The awkward path to serendipity

Lisa Rossi
7 min readSep 10, 2020

Everyone is beautiful.

They are beautiful in a way I can’t understand.

I’m on a Zoom call with aspiring and working entertainment professionals from around North America, but most are clustered in Los Angeles. I’m in Des Moines, Iowa in my finished basement, with it’s lacquered wood paneling from the early 2000s and a little boy’s basketball hoop perched upon a door in the background.

I’m asking myself: How did I get here?

I’m learning comedy from the L.A.-based Groundlings Theatre & School, the same place of improv and sketch comedy that trained my hero, the comedian and actress Melissa McCarthy.

I only realized she was my hero in the last year.

Because I’ve blown up my life. I try not to say it like that in Zoom introductions. My elevator pitch is smooth. Hi, I’m Lisa Rossi. I’m here because I run a company that trains professionals in using a process of innovation that unlocks breakthrough ideas. I need improv (a form of live theater where performers act out unscripted stories) to loosen people up during these trainings. And I’m here to learn more about it.

I need improv to loosen myself up. I was a journalist once. For 20 years, actually. I quit about two years ago. I did that after completing what I believe is the most prestigious fellowship that journalists can attain. I was at the Stanford John S. Knight Journalism Fellowship, with one of its key goals of building change agents. At the beginning, I thought this fellowship would build me into a person who could reinvent the financially beleaguered industry of local news, to put its broken pieces back together.

But then one day, I took a comedy class at a dark theater in mid-day in San Francisco. I’ll never forget the moment when my friend Michael Grant was thrust in a scene that required everyone to give voices to inanimate objects in a child’s nursery. Michael slumped down on the floor, splayed his legs in front of his body, and dangled his head down.

Cecilia Wörthmüller, Michael Grant, Lisa Rossi, Janna Bubley and Jessica Chow at an improv workshop at the Un-Scripted Theater Company in San Francisco. Photo by André Natta.

“I’m a teddy bear,” he said in high-pitched voice that I had never heard come from him before. “And nobody ever plays with me.”

I cracked. My world cracked.

This was just …. beautiful. And hilarious.

I was a journalist once. I searched for stories that would change people. I wanted stories to show people truth, and in some grand way, light. I wanted words to be transformative in a path to justice.

One day at my fellowship, I was assigned to tell my cohort of journalists from around the world my own story, something we each did throughout the year to build our community. We all gathered into a room with couches and a large screen at the front to display slides. I sat at the couch in the front and they circled around me.

My heart thumped when I told them that my career started at a small county weekly in rural Iowa and progressed to covering national presidential campaigns for the Des Moines Register.

That sounded good. Maybe I was going to be ok.

I then told them I covered 9/11 at age 20. My voice wavered and my mouth went dry. They could all see it happening. I placed my hand on the box of Kleenex and didn’t take one out.

Silence. Awkward silence.

I struggled because I was silencing myself, holding back the secret that I almost left journalism immediately after covering 9/11 because I had panic attacks at night and could no longer understand what it meant to have friends.

I didn’t die, I thought. I wasn’t a rescue worker. I didn’t fear for my own life in the way Muslim Americans endured post-9/11. I was just the observer. And I was being dramatic. It’s the story I told myself that allowed me to drag my heart back in the newsroom and try again and try every day, even as my ability to cope with this career began to actually crumble for real. I remember one work day about four years ago, I spent 13 hours on social media researching two local police officers who had been ambushed and shot in their cars. I came home unable to speak, silent tears running down my face.

I was done.

And I was also going to Stanford.

I remember the director of the JSK program, Dawn Garcia, introducing me to the concept of serendipity. I interpreted the message as an opportunity to give myself some free time to consider different paths to my goal of telling the truth. Who says you have to change the world in just one way?

Near the end of my fellowship I nearly accepted a big job at a university that looked oddly similar to what I was doing before.

I was *this close to kicking serendipity in the face for a title that would look good on LinkedIn.

What got me in the end was the realization I dreaded that job. Every day would be a struggle and one I wasn’t confident I could withstand. I dreaded the phone calls to even talk about this job. I had changed before I had even understood how I had changed.

With a mix of shame, fear and excitement, I turned the job down and moved back to Des Moines, Iowa. It’s where I now sit, two and half years later. A woman on the other side of the Groundlings Zoom call is on a couch, her arm draped over it, soft lighting on her face. She’s a make-up artist. A man is in a room full of books. He’s a teacher and when he moves, his arms pop out during exercises with such electric energy that I have to laugh.

I came back to Des Moines and started a company with my business partner Nathan Groepper that teaches people the essence of what I loved in journalism: Listening. Only now, we train others in listening as a path to personal understanding and creativity. We are building and growing and nowhere near that established career I left behind to chase serendipity.

In the darkness of an Iowa winter, I signed up for my next improv class. I fought through my shame of failure to “make it” as a journalist while a quiet man named Eddie transformed himself into an octopus and flailed his arms around and rolled his tongue in his mouth. I joined an improv troupe and performed in a coffee shop theater with dust on the floor and nobody but my own husband and another partner of a troupe member in the audience. I auditioned for a spot on a comedy club house troupe and didn’t make it. I performed stand-up and sometimes people laughed and sometimes … they didn’t. I took more classes, I built my business and I worked on myself in therapy.

Andrew Tatge, Lisa Rossi and Mark Hoag, members of the Alley Cat Improv Troupe, performing in the Java Joe’s Theatre in Des Moines Iowa. Photo by Danny Carman.

And a few weeks ago, lonely in the middle of a pandemic, I auditioned for the chance to train with the Groundlings Theatre. And I made it.

During our first session together, our teacher, Tom Blank, asked us to take turns describing objects. Many of my fellow students, myself included, liked the concept of gloomy, decaying items, old mysterious things like rusty swing sets.

Tom urged us to avoid these judgmental adjectives like “old” and “musty” and instead describe the objects we imagined as they actually are. I recall how he said one student once thought of an object that was a pink retainer box with a My Little Pony sticker on top. I understood that an audience member can picture that with more clarity and meaning than she can picture an “old” retainer.

He then quoted artist John Singer Sargent, known for his portraits.

“I do not judge. I merely chronicle.”

For a second, my entire world went on pause.

My computer was balanced on a tower of books, a set-up that allowed me to be seen as I moved in class. Right next to it was a paper towel. I searched for something to write with and found a Sharpie. I wrote the words down as fast as I could, struggling as the marker scraped against the grooves of it.

“I do not judge. I merely chronicle.”

This sounded just like the advice I was given as a student journalist in the classrooms of Seashore hall at the University of Iowa. Like, almost verbatim.

I’m yet again, in a place that’s seeking to tell stories that reveal deep truths. My story of grief and shame that I quit something, I realized, was completely and utterly false.

Looks like serendipity got me after all.



Lisa Rossi

Obsessed with the growth mindset, design thinking and telling great stories.