It helps me to visualize on the watch my calendar events for the whole day (and using always on display) . I made my own design (using Watchmaker) but it's the same idea as Samsungs "My Day" and this: https://play.google.com/store/apps/details?id=shu.gear.calwatchanalog&hl=en&gl=US
(I haven't used this, just got inspired of it. Watchmaker has access to the coming 4 calendar events.)
I've been testing out Trello. Have you checked that out? I'm a huge planner/organizer. The things I like so far about Trello are that everything is in front of my in one view, however I choose to organize things - Work | Finance | Family | etc. Drag-and-drop functionality makes things really easy. You can add notes/comments on each item (called 'Cards'), and assign dates to them. I'm liking it so far.