For Destination Imagination alumna Jackie Stewart, discovering the Improv Challenge led to meaningful friendships, a career shaped by creative problem-solving, and a strong commitment to giving back.
Growing up, Jackie Stewart was familiar with Destination Imagination (DI). Her siblings participated in the Challenge Experience, but she felt that the Challenges they worked on never quite captured her interest.
That changed during her sophomore year of high school, when a friend invited her to join an established DI team that needed another member. The team participated in the Improvisational Challenge, which Jackie hadn’t realized was an option.
As it turned out, Improv was exactly what she’d been looking for.
“Improv is what made DI click for me,” she said. “Growing up around lots of theater kids, I never wanted to memorize lines and dress up for a show. Instead, creativity and joy for me was getting a set of rules and seeing how far I could stretch them.”
Rather than following a script, Jackie could take a prompt, explore different possibilities, and make something entirely her own.
“Improv checked all the boxes, and because of that, I was able to push myself out of my comfort zone in a way that felt comfortable for me.”
Finding a Place to Belong
Although improv drew Jackie into DI, the relationships she formed with her teammates became just as important.
Growing up with social anxiety, Jackie found that making and maintaining friendships often required considerable effort. Joining a team whose members had already spent years together could have been intimidating. Instead, their invitation made her feel welcome.
“Them inviting me to join meant that I had a space to feel wanted, especially since they had been a team for such a long time,” she explained.
Over the next three years, those relationships helped Jackie build confidence and become more comfortable expressing herself.
“My team gave me a place to truly be myself with people who accepted me and gave me space to grow.”
That sense of belonging extended beyond her own team.
During her first year in DI, Jackie’s team advanced to Global Finals in Knoxville, Tennessee. Her brother’s team qualified that year, too, making the experience even more memorable.
While the event brought together teams from around the world to share their creative solutions, one of Jackie’s favorite memories happened after the Closing Ceremony.
Trading Affiliate T-shirts with students from other states and countries is a popular tradition at Global Finals. Jackie remembers meeting a group of girls from Poland and exchanging her Michigan shirt for one of theirs—a keepsake she still has today.
“It truly reminds me that DI isn’t about where you come from, and that we all have something in common.”
From Team Member to Volunteer
Jackie’s involvement with DI didn’t end when she graduated from high school.
For the past eight years, she’s continued supporting DI as a volunteer and Appraiser, helping create the kinds of experiences that meant so much to her as a student.
Her decision to return was partly inspired by the adults who supported her own team.
“We were a team that had a consistent Appraiser (shout-out to Mr. Currin!) who did it every year without fail,” she recalled. “We were really lucky to see how much dedication the volunteers put in, and it inspired me.”
Jackie wanted to help create those same experiences for other students, whether that meant sharing a silly joke, writing notes as an Appraiser, or watching teams bring their creative solutions to life.
Over time, she developed an even greater appreciation for the volunteers who make DI possible.
“Now that I understand just how critical volunteers are to the program, I feel an even stronger motivation to continue,” she said. “I want DI to thrive so young creatives can keep being creative!”
That commitment has taken her beyond her local tournaments.
When Jackie volunteered at Global Finals for the first time, she saw the impact of her work on a much larger scale. From managing long merchandise lines to cheering on teams at Closing Celebration, she experienced firsthand how many people work behind the scenes to bring the event together.
She returned home feeling proud to have contributed to an experience that gave students opportunities to learn, grow, and connect.
“I truly just feel DI is such a great resource for kids all over the world, and I can only hope to be a small supporting role in keeping it going strong on every level.”
Bringing DI Skills Into the Workplace
Today, Jackie works as a Process Expert, collaborating with colleagues, researching solutions, and finding creative ways to improve processes.
To Jackie, much of her work feels surprisingly familiar.
“My day-to-day feels very much like a team practice,” she said.
She compares long-term projects to DI’s Team Challenges. Much like she did as a DI participant, she starts with an outcome to work toward and figures out how to get there. Even presentations remind her of preparing a DI performance.
And when something unexpected needs to be fixed quickly? That’s an Instant Challenge.
“I’m given a broken process, and I find a way to fix it as quickly and efficiently as I can,” Jackie said. “I am crafting together creative solutions that haven’t been brought to the table yet.”
She also brings the same curiosity and willingness to question assumptions that she developed as a DI participant. One of DI’s longstanding principles, reinforced in every Team Challenge, encourages teams to think beyond assumed limitations. As long as an idea doesn’t violate the Challenge requirements, it’s worth exploring.
“Sometimes, I even get to poke holes in our processes, just like we did in DI when we’d debate with our teammates: ‘If it doesn’t say you can’t, then you can!’”
For Jackie, creative problem-solving didn’t end with her final DI tournament. The skills she developed continue to shape how she approaches her work every day.
Finding New Ways to Give Back
Earlier this year, Jackie took another step in her DI journey by joining the organization’s Alumni Council.
“I felt the Alumni Council was the right move for me because I wanted to go beyond my Affiliate when it came to supporting DI,” she explained.
Through the Alumni Council, Jackie hopes to strengthen connections among DI alumni, encourage more former participants to get involved, and find new ways to support the program.
She’s also keeping the door open to whatever comes next, whether that’s returning as an Appraiser, serving as an alumni volunteer, or someday experiencing DI as a parent.
For someone who once wasn’t sure the program had anything to offer her, DI has become a lasting part of her life.
You Might Find Something You Didn’t Know You’d Love
When Jackie thinks about students who aren’t sure whether DI is right for them, she remembers how she felt before discovering Improv.
She knows firsthand that finding the right Challenge can make all the difference.
Her advice is simple: Don’t rule it out before giving yourself the opportunity to explore.
“DI can be whatever you want it to be,” she said. “Find a Challenge you connect with and give it a shot to see just how much you can make it yours. You might just find something you didn’t know you’d love.”
For Jackie, one invitation to join an Improv team led to meaningful friendships, opportunities to explore her creativity, and years of volunteering with the program that helped her find her place.
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