I'd say when you have learned what proper portion sizes are for your required needs.
If you can guess quantity and then weigh food and be really close, then good job.
If really bad still, better keep weighing and logging until you get it down, keep practicing.
As to your mental makeover to still eat good - sounds like you made too many changes to your diet then.
If you have very reasonable items you cut out of your diet to lose weight, then you really didn't make sustainable changes.
Smaller portions of things you do enjoy, or figuring out how to include them and what else must be adjusted, is more sustainable.
The more different and miserable you've made things, the more likely you'll have to keep logging.
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