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I also struggled with contexts because, like many others, I can usually access any tool at any time and so really only have one physical context. So I asked myself, what purpose does context serve? And the answer I came up with was, when the time comes to pick a task to do, context helps you pick from those tasks that are right for that moment while filtering out the rest. That led me to these contexts:

Errands - I want to see this tasks when I'm on the go
Weekend - I want to see these tasks when I have a chunk of hours free
Quick - these are for small chunks of time
Fun - these aren't really "tasks" but fun stuff I want to remember to do