It really depends on more on how many servings you are talking about. The most accurate point calculation is going to be doing the math for the entire amount eaten, but short cut estimating isn't a problem when you're only talking a serving or two (even per day).
I had a leader (of all people), who kept track of all of her calories, fat, and fiber for the WHOLE day, and then did her point calculations. While there's nothing "wrong" with her way, if it works for her, I think it would be counterproductive for me. One of the biggest advantages of the points system for me (over say calorie counting) is that I do not sweat the small stuff as much. When you're working with calories (or at least when I do), it can become obsessive (is this apple 45 calories or 67?) By using bigger units (points) it's a little easier to keep things in perspective.
Our weight loss isn't going to be jeopardized over one or two points, but if your weight loss stalls, you may want to reevaluate your point calculations, food measuring, etc, but otherwise whichever is most convenient at the time is fine (even if you're not completely consistent with the method). For example, there are some foods I have memorized the counts for. If I double the serving, I just double the points. However, if I am having to calculate the points anyway, I always calculate for the amount I will be eating. Works for me anyway.
Colleen
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