I'm a vegetarian and I calorie count. I don't track every calorie, nor do I write down my food, but I am VERY honest with myself about the calories in my food and pay VERY close attention to it. Primarily, I cook for myself, estimate the calories in the whole recipe (I know the calories in a cup of dried lentils/beans by heart!) and then divide the recipe into at least as many servings as need to get to a target number of calories.
For example: I want my lunch main dish to be at least 200 calories, but no more than 300 calories, so I make lentil soup, consider the ingredients, come up with "total calories in the recipe" of 1200 or 1400 and divide the recipe into 6-7 servings. Voila!
It is fairly simple once you start paying attention, though I think with things like meat and cheese and grains and starches like potatoes, weighing and measuring is more important.
I count out the number of croutons I'm allowed to have (six, precisely) and the number of olives I'm allowed to have. I don't weigh and measure veggies, but I do pay attention to the calories in my fruit servings.
The MOST IMPORTANT PART of any plan is that you plan ahead. I don't know what your schedule is, but during the week I work late and don't have time to cook regularly. I prep my salads and cut veggies primarily on Sunday (with a secondary prep night mid-week, which is usually AFTER I have eaten dinner). I have dinners ready to go when I get home so I don't have to worry about being frantic and hungry and wanting fast or convenient food.
Also, particularly early in the process, I gave myself permission to get a take-out salad or use those pre-packaged cut veggies or pour-out salad implicitly. My local grocery stores makes nice garden salads with loads of veggies that are $5 a pop. If I didn't have salad prepped I would run into the grocery store and get one of their pre-made salads and a bad of lettuce and turn it into a couple of days' worth of salad (lettuce alone is not a salad in my opinion).
I always have food at home that can turn into a quick dinner that I needn't think about. These are generally pre-made tofu and/or veggie burgers that I can pair with frozen veg or cut veg or whatever, something easy that requires no thought and little prep time, but that I actually like.
I have also researched calories in fast food options, and in the casual restaurant chains, and have some places that I know I can go to and get a meal that is vegetarian and is satisfying and is within my calorie limits. There aren't many, but I have those places always ready if I need them. Pita Pit, Subway, Ruby Tuesdays. Even Taco Bell. Panera for sure.
I NEVER fib to myself about the calories in food now. I did that alot before. I don't assume something is healthy if it sounds healthy. I LOOK IT UP.
And I NEVER have open bags of chips (even baked ones) or other tempting, mindless foods in the house. That doesn't mean I don't EAT chips. I do, pretty regularly, and certainly with lunch on both Saturday and Sunday. I just buy big bags of single-servings. Not necessarily 100 calorie packs, they may be 90 or 140 calories, but single-serving packs.
Or, if I want something like pop chips and they don't have single-serving bags, I search through all of the bags available to find - not the food with the lowest number of calories per serving, but the food that appeals to me that comes in the smallest PACKAGE. 3-4 servings maximum. It is easier to portion out 3 servings over time than ... 12! in a big open bag of food your brain sees as insufficiently memorable to stop you eating.
That's true of things like frozen french fries, too. I do buy those. I like fries. I just bake them in the oven and they are fine, but I buy Cascadian farms shoestring fries almost exclusively because they come in a 5 serving bag rather than a 12 serving bag. There's a certain strategy to that, as limiting access to those foods makes it harder to overestimate them and overeat them.
So: I think any plan can work, as long as you take the time to plan ahead and map out your strategies for dealing with stressful moments. Think about them ahead of time and have a plan that you can just implement and it is MUCH easier to make good choices than when you are stressed and starving and grumpy.