Next in Line is a weekly newsletter for advisors, brought to you by Herbie, covering the practical yet consequential interaction between estate planning and family dynamics.

When David and Linda came in to update their estate plan, the conversation moved quickly through their finances. The difficult part began when they started talking about the children.

Their oldest daughter owned a successful veterinary practice. Their youngest son had been with the same engineering firm for more than a decade. Neither worried them.

Their middle son, Ryan, did.

Ryan was charismatic and generous, but he had never been good with money. He had cycled through failed business ventures, accumulated credit card debt more than once, and spent years battling a gambling addiction that had ultimately ended his marriage. Although he was doing much better, his parents knew that recovery was rarely a straight line.

Linda finally said what both had been thinking: "If we handed Ryan several hundred thousand dollars tomorrow, I honestly don't think he'd have it a year from now."

She immediately looked guilty for saying it. Yet, the truth was that David and Linda weren't trying to leave Ryan less than his siblings. They simply wanted to know whether there was a way to leave him an inheritance without putting it at risk.

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