One of the best things I learned while I was on staff at Bay Hills Community Church was also probably the most embarrassing things I had to endure when Dave and I would go to conferences, meetings, restaurants, etc. He would always ask for something free.
Dave is probably one of the cheapest people in the world. That's not a exaggeration. He will admit it and I think he actually takes pride in it. Don't get me wrong, when it came to being able to get what we needed to reach people in the Bay Area, he would spare no expense (at least for me), but personally he's super cheap. I was always embarrassed when he would say "can I get it for free" but always happy if he got me something for free.
I've learned in the past few years that it never hurts to ask. I've always thought that I would look like a freak if I walked up to someone and asked them for something. It took a while for me to realize that the worst thing that could have happened would be that they said "no" and you'd be in the same boat you were before. You have to forget about appearing to be cool.
The night before I got married, my groomsmen and I were staying at the Grand Hyatt in Buckhead (a nice hotel in Atlanta). When we were walking back from the ESPN Zone where we spent my "Bachelor Party" we saw P-Diddy, or whatever we're calling him now, outside of the hotel probably getting ready to go out as we got ready to sleep. My instinct was to play it cool and act like we didn't care he was there. That's what we did and guess what, I don't get to tell the story about how I met and partied with P-Diddy the night before my wedding.
You never know what will happen when you ask a question. You always know what will happen if you don't: nothing. Don't waste great opportunities to meet people, get free stuff, or have experiences you never thought possible. Just ask.
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