I just checked, and boy, my oldest DayOne entries seem to be from 2005, probably imported... about 10K of entries all in all. I use DayOne and Stoic and despite still thinking that D1 could improve in many small ways (Find/Replace, compressing images, indexing on the iPhone and mostly the way «on this day» is handled on various devices), it is the best app for just writing down your thoughts, organizing them, adding images etc. It could be better, but it is a very good solution so far. Stoic offers a more prompted approach and I like the app and the way the developer works on it quite a lot, but not as a diary, more as a mood tracker. It will be neat to see where Apple takes its own journal, which with deeper integration could really become amazing, but probably will not... because Apple almost always develops software that sticks at about 80%. They often do not go the last mile or leave software development when it feels baked. And it is the free developers who come up with solutions that give you the last 20% you need. Like Fantastical vs Calendar, it will be interesting to see if DayOne can survive this ( I have no idea about the user base and health of the company as it has been bought by Automattic) or will use this to offer a better solution and make people jump from the Apple standard software to something more tailor-made.