Dreaming Out Loud (About Philanthropy)

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A recent conversation with someone close to me got me thinking.

This person has it all figured out. Pre-paid funeral. Beneficiaries named on every policy, updated and correct. They have taken care of others for many years, including an adult with severe mental-health challenges. Worked hard, saved for themselves to retire the way they wanted, with travel, joy, and warm weather. And they’re the kind of person who has quietly and generously supported causes they’ve loved for as long as I’ve known them — never asked, never announced, just consistently there for the things that mattered to them.

We started talking about it all to make sure their ducks were in a row. Most of it was. But nothing in the estate plan reflected any of their philanthropic aspirations or the sustained legacy they wanted to leave behind.

Not because they didn’t care. Because no one had ever asked them to dream about it.

I think this happens more than we’d guess. People spend real effort getting their affairs in order — the policies, the beneficiaries, the paperwork — and somehow the causes they’ve spent a lifetime showing up for never make it onto the list. The generosity was real. It just never got invited into the plan.

There’s a universal truth in that: We’re often better at tending to our obligations than to our loves. We name the beneficiary. We rarely get asked to name the legacy (outside, of course, an ethical will).

So we talked — about a social-services organization that offered meaningful advice during a challenging time, but because of circumstances, never got to make good on their ideas. About a long-defunct synagogue, now with a small operating cemetery only, that gave comfort during the loss of a loved one. And about an education organization that mirrored their professional life and values, enhancing the lives of those most vulnerable. It was a conversation that brought us both great joy and comfort.

Legacy like this is what I love to dream about — to think about what has always touched your soul. The places and people to whom you want to leave a lasting thank you, an organization that gave you comfort and hope, a location that has sparked feelings of deep gratitude. How might you say thank you in a way that is truly felt?

That’s the actual work I love to do. Not just writing proposals. But sitting across from family, friends, clients, whoever’s willing — and asking the question nobody else asks: Given everything you’ve cared about, what do you want your name to keep doing after you’re not the one doing it?

I’d like you to think of someone in your life who’s generous like the person I referenced at the beginning — quietly, consistently, without needing credit. Have they ever been asked what they want that generosity to become? How they want it to endure? If not, you might be the person who gets to ask. And if you’d like company for that conversation — with them, or about someone you love — I’m here for it.

Shabbat Shalom, 

Kari