem or obstacle for as long as it takes to conquer it and then move on.

In many cases, I can’t even get a good bearing on when or how I solved a problem. It just stops showing up in my writing. I have to rely on my memory to work out what happened. It feels like only ever getting to read the first half of a story; the writer moves on before offering a resolution.

On that note, it would also be nice to revisit how I felt when things were positive. 

I got good at sharing my feelings about adverse circumstances but only spent a little time focusing on my wins or things that were going well. Being able to balance that would have been nice.

Overall, I’m glad I can revisit young Kasim (or old Kasim?) and get a soft reminder of where I came from and how far I’ve traveled. The journals are a gift I’m grateful for. I’ll take this learning opportunity and improve my entries for future Kasim. 

Do you journal? If so, what advice would you give to people about to start?