Tired of starting over!

I think the most important thing here is to accept you will have to monitor your eating habits for the rest of your life. Some days will be better than others but aim for making portion control a habit rather than a temporary punishment. Eat what you like but not more than within your daily calorie needs. You may have to change your food shopping, cooking and learn to automatically ask for to-go boxes at restaurants. You’ll have to weigh and measure food to learn what a real serving size is. Read the labels too.

It doesn’t have to be awful - just mindfulness. It’s an education in taking control of your health. If you think of successful weight loss having an end date when you reach goal, the weight always returns.

Agreeing with @jtophinke, the calculators and gadgets have limits. We really don’t know how many calories we are burning unless hooked up in a lab. The calculators are based on statistics and averages but no one is exactly average. Calculators provide starting points, but we all have our own bodies that react to things in unique ways. Plus, there are always going to be calorie counting gray areas.

Why am I going on about this? Because if you read this board much you’ll see lots of people go to pieces when the numbers put out by the calculators don’t line up with reality. Weight loss takes 2 things- eating in a deficit and living with it. Folks tend to go all in on the deficit try to beat themselves into living with it. Don’t do that.

And forgive my nitpicking here. I think you’re on the right track, any loss needs to be recognized as weight loss success. Don’t agree that any loss is amazing. That’s an exaggeration. But failure to count that .2 lb loss for the week as a step in the right direction is a big problem for a lot of people.
We need to beware of our own brains. Personally I think our brains hate weight loss. Our brains will turn any mistake in total failure if we let them. Our brains will even take that .2 lb loss and make it seem like a 5 lb gain.

Last thing- I’ve maintained my 100 lb loss since 2006. Not a typo. I lost my last 35 lbs on Weight Watchers. WW is really just calorie counting dressed up for copyright protection. Not promoting their program. But going to the meetings I saw the nonstop stream of people coming back having regained everything they lost. Frequently everything plus more. I vowed not to get into that group.

This gets to the importance of having a routine we can actually live with. Don’t make changes to move the scale short term. I didn’t regain in part because I kept everything I was doing in place for 5 years. I eventually quit keeping a food diary for long periods. But if I start gaining, I start logging. And my food scale (I’ve gone through several) is always out on the kitchen counter and gets used every day. If you don’t want to regain not much will change at goal weight. Good luck.