In a session today in Aspen at the Council on Communication Management’s conference, a speaker talked about taking a career mulligan. He asked everyone in the audience to think back on our own mulligans.

My first, not my last, was a doozy. I was fresh out of college and working as a peon in a small PR firm. My abusive, yelling, horrific boss was running a big shopping mall give away. Printed cards were individually printed with scratch-off numbers and there was one number that would win the big prize. The boss lady (I use that loosely) demanded that the winning card and the box it was in be clearly marked for identification. What did I know?

After several weeks, the client got antsy and wanted the winning card to come out. We trekked to the mall. With the client standing there, the boss yelled at me to bring her the winning ticket. I went to the stock room, found the box and the ticket. Again, what did I know?

As I walked toward her with the singular ticket she shrieked at me “NO, NO, you can’t bring THE ticket! That’s against the rules!” The strict rules about such random drawings is that you can’t know when you’re handing out the winning ticket. Then, it wouldn’t be fair and could wind up in court.

I was crushed. I didn’t understand the strategic issues and had made a blunder in front of the client. For a time I blamed the boss and the firm, which I actually left shortly after this mulligan. Later, I realized that I needed to be more strategic about my thinking in order to not take another such mulligan. I couldn’t rely on anyone else around me to see these coming.

I’ve taken other mulligans since then, but that’s the one I’ll always remember.