We were lucky to catch up with Jessica Henkin recently and have shared our conversation below.

Jessica, thanks for taking the time to share your stories with us today Have you been able to earn a full-time living from your creative work? If so, can you walk us through your journey and how you made it happen? Was it like that from day one? If not, what were some of the major steps and milestones and do you think you could have sped up the process somehow knowing what you know now?

My upbringing was complicated. Creativity ran through my family, but so did hardship—my parents and sibling struggled with substance abuse and financial instability. Somehow, through some magic of the universe, I became the first person in my family to graduate from college.

I had dreams of studying theater, but I also knew I needed financial stability—and I didn’t want to rely on anyone else to provide that for me. So I prioritized finding a full-time job with benefits as soon as I graduated.

An internship working with young children with autism led me to special education—a field that was still emerging in the 1990s. Around the same time, I discovered improv theater. That passion eventually took me to New York, where I pursued improv at night and taught during the day.

Later, I moved to Baltimore and joined the Kennedy Krieger Institute, eventually becoming a special educator in the public school system. Evenings were for improv, this time with the Baltimore Improv Group.

About 20 years ago, my friend Laura Wexler invited me to collaborate on a live storytelling event. Laura was a narrative nonfiction writer, and she thought my improv background would complement her skills.

Together, we created The Stoop—a live show and podcast that has grown steadily over two decades. I think one of the reasons it’s endured is that it was never our main source of income. Because we weren’t chasing profit, we could protect the creative integrity of the project. It’s remained true to who we are—both as artists and as entrepreneurs.

Is there mission driving your creative journey?

With The Stoop, our mission is to lift up Baltimore through the power of true, personal oral storytelling. We believe that when people share their real experiences—messy, funny, painful, or profound—it fosters empathy, understanding, and community.

We encourage our storytellers not to worry about delivering a flawless performance. It’s not about perfection. It’s about presence. What matters most is sharing your truth as fully and honestly as you can. We ask people to take the risk of being emotionally open and vulnerable on stage, because that’s where the magic happens.

When someone stands up and speaks from the heart—warts and all—something powerful occurs. Walls come down. Audiences lean in. People laugh, cry, nod in recognition. That moment of raw human connection is the heartbeat of The Stoop.

It’s not just storytelling. It’s soul-sharing. And in a city as layered and resilient as Baltimore, we’ve seen again and again how those moments of connection can ripple outward—building bridges, changing perspectives, and reminding us that we’re not alone.

That connection is the true power of The Stoop.

Contact Info:

• Website: https://www.stoopstorytelling.com
• Instagram: stoopstorytellingseries
• Facebook: stoopstorytellingseries
• Other: https://www.wypr.org/podcast/the-stoop-storytelling-series

Image Credits

Photo by Aaron Curtis. There are more photos to choose from here:
https://www.flickr.com/photos/stoopstorytellingseries/albums/72157625089486211/with/52491002254