This is more or less the strategy I am taking for my weight loss.
I don't count calories religiously. I've been around the weight-loss block enough times that I know what healthy foods and healthy portions are, I know how much I can eat to lose weight, I know what foods I have trouble eating in moderation. I do count a few days every month or two, just as a reality check, to make sure my portions aren't creeping when I'm not paying close attention. But for the most part I just plan to eat sensibly, keep lots of fruit and vegetables around, and try to make the right decision each time I am faced with a food decision.
The reason I've taken this approach this time is that in the past I have great success with meticulous counting for six months or so, and then burned out on it, moved on to some other enthusiasm, and eventually gained all the weight back with interest.
This time I decided not to let weight loss take on the obsessive nature of my other enthusiasms, so it would not become something I tired of.
The trade-off for me is that the weight loss is a bit slower. I have lost about 45 pounds in the last year, and it takes a lot of patience to grind through times when I don't have as much focus and the weight stops coming off. The upside is, I am still at it after a year, which has not really happened before.
Plus, I'm 45 pounds lighter than I was last year, which is better than not having lost at all.
Will it work in the long run? I don't know, the jury is still out. And I just keep telling myself I'm in no hurry. My rate of weight loss may not impress anyone, but it's still loss, and if I lose another 50 pounds in the next year I'll be a whole lot closer to goal than if I burned out on meticulous focus after six or eight months.