This is one of those places where everyone has to find what works for him or her. My experience has been that the most successful people are able to be "strict" about following the game plan set up, yet there has to be some flexibility built into the game plan in the first place that works for you.
For me, I need to be logging my calories, tracking my food intake. Otherwise, I just don't pay attention to how much I've eaten, the timing, or the macronutrient breakdown, & then I slip into bad habits - e.g., not eating enough early in the day or during afternoon time in my office, which means that I make poor nutritional choices later in the evening when I try to catch-up. I do like eating a lot of the same foods (and I stick to the same foods for certain situations - breakfast, post-workout, etc.).
However, I could not plan meals out for an entire week! Instead, I keep healthy food choices around my home, with me at work, and I keep in mind what nutritional breakdown I'd like to achieve (caloric range, target protein, and so forth). By tracking several times a day (very quick on my computer), I'm able to stay on track and make adjustments. I try to go "off tracking" about once per week, when I try to eat healthy but not nearly as "strict" in recording everything. Again, it creates more flexibility for eating out or wiht other people. The totals vary day-by-day, but the overall effect is pretty good.
Good luck!