It Takes Chutzpah

A friend was recently telling me about the unexpected twists and turns she encountered on a weekend trip she had been planning for months. A last-minute, unexpected event delayed her departure date. I said: “So you had to pay a change fee?”, and she said: “I called the airline and told them it was a hardship. They waived the change fee and found another flight.”

When she arrived at her hotel, she presented her hotel-chain loyalty card. I said: “I never think about doing that. It seems like too much trouble,” and she said: “The front desk clerk announced that I had been chosen VIP loyalty customer of the day and I received a free upgrade to a fabulous suite.”

Finally, on the day she was returning home, she had a couple of hours to spare before leaving for the airport. She thought she could use the time to take in one of the local attractions, but the time for obtaining tickets had passed. I said: “Oh, that’s too bad,” and she said: “No. I saw a park ranger standing there and told her I’d really like to see this attraction before returning home. Was there anything she could do for me? She handed me a ticket for the next tour group.”

“How in the world did you get so lucky?” I exclaimed. “It never hurts to ask,” she said.

My mother used to say, “Boy, that person really has chutzpah” when they asked for something above and beyond what was offered. She was big on following the rules as they were laid out, and this apple didn’t fall far from the tree.

How often have I missed out on something because I think it does hurt to ask? I’m a risk-averse person, and my strategy for addressing the risk of being rejected is AVOID. If I’m not sure a business offers a AAA discount, I’d rather pay full price than to ask and be turned down. I avoid yard sales that don’t have tags on the merchandise because I hate to haggle over price. And car shopping . . . don’t get me started.

But could my lack of chutzpah be holding me back?

I looked up some synonyms for the word and found it has both positive (boldness, self-confidence, self-assurance) and negative (impudence, rudeness, pushiness) connotations. I think it’s weird that one word can be seen in two such different ways. Why not just choose to see it in the positive rather than the negative light?

For instance, as a project manager, I frequently have to learn new aspects of the organization or software because I’m not an expert in the product of the project. I will often hesitate to suggest a new way of looking at something, because I think I don’t know enough about the subject to offer an opinion. But at times I have chosen to do it anyway, and the worst that happened was that people rejected the idea. Who’s to say that people didn’t appreciate my boldness rather than judge me for my pushiness?

I’m going to promise myself that the next time I feel afraid of being pushy, rude, or impudent, I’ll picture myself as self-confident, self-assured, and bold instead. I’m hoping to uncover some unexpected opportunities in the process.