So I'm currently on my fifth or sixth attempt to lose weight. Historically, I've tracked my calorie intake for a few weeks or a few months, lost a few pounds, fallen off the wagon and gained it all back.
There are a number of things going on this month that I'm choosing to participate in that are going to have to be cheat days or cheat meals. Without disclosing too many details, my workplace is holding an event where there's going to be a lot of free food. Another one is that I'll be traveling for work for a few days and I'll be eating out since I won't have access to a kitchen.
Progress, not perfection is the mantra I've been repeating. I'm gonna want to stop counting calories on the work trip - a work trip was the hurdle that made me give on my last weight loss attempt. I'm trying to give myself some grace - it's okay if I gain some weight, because I can lose it again if I keep tracking my intake. Even if I don't limit what I eat at all on the trip and the other events, if I get back on the weight loss wagon that's still progress.
You are doing great just by accepting the fact you need to lose weight and putting honest effort into it. Baby steps... don't go from zero to hero (~insert the song from Hercules here~).
I personally don't do calorie counting, but give myself objectives. My current objective is to eat more green vegetables, and lean protein (chicken, egg whites, white fish...) three times per week. Just three times. I put a littlke circle in my agenda when it worked, and can pat myself on the back when I succeed at the end of the week.
I also plan my cheat days ahead of time. If I know I am going to have a cheat day (like this Saturday, when I will be attending a wedding), I put it in the calendar. When I am tempted to order food, or make something fatty, I check the calendar to see if my "alotted cheat meal" has already been claimed for the week.
The single hardest thing to do, for me at least, is listen to your body. Are you actually still hungry when you are going back for seconds? Thirds? Or do you crave the food, the pleasure of the tasty flavors, the reassurance of a tummy well filled (stuffed, really)? I try to use smaller plates too, to force myself to eat smaller portions, and make that evaluation when I empty my first plate: am I still hungry, truly hungry?
Be gracious with yourself. Chances are, you built the "bad" habits over years and years of mindless behavior with food. Now you need to dedicate years and years building mindfull ones.
Anyway... there's my two cents of wisdom. Good luck!