7 Things I Learned from 365 Days of Journaling

Author’s image of a custom notebook
1. I use the app Journey on my Android phone. I bought their premium one-time purchase option a couple of years ago.
2. I also use their web app www.journey.cloud on my desktop without buying a subscription.
3. The loose purpose of my journal is to make a log of anything that happened on the day and whether it meant anything. See Lesson #2 below.

#1 You don’t have to write everyday to maintain a daily journal

The big epiphany that allowed me to succeed for a year was writing an entry for a previous day. I had missed a day early on and I wrote an entry for it later.

The idea that I must write on the day itself was an unnecessary assumption tacked-on to the project.

At the time, I’d never gone back to write an entry because it felt like cheating. I had an unhelpful thought pattern:

Side note: making notes helps

Of course, when you catch up to entries for previous days, you’re going to forget things. Notes help, and I try and jot down bullet points within a day or two so that I don’t lose too many details.

#2 Your journal is supposed to be whatever you want it to be

Is there a correct way to journal? Yes. But the correctness depends on your goals with your journal, not on prescriptive templates.

Portion of author’s journal entry about the Enneagram

#3 The benefits of a daily journal are proportional to your days

My journal takes the form of a stream of events of the day followed by my feelings. Because of this, a lot of entries are mundane.

I felt the benefit of the journal when I was able to make peace with significant happy and sad moments in my life.

The really meaningful entries come with your heavy days. Those days will feel really special, and you want to be ready for them.

  • July 19th — my first ever major surgery to remove a previously exploded appendix.
  • July 28th — my last day at a job that gave me the gift of responsibility and trust for 2 years.
  • February 11th and 12th — my grandfather passed away and I traveled with my cousins to scatter his ashes.

#4 Journaling helps you close mental tabs

Yogesh, a former colleague, introduced me to the phrase “closing mental tabs”. I remember relating to that phrase hard. It felt like an apt metaphor for the way anxiety works.

A sample of the author’s template for a brain dump

#5 To succeed, find the path of least resistance

My journaling app reminds me to log my entry at 9pm everyday.

Author’s example of a dud entry.

#6 Revisiting your journal is incredibly moving

I had an empirical list of joyous moments that showed me evidence of a good life, and evidence beats insecurity.

The app I use hits me with daily throwback entries in the morning. It shows me any entries from the same date in previous years, as well as the entry for the same date in the previous month.

Author’s example of compiling the top moments of the year

#7 Systems are better than habits

This 1-year journaling project, despite no dramatic planning, is the longest personal project I’ve ever done.

Author’s journal entry after completing a 1-year commitment



Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Vaibhav Gupta

Professional technical writer, 2x Distinguished Toastmaster. I write about mental health and self-awareness. Also see https://medium.com/thorough-and-unkempt