How I Lost $100.00 to My Boss

There was a time when I could say the words “I am always right,” and, without ego, be correct. It has been reassuring to me knowing that I have a mind like a steel trap. I feel in my old age that my steel trap is getting a little rusty…

I was sitting with my boss at an awesome Middle Eastern/Mediterranean restaurant. We had finished our meals and were talking about the latest in Search Engine Optimization when the bill arrived. My boss looked at the bill, then up at me intently. “It’s your turn to pay,” he noted sternly. “No way, I paid last time. It’s your turn to pay.” He huffed, and emphatically said, “I’ll bet you $100 that I paid last time.”

Suddenly, I was at the poker table. I was sure I had the winning hand, and I had some decent cash on the table to represent it. My boss just went all in against me, with amazing confidence. People who go all in with that much self-assurance probably aren’t lying, especially if they don’t play poker, right? I should have folded right there. I should have said, “I’m pretty sure I paid last time, but for argument’s sake, I’ll pay this time and we can figure it out later.” For some reason, however, I decided to trust my brain and try to call his bluff.

“Fine. $100.”

Man, worst hundred bucks I’ve ever lost.