Then I obviously got lazy. And while I sometimes still think I can estimate how much I am eating, I am probably wrong, because my bathroom scale says something different. My key takeaway is that it takes quite a bit of effort, but once you got into a routine, it's not hard.
Edit: Also, while I might have tried to ditch "wasted calories", I didn't put too much effort in eating healthy. One step at a time.
I love almonds and because I love them so much, if I don't portion them out then I end up eating 2-3X the calories that I thought I did so easily.
I pretty much eat 1k calories per day during the week and then 2-3k on the weekend.
It took constant lowering of calories over a year to get to this point but being hungry just feels normal and natural for me. There must be something with fat adaption going on as I never feel low on energy. Eating during the week has been completely divorced from a pleasurable activity to me too. Chicken breast, nuts, vegetables, not much else during the week. It is just easy at this point for me to wait to eat for pleasure on the weekend.
The killer for me was breakfast cereals. The box shows a full bowl of whatever, full to the brim etc. in reality the pictures are probably 5 or 6 or more servings - a single serving would barely even cover the base of the bowl and even then be 200ish calories before milk.
If you just pour yourself "a bowl" of cereal without thinking or weighing then you're probably having 1200+ calories (or about 50% of your entire daily quota) even before you add milk or anything else, just for breakfast.