I am the world's WORST estimator. I have no idea how tall people are (taller than me, is usually about as accurate as I can get), how many people are in a crowd or at a party, how heavy something is, or how much something costs. Even after 10+ months of measuring and counting calories, I still have no idea what 28 grams of hummus looks like - and I eat that almost every day! I think the "estimation" center of my brain is missing.
Because of this, I have become best friends with my digital food scale and my calorie tracker. I'm approaching goal, but have no intentions of giving either of those things up once I get there. If people want to think I'm weird/OCD/obsessed, that's fine - I can be all of those things as long as I am at a healthy weight for me.
Over Christmas, I'm going to be a my sister's house for 10 days or so, and am bringing my food scale with me. I know I'm going to take some grief for that from her, because she doesn't really understand how much of a lifestyle change this is for me. At the same time, my dad has Type II diabetes and my sister (37 years old) was just placed on medicine for hgh blood pressure. If being super-vigilant about my food portions helps me avoid the same fate, I'll take her ridicule with a smile.