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You're Not Bailing Out Your Adult Child, You're Buying Proof

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05.08.2026

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Somewhere between 'just this once' and now, that became the policy.

Your kid isn't testing your love. They're testing a rule nobody ever wrote down.

Are you providing money to truly help (and is it really helping)? Or is it hush money for your own guilt?

Carol looked up at me on our virtual call and said, "Hold on, you want me to do what?" I gently further encouraged her by repeating my prompt. She then wrote each number in the left column first. That's right, I'm talking about every transfer, loan, and rescue to her son over the past year, totaled up on a legal pad. But what actually gave her pause wasn't the list of numbers or the total dollars, for that matter. Rather, it was the second column I'd asked her to add to the right: one word (specifically, the feelings) next to each entry, for what she felt in each moment she said yes."Relief," she wrote next to the first one. "Dread" next to the third. Then, beside the largest number........

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