7 Things I Learned from 365 Days of Journaling

Vaibhav Gupta
8 min readSep 21, 2021


Author’s image of a custom notebook

Something, never mind what or why, clicked into place on September 14th, 2020 and I started writing a daily journal.

Before that, I’d been writing for two and a half years with no regularity or structure. On that day I started taking it seriously. There was no moment, no big decision, no grandiose commitment. I just started and tried to keep going.

I’ve since written 370 entries in 365 days. Here are the 7 lessons I learned.

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:

“Whoops, you missed a day. Don’t be inauthentic now.”

But in September, that changed because I acknowledged the bigger picture of the habit I’m trying to create. That helped me brush off any guilt about inauthenticity.

By now, people in the self-improvement game understand that perfectionism is the enemy. We tack on rules and requirements to our endeavours and when we fail, we give up entirely because it is too hard.

My goal here was to record the events of my life day to day. That’s it. The idea that I must write on the day itself was an unnecessary assumption tacked-on to the project.

Now I routinely let a few days go by before writing entries for all of them in one or two sittings. The biggest gap I had this year was when I got appendix surgery in July, and I didn’t feel like recording my feelings at the time. Eventually, I was catching up to about 12 days worth of material and I managed to do it over 3 days.

Taking off the pressure to write every day made it easier for me to stick to this project.

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.

I captured anything I found interesting, from what work I did or didn’t do to a tidbit of conversation that caught my attention. I did this because…

#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.

As an Enneagram Type Four, paying attention to my feelings is important to me. That plus the fact that I’m a professional writer means that my journal entries are long and descriptive. That’s what is right for me.

Portion of author’s journal entry about the Enneagram

If you don’t want to do that, good news! You don’t have to!

Your journal can simply be your work log, in which case you might want to create a bullet journal. If you’re looking for a simple way to process your day, you may want to use a 5-question format like in Five Minute Journal. If you want to process a particular project, you can create a template and follow it.

(Reach out to me on Twitter or Linkedin if you’d like help in creating a custom template for your own journal.)

What are you trying to do with your journal?

#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 can, of course, find a meaningful lesson in making coffee or having another day at my day-job, but that lesson may not be particularly significant.

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.

Most human beings are not very good at processing their emotions, because we’re not encouraged to do so. Having a journaling habit means you get a lot of practice.

This is because writing is a more articulate form of communication than speaking or thinking. When you empty your mind on to paper and arrange your thoughts, you find patterns and create meaning. By doing so, you live a deeper and more satisfying life.

When I created entries for every day, I was practicing exploring my emotions. I built up my ability to process feelings and keep them in check. As a result, I felt more composed and happier than normal this past year.

I noticed that I would put off entries for significant days, such as:

  • 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.

When I came back to fill up the gaps, I saved those for last. Those dates, and a few others, were significant and heavily emotional. Writing about them was going to help me let go of them.

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

But beyond that, even the daily habit had its benefits, because whenever I finished an entry, I felt a lot of relief. And that is because…

#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.

Whenever I get overwhelmed, it is because I am tracking and worrying about too many things. I keep Google Chrome Tabs open in my head.

Journaling allows me to close these mental tabs. Whenever I catch up to my journal, I get an immediate, physical sense of relief. I log things, events, responsibilities, and worries, so that they become permanent and can be safely taken off my mind.

In fact, because my daily journal is often about things that have already happened, I have a separate format I created for processing overwhelm. It’s called “What’s on your mind, Mr Gupta?” and it’s a format that I’ll explain in another post. Here’s a sample.

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

Of course, if I’m going to write this much, how do I do it more times than not? How do I keep the habit going?

#5 To succeed, find the path of least resistance

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

When I ignore the reminder is when the journal starts to pile up. I’ve found just clicking on the notification is enough to get me to write the full entry for the day, or at least jot down notes so I fill in details later.

It’s easier to click and get started than it is to let it pile up.

When I’m catching up to my journal, I’ll do it on my laptop in a longer writing session.

It’s easier to type on a laptop than on a phone.

I’ll also occasionally let an entry be simple and have no details. Out of the 370 entries, about 10 are short and meaningless. They literally have the text — “I don’t remember much else” or “I didn’t do a whole lot else today.”

Author’s example of a dud entry.

In the interest of the bigger picture, it’s better to occasionally allow yourself to produce a dud. Otherwise, you end up creating artificial rules to tack on to the project and risk stopping altogether.

It’s easier to create a few duds and keep going than it is to try and knock it out of the park every time.

#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.

I try and read those everyday, just because it reinforces the habit, but also because it gives me a gift. It lets me see how far I’ve come with my mental health, my lifestyle, and my ability to process my thoughts.

Having 4 months of journal at the end of last year also helped me compile a list of top moments of the year, and I was able to feel really proud of myself. I had an empirical list of joyous moments that showed me evidence of a good life, and evidence beats insecurity.

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.

Although I’ve done bigger things, like Toastmasters, I had colleagues and friends along the way. I had people to help me, and I had people I could help — both of which are incredibly motivating.

My journal benefited no one but myself, and was done with no help. To be able to do something so significant for myself is a very strange, foreign concept. Because I persevered, I was able to better understand what goes into sticking with a project until the end.

Journaling is not a habit for me. I frequently don’t feel like doing it, and often skip the day. Some days it feels like an obligation. If the effort-reward ratio was any less, I’d have dropped the project.

But because I was able to recognize artificial rules and emotional patterns, I realized I could find methods to work around them. By creating those methods, I developed a system, and a system minimizes the mental load of your projects.

The 1-year journal is not the only project I’ve been able to complete from having a system. In this past 1 year, I’ve done a lot. And I’m so happy that I chronicled it all.

Here is the entry I wrote when I finished the project.

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

And if that isn’t meaningful, I don’t know what is.



Vaibhav Gupta

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