The Hardest Thing

It isn’t figuring out how to solve the problem,

or deciding what approach will work best.

It isn’t sussing out what tactics to use,

or who will be your partners and your competitors.

It’s not figuring out product-market fit,

and it isn’t even hammering out how you’re going to convince skeptics of your story.

The hardest thing is figuring out what’s really important to you.

The things you want to work for.

The things that are worth sustained energy and sacrifice.

It’s the act of clearing away the dross, of quieting the voices that are the noise, not signal, streaming through your head.

The moment you state your goal is the moment you can’t hide from it.

It’s the moment you have to stop pretending that you don’t know exactly what it is that you are here to do.

The humanity ante

The “ante” in poker is a bet that every player has to make before the hand is played. Before the cards are dealt, each player puts some money on the table – usually a small amount – and this makes it harder to fold one’s cards and walk away. The ante puts everyone a little bit on the hook for each and every hand.

In some games, it’s customary for the ante (called the “blinds”) to rise as time passes. Late in the evening, the blinds get big enough that they change the character of the game: players have to pull out a whole new set of tactics and strategies when the blinds are huge.

A similar dynamic is at play when two people sit down across the table for a first conversation – or for their first important conversation. While the rules of this game aren’t as explicit, there’s an ante that each player puts on the table from the outset. This is an emotional ante, a statement of how human you’re going to be in this conversation and in this relationship. You can see the first glimpse of this ante as the players answer questions like “how are things going?” and “what’s been happening on your end?”  The true question you’re answering is: “how real are you going to be?”

I’ve increasingly found that most people will match the humanity ante I’m willing to put on the table. Hold my cards close and they will too. Be willing to take some risk, to show my own humanity – in the form of being willing to share my challenges or flaws, my dreams or my frustrations – and they will also.

This is basically the opposite of what we’re taught in big institutions. These institutions exert a strong socializing power that slowly and deliberately beats the humanity out of us. The message is: be as un-human as possible, because that’s what it means to be a professional. (This is the same reason the emails from these institutions are so unreadable).

Part of what we have to remember is that to do anything that matters we must dare to do emotional labor. And for us to do that emotional labor together, the first step is that we show up as full human beings.

Ante up.

Subway Portrait

“Excuse me, m’am, may I draw your picture?” he says, white pad on his lap, fingers stained with charcoal.

“Pardon me?” says the woman sitting across from him on the subway, looking confused and a bit taken aback.

“Your picture…is it alright with you if I draw your picture?” he reiterates.

“Uh…sure.”

And then, as his hands glide across the page, his patter begins, not interrupting the drawing, which has to be complete in the two minutes before the last stop.

“This is what I do,” he says, “I draw pictures of people. Portraits. Been doing this for years, I’ve drawn 800 portraits of New Yorkers so far.”

She takes the bait: “All in one day?” she asks. Her guard is dropping just a little bit.

“No m’am, that would be impossible. Anyone who tells you they’ve drawn 800 portraits in one day, they’re lying to you. No, I’ve drawn 800 portraits since I started, and that’s why I can draw them so fast, because I’ve done it so many times. I’m an artist, you see, an artist. Don’t you like how that looks?” (he holds up the already – amazingly – half-finished sketch, which has gone from a few lines to, instantly, a pair of eyes, an outline of a mouth, a bit of expression, in about one minute).

She smiles, recognizing her likeness, the shape of her face, the crinkles around the outside of her almond-shaped eyes.

“See I knew that would make you smile! Now I can get that smile in the picture… Now I’m gonna give this portrait to you, that’s what I do, I’m gonna give it to you either way….Lots of people like these portraits, they hang them up, in their offices usually…And a lot of them pay me for them, even though I give them to ‘em either way, a lot of people pay me $10, or sometimes even $20…

(almost to himself) “Yeah, I try to get 10 people in a day to pay me $10 each, that’s what I try to do. Last guy I did this for he handed me a $10 bill, yes he did. And don’t tell me I’m not an artist, see? Artists make people smile and that’s what I’m doing here, I’m making something that will make people smile.”

Just a few more seconds for the finishing touches, and:

“So here you go, beautiful, here’s your portrait I hope you like it.” he says, handing it to her.

And she does.

And she pays $10.

 

In review: to create a situation where someone gives or buys, you must first create joy, a story, connection, a thing of beauty.

And in situations, like philanthropy, or busking, where it’s not clear what something is worth, it’s your job to tell them, to frame it for them, to say: this is what people who are happy and feeling a sense of connection in this moment typically pay. This is what the last 10 people did.

“I’m going to give this to you either way, but you gotta know that everyone else before you who liked their portrait gave $10 or $20 and hung the portrait in their office.”

Sure, she could decide not to pay, but if she does pay, you can bet it’s not going to be $1, which is what most people on the subway get when they ask for money.

His starting point was a $1 portrait. The story about the portrait, and the story about what people who like portraits pay, that’s what’s worth the other $9.

Individual and Institutional Fundraising

Over the past six months, a greater proportion of the fundraising I’ve been doing has been institutional rather than individual. By “institutional” I mean fundraising from people who have been charged with donating somebody else’s money – whether or not it’s a formal, recognized institution (e.g. a large private foundation, a corporation, etc.).

In both individual and institutional fundraising, there’s a strategic element and a people element. The strategic conversations are around goals and outcomes and what success looks like. The people element is around what motivates a person to take action – the story and the emotional elements that move people to act, as well as the interpersonal dynamics that are always at play.

The one thing that is missing from these institutional conversations, which easy to miss if you’ve not experienced it directly, is a deep, personal element. In my experience, real, substantive conversations about real, substantive philanthropy nearly always get personal: they touch on motivations, hopes and fears, aspirations, and legacy.

These conversations require something different from the person doing the fundraising: a comfort getting into that murky space where they, too, are more open, honest, and vulnerable than would ever be expected in a purely professional context.

My hunch is that the reason most people don’t wade deep into individual, big-ticket fundraising is either because they don’t understand how deeply personal these conversations have to be, or they are unwilling or unsuccessful at going there. This means that if you have the courage to take that leap, along with openness to do the real work that this leap requires – to learn about yourself, to understand your own motivations for doing this work, to help people talk about their own purpose – you’ll soon be part of a very small group of people willing to take it to another level. This path is a heavy lift, a long walk that requires emotional labor and has the potential for a serious personal and professional payoff.

Of course your other option is to sit safely at a desk replying to yet another formal request for proposal, hoping that your program will be the one out of 1,000 that’s picked out of the pile.

This is one of the greatest blend-in or stand-out opportunities in the nonprofit sector.

TGIM

“It’s almost there. Today’s Thursday,” I hear a fellow passenger say to her friend as we all walk off the train. Yet another person counting the seconds until the weekend.

(At that moment, she had 115,200 seconds to go.)

On and on we tromp down the endless treadmill, until, perhaps, we step up and step off.

It is especially rare to wake up one day and muster the courage to jump off alone. The treadmill’s moving too fast, and we might hurt ourselves when we jump.

What gets us there is the slow, consistent work of finding like-minded people to dream with, to experiment with, to discover what a different world might look like. We draw our courage from them, as they do from us.

When the moment finally does come to leap, we are surrounded by a community trust, that catches us, shows us the way, and cushions the fall.

Happy Monday to you.

What we need from you

What we need from you isn’t better thinking, more analysis and caveats, the low-probability risks you’ve explored, and how you’ve smoothed the edges.

What we need from you is the fearlessness to put your best ideas out in the open,

unadorned

for everyone to see.

Not more smarts, more courage.

The hard parts

The parts that are uncomfortable

The bits that no one else really wants to do

The things that make you feel exposed

And stretched

And outside of your comfort zone

The things that make it clear that what you thought it was going to take to get this done wasn’t right at all.  The funding isn’t there. The strategy hasn’t been sorted out. The roles and responsibilities aren’t clear enough. The team is too small and it doesn’t have all the right skills.  We’re just not where we need to be, and fixing things is going to be a heck of a lot harder than we expected.

All this really messy stuff?

That’s why we need you.

It’s because it’s hard that the work hasn’t been done….yet.