: Re: How do I figure out what "challenges/issues" my character could encounter/go through? I will supply you with some character information and some context for my specific project, though I'm thinking
As Anne Lamott would say, we all have our own "mental illnesses", and they usually stem from our experiences. If your hero is a "bad boy" who inherited a bunch of money, has a company, and who seems to have a thing for the secretary, consider how these aspects of his life came to be: If he inherited money from his father, would that affect him positively or negatively? Would he invest carefully, or blow it all on his wants rather than his needs? Would he take responsibility, or dodge it and thus incur the wrath of others?
Going further into his past, you can consider how his childhood caused certain "bad boy" problems in his adult life. If his dad was off making money, did he have time for his son? Did the son (ie. your hero) begin to act out to get Dad's attention? Did that carry over into his adult life? I find that character's internal issues usually create external problems for them. If you let your bad boy hero act the fool, he might get into trouble with someone else and, by consequence, help the story progress.
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