I used to pride myself on not asking for things. I wasn't exactly a Spartan lad with a fox inside my clothes, but I was generally self-sufficient and stoic and probably a little martyred and put-upon. So attractive. But better than being a schnorrer.
Then one day last year, my basement flooded. Bottom dropped out of the water heater and my plumber, a really good guy, said: "You don't want to pay my hourly rate to wet-vac your basement."
A contractor who has done lots of projects for my family was working in our office space and I asked if he had a wet-vac. He said he did, then asked: "Do you actually know how to use it?" I didn't. He and his colleague then cleaned up my basement for me. All because I asked.
I found this amazing. I mentioned it to a woman in my life who offers me much wise counsel, although it's usually about nutrition and how to cultivate good behaviors so that eating well is something you do almost mindlessly. She said: "Most people like to help other people. And you pride yourself on never asking, you deny other people the opportunity to be kind to you."
The insight lodged in my head. It was a real lightbulb moment for me. So in February, when I saw Brian Koppelman, most recently the creator of Billions, I walked right up to him and said: "I've heard you on The Howard Stern Show and I would give anything to be on The Wrap-Up Show."
Brian Koppelman made this happen. I had a blast. And it was all because I ASKED.
(If you need background on this, ask me in person. Long story short: I love The Howard Stern Show and have been listening for 20 years. There are a lot of reasons to love it, but it's currently THE best place to hear creative people talk about what they do and how.)
Next week I'll tell a story about a person so kind, so gracious that I literally cried when she offered, out of the blue, to do something nice for me. In this case, I didn't ask. But I still think there's something to asking for things you really want.
Just don't be a schnorrer.