John Knowlton, February 18, 2026

This piece was originally published in Trusts & Estates on February 18, 2026.

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The first generation makes it, the second generation spends it and the third generation loses it. You’ve probably heard some version of the “Shirtsleeves” proverb. Shirtsleeves to Shirtsleeves in three generations is the American form. Brazil’s version is “Rich father, noble son, poor grandson.” Whatever the details, this proverb captures the essential truth that many families struggle to maintain wealth for multiple generations. And beyond wealth, many families are challenged to maintain a sense of identity: the essential concept that we’re a multi-generational entity with a common purpose. 

Traditional estate-planning tools are used to prevent assets from being wasted. Wills and trusts often contain strict conditions and qualifications that beneficiaries must meet to receive distributions. These conditions are often called “control from the grave” or even “dead hand control.” Instead of a lump sum payout to beneficiaries, the grantor stipulates partial or periodic payments. Each payment depends on requirements such as completing college, maintaining sobriety, having steady employment or other lifestyle factors. These mandates may be well-meaning but can induce resentment among beneficiaries, may become meaningless over time (“you must run the record shop” doesn’t make sense after that industry disappears) and impose a significant administrative burden on the trustee. 

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