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I have this problem - I like talking to friends but I'm not so good at long distance friendships. I often find myself waiting for the right mental space to respond to friend's emails, by which time the moment has long passed. I find myself with reams and reams of flagged, starred or marked as unread emails that I always mean to get around to but make myself avoid.

Putting this into Omnifocus is a laborious and neverending task. I'd have an inbox full of "Respond to David", "Respond to Sarah", etc ad infinitum. Then I'd have to remake the actions again whenever they responded. Either that or I could say 'respond to all outstanding messages' - an impossibly ambitious task no matter how much free time there is.

I came up with a system to help me with this. I can take weeks and months to respond to emails so why not accept that rather than fight it? I now have a task in OF that is simply "Reply to one major outstanding message" that repeats 1 day after completion. I'm just trying this out for the first time recently, and so far it's worked quite well - OF never overwhelms me nor leaves me alone. I'm going to experiment with having it repeat more than once a day or perhaps change the task to "Reply to 2 major outstanding messages", but I think this might help me finally get back to those neglected people. I'm thinking as well of having a task that repeats, say, every 5 days to tell me to message someone I haven't spoken to in a while. This might seem oddly mechanistic but it makes OF get one step closer to being the holistic productivity solution it wants to be.

Any thoughts on this? Does anyone else have this problem?