Chicago Memories

Chicago Sign

I love the city of Chicago.  The first time I came here, I called home and told the hubs, “I think I could move here!”  It was April.  He told me to come back in February and then call him. 

I’ve been back many times and from the moment I get off the plane in O’Hare, it feels like I’m home.  I don’t even feel that way when I go to San Francisco and it tops my list as my most favorite city.  Chicago always comes in second…go figure.

So I’m back this week for work.  This time it’s just me, alone, in a hotel room the size of my walk-in closet with a bathroom the size of my pantry.  It’s very nice, just very, very small and very, very, VERY expensive.  No matter, I love it here.

Chicago Trump

Last night as I walked up Michigan Avenue and snapped these pics, I started thinking about my last trip here – about 10 or 11 years ago.  I was with my team and we were presenting a class.  I remember being more concerned with where we were going to drink than the class we were delivering.  There was a reception after the first day and when it was over, I went to my room and did some work and then came looking for more drinking buddies.  No one was there.  I remember thinking, “What’s wrong with me?  Why is it never enough?”  I also remember feeling very, very alone.

I sensed my boss knew what was going on because she specifically told me not to go out drinking with the class participants.  I remember thinking, “What is HER problem?  I’m a grown ass woman!”  She knew I was out of control and was just too polite to really call me out on it.  I likely would have imploded if she had actually said anything anyway.  Remembering those times brings a special kind of shame to my heart. 

Last night I sat with that shame.  I let it wash over me.  I let it drift from shame to guilt because, to paraphrase Brene’ Brown, guilt says I’ve done something wrong, shame says I’m wrong.  I’m sick to death of shame.  But guilt is part of me and I have to honor it in order to move past it.  So I did and by doing so, I was able to see this city I love with a new perspective. 

Wanting to soak up some local color, I stopped for dinner at a little dive of a neighborhood restaurant/bar in the basement of a building.  It was fairly early so the place was pretty much empty except for several “regulars” at the bar.  This was just the kind of place I would have LOVED in my drinking days.  As I waited for my deep dish pizza (so much for my eating plan), I watched and listened to the folks at the bar and, rather than feeling envious of their ability to drink, I just felt a deep sense of sadness.  Not for me…for them.  Why weren’t they on their way home to their families?  What would bring them into the basement to drink when the weather was so beautiful?  Why not get a jump on traffic or rush hour?

As I listened to their conversation (it wasn’t hard…you know how loud we get when we drink), it became even sadder to me.  They spoke of kids and wives and husbands.  They discussed Halloween and parties and weekends.  Why were they wasting time in this dark (and cozy I have to admit) place instead of making their way home? 

The longer I sat the more they drank.  No one else came in.  The bartender knew each by name and brought their drinks before they asked.  A familiar pattern to me.  After I finished my meal I overtipped the waitress and made my way out of there, silently bidding goodbye to the locals.

And thanking God that I was no longer one of them.



14 thoughts on “Chicago Memories

  1. I’ve only been to Chicago once…. in December!!! It was hellishly cold – I remember these sharp ice crystals embedding themselves in my face. I flew in from Rhode Island with an American friend. He had an old college pal in Chicago who in the coldest wind known to mankind tried to give us a guided tour! Luckily my friend after a while said “I don’t give a sh**! Find me a bar with a big fire!”

    We went to Buddy Guy’s club and I got to play pool with Otis Rush – who for anyone brought up on Clapton and Gary Moore was like meeting God. Such a nice guy – I was sad when he passed away

  2. I think you are right. It is ok to feel the guilt, the regret, and let it go.
    The person we are today is not that person. But we take the lesson and learn from it, so that as we know better, we do better.

    Enjoy your trip.

    1. I’m in with Mrs. D! I love Chicago, but have only been once, so I really need a tour guide. Sherry’s Sober Chicago Tours 🙂

      Just this morning I looked at a picture taken of my family in Disney World. I was still in active addiction. I did not drink (excessively) on that trip, but my mind was so focused on it, every time I see a picture I am filled with shame. I want it to be guilt, but it is sadly still shame.

      So thank you for this post, maybe this is the permission I needed to transition from shame to guilt. We’ll see how it goes!

      1. It will turn into guilt one day. Then you’ll have to figure out what to do with that too.

        Why oh why do we do that to ourselves?

        Keep trying and so will I.


  3. This is such a beautiful post, and I’ve always loved that quote from Brene Brown about shame vs. guilt. I didn’t realize until I read that how much I was affected by shame while calling it guilt. Hmmm. This post makes me want to do a grand Chicago tour. I’ve been a few times for work but not enough to thoroughly enjoy it. My dad used to travel there frequently for his job when I was a kid, and he always brought home cool gifts and beautiful stories.

    AND…San Francisco is my top all-time favorite city!! I love it so much. I was a flight attendant back in the day and I used to adjust my schedule all around so I could get the LONG layovers there. Three of my best girlfriends and I went there for my bachelorette party; Gil went with me on a few layovers, and now I want to go back for vacation and take my kids.

    So glad to hear you’re moving past shame – you’re definitely NOT wrong.

  4. Oh, how I LOVE Chicago too! I have been there at least a half a dozen times, and have always been pretty much drunk and hungover the entire time I am there. EVERY. TIME! It’s always like that, because the people we go with all party hard. Especially on vacation! We may be going again next Spring, and I won’t even know what to do with myself there. It will definitely be a whole new experience, and one to remember too! Imagine that. So glad that you were able to do that too! How awesome for you to be able to appreciate the city in such a different light. I am always amazed at how I think I want to drink, then I watch/listen to people drinking, and I realize how much I don’t want to be like them. There is a fine line between having one or two social drinks on occasion, and then drinking like we used to.

    1. Exactly. I don’t know what one or two is! Even now if I think about drinking it’s about drinking a bottle – not just a glass.

      Chicago was even more beautiful sober.


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