Every waking moment that I am outside of my apartment in NYC, I am constantly asked at every corner, subway stop, and on every train for some change. I normally don’t carry any cash or change so its very easy to avoid any awkwardness.

I’ve lived here for just over a month and every day the same thing, “change?” over and over again. That is until a few days ago. An obviously homeless man walked up and asked me for twenty dollars. I was shocked but instantly compelled to pull out my wallet and give him my only twenty.

In an instant this man had done something to me that led me down that path. He stood out from the crowd by asking for what he really wanted. He started an internal dialogue inside of me “should I do it? twenty bucks is a lot of money! but I’ve had those times when twenty bucks would seemingly fix almost anything”.

I handed over the cash and he said “thank you kindly” and then he walked over to the a deli and ordered a sandwich.

In reality the story at hand isn’t about him or me for that matter. It’s about you. How many times have you asked for less than you really wanted and gotten exactly that. As a designer under bidding a project, or for a birthday asking for a sweater when you really want a pony. Chances are if you ask for a sweater you won’t be getting a pony so why set yourself up for failure. Ask for a pony and you never know what may happen.