Journaling

As with all advice, ignore this if it doesn’t work for you. This has worked for me:

Keep a journal.  It helps you learn about you.

I'm not going to make the case for why you should journal. There are tons of articles and sites out there to tell you why journaling is good for you, how to do it, what tools to use, etc. If you don't already know why, dig around.

So let's assume you're open to the idea of journaling. The useful questions immediately become: in actual practice, why? how? what works? what doesn't? I can answer those from my own experience, which might be useful.

Why:

I think of my journal as a "tool for thinking", and as a way of remembering events important to me in the moment that my poor memory would otherwise lose.
The act of writing helps me organize my thoughts, refine what I believe, and learn from my experiences over time. Something about getting those thoughts into concrete words helps clarify them. (“Hold on. That doesn’t make sense..”)
Having a multi-year archive of those things important enough to me that I’ve written about them has proven to be an essential tool for my growth and development over time. (“Man. What was I thinking?” ... “Oh.”)
I know there are other reasons that people journal. Therapy. Gratitude tracking. Recording daily events. Dozens of others. Those are all legit, but I can't really comment on them.

How / frequency:

I journal compulsively.
I do not have a daily journaling habit.
I do not write at any particular time of day.
I write when I need to or want to.
Sometimes I write every day for weeks.
Sometimes I write a few times in one day.
Sometimes I go months without making a note. But I have always come back to journaling after a dry spell like that.
Today I have roughly 3000 digital journal entries spanning about 30 years, so roughly 100 entries a year.

How / content:

I have found that I largely create three types of journal entries.
- Records of what happened, which I refer to as a "diary". Trip diaries, notes on a conversation, stories from an eventful day. Maybe a photo. Journal entries that are nothing but diary make up perhaps 10% of my journal entries.
- Most other entries are “thinking", or "thinking out loud onto paper”. (Ironically neither actually out loud, nor actually onto paper, but that's how I think of it...) This usually means I’m trying to figure something out. These thoughts can take all kind of forms: ideas, reflections, brain dumps, rants.
- The third main type of entry I have is planning, which is arguably a subset of thinking. It's working through the ideas of some new system, or some way of doing things, or what I want from a particular project I have in mind. I do that often enough that it's a clear third type.
Often and thinking overlap in the same journal entry. “Here’s what happened today, now I’m going to reflect on that, and hey, that gives me a few ideas”.
A key point here: the term "journal" tends to imply some kind of daily or regular recording of "here's what happened". You'd expect the Lewis & Clark expedition journal, for example, to have entries like "found a good water source" or "ate a moose" or "half the party died of dysentary yesterday, what a drag". Not "I'm feeling lonely" or "I just had the greatest idea for a new wagon wheel design". However, the majority of what I've found I want and need to write about over the years has been in the latter category. Both kinds of entries are useful.

How / tools and organization:

I used to journal a little bit in paper notebooks, because those look cool. But, in practice, writing in them was far too slow and messy. I quickly migrated to a digital journal tool once that was possible.
Like all of my core tools, my journal app needs to meet my basic digital tool requirements.
I've used many journaling apps over the years. Today, I'm using Day One, an app that’s pretty good for journaling. Among other things it also lets me record photos (often a white board capture), search entries, and tag entries with various category types. (Knowing me, I'll switch tools in the next year, because I think there's a new one that handles tagging better.)
Day One also lets me have multiple "journals" in the app, where a journal is a set of related entries. Entries can only be in one journal, so it's metaphorically like having different physical journals on your writing shelf, then choosing the one to write your current entry into. ("Chemistry Experiments" or "Recipes I've Tried"?)
I have two main journals in Day One. One for "Personal", one for "Work". I tend to find that those two topics separate fairly cleanly, and you want to keep the work crap out of the non-work stuff.
I also have several "special purpose" journals that I use to organize very specific topics. These vary a little over time and sometimes I have a bit of a struggle with "is this topic worthy of a journal, or is it just a note in my note system?", however, here's my current set of other journals:
- Medical: recordings of health-related events, notes from doctors visits, etc
- Letters: letters I wrote to people, letters others wrote to me, cards, and so on (this overlaps a tiny bit with normal email, but in practice, letters are a bigger deal than email)
- Planning: Annual and multi-year goals, thoughts on habits, initial ideas for projects, etc. Once a project becomes real, I handle all the notes and planning for that in my notes system.
- Ideas: I used to keep a separate journal for ideas. I have so many, and they're so diverse, that I've pulled these out of my journal system and moved them into a different tool for idea tracking and organization.
- Meditation: A log of thoughts collected during and after meditation sessions. Pulling these out as its own journal helps me see meditation-related trends over time.
I have fortunately kept all of my digital journal entries in one application (migrating a few times over the years), making them very easy to find and search.
I try to keep all other writing out of the journal. So, things like to-do lists, the real details of project plans, trip preparation, essay writing, etc - these go elsewhere, usually into my notes system. That way, I can count on the journal just being a record of stuff that happened and what I was thinking.

How / In Practice:

There seems to be some kind of weird pressure on people to journal daily or regularly. To end every day with a wrap-up. To capture every moment of gratitude to bottle up your happiness for use later. Enh. None of that works for me.
I find, rather, that I sometimes just need to write. I know what that feels like in my head now. Some of that feeling has probably been a part of me since I was in my teens, some of that has been learned over time, as I began to realize just how bad my memory is, and just how much writing helped me sort stuff out. Here are the triggers I'm aware of that bring me to typing into my journal:
- Recording an event. On the flight back from a trip, I often journal about what happened, what worked, what didn't. After something particularly crazy at work, I may unload the raw story into my journal.
- Logging something I'm tracking. I've learned to take notes about medical events regularly, because they're incredibly useful later. I'll often find a table not far from the doctor's office to write in shortly after an appointment. After meditation, I often need a place to unload thoughts, so I usually keep an iPad near.
- Unloading my head. I often find I've got thoughts swirling around, issues bugging me, a complex emotion, an idea burbling along, just a pile of chaos that needs figuring out. Sometimes it takes a white board to sketch it, sometimes it takes a journal entry or two or three to disentangle the chaotic mess. Sometimes I disable auto-correct, open a blank entry, close my eyes, and type as fast as I can to capture all the nonsense before it fades or overwhelms me. Cafes, coffee, and headphones help.
- If I go too long without figuring out where I am in a journey ("what's the point of it all? what am I trying to get done in the next month? what am I going to do about this hard decision facing me?"), I get a little lost. Sitting down on the couch or in bed and writing about where things are and where they need to go helps put it all in context for me.
I often write in coffee shops and libraries. I sometimes write at my desk at home before wrapping up the day, or on an iPad in bed. I never write on my phone.

Almost everything I've talked about is about the writing. That process alone is worth journaling for me, because the act of writing helps me figure things out.

After you journal for a while though, you have a pile of journal entries that serve another purpose: reminding you of things from your past that you probably forgot. Having a medical log I can search has been critical. Going back and scanning entries from my last job can occasionally can be really interesting.

My top two broad insights across 4 decades of journaling:

At the core, I’m basically the same person I was in my teens. Same kinds of worries, same kinds of hopes, same kinds of tendencies. My top motivation at work back then was to do something that I felt mattered and pushed me. Same thing now. I got intensely frustrated with idiots at work. Same thing now. I never felt like I was quite good enough. Same thing now. Except that I've learned that that's how I tend to assess things no matter how well I'm doing, so now I give myself a break.
It’s an invaluable tool for me for learning about myself. I can go back and say “if I’m the same person, how did I deal with this challenge before? how did that work out? What should I do differently this time?”

So... for example, I can tell from my diary that no matter how many times and how many tricks I’ve tried to convince myself to journal daily, I just don’t. Doesn't matter. I won't do it. So, now, when I think "oh, hey, I should have a resolution to journal daily!", the part of my brain paying attention to this stuff can say, "yeah, no. Don't create arbitrary expectations for yourself again. No need. Journaling is working just fine for you without that nonsense. Do what works for you".

... and that's what works for me.