Are you sure this is a technology problem? I agree that any technology platform is going to favor whoever is paying for the technology. So I agree that the big data companies aren't your friends in this regard. On the other side, the decision about what color dress to wear today is a very insightful one to consider. Since how we dress affects our self-image and our emotional state, and it depends at least partially on weather, culture, social status, tasks to be done today, expectations of who we meet today, what we want out of those meetings, and many more things, it's a hard problem, probably too hard to technology. Tech can't know that you're feeling a tad self-ware today, and so you need to wear that power-suit that got you compliments that one day last month.
Instead, I think this problem is one of personal cognitive load and attention budgeting. These are nicely addressed by various philosophies and lifestyle choices (think Buddhism, Danish Hygge, Ancient Greek Stoicism, the modern Simplicity Movement as just some examples).