Keeping track means having a record of what happened: the evening you read, the day you put money aside, the call you made. It doesn't need a score, a streak or a judgement on how the week went.
A record, not a grade
A record answers "what happened, and when?". A score answers "how good was it?", and that's a question only you can answer, with everything a score can't see: the week you had, what else needed you, what you chose instead. So UpWill keeps the record and leaves the judging out.
Make it a sentence
The easier a record is to make, the more likely it is to exist. In UpWill you say or write what happened in your own words ("used 40 minutes for the guitar tonight") and the update goes to the plan it's about, with Undo. The note stays in My Diary as you said it.
A line for each plan
My Life shows each plan as a line across two weeks of dates, with a small dot on the days something was recorded. The same dot for any update: it marks that something happened, not how it went. Money used and money added look the same, because a record isn't a verdict. Tap a day to see what was recorded.
Empty days are just days
A day without a dot isn't a failure, and nothing resets. Plans pause, weeks fill up, priorities move. The record is there for when you want to look.