One central difficulty with my present journaling habit is that it is brittle. If I miss a couple of days, writing a new entry feels daunting because I have lost the context of my life. How do I regain it?
Fundamentally, I have three options:
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Suck it up and write a long entry whenever I miss out. I have a friend who does that, but it does not work for me.
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Have a "today" rule. Treat any day that I did not journal as a complete loss. This has two advantages: i) the barrier to re-entry is always low ii) I have a strong incentive to write each day. Still, it seems drastic. More reasonable is a "this week" rule.
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Write a "return to journaling" prompt which I follow any time I haven't written for a bit. I'll iterate on this approach, but here is one attempt:
Think about each day in the past week that you didn't journal about. Briefly list any events which you can remember for that day. Optionally, a) choose 1 to 3 events to describe in more detail b) write a normal entry for today.
Notes on part 3:
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This type of entry doesn't get quite as deep, but that's okay. I can write more deeply the next day if I want.
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The whole experience, including the optional parts, can be a bit long. Prioritizing the first part is helpful, but less fun.
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It might be worth compiling prompts for other types of difficult journaling situations? (i.e. a 2 minute starter prompt for days when I don't feel like journaling?)
Two broader lessons?
First, it's worth noting that this method is tailored to my goals as a diarist. I tend to appreciate comprehensive journal coverage over lucid analysis (in part because I am more likely to forget the existence of an event than my feelings about it). I am more willing to sacrifice the quality of an entry in exchange for less friction.
Second, I think most of the value comes from realizing that this friction was an issue in the first place, and brainstorming a solution. One question I am curious to reflect on (and maybe you should to): how can one learn to recognize little areas for life design?