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Well, That Was a Mistake

July 23, 2026

Don’t want to read? Take a listen, here.

That was my thinking recently when my blog didn’t go out as I intended — rather than being embedded fully in the email, both the title (“It’s About Time“) and the content itself were missing. It instead invited readers to see more by clicking over to my website. While I am always happy to have visitors, I personally do not like having to click over to read things (or listen, as the case may be). And yet… many of you still clicked over to read it! Not as many as each week, but plenty of my “regulars” even sent me notes about the book I referenced by Rabbi Alan Lew, or asked about our outdoor couch. If you feel like summer is slipping away, you might want to give it a quick read.

Basically, the experience was a light case study in the law of unintended consequences. We are all familiar with things that don’t go as planned — or, just as often, that go exactly as planned, but whose results or second-order consequences run against the spirit of the original decision.

That’s often true in philanthropy. Donors may be drawn to one specific function of an organization and lock in their support to that single area. But by tying a gift to a very particular purpose for a very long time, they can inadvertently freeze that organization in a moment that’s long since passed — shifting its focus away from a more pressing or ongoing need, or leaving it unable to respond to a need that didn’t exist when the gift was made. There’s a real push-pull here, which is part of why I care so much about the trend toward general operating support. In many cases, with the appropriate trust and due diligence, general operating support lets the professionals and governing board of an organization decide where and when to deploy resources — not a single funder, frozen in time.

Restricted gifts, and endowments, are often important, always well intended, and usually effective. But sometimes, not so much. I think of religious institutions with endowments for pre-schools — not restricted more broadly to programs serving ages 0–5, which would have aged better, but tied to a specific school long since closed. Donors many generations removed have no idea what their forebears intended, and the funds just sit there, dormant and ineffective — almost certainly not what the original donor wanted. I think of agencies that closed or merged, where new staff know only the letter of an outdated but legally binding agreement, with no sense of the spirit behind the gift.

At the same time, I think of organizations I know that have turned down major, transformational gifts outright, because the restrictions would have hamstrung them from doing what they and their board had determined was the priority or organizational focus. That kind of decision takes real conviction. Restricted giving plus a posture of scarcity rather than abundance makes it rare for an organization to say no to money on the table. But responsible giving asks us to think a few steps ahead — to the second and third-order effects of a gift, not just the first.

This is my long(ish) way of saying “be careful what you wish for,” and of encouraging you to be thoughtful about the intent behind both your commitments and an organization’s goals and objectives. So I want to ask — is there a gift you’ve made, or received, that no longer fits the moment it was written for? And what would it take to let it evolve? As always, I’m here to talk it through with you.

Shabbat Shalom

Kari Alterman

Kari

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Earlier Dispatches

  • Well, That Was a Mistake July 23, 2026
  • It’s About Time July 16, 2026
  • Dreaming Out Loud (About Philanthropy) July 9, 2026
  • On Patriotism and Pride July 2, 2026
  • Seen. Named. Celebrated. June 25, 2026
  • Same Pieces, New Pattern June 18, 2026
  • Continuing Education June 11, 2026
  • Who (or What) is on First? June 4, 2026
  • One Year On My Own May 27, 2026
  • Have You Met My Dog? May 20, 2026
  • When the Routine Breaks May 13, 2026
  • On Em Dashes and Technology May 6, 2026
  • I’m Not a Philanthropist! April 30, 2026
  • You Don’t Know What You’ve Done April 22, 2026
  • On Spirituality, Legacy, and Dining with People Who Change You April 15, 2026
  • On a (Somewhat) Lighter Note April 9, 2026
  • Sunrise, Sunset: On Knowing When to Let go March 30, 2026
  • On Legacy and Aging March 24, 2026
  • When the Walls Close in March 17, 2026
  • No Occasion Necessary March 11, 2026
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