I can imagine this using some sort of "somethingnew" list (from e.g. www.reddit.com/r/somethingnew) or maybe you can feed it a list of things you always wanted

I can imagine this using some sort of "somethingnew" list (from e.g. www.reddit.com/r/somethingnew) or maybe you can feed it a list of things you always wanted to do but (typically) never got around to... so you give it some tasks, maybe specify a condition (weekends or during the week?) and next thing you know, it tells you to do that task the next time those conditions are met.