Lesson #1: Plan Ahead

My friend Sarah came up from Indy to visit this weekend, so I thought it would be the perfect time to begin my challenge. We could experience Chicago together. As I began to research things going on around the city, there were so many options to choose from. I'm not much of a planner, and like to be super spontaneous- especially when it comes to entertaining myself. This proved to be a problem this weekend. By the time we decided what we were going to do, and went online to purchase tickets, everything we wanted to do was sold out!



On Saturday morning we decided to walk the dog down to the lake and then grab a quick brunch at Emerald City Coffee. After doing some more research, we decided to head to the St. Alphonsus Oktoberfest. If we were going to have some drinks, it may as well go to a good cause! After that it was decided that we couldn't go an entire Saturday in September without seeing some college football. So, off to Houndstooth it was. After a little more bar hopping, we decided to get all dolled up (the girls decided this) and just bar hop through Wrigleyville.

The first weekend of my challenge didn't quite deliver on trying something new and exciting, but my friend did get to experience a part of the city she had never been. Plus, it's always a good time when Sarah is in town!

Week one didn't go without a lesson though- plan ahead. I already know what I want to do this weekend, so weather permitting, I'll actually have something to report next week!