“Trust me,” my younger son said–sincerely. Yet there were countless mishaps with money, related to disorganization and unreliability. The freelance web design job that was going to earn him $750 for ten hours’ work turned out to take sixty hours—and then weeks more before the clients finally paid. His optimistic rent check, mailed to a landlord in expectation of being able to beat it to the bank with a promised payment from a client, bounced. Cell phone and internet were cancelled at various times for nonpayment, leaving him—unless rescued hastily by his mother or myself—without a way for prospective clients to reach him. Time and again, we found reasons to keep the wolf from his door—usually extracting nominal assurances that he’d learned a valuable lesson. Our son’s “trust me” had long since acquired the opposite meaning to us: a red flag.

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