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I've only assisted a couple of souls "cross over" so perhaps my experience isn't as broad as some others who have responded.
From what I've seen, the only thing holding back a spirit is either fear or love. Fear can be fear the "judgment" they believe awaits them, or fear can be of the unknown or of being all alone. Some are so attached to someone in the physical realm that they just can't bear to leave.
I believe it's important to reassure spirit that moving forward is not a one-way ticket: they can come back to visit loved ones. Spirits do that all the time.
One young lady we helped move along was terrified and alone... until we told her to call her mother to come help. As soon as she thought of her mother, the mother came to comfort and escort the young lady across.
Another young lady passed as the result of drug use, and was so scared of what awaited "people like her" on the other side. She refused to enter the light, avoided guides who tried to coax her to go forward. I spoke to her mother and found that his girl had major trust issues, especially of males. So the mother asked the girl's friend, who had passed a few years earlier, to come to her aid. Sure enough, once the young lady saw her friend her fears vanished and she was able to muster the courage to move forward.
From what I've seen, most of the soul growth, life review, and self-examination takes place on the other side, not while spirit lingers in the physical realm. The recently departed spirit, especially of one who passed under negative circumstances like suicide, would not be in any condition to benefit from a life review at that point. They would still be caught up in the transition itself, the sudden ripping away of the world they knew.
If I were in your situation, I would ask this spirit why he feels you are the one to help him. The reason isn't actually to understand his reason, but to get a chance to size up his sincerity. A spirit who wanted to cross over would normally have already done so. There is no magic to it. It's the natural, normal progression from life to afterlife.
So why is he lingering? Is he truly lost and confused and scared, or is he some sort of trickster spirit just out to have some fun, playing on your helpful nature?
Assuming he is sincere, talk with him to find out what he is afraid of and who he trusts enough to go with them to the other side. After a chat, suggest he call that trusted person and help them visualize that person answering the call. Often that trusted person is their mother, grandparent, or a dear friend.
Then just send spirit along with love, and maybe wish them a fine journey.
Spirit will have plenty of time to review this life and come to understand their successes, failures, and both good and bad decisions. On the other side. Where time isn't as we know it, and where there are loving kind souls to help them understand.
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