The Red Boots and I tromped all over Chicago last week. We attended the 2012 Association of Writers & Writing Programs (AWP) conference. We visited my cousin, who lives there and is recently involved in the city’s stand-up comedy scene. We passed out postcards and told everyone we could about Under the Gum Tree.

The Red Boots and I were a lonely 2 of 10,000 attendees.

Not even wearing the red boots seemed to help dissuade feeling overwhelmed, nervous, exhausted, outnumbered, lost in the crowd and even frustrated.

See, the thing is that I can muster up the boldness to wear The Red Boots once, but I have to muster it up all over again next time. But wearing The Red Boots for the first time should give me the strength to wear them again, because I know it’s something I’m capable of. I’ve done it before, I can do it again.

Once I started wearing The Red Boots, I wanted them to be magical. I wanted them to give me super powers. I thought that simply by wearing them I’d change, just like Clark Kent or Bruce Wayne. I wanted an instant phone booth transformation¬†that would allow me to, when dealing with major health issues and emotional trauma last year, share candidly with anyone and everyone who asked, “how are you doing?” The Red Boots should give me the power to honestly say, “really awful,” and then continue to share why. Not because I wanted sympathy, but because I wanted an authentic connection with people around me.

Instead, what I’m learning is that it took time to work up to wearing The Red Boots: they sat on the floor in my closet for almost a year before I wore them. I remember looking at them every day, thinking about how to wear them, what outfit combos to pair with them. That year got my mind used to the idea of wearing The Red Boots, and I had to be mentally comfortable wearing them before I could be physically comfortable wearing them.

And I still have to give myself time to work up to wearing The Red Boots — whether that means sharing about deeply personal and painful things or peddling my magazine.

Because the truth is that in the midst of said emotional trauma, I would have broken down crying every time someone asked how I was and I certainly didn’t have the strength to deal with that.

Because the truth is that, while I may be known for wearing The Red Boots, they aren’t magical and there’s still a certain amount of gearing up for vulnerability and shameless self-promotion that goes on behind the scenes.

Time gives me the distance I need to process, adjust, accept, move, write, and tell my story…when I’m ready.

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4 thoughts on “What Chicago taught me about mustering up the boldness.

  1. I tried to send this as a reply to your email but it was invalid somehow.
    Happy Day
    Boldness, It’s taken 50 years and Breast cancer and I am still struggling. I am the sole parent of two children, one in college, and my ability to work in more creative capacities in hampered by that. I would like to write, create works of art, craft and cook. I do all of these things in a smaller scale and not for profit actually the oopsite because you have to buy supplies. I am a very talented large scale Garden Designer which is a creative outlet and pays the bills but I am ready to explore some of my other talents/desires. Why does it have to be so hard. My work (Beautiful! For garden people) My blog page, good for a laugh or two (check out my red dress in my profile pic)

    Keep on walking,
    All my best, Simone

    1. Thanks for sharing, Simone! Isn’t it amazing to reflect on our experiences and see where time has taken us? That distance really helps to put things in perspective sometimes. But it’s definitely easy to loose track of that in the midst of struggling.

  2. Janna, that first comment is from my dear, sweet, bold, sassy sister! I just came back to this post to comment and was a surprise to find her here. Synchronicity.

    Sometimes when I read inspirational stuff on boldness or similar themes, I’m turned off by the unabashed approach that is often used, because there is an internal timing for each individual. That timing is unique to us and can’t be determined by some external source. It is great to get inspired and take leaps, but really what gets you there is the step by step and day by day.

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