I see many power ups that will tell me how much time it took me to finish a task, after the fact. What is the best way to n block out my day in advance, estimating how much time each task will take. This will let me know if I am using all available time or if I am adding too many tasks to my day.
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It might seem odd, but I use Cronofy. It's a calendar PowerUp. It has pseudo-2-way syncing, in that, if you add a card to the board, it'll sync to Google Calendar (or any other calendar of your choice) and you can edit in the calendar. It won't pick up calendar events and add them to Trello though, hence being a limited 2-way sync.
Cronofy is free for 1 board > 1 calendar, but the paid version, which gives unlimited boards > unlimited calendars is very reasonable, at $24 a year (personally I'd pay more than that for paper diaries through the year, but that's just me!)
I can link my board to my calendar, create a card for the task that I want to do and set a due date and time, hop into my calendar and see the card as an event. From there, I can move it around (which will change the due date and time on the card in Trello) and set a duration (in Google this is done by hovering your mouse over the bottom of the event and dragging it down). When you change the duration within Google Calendar, that syncs back to the card and adds a little box on the back of the card with the new duration on it.
That way, your calendar will be blocked out exactly as you want it to be, and all events will be linked to your Trello board. If you change the title of an event, this will sync back to the title of the card, likewise, if you change the description in a calendar event, this will sync back to the card description.
It's not the ideal solution, but I thought I'd mention it in case it's useful!
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