Stages and conferences calls

How the “rules” of storytelling work for philanthropy

By day, I work hard to transform the field of philanthropy. By night, I’m on stage as a performer, sharing true stories about my life. My performance work is overtly creative — there are no screens, spreadsheets or conference calls. When I have a mic in hand, my language is decidedly NSFW. My stories are about personal parts of my life: love, sex, dating, spirituality, womanhood, and the occasional tale of mundane moments that make being a human hysterical. The stories I experience in daylight are different, and I spend a lot more time listening. I listen to remarkable stories of the grantees I work with at Kindle Project. I hear stories from Indie Philanthropists who stretch beyond their comfort zones and take risks to make the field of philanthropy more effective and to make their grantmaking meaningful.

The other day I was co-facilitating an all-day storytelling workshop to a group of 30 health-care professionals. We started the day off with some tips to think about when crafting a true story. They are rules I use for my stage performances but they apply just as easily to any setting where you might find yourself conveying a story — say to your boss, client, or Tinder date. As I was explaining my handy set of rules to this group I had a revelation — Hot Damn! These rules apply to philanthropy. I can’t believe I had never seen it before.

It may seem like I live in two disconnected realities but, really, there are very clear parallels between my experiences with philanthropy by day and telling stories by night. Despite the obvious differences, both my daytime and nighttime professional lives require the same skills and offer similar challenges. Both fields need the truth, even when it’s hard. Especially when it’s hard.

Here are my top five storytelling “rules” for the stage and how they can work for philanthropy:

1. The story has to be true and has to have happened to you.

One time on stage I told the story of how a dear friend met her husband. I played a very minor role in their fantastical union. But still, the story didn’t quite land because it wasn’t really about me. A story about a traumatizing haircut had me connecting more with the audience. You catch my drift? Your personal experience makes the narrative sing. Thanks to The Moth for popularizing this rule above all others.

For philanthropy, this is about transparency. There are acres of room for improvement in our field in being transparent about where our money comes from, where our investments are, who our collaborators are, and what processes we use for making funding decisions. Also, and perhaps even more importantly, if we’re funding in a community outside of our own, how do we assume to know what’s best for them? As a first step, we talk with this community. We build relationships. We make them decision-makers or, at the very least, we listen to their stories and let them shape our thinking, feeling and decisions.

2. Don’t bring notes on stage.

The one time I brought notes on stage, I bombed. It’s not because my story wasn’t good. It’s because it made a firm shield between me and the audience losing any glimmer of hope for authentic connection and the magical sneak attack of vulnerability. In my case, that ended up with me yelling at an audience member who laughed at my reverence for Michael Jackson’s music. Not my proudest moment. Notes can masks important truths. Beware.

In philanthropy, this is about authenticity. It’s about being absolutely present with our teams, colleagues, and grantees and being straightforward about our discomfort, frustration or challenges we might be facing. It’s about building real, trusting relationships and bringing our full, messy selves to this work. As funders, we expect that grantees will be open, honest and clear, yet we are rarely held to the same standard. Authenticity makes transparency that much easier. Every method of Indie Philanthropy has its challenges — facing those with authenticity makes working with those issues a lot less bumpy.

For the sake of TRANSPARENCY and AUTHENTICITY — A photo of me on stage, likely in shock and delight at the personal truths I’ve decided to reveal in the moment.

3. A good story needs a beginning, middle and an end.

This is more of a perpetual note to self since I find classic narrative structures to be challenging so I eschew them in favour of spontaneous revelations and rants, keeping my fingers crossed that one such revelation will occur from an alchemical reaction with the audience.

The field of philanthropy loves to talk about impact and metrics. We need smart maps and smart goals for our philanthropic organizations. Sure, we know this to be true. But, we also need to be nimble with our plans. If we are too rigid in our structure we don’t have the room to respond to inspiration or crisis. And then we’re at risk of getting so carried away with metrics that we lose sight of what really matters in philanthropy — the stories of how our grantmaking made an impact on individuals, communities, systems and movements.

As a storyteller I believe wholeheartedly in the power of anecdotal evidence. I believe that stories contain the important truths necessary for real transformation. I have learned to swoon over well executed data, metrics and reports because they do reveal some very hard truths about our field. I have a dreamy project on the back burner of my brain that will somehow turn the stories of the movement of Indie Philanthropy into hard data, ready to inspire the masses. Thanks to Giorgia Lupi at PopTech last year for reminding me that “data is about people, when it matters.” Structure matters, but to me, stories matter more.

4. Never tell a story that involves details about someone else that you wouldn’t say to their face.

I learned this lesson the icky way. I told a story of details about a date I was on that I found…unsavoury. Details that were comedic but never details I would have revealed to this person that I didn’t enjoy. It would have hurt his feelings. I didn’t say his name on stage, but the icks were there regardless. They still are. The icks are never worth a laugh. This is just a good life rule thrown in for good measure. It’s about integrity, courage, and tact.

Our field of philanthropy is a tough one to navigate sometimes. There are organizations or practices that we not only disagree with, but that might even grind our gears. How can we continue to work together to make our field better? We do that by reaching out to those that seem like unlikely allies to build community and find opportunities for collaboration across our perceived differences. This is where we start to build a movement.

5. It’s okay to chuck all the rules into the bin.

I’ve never been all that great at following rules and favour spontaneous inspiration over carefully crafted performances. Maybe that’s because I have a complex resistance to rehearsing and feel envy for those that do so with care. Sometimes, a story will just come to me in the moment of a show. So, I’ll run with it. Sometimes I bomb, sometimes I don’t, but I’m always happy to take a chance on telling a story that I didn’t know had to come out of me. Having the freedom to chuck out a set of rules or plans means that my brain space is free to let my imagination do the work.

As per usual, bell hooks helps me out in expressing exactly what I’m talking about:

“Definitions are vital starting points for the imagination. What we cannot imagine cannot come into being.” — bell hooks

I’m going to repeat that last one, “What we cannot imagine cannot come into being.” Hello?!! We need imagination if we’re going to work to make our systems and lives better. Sometimes the rules just don’t matter. When we created the Indie Philanthropy Initiative our little tagline explained the concept behind our project so perfectly: Funding, Reimagined.


Here’s the thing, mainstream philanthropy wants to present itself with a shiny bow on top — we gave this much money, and it amounted to this much “good.” Why I’m so passionate about Indie Philanthropy is because it’s about acknowledging what a mess it is to have substantial amounts of money in an unjust system. It goes beyond just noticing what gives us the icks about this system and shares so many ways to work within, around, and outside of that.

Indie Philanthropists face the power dynamics that come with privilege, and they take intelligent, imaginative risks and act with bold integrity. They are also humble enough to accept when there are mistakes made, and then learn from these mistakes to do better.

A truth for stage life/philanthropy life found behind a mobile toilet on Lundi Gras in NOLA.

Indie Philanthropy is a good story. And we all know that any good story is not about two perfect people who meet, have no conflict, have everything be flawless and easy and then live happily ever after. A good story includes risk, fear, sadness, obstacles, and honesty about the truth of what it is to be alive. Mainstream philanthropy is often tempted to ignore these truths — Indie Philanthropy wants to expose them, revel in them and empower practical ways of working with all of this.

Changing culture can be really hard. It can take decades. And in my lifetime it’s very probable that I will not see philanthropy in the place that many of us are nudging it towards — the democratized, power-sharing and redistributive place it needs to get to if we are to make lasting social change. But with transparency, authenticity, collaboration, imagination and a little wiggle room, it is possible that we can move it a hell of a lot closer.


Learn more about : me, Indie Philanthropy, Kindle Project