The Plot Thickens

Two years into this business, I have a confession: I’m getting pickier about the work I take on. 

I’ve realized I like philanthropic advising best when I get to stay for the whole story - not just helping a family solve one particular question or complete one particular project, but sticking around long enough to understand the history, relationships, personalities (oh, the personalities…), and decisions, often across generations, that brought them to where they are today.

It’s a little like a really good TV series. There’s context that carries from episode to episode. Inside jokes that would make absolutely no sense to someone who just tuned in (all hail Arrested Development). Drama, levity, shifting relationships, unexpected plot twists, and characters who occasionally surprise you.

When I started my philanthropy advising practice two years ago, I said yes to lots of different kinds of work. I took on ongoing advisory relationships, but also many discrete projects. Each engagement taught me something, and after two years, I’m now crystal clear about where I want to spend my time:

Ongoing work with family philanthropies, supporting private foundations and holders of large donor-advised funds where I get to stick around as the story unfolds.

This philanthropic capital is being used as a symbol of family values. The decisions can be complicated, the family dynamics can be fraught and the stakes are real. I find joy preparing for and leading the quarterly board meetings, setting the grantmaking calendar, facilitating conversations about which organizations to support and how much to give. I am present for the moments when trustees disagree, and when they find their way back to common ground. I’m in the weeds on next-generation engagement and any subsequent cultural misalignments. There are annual rhythms that give family philanthropy its structure while leaving room for the unexpected. Over time, context accumulates.

So I’m making a more deliberate business decision about where I put my time - I’m saying ta-ta to the standalone projects and will only be accepting long-term partnerships with family foundations and large DAF holders. I am focusing where my heart is: earning trust, creating the systems and rhythms that make philanthropy easier, managing the details and being there as families and priorities evolve. 

I’ll still be tuning in long past the pilot episode.