I just went from 305 to 265, plateud there for a bit, almost back to my prior eating habits.

After about a month at 265, I got back into the groove of loosing weight and I'm down to 254 currently.

I switched what I could to a low calorie supplement. 2% milk to skim milk to vanilla almond milk to unsweeted almond milk. Even now I rarely drink that and drink mostly water, but if I'm craving some flavour in a drink I'll have a Rockstar Burner or Rockstar Lemonade to kill that (10 calories or so). You can have a zero calorie soda instead. Don't drink it all the time, just to kill the craving.

The biggest thing is cutting down your portion sizes. I know I use to cook something like hamburger helper and go into it thinking I'm going to eat the entire thing that night, maybe save a bit of it for breakfast the next day. I changed my attitude to take a quarter of what I made at most, wait a bit to see if I actually was still hungry or just bored, and save the rest. I eventually turned what I cooked into chicken, rice, steamed vegetables, having a banana with supper, maybe some yogurt as a dessert. I would make two sandwiches for lunch. Cut that down to one sandwich, with smaller slices of bread so I didn't put much into it. I started using my smaller plates instead of the bigger ones. Instead of buying a bag of chips I would buy a bag of crispy minis instead, in case my snacking would get out of control and I finished off the bag. There's only about 400 calories in a bag so I wouldn't have done so bad if I finished it off.

Basically, work on your portion sizes. Then work on swapping in items that are filling but less calories. Drink lots of water to help you stay full and if you have bad self control, limit what you can conveniently eat in a sitting.