A few years ago I got the pro version of the app Daylio. At the time it was essentially an emotion and activity tracker; every day at some time, it would prompt you to choose how you were feeling on a scale from “rad” to “awful” (with some emojis and colors to illustrate the various feelings) and then mark which activities you had done during the day. The idea is that by keeping track of which activities made you feel a particular way, you could optimize for doing those activities more often.

As with most of these mindfulness apps, YMMV. In my case, I would do it somewhat reliably for a few weeks, but then I would miss a few days and I’d stop. Upon reflection, like with most things that don’t get traction, it basically suffered from not having enough utility justify the time investment. The different categories of activities were often hard to map onto what I did everyday or what made me feel a particular way, so I spent an inordinate amount of time coming up with new categories or rearranging past categories just to be able to write down something that I basically already knew.

That being said, on principle I am a fan of these kinds of mindfulness apps. I’m of the strong opinion (formed mainly from my own experience dealing with stressful things) that the key characteristic that separates happy, healthy people from their peers is a high degree of metacognition,¹ and habits which encourage metacognition seem like a net good.

So when I recently got a new phone and made the leap from Android to Apple (this was an unrelated change that was primarily done so that I could use this particular app that my company required) I figured I’d reinstall Daylio and give it another shot. The experience this time around was dramatically different. As of today, according to the app stats, I’ve been journaling for 77 consecutive days, or a bit over three months. What’s more (or maybe, the reason for this relative longevity), the quality of journaling is significantly higher, and I find myself reviewing what I wrote down on previous days, cross-referencing thoughts and actually spending five to ten minutes a day “thinking about thinking”.

What’s Nice about Daylio

From what I can tell, the “killer features” of Daylio compared to other journaling mediums are:

1. Daily reminders to fill out a journal entry, which you can set to alert you at a particular time, when you are most likely to record something useful.
2. Recording long-form text with an actually good text editor.
3. Prompt templates which can be customized.

Some other features which are less useful, but still nice to have:

1. Adding photos to journal entries. This was a nice feature when I went on vacation and wanted to have a visual memory of what I did.
2. Statistics reports, for things like daily streak, number of words, and mood. This seems more like gamification, but gamifying activities which you actually want to engage with seems like a good idea. There’s actually a little “achievements” part which tries to reward you for using different features, but I guess I’m not motivated enough by those sorts of things because I haven’t really diversified my usage of the app that much.
3. Cloud backups, to preserve what you’ve written from a long time ago.

Some features which I’ve found not useful at all:

1. I’ve basically completely phased out the “what did you do today” categories, since the utility seemed to be so low. It’s a lot easier to write down open-form journals.

What I Usually Write About

As I mentioned above, one of the really good features of Daylio is their text editor and prompt templates. In my case, I’ve basically settled into mainly using two templates, sometimes choosing a different one depending on what’s going on in life. I call the two main templates “Morning Brainstorm” and “Evening Reflection”. The “Morning Brainstorm” one looks like this:

- What did you do yesterday?
- What do you plan to do today?
- What do you want to learn about?
- What do you want to create?
- What ideas do you have?

And the “Evening Reflection” one looks like this:

- What did you do today?
- What do you plan to do tomorrow?
- What did you learn today?
- What ideas do you have?

The main things I like about these prompts are:

1. They use bullet-points instead of long-form text, which gives them more of a “brain dump” feel and encourages me to write down more than I would otherwise.
2. There’s always a prompts about what ideas I have, which usually forces me to sit down and come up with an idea (not something I was previously in the habit of doing every day). I really think this helps break the monotony of just doing whatever I do every day, and “ideas” is broadly-phrased enough that it encourages general metacognition.
3. There’s continuity between days, so that I can check whether or not I actually ended up doing the things I said I wanted to do yesterday, and figure out where I need to pick up today.

There are also a few other prompts. I particularly like the gratitude entry, which has questions about what you’re thankful for. When I was recently on my honeymoon with my wife, I found that taking time to be grateful made the experience a bit richer and resulted in me being more present than I might otherwise have been.

Behavioral Changes as a Result of Daily Journaling

People don’t usually brush their teeth so that they’ll have clean-feeling teeth; usually, you brush your teeth so that you don’t get cavities. It’s the sort of activity that pays off long-term, and it’s hard to do it every day unless you’ve built it into your routine (speaking of which, I’ve just realized that I need to brush my teeth today). I think something similar can be said about journaling; the true value of having a journal is when it becomes a habit that you do on a regular basis.

One of the most immediate things I’ve noticed is that the practice of having to express my thoughts every day has made my commmunication with other people clearer. When I first started journaling, I noticed that I was having a strange word-finding difficulty when I talked to people. On reflection, I think it was a consequence of spending so much time writing code - the way that you form mental structures when writing code is pretty different from the structures you form when communicating, so when you’re really used to using the former it becomes harder to transition to the latter. I’m not sure if it was the practice of writing every day, or the fact that by thinking about my day I actually started to notice that it was a problem, but I’ve since found my communication to be much clearer than it was previously.

Another change that I’ve noticed is that I’ve started spending more time ruminating about things. I directly attribute this to forcing myself to come up with a new idea every day. I’ve somewhat internalized the fact that it’s actually fun to come up with new ideas and just imagine things. It’s almost like a psychological cheat code - if you’re sitting on the subway or taking a walk somewhere, and you’re bored, you can literally just start imagining things to entertain yourself and scratch your curiosity. Who would’ve thought!

Behavioral Non-changes

One thing that definitely hasn’t changed as a result of daily journaling is my general productivity level. Maybe as a consequence of the “hustle culture” stuff, it seems like all the mindfulness apps have some incentive to advertise themselves as a way to make you more productive. But I don’t think daily journaling has had any impact on my overall productivity. If it has, it’s likely only in the sense that I spend more time doing things that I’ve actively chosen to do, which hopefully means they are things that will be more valuable to me over the long run.

Another thing that I haven’t noticed change is my attention span.² I think this is mainly a function of the amount of time I spend journaling compared with the amount of time I spend dicking around on the internet; one just clearly dwarfs the other, which is unlikely to change the fact that I’m basically a professional internet user, so even though I’ve been able to set aside time to journal every day, I haven’t noticed that it’s made any impact on my larger ability to focus on things. The only thing that seems to work in that regard is getting enough sleep, doing semi-regular exercise and working on problems that I find challenging and stimulating.

Hope for the Future

I think it would be cool to have a year’s worth of daily journals. There’s something appealing about the long-term coherence of my life between two different years; like, knowing what I was doing and how I felt on the same day one year ago. It’s like when memories pop up on your Facebook feed, but less engineered.

Also I hope that the app doesn’t randomly crash or die and delete all my data, or get hacked and release all of my inner-most thoughts to whoever wants to read them. To be fair, that’s usually on the back of my mind when I’m writing new entries, so I tend to shy away from writing anything that would look embarrasing if it were surfaced without my consent.