I begged for money on the streets and THIS is what happened.

I wish I could tell you that the title of this post was some kind of joke. But it’s not.

I literally took to the streets of DC today to ask strangers for money.

My business coach takes sick pleasure in pushing the limits of what I will tolerate, all in the name of helping me grow my business, of course.

At 1:20pm he sent me into the streets of Washington DC with nothing but my phone and told me to come back in 90 minutes with at least $50.

The rules were that I couldn’t use any money that was in my wallet and that I couldn’t sell any existing product or service of mine and I couldn’t ask anyone I know for money.

With optimism in our hearts and naïve enthusiasm my partner-in-capitalism, Dawn, and I hopped in a cab to the highest concentration of people the cabbie could find — the National Mall.

We were in it to win it until we actually got out of the cab and realized we had to ask strangers for money.

The timeline went like this.

1:45pm | Told middle-aged man the truth about why we were asking strangers for money and asked if he had a dollar for our cause. He smiled the kind of smile that implied he thought we were certifiably crazy. He told us he did have a dollar, but he wasn’t giving it to us. #movingon

1:50pm | Found a young couple trying to take a selfie in front of the Washington monument. Offered to take their photo. Told them the truth about why we asking for money; asked them for a dollar. Got a dollar. #winning

1:55pm | Second attempt at the kind-stranger-who-wants-to-help-you-take-your-picture strategy. They didn’t speak English. We didn’t even bother to ask them for money. But we did take their picture. #fail

2:00pm | Made a discouraged third attempt at the kind-stranger-who-wants-to-help-you-take-your-picture strategy with a family of three. They told us they spent all their money at the food trucks. They may have been lying, but they were so cute I forgave them. #epicfail

2:05pm | Decided to switch strategies. Wandered over to the food trucks, asked a man running a food truck where we could find a bar full of drunk strangers who would be friendly enough to give us money. He suggested Georgetown. In the business world I’m calling this a win, the man gave us a referral just because we asked. #almostwinning

2:15pm | Caught an über to Georgetown, walked into a bar. Asked the bartender where we might find friendly drunk people who might give us money, because it didn’t seem like that was going to happen at that particular bar. We told him our truth and he told us to just go to an ATM, lie about it and call it a day. #whataschmuk

If I had done that, I wouldn’t be writing this story.

That bartender sent us to another bar full of old guys. He said they would surely buy us a drink and give us money. We went, but it was swanky and we totally chickened out for fear of getting kicked out.

2:45pm | Got back in an über totally defeated and making lots of excuses.

Here’s what I learned about myself:

In business and in begging for money on the streets, I have a lot of strategies and sometimes I give up before I give them a fair chance.

I am really comfortable asking for referrals.

I can be a judgy bitch, I make a lot of assumptions about whether or not people want to talk to me or work with me and I make decisions based on those assumptions and that, my friend, is no way to live. So I’m going to stop doing that now.

Laura Diaz is the CEO and Senior Brand Consultant at Kiss Me Creative where they make client love all day long. Her super powers are efficiency, follow through and creativity based on sound logic. She enjoys long sips of coffee and short lines at Starbucks.