Any thoughts on the best time to journal? I've been doing it right before bed, but sometimes I get so tired I'm not really into it. I could try in the morning with my coffee, perhaps. At least now since I'm working remote and my commute is a hop, skip, and a jump.
My longest entry to date was done one evening while I enjoyed a pour of bourbon. Not sure if it was the bourbon, or the day in general.
Whenever works well for you. In the morning with your coffee, at lunch time, or in the evening with a relaxing beverage, whenever some sort of thought gets stuck in your head, when you encounter something that you want to remember, any of the above in any sort of combination.
Personally, I would recommend that you start by setting yourself up so that you do at least one session at the same time every day, just to get yourself into the habit and then start riffing off of that.
Speaking as a history buff myself, I like the concept of a commonplace book. Leonardo da Vinci used notebooks to great and lasting impact. Going back even farther, Marcus Aurelius and his collection of writings referred to as "Meditations" is probably what I would personally consider to be one of the oldest form of journals.
As with shaving and coffee, it's all about what you make of it and how you like it (with apologies to The Bard).