Show Me the Money: The Dirty, Lonely Business of Fundraising

Never in my wildest dreams did I think I’d work as a fundraiser.

Some people call it a development professional, director of advancement, or even shnorer. However you slice it, my job is to ask people for money — and pray they say yes.

When I was a kid, there was this Rabbi-type that would visit our house about once a year. He always came with a big black briefcase stuffed with papers. His suit was always creased. His beard always sprinkled with dandruff that floated into neat piles on his shoulders. He sat at our kitchen table and exchanged pleasantries with my parents, this meshulach as we called him. I don’t know what they spoke about, but it was always quick — and resulted in my parents giving him a check.

Throughout my childhood, we diligently watched the Jerry Lewis telethon. The comedian-turned-master telethon host and his all-star cast sang and danced and implored for pledges, all while holding tight to our heart strings. And then the crescendo: a sweaty, passionate Jerry Lewis, his bow tie loosened after hours on TV, yelping for joy as the final numbers — always more than the year before — were displayed on the tote board. “G-d bless you all! G-d bless you all!”

Once, as a young adult, I watched some taped sessions from the Shluchim convention, a gathering of approximately 4,000 Chabad emissaries from around the world. The workshop was on how to be an effective fundraiser — from making new contacts, to developing relationships, to gaining attendance at community events, to securing donations. “Is this what it means to be a Shliach? Pshht,” I (naively) thought to myself. It all felt so commercial to me, so impersonal.

Somehow, raising money seemed liked a dirty business. From unkempt Rabbis, to overly-excitable telethon hosts, to how-to sessions for spiritual leaders, asking for money seemed disingenuous.

And then — it became my world.

During the first year of the school I co-founded, Lamplighters Yeshivah, we only needed to hold one fundraiser: an end-of-year concert that brought in the exact amount of our deficit for the school year ($36,000… those were the days).

During our school’s second year, things shifted. We lost some families mid year and with that, thousands of dollars in tuition. I was quickly confronted with the harsh reality that to keep my dream afloat, I would need to fundraise — a lot.

I was so naive then. I thought it was so easy. And in certain ways, it was.

A crowdfunding campaign to fund our renovation. Meetings that resulted in some gifts. Donated materials. I had no how-to manual, no real sense of how the numbers would take on a life of themselves as the school grew. I believed in our cause to the depths of my being — obviously others would too, right?

Yes and no.

Imagine pouring your heart out to someone, pitching something you feel is truly revolutionary, and they just look at you, completely unmoved.

Imagine spending hours crafting an email to someone and getting no response in return.

Imagine practicing saying numbers over and over again so they feel natural coming off your lips — a thousand, ten thousand, a million dollars — yet still feeling slightly awkward every time you say them.

Imagine getting to know someone and sincerely wanting to connect to them — while you wonder how they can help you.

Imagine navigating all this as a woman in a male-dominated world of l’chaims and farbrengens and hobnobbing at events, an unspoken barrier in almost every encounter.

Of course, there have been many moments of incredible triumph, like a match drive in which we raised $200,000 for Lamplighters in 24 hours. Surprise gifts that arrive just in time to cover payroll. Relationships with people who are so incredibly supportive, so full of wisdom, their friendship worth more than all the money in the world.

Its so strange. Me, who has such a hard time asking for help. Me, is so scared to need. Me, who when feeling vulnerable, pretends to be so tough.

Now my job is all about the vulnerability I seek to avoid in my personal life. I hold the weight of 92 children and 26 staff members on my shoulders; of growth and expansion and strategizing for the future; of plans to buy a new building and scholarship funds and growing bills and salaries I wish I could raise more and more. And of course, I am not alone — but you better believe it sometimes feels like I am.

A couple of months back, I attended a conference for educators and leadership of Jewish Day Schools across the country. I joined workshops on all sorts of things related to raising money and creating a “culture of philanthropy” at our schools. The facilitators, all experienced development professionals, shared organizational tips, scripts, giving tables, and more. How to empower our boards to get involved? How to steward our prospects? How to make that “big ask”?

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But beyond all that, here’s what I really wanted to know: Why wasn’t anyone talking about how lonely this job is?

Cold calls, emails to people you don’t know, conversations with people who don’t answer back. The constant wonder how you’ll meet someone new. Ready to stuff your life’s passions into a ready-to-consume sentence about 1 minute long.

I am always in a position where I need something from someone. There are constant ups and downs. My job is never to accept the first “no”– and I am constantly fight to bounce back from rejection.

Yet in the loneliness, there is the potential for such deep connection.

Because to be a fundraiser is to truly listen to people.

To be patient.

To show authentic interest in another person.

To have no shame.

To be humble and recognize you are working for a deeper mission.

To be open to the blessings that continuously flow from a Higher Power.

To be willing to be vulnerable.

To ask for help.

To allow someone else’s hopes and dreams to become your own — even if just for a heartbeat.

Being a fundraiser is to appreciate the magnitude of generosity when someone chooses to give of his or her hard earned livelihood to your cause.

And, yet, who really is the giver? Who, in this relationship, is ultimately the receiver? It’s not so clear.

And in life, aren’t we all constantly walking this delicate tightrope, at any given point both the nurturer and the taker, balancing seemingly opposing roles in all our relationships?

One of my first gifts came from a person who was “looking for a cause to be passionate about.” Nine months pregnant with my fourth child, I walked him over to the renovation site of our school, about to start its third year. In a room full of sawdust and wood beams he began to believe in our dream. He saw where we were headed- and how we need him to get there. And when he tells me time and time again over the last three years how much we’ve given him, how supporting our cause has enriched his life, how this is now his dream, too — I believe him. I know its true.

So no, its not a wholly dirty business. In fact, as hard as it is, its one of most rewarding things I could do. It’s more holy than dirty.

Every day, I am connecting with benevolent souls who have become my teachers, bringing generosity to life in a way that regularly brings me to tears.

Every day, I put my heart on the line, making myself soft and vulnerable- against all my defenses- for something I truly believe in.

And every day, our dreams – of givers and receivers alike – are becoming more and more actualized, more and more alive in front of my face — one hard-earned dollar at a time.