Well, other than when I was on StB, these days I use my past experience of counting cals to make an educated guess as to how many I take in. So I don't count every day. I have a very good sense of how much and how often I should be eating for gaining, maintaining, etc. Every 3 weeks or so I track on Fitday for a couple days just to see if I'm in still in line.
I think you can definitely do it without counting if #1 - You have experience and #2 - You are following the general guidelines of something like Adam's Diet.
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