Day 8 – 11: Cultural Chicago | Max Woolf

Max Woolf is a motivational speaker and career coach for Gen Y and beyond. Max speaks to organizations, groups, sports teams, and individuals to help them maximize their potential, live life more fully, and discover their passion and purpose. He has developed a new context for living that invigorates life experiences and improves quality of life called Living at the Edge.

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Day 8 – 11: Cultural Chicago

Published on 08 September 2007 by in Blog, Uncategorized


Before arriving in Chicago, I had high hopes of enjoying the many cultural attractions of the city. I had envisioned a few days packed with history and art. I hoped to take trips to the Art Institute, the Sears Tower, the Field Museum, the Chicago Tribune, and Wrigley Field. I had promised myself that during my visit to Chicago, I would get a true in depth understanding of the city, the people and the lifestyle.

Interestingly enough, I think the picture of this taxicab sums up the reality entire experience:

After this ten minute cab ride, I quickly adapted my original assumptions of “culture” to fit the reality of my visit to Chicago. The cultural experiences I had envisioned were only a figment of my imagination. The true nature of Chicago was in a different realm than I had originally thought. We went to the Watertower to go shopping for sunglasses, we went to the Navy Pier to play miniature golf, and we went to the Signature Room on the 95th floor of the Hancock Tower for drinks.

So, in reality, my cultural venues had more to do with the true “nature” of Chicago and less to do with the history and art that I had originally surmised. In fact, I probably learned more about the Chicago culture in those few choice interactions and moments than I would have at the museums and historical landmarks. I was able to get in touch with the people in the present where they lived their lives: shopping malls, recreational games, and local bars.

The Hancock Tower: Home of the Signature Room!

The city of Chicago from the Navy Pier: Home of my miniature golf victory!

The Watertower: Home of Brett’s new sunglasses!

And in the end, the joke of it all is that the venues don’t matter and the culture is a moot point because it’s all about the journey! No matter what we did or what we saw, we were living the dream. It turns out that the Party Cab that we stumbled upon had the only message that we needed to find in Chicago. And we found it! It’s all about the journey! Don’t ever forget it!

One Response to “Day 8 – 11: Cultural Chicago”

  1. Misha says:

    Dude, you’ve already been to the Sears Tower, Navy Pier, and probably some of the other places you just went again — you haven’t forgotten the epic journey from Boston to Chicago to visit Ben and back again, with John Anderson, JokeWoolf, Chunghovan (and his gatorade/urine bottles), HAVE YOU?