Because of the people-pleasing nature of myself, I will rarely be the person who starts asking for discounts or deals on things. Even if it’s at a garage sale and it’s what’s expected, I often won’t do it.

However, throw a little competition in and suddenly I can become a savage bargainer.

I’m similar in most sports contacts. I am competitive, but not a physical player at all, but if I start playing basketball with a guy who’s 6 inches my height, I play up to that level, which often means playing more physical. Not fouling, but doing everything possible that a smaller guy can against a big guy.

I gave myself a competition this weekend. My wife and I were planning to go to KC, and I thought, how can I get the best deal possible on lodging? I looked and most Airbnb’s were going to be over $500 (or they looked way more sketchy than I was comfortable with), and the cheapest hotel I found was $450.

I researched hotel discount tactics and went from there. Originally thinking that I was going to wait until I got to the hotel to ask for the bargain, I changed my mind and decided to call the local hotel to see what I could do.

After following through with some of the steps, I was able to drop the price of the hotel by almost $200. It felt terrible and great all at the same time. I almost felt like I had swindled the man on the phone out of money, but being able to have an extra $200 was not something I was going to complain about!

What would make you a bargain man/woman?