Every so often I can make it happen, but most times I'm struggling regardless of how much prep time I give myself. Feel like it might be related to ADHD? Either way, I'm so bad at it 
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I have a lot of anxiety when I'm running late for something so for me going out usually goes like this: Well it should take 40 minutes to get there. So I'll leave an hour before to be on the safe side. No actually, id better leave 15 minutes before that, just to be double safe.
Oh, I arrived like forty minutes early?
. And the person I'm meeting is running thirty minutes late? 