I'm not sure if I'm a pessimist but I have been guilty of underbolusing. Like you, I'm not always sure how many carbs are in unknown food. But I was also guilty of not using enough insulin at home because it was making me gain weight. I got yelled at for my A1c of 7.4 at the endos so I am being better. Of course episodes of hypoglycemia are becoming more common again. Guess I can't win!!