I believe I answered before with a similar question about discipline and suggested several books - Between Parent and Child by Haim Ginot, How to talk so kids will listen and listen so kids will talk by Adele Faber, & Smart Love by Martha Piper that offer kind and respectful ways to resolve everyday conflicts with our children. I agree with them in that 'time out' is disrespectful, demeaning, belittling, and humiliating. Fear of punishment (or reward for accomplishment for that matter) does not teach a child to behave properly.
We use 'Time Out' pretty much as a medicine for everything and bitter the medicine quicker the results. Sure we can get the short-term 'outcome' we want with our forceful tactics because we have the role power and our kids are too young to compete with us and they have nowhere else to go. We raise the bar the more we see them becoming independent and raising their voice.
A 'time out' will not teach a child the long-term value of respect, kindness, and responsibility. We teach these values by modeling the behavior. The bottom line is to find the middle ground in a way that their needs and our needs are met. When we acknowledge and validate our kids' feelings and seek to understand them respectfully, then, they will do the same. Our display of power only makes them defiant or submissive. How many 'time outs' or other punishments should a child be given to get to that stage is up to us.
The best way to encourage and reinforce the desired behavior is to consistently give kids specific praise on their positive qualities. They would love to do more of it. We also need to be careful NOT to point out the negative at the same time with positive. The positive will lose its value and negative is already negative. Albert Einstein said that for every negative thing we say about our children, we must say at least ten or eleven positive things about them to neutralize the impact of negative on their self esteem. The research has shown that by the time our kids are eighteen, they hear at least 18, 000 negative statements about them. We can only imagine 198,000 positive statements we would have to think about to say to our kids! Here, I recommend another book title - Discover your child's learning style by Marriemma Willis (sp?).
An occasional 'time out ' to either separate ourselves or the child from the situation if the child is hitting or biting is the only situation I can think of, other situations should have logical consequences. For example, if child does not want to put on a jacket to go to park, just let him go without it. Just kindly say that I will take it with me in case you feel cold later. He will feel acknowledged and will get a logical consequence if feeling cold later. And that is when we should refrain from saying, 'I told you so' as again it is demeaning. :)
Please don't be so hard you self for trying to be an ideal parent and have your child be the good child in an attempt to 'please' our society. Your child will outgrow most of his immature behavior 'in time' but not with 'Time Out'. ;)
Best,
-Rachna