I'm a long-term calorie counter (This is my 8th year doing it) and I used it to get to my weight loss goals and to more or less maintain for the past 5 years. It's such a habit that when I don't weigh my food or track calories, I feel like something is missing. I even track binges, so if you looked at my app you would see the 3500-calorie days as well as the perfect days. I like tracking whatever goes into my mouth.
As for how I do it, I weigh my food more often than not. I rarely do cup measurements unless I'm baking or something. I find using measuring cups and spoons a bit "extra" and messy and it's just easier for me to zero a plate and put my food in it or weigh my plate with food in it and then once I'm done. I think it's much easier to weigh food as a calorie tracker and I think it becomes a habit the more you do it. I started weighing my food in 2009 and I still weigh 95% of what goes into my mouth. I have a small scale at work, one in the kitchen, another in the family room, one at the dining table, you get the picture. Food scales are pretty inexpensive and they have the really flat and discreet ones. At first people thought it was odd but now they're used to it. I'm definitely the person that weighs my slice of birthday cake at the office do, or weighs the chocolate chip cookie or a muffin. A lot of people feel really constrained if they don't know where the cake or muffin came from or if they're not the ones that baked it, but I think that mentality is what makes calorie counting seem very hard. If I don't know what went in the chocolate chip cookie, I just weigh it and look for the calories in a chocolate chip cookie of a calorie counting app. On some apps, you may see different values, I'd typically go with one of the higher calorie values I find for a home made or fresh baked chocolate chip cookie- better to overestimate than underestimate if you're trying to lose weight. The same would go if I was having lasagna or potato salad or something else I didn't prepare. The thing about calorie counting is that after weighing your food all the time for a long time, you begin to be able to estimate what things weigh and how many cups of something you're having. I would never get into the habit of counting just by sight. At home or at work or in a controlled environment, I ALWAYS weigh. But estimating by sight or perceived weight what you are eating can serve you well on the few occasions you're away from home at a party or something.
I keep track using an app because there's no way I could cope writing everything down and doing the math. Since losing most of my weight and getting more into fitness, I also somewhat care about my macros (proteins, carbs and fats) and even though I'm not militant about it, I like to not depend on sugar and carbs for most of my calories. App-wise, I started using My Fitness Pal (MFP) this year but prior to that I used an app called Tap & Track for 7 years and I quite liked it but it got kind of outdated because the developpers never updated it. I find MFP a little unreliable sometimes because you need to have data or wifi to really use it and also because there's a lot of user input, sometimes I find the calorie information to be incorrect, but for the most part it's fine. Just don't give in to the temptation to select the lowest calorie value listed for a certain kind of food.
Is there a time, I don't count calories? Sundays have always been my cheat day/rest day/eat with family day, so I typically don't count my calories on Sunday. Also, I'm a lot more loosey-goosey when I'm on vacation unless I'm in a self-catering situation. I went on a cruise and I tried to count and it became ridiculous trying to track all the different bits of this and that I was trying. That said, immediately I was back from my cruise, I was back calorie counting, not because I was trying to lose weight, but because that's just what I do. I now find it as odd when people just eat without tracking as people find me for having a food scale on my desk at the office. I now eat mostly paleo and whole foods and have done Whole 30 all of which people say is supposed to give you freedom from tracking and counting but even through those programs, I've found that nothing empowers me with knowledge about my diet and weight and frees me to make food decisions like calorie counting does. It's not just about the calories, tracking your food gives you a lot of insight into what you eat, how you eat and even how what you eat makes you feel and what you want to change. I hope this helps and let me know if you have any more questions.
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