I'm only half-kidding about the "obsessively" part! Due dates can be a slippery slope... I look at my context lists several times throughout the day (just because I read through it this morning, if I've now got 10-15 minutes, I look through it again - I really try not to rely on my memory anymore!).

I still put due dates on some actions, and even put reminders in my calendar; whatever I need to do to get a particular project or deliverable off my mind. But I rely more on consistent interaction with my system than anything else.

If you hired an assistant and just spoke to them once a week and asked them to remind you of things, then you wouldn't have a very rich relationship with that person. But if you're checking in with them throughout every day, you can shuffle, re-negotiate, and strategize in the moment...