I usually ask these as questions on Quora. Quora is incredibly tolerant of even inane questions, and has the benefit of allowing others to provide feedback (in the form of answers and comments to the question). If a question has already been asked, then you will also be able to read what others have written in response and/or follow that question for future answers. Quora also has the option of anonymizing questions. I've found that always converting my thoughts into questions has made me very conscious of what sort of questions are interesting to ask (not that there's anything right with that).

Another idea is to practice this with writing down dreams. After waking up, I often think "It's not really worth writing that dream down anyway", whereas in reality I would find it quite interesting if I came back to it later. Forcing oneself to write thoughts down even when one is not inclined to may lead to more sedulous record-keeping. (But this is just speculation.)