The Money's Not the Problem. Holding Onto It Is.
As a culture, we’ve conceded that money is complicated (to wit,"Mo Money Mo Problems,” the #richpersonproblems memes).
I work up close with that complexity, advising philanthropists on how to give freely.
Here’s what I see — and what might help if the money sits uneasily with you too.
Old money, new money: same doubt
People who inherit wealth grapple with feeling — correctly — that they did nothing to earn what was handed to them. They can feel burdened by a family’s legacy or ashamed of how the money was made in the first place.
Those who made it themselves — through shrewd investing, entrepreneurship, joining the right unicorn at the right hour — feel the weight too. It isn’t quite impostor syndrome. It’s closer to terror: that whatever they did the first time was a fluke, a lightning strike unlikely ever to land twice. It’s the one-hit wonder or the novelist whose first book was a sensation and who now confronts a blank page, wondering if the well has run dry.
It shows up for different reasons, but old money and new money often share an uncomfortable question: Do I deserve this? At some level they already know that they hold more than they need, and that the surplus could do extraordinary things elsewhere.
Why we give
Maybe I’ll feel better if I give some away. Though in practice, giving almost always feels good, philanthropy-as-a-salve is too easy, and it isn’t the point. In reality, the point is that the discomfort around money signals something about your values, and it’s on you to pay attention and put it to work. No amount of rationalization will ever make I deserve this feel entirely true.
What philanthropy does is let you reframe your relationship to wealth as stewardship — and then act on it. It stops being about you and becomes about what the money can do when it’s outside you and beyond your control.
But it isn’t clean.
Here’s the part nobody in my line of work likes to say out loud: giving doesn’t fully dissolve the discomfort, and sometimes it sharpens it. The moment you become a donor, you get cultivated: courted, thanked, seated well, made much of.
And cultivation quietly reintroduces the very doubt giving was intended to relieve: Are these people warm to me — or to my capacity? Anyone who has been on the receiving end of a development office knows the feeling. Giving helps. But it isn’t clean. I’m not going to pretend otherwise.
The relief of giving without strings
The complaints add up to one thing: disappointment.
And disappointment breeds control. Burned a few times, a donor holds on tighter — restricting a gift, prescribing an outcome, dictating where every dollar lands. Or they stop giving entirely. The grip feels like insurance against being let down again.
It rarely works, and it exhausts you besides. One might think that anxiety around having money is about scarcity — the fear of losing it. Some of it might be.
But that’s not the fear I hear most.
Rather, from donors up and down the spectrum of giving, I hear complaints I could set to music:
The organization goes silent the moment the check clears
They only ever call when they want more
The person I trusted there is three hires gone and no one there knows my name
Most maddening of all, no one can tell me what the money actually did
The person best placed to judge how the work should be done is almost always the one doing it, not the one signing the check. Put the discipline up front — choose organizations you genuinely believe in — and then let the trust follow.
This is why the MacKenzie Scott model lands the way it does: she gives without restriction, backs the organization’s own expertise, and gets out of the way. As a bargain, she sidesteps the whole ritual of being cultivated. Donors who give this way describe a freedom that’s hard to put into words. The relief isn’t about the money. In fact, nothing has changed day to day: same houses, same trips, same comforts.
What has changed is that they’ve stopped holding on. Imagine stopping the mental machinations and emotional contortions it takes to justify everything you’ve been given. It’s true liberty.
A personal reflection
We all fall short. At a gala recently — for an organization whose work I truly admire — I was irritated that we weren’t listed at the right level in the program or seated where I thought we should be. My pique was quickly followed by shame: Physician, heal thyself! My first reaction wasn’t letting go; I was putting myself back at the center of something that wasn’t about me at all.
And that’s the whole thing, isn’t it?
It’s tempting to sort giving into guilt on one side and vanity on the other: the dichotomy of expiation or attention. But that misses the person I find most poignant: the one who genuinely wants to do good and still can’t loosen their grip enough to let the good happen. Good intent isn’t what saves a gift — letting go is.
You can want the right outcome with your whole heart and still strangle it — by prescribing, restricting, steering from the outside. Knowing the trap doesn’t lift you out of it: I know it cold, and I still sulked over a seating chart. What did it matter where I sat, or who knew what I’d given? The point was never to perform giving. The point was to give.
So, don’t hold on so tightly. Let go.
Remember that the money is apart from you, not a part of you. Let it out into the world to do its work — and everyone, you most of all, will be better for it.