For too long, nonprofits have relied on reactive fundraising—chasing grants and emergency appeals. Today’s foundations demand more, prioritizing organizations with sustainable strategies over those operating crisis-to-crisis. The $68 trillion wealth transfer presents unprecedented opportunities, but only for nonprofits with modern planned giving programs. As Trump-era policy shifts demonstrated, diversified funding models provide essential resilience. Organizations clinging to outdated methods—like complex calculators and printed newsletters—are losing to those focused on donor relationships and digital engagement. The future belongs to nonprofits that plan strategically, not those that plead desperately.