Observation of any event or process without getting involved is the best way of understanding. When a person gets involved, understanding of an event can be different and biased based on own beliefs and experiences. It is very important that observer must be a detached and does not have any emotion about the observation.
Normally we believe that only our body is “self”. But most of the time this self is extended to other human beings or even to objects. We may feel more pain than the subject itself if that subject is our beloved person ( child, spouse or lover). In an object, Even a scratch on a new car is more painful and lasting than the scratch on our own body. If we have a habit of connecting with somebody, it may not be a good thing all the time. If we observe something and note down things as a plain observer, we are better in explaining or understanding that stuff. Take an example of Kama Sutra which is written by Vatsayana. Now Vatsayana was known to be bhramacharya (unmarried and practiced abstinence). Kama Sutra can only be possible by a neutral person who observes and notes down carefully without getting any pleasure or involved in it. I also read recently a priest who was never married himself has written a famous book on how to be sucessful in marriage. His explanation was that he met so many couples and counsel them for their problems in marriage that he becomes the master of marriage. If he himself was married, he might have a biased opinions or confused beliefs.
Now same is true with our own self. Normally we are always involved with our own self through out our life journey. This is the reason most of the time we believe we are right. Even if we think we were wrong , we might have lots of reason to defend ourselves. So we have to detach from our self to understand the whole event and the role we are playing. In any event, Imagine yourself observing the whole activity as an another observer floating up on the ceiling or up above. Normally this looks easy in dreams or remembering any past events. You are observing the whole scene as another observer. If you are lying on a bed, thinking about some past events. It is very easy to see how wrong you were in certain past incidents. You may burst into an inner laughter which is a good sign. This is a simple way of judging yourself as another person. Slowly you can imagine yourself in any live situation and give live feedback mentally about yourself. Pretty soon you will get used to it and start truly judging yourself.
Real out of body experience may be difficult and can only be achieved thru higher form of meditation. It can be induced with banned drugs like ecstasy. But this process is just an act and might help you in great deal to rewind your past experiences and may think how foolish you were at certain times. Slowly you can think of yourself observing your moves which will help you better aware of the situations. Just look up in the sky or roof and imagine you are watching from above.