Her Giving Goes Through Fidelity Now

She said it, last March, over coffee at a small bakery in Brookline.

You had been steward of her file for six years. You had taken her, twice, to lunch. You had sent her, on a Tuesday in November of 2023, a careful handwritten note about her grandson's first viola recital, which her daughter Anne had mentioned to you in October, in passing, in a way that had felt private and worth carrying.

You raised the coming campaign. She lifted her coffee, with the careful slowness of a woman in her late seventies, and said, very gently — I should tell you, since 2019, all of my giving goes through Fidelity now.

You nodded. You did not understand what she had just said.

You said, Of course, Mrs. Hollis — that's wonderful. You closed the meeting. You walked back to the office in the rain. You did not put a note in the file. You did not change anything about her cultivation plan. You did not, anywhere in your day, write down the word DAF.

What the sentence actually meant

Mrs. Hollis is, right now, sitting on a balance of two million one hundred thousand dollars in a Fidelity Charitable account. Her quarterly recommendation — the second Sunday of every February, May, August, and November — is, on average, thirty-eight thousand dollars distributed across eleven organizations. In the most recent four quarters, she has granted twice to a literacy program in Lowell, three times to her seminary in New Haven, once to her late husband's medical society, and twice to a small animal-rescue program in Maine she found through a niece.

She has not granted to your organization since 2018.

She still gives you fifteen hundred dollars a year. She writes the check from her household account at Cambridge Trust on the Monday after Thanksgiving, because that is the date her late husband Richard used to do it, and because the small motion has come to feel, in his absence, like a thing she is keeping warm.

She is not, in any honest accounting, a fifteen-hundred-dollar donor. She is a two-million-dollar donor. The check at the kitchen table is a tribute. The grants from the drawer are the giving.

You did not know there was a drawer.

The money that is and isn't there

Donor-advised funds, in the spring of 2026, hold something on the order of three hundred and thirty billion dollars. That is not, as is sometimes claimed, more than every operating American foundation combined — the foundations still hold well over a trillion and a half between them. But three hundred and thirty billion is its own kind of number. If you took it in hundred-dollar bills and laid them end to end, the trail of money would wrap around the Earth three times — and you would still have enough left over to run a ribbon of hundred-dollar bills off the edge of the sky and all the way to the Moon. The annual payout from those funds is, in any honest reading, lower than the sector likes to admit — a great many accounts grant only a small fraction of their balance in a given year, and a meaningful share grant nothing at all.

What this means, in plain English, is that a generation of major donors has quietly moved their philanthropy into a side room you have not been invited into. The kitchen-table check, which the development office is still designed around, has become — for the donors who can give the most — a small ceremonial gesture. The actual giving happens, three or four times a year, from a laptop, in soft slippers, on a Sunday morning, in a column of recommendations the CRM cannot see.

The development office that does not understand this is, right now, in 2026, structurally fundraising in the wrong room.

The four things she told you in nine words

When Mrs. Hollis told you, in March, that her giving goes through Fidelity now, she was telling you four things simultaneously, in a single nine-word sentence, none of which the file recorded.

She was telling you, first, that she has decided to give serious money in her lifetime rather than at her death — that the DAF is, for her, a kind of living estate.

She was telling you, second, that her decisions about where the money goes are now made quarterly, and not at the kitchen table on the Monday after Thanksgiving. The annual cadence your office is built on no longer maps to her calendar.

She was telling you, third, that the recommendation form has a small search field, and that the only organizations that appear in the column are the ones she has thought of in the previous ninety days. If she does not type your name into the search field, you are not on the page.

And she was telling you, fourth, in the kindest possible way, that she would like to type your name into the field, if your organization gave her a small careful reason to remember it on a Sunday in February. She was, in nine words, asking to be courted differently.

You said, Of course, Mrs. Hollis — that's wonderful. What she heard was we are not built to fundraise from where you live now. She paid the check. She went home. She granted forty-two thousand dollars the following Sunday to the literacy program in Lowell, which her grandson's tutor had mentioned in the car the previous Tuesday.

What you should have done by Thursday

The Thursday after that coffee, you should have written a note.

Not a thank-you. Not a stewardship report. One paragraph, on cream paper, that said something like — Mrs. Hollis, it was a kindness to see you Tuesday. If you are recommending grants quarterly through Fidelity Charitable, would it be welcome to send a one-page update on the second Friday of January, April, July, and October, so the work is fresh in your mind before you sit down to choose? No newsletter. No appeal. Just one page, in plain language, on what changed last quarter.

That note costs one stamp. By year three, it would have changed her giving to your organization by roughly a hundred and seventy thousand dollars.

You did not send it because you did not know what she meant. The CRM, which knew her as a fifteen-hundred-dollar annual donor in segment 4, did not know either. Diane, who would have known, retired in 2017 and now lives in Wellfleet.

The grant recommendation is the gift

The donor decided, in 2019, when she opened the account at Fidelity. The donor is no longer deciding whether to give. She is deciding, four times a year, to whom.

That is a different question, and the institutions that win on it are the ones that have made themselves small-handedly memorable in the ninety days before the recommendation window opens.

A piece of mail in January. A handwritten thank-you from the program director in April. A phone call, in July, from the executive director, who has remembered that the granddaughter's recital was last spring. An invitation, in late October, not to the gala — to a small breakfast for the donors who have been with you for ten years.

Four small motions, against the quarter, on the donors who have said the sentence. That is the work.

A small honest line about Rōmy

Part of why we are building Rōmy is that the sentence she said over coffee in March is sitting, in some form, in the public record. The 990-PF of the small Hollis family trust her late husband opened in 1998, the one she still uses for the larger life-of-the-donor gifts, lists every grant recommendation she has made since 2015. The grants to the literacy program in Lowell are on it. The seminary in New Haven is on it. The Maine rescue is on it. The fact that she has not granted to you since 2018 is on it.

The portrait Rōmy returns when you point it at her row is not a wealth score. It is the small visible map of where her giving actually goes — and the soft careful list of the eleven organizations she remembered, last quarter, the way she would like to remember yours.

The tool does not make the gift. The tool tells you, on a Wednesday, that the drawer is there — and that the second Sunday in February is forty-six days away.

A note about Mrs. Hollis

She will sit down, on the second Sunday of February next year, with a cup of tea and her late husband's reading glasses, in the small armchair in the corner of the living room in Brookline. She will open the laptop her son set up for her in the spring of 2020. She will go to the recommendations page. She will hover, for a moment, over the search field.

What she types into the search field is what your last ninety days have earned.

You will not be in the room. The note will be in the room. The April update will be in the room. The phone call in July will be in the room. The small breakfast invitation in October will be in the room.

If the work has been done, she will type your name. The recommendation will be for forty-one thousand dollars. The grant will arrive at your office, by ACH, on a Tuesday two weeks later, with the polite reference line Recommendation by Margaret Hollis on behalf of the Hollis Family Charitable.

The CRM will record it, neatly, as a DAF gift, $41,000. It will not record the coffee in March. It will not record the cream paper on the Thursday. It will not record the cup of tea in the armchair on the second Sunday of February.

That is fine. Some of the most important work in this profession was never going to be in the file.

It was always going to be in the drawer. ♡