Street Fundraising: highs, lows, sadness, and excitement

Today, I started my new job as a street fundraiser. From 11 a.m. to 6:30 p.m., I was one of those annoying people on the streets that stopped everyone and asked them to donate to a charity. Let me break down what was possibly the best, worst, most tiring, most fun, most social, most depressing day of my life.

In my 7 hours in the field, I'd say I tried to talk to 350 people. There were a couple techniques I used.

(a) Wave either one or both my hands from 20 feet away to get them to notice me, and say "Hi!"
(b) Move so I was in their path, extend my hand, and say "Hi!" when they were close enough.
(c) Bow down, or fling my hands out in a hug-like formation, and say, "Hi!"
(d) Tell them their dress / skirt / hat was cute.

Of those 350 people, 15 of them stopped to have a conversation with me. The other 335 did one of five things:

(a) "No thank you, I'm running late / have work / can't talk"
(b) Took out their phones and stared intensely at them
(c) Looked straight ahead and, with great willpower, tuned me out
(d) Veered at an angle away from me, and gave me a tiny, tiny smile of acknowledgement
(e) Smiled and said, "Not today."

Of the 15 people who talked to me, I had some pretty interesting conversations.

One girl walked by me, and I yelled, "Are you a native New Yorker?" I had to follow her down the block, and turns out she was born in LA, lives in San Francisco, goes to HBS, worked at Goldman Sales and Trading, and has a boyfriend already.

Another was this MIT 2011 grad who was walking to Equinox gym for Brazilian jujitsu. There was a Parsons student I walked for two blocks with. A Columbia student who had been approached multiple times. A nice Indian man who said he'd come back but never did. A black woman who was in the middle of filling out the form before she refused to give me her credit card information. The rest don't really matter.

I signed up one person my first day. He was a beer salesman (niceeeee), half-Filipino, and told me I had a great pitch. I was happy. It means I have 3 more days on the streets before I could potentially be fired.

There are two lessons I learned from the day. I'll run them down in importance.

1. White people won't stop for me. It's just a fact. Of the 15 people that stopped for me, 13 were minorities. Asian, black, Latina, European. There was one nice young lady and one nice older man who were white. That's it. Either I'm subconsciously psyching myself out when I'm approaching them, or I'm just not attractive and familiar enough to pitch them. If anyone has any insight into what the f*ck is happening, I'd love to hear it.

2. It's really easy to get sad on this job. In one hour, I have an average of four conversations, all usually less than a minute. That means the other 56 minutes are spent either getting rejected, smiling and waving before I get rejected, or standing around waiting for a person to come so I can (likely) get rejected. It was the worst between 3:30 p.m. and 5 p.m., when literally one person stopped for me. I felt like shit. Like I wasn't a worthwhile human being. I questioned why I took this job in the first place. I asked myself why New York was such a mean place. I wondered if I cared enough about the organization, and whether it was showing in my pitch. I resigned myself to a "0" sign-up day, until my coach snapped me out of it. I got my first sign-up immediately after.

For the next three days, I need to average one sign-up a day. If I was pushier (I don't know, I'm not sure I can bring myself to do it), I could have gotten 3 today. Maybe. It's all about rapport -- developing it so they're comfortable enough talking to me in the sun for 10 minutes, giving me their credit card on the street, and sponsoring a child for two years. That's a Big Deal. I'll get better.

Immediately after work, I attended a GrubWithUs dinner down the street. It was surprisingly lively and fun. The people were great. I ended up staying for 3 and a half hours. On the subway ride home, I fell asleep. And now, I'm going to check my email for the first time in like, 22 hours.

This job is tiring. The biggest difference from a desk job is that there's literally no "Off" button. I can't switch my browser window from Excel to ESPN. I have to be On every second, because I'll never know when that one good person will come by. I'm engaged 100% of the time, in one way or another. And, despite how tiring it is, I think I might love it.