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My Two-Thousand-Dollar T-Shirt

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Every so often I stumble across a neatly folded red t-shirt tucked way back in my closet when I’m organizing or looking for something. I’m always compelled to unfurl it, and unfailingly get lost in memories. It’s my two-thousand-dollar t-shirt. I’ve never worn it. I’m not even sure I’ve ever washed it, but I have considered having it framed because of the price.

In spite of the sage words of my grandma, I never liked to stand out, preferring a safe place huddled in the masses. It wasn’t that I didn’t know how to sparkle—intentionally or not—but that there was no expectation of it. I had developed a quick wit over time and by my mid-20s knew when—and when not—to use it.

I began hearing “you should do stand up comedy” around that time. Though I didn’t have anything against the idea, I had no concept of how to begin. Besides that, it looked terrifying. Alone. On stage. Dying. Being heckled. Scary stuff that I wasn’t ready for.

But I had the benefit of living in the home of The Second City. And as I heard the “stand up” comment more and more, I began to understand that it was misunderstood by many people to mean improv comedy. A couple of years later my bestie and I began to consider seriously signing up to take classes at the venerable improv comedy institution.

Once we had decided it was time to pony up the $2,000 fee, we reported to 1616 N. Wells on March 15, 1997 (and still it feels like only a couple of years ago). My nerves were atwitter and my IBS went beyond teasing me to blatant torture. It was a sensation that never let up as class approached each week. It was terrifying—in the way only something that exciting can be. 

It was during the two years of weekly three-hour classes that I learned—or perhaps remembered—to be fearless. Unlearning how to think on stage and, rather than act, react; figuring out “the game” of the scene each time. I learned how to trust my stage partners and to heighten the scene in accordance with the rules set forth by the progenitors of the very stage on which I was standing. I had three different weekly sessions which took place on the hallowed Main Stage, where the likes of Belushi, Nichols and May, Carrell, and Fey performed.

Attending classes at Second City was without a doubt one of the most special and defining experiences of my life. It was the scariest and smartest decision I’d ever made. It ever-so-slightly changed the direction of my life, and my perspective as well. What I experienced each week in class found its way into every aspect of my life. The teamwork I learned caused my performance at work to increase exponentially. I began to look at “problems” as “challenges,” where the key lay with finding the game. Improv became a metaphor for life.

The satisfaction and intensity of being fearless on a weekly basis propelled my life forward at an accelerated rate. But I have to say, it wasn’t the most valuable gift by any means. Aside from “graduating” Second City with a sense of accomplishment, I left with four of the closest friends I’ve ever had. As I look back on my tenure there, the rules I learned on stage give way to the long-lasting and harassing friendships that were formed while learning them. At the time in your life when most people aren’t in the position to make new friends, I made some incredible ones. Another reward of fearlessness.

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About Ron Stempkowski

  • Tina

    Ron, You are spectacular and you ARE fearless! Some of the best memories of my entire life were made on that stage with you — and in those “apres classe” sessions that came so highly recommended!

    MUCH love to you and your faux-dark hearted self!



  • Jim


  • Kim

    How awesome! You are such a wonderful writer. I’m so glad you are doing what you so enjoy.

  • Mindy

    Awesome story as only you could tell it. And as always, you pass on such amazing nuggets of inspiration through those stories.

  • Louise K


  • Ross

    The owner of the $2000 shirt obviously hates attention as he shuns the expensive shirt. His reason was that he hates being the center of attention. Well, I can only guess if it’s a $2000 shirt, it must really live up to its price and that in turn, will turn heads. However, his story has a strong message. If you’re always afraid to take the plunge, then you’ll never know what you’re missing. The author decided to sign up for classes and trainings to be a comedian when in fact, if he hates attention, will be a huge NO for him. Yet, he took that leap and came out from the experience more confident as he met interesting and fun people along the way. A lesson that we all must ponder on..