Convenient Again
A woman sits at a desk covered in stacked papers.
She is literally jailing herself in.
When your office is next to the largest, most powerful name in Boston, who happens to be your boss, you build a screen.
She was all in.
I was not.
And I think we both knew it.
The first time I met him was at an event.
I was transfixed.
Who is this guy?
Not the image. Not the magnetic CEO people hurled themselves at across the room.
Who is he really.
He was like everyone else who sat in that seat.
Except maybe kinder. More genuine.
Because he didn’t need anything from anyone.
He was in the privileged position to really choose. Who he was, what he wanted, what he wanted his life to mean.
Someone told me he took after his mother. Generous. Kind. Big heart. You could see it.
When I was hospitalized he called.
He had also arranged a hospital room with a view for a former colleague who was actively dying.
He did these things knowing there was nothing he would get in return.
But there was a larger dynamic at work.
Someone else said: of course his father is agitated. He gave this city, this organization one of his sons.
That is what made philanthropy different at this organization.
All of Boston’s elite flooded to it. To have a piece. To lend a monetary favor. To share their name next to the organization.
Did they genuinely give a shit?
Maybe.
As the money flooded in, the kids thrived.
The programs were real. The impact was measurable. The mission was being served, not because the donors came for it, but almost in spite of the fact that they didn’t.
I used to wonder what would happen when he left. Whether the money would follow the mission or follow the name.
I had been in this exact center before.
To learn about adoption. To begin that journey.
I sat at a table. Children racing around. Volunteers milling. Staff laughing. Kids engaged in projects.
A six year old girl asked me for help with glue.
Her hands wrapped around the bottle. Mine wrapped around hers. Both of us squeezing together.
I came back to the place where my adoption journey started.
I thought I could heal through the kids.
Maybe that is why I stayed as long as I did.
One fall evening we hosted a private dinner for some of the city’s wealthiest donors.
The development team planned it. Cultivated it. Built it.
When the dinner began, leadership stood behind a curtain.
My boss among them.
Literally.
The donors sat in the spotlight. The names that mattered occupied the room.
The women who had created the evening disappeared from it.
The kids still benefited.
The mission was still served.
The stacks of paper were her cage and her preservation.
I would not be caged.
But I could no longer pretend I didn’t understand the performance.
I stayed until I could find another role.
Not because I stopped believing in the kids.
Because I could no longer afford to keep paying what it cost me to believe in the institution.
Years prior I had worked for another organization.
One of the ones that found me inconvenient after the birth of my daughter.
The exit was cold.
One day my former assistant called.
He is on the phone trying to get to your CEO.
I smiled. I knew what was coming.
An email from a former cabinet colleague. She wanted to meet for lunch.
I cared for her. I respected her.
But I knew, the second I opened the email, that this was not about reconnecting.
This was about ascertaining my feelings. Creating an opening.
One hour before we were supposed to meet, I emailed her and cancelled.
I had been a pawn enough in his game.
I cannot remember if she attempted to reschedule and I declined.
What I remember is this:
The CEO at my new organization had so much power that a former president was willing to humble himself enough to work to get to me, through a former colleague I trusted, to get to him.
Convenient again.
Not because anything had changed about me.
Because of the room I stood in.
Performative Philanthropy: The practice by which institutional donors, boards, and civic elites direct resources toward mission-driven organizations not primarily in service of the mission, but in exchange for proximity to power, social legibility, and the cultural currency of generosity.
Trust the reader. Cut until it hurts. Earn the silence.