ORLANDO, Fla. — Drycleaning owners can often struggle with workplace conflicts or find themselves frustrated by what they see as a poor work ethic with their younger employees. However, the problem often isn’t a lack of dedication or effort, but a fundamental misunderstanding across generations.
During her 2025 Clean Show presentation, Jessica Stollings-Holder, author of “Regenerate: A Guide to Connect Generations,” challenged attendees to rethink how they view and engage with their multigenerational workforce.
Her message was clear: Understanding the unique experiences that shape each generation can transform workplace dynamics from frustrating to empowering.
“Sometimes, the words and phrases we use can have a totally different meaning depending on the time and context that we grew up in,” says Stollings-Holder, illustrating her point with a simple example: Ask people about “the moonwalk” and you’ll get vastly different answers depending on their age — it’s Neil Armstrong’s moon landing for some, Michael Jackson’s signature dance move for others.
The Challenge of Change
The speed of technological and cultural change has been staggering, and this is particularly true in how we communicate. Stollings-Holder walked her audience through the evolution from families gathering around radios for news and entertainment, to the TV era where viewers physically changed channels, through the dial-up internet days, to today’s smartphone and social media environment.
“In today’s world, you can call a young person all you want, and they’re not there, but then you do what?” Stollings-Holder asks. The answer from the audience was immediate: Text them.
This change of pace means each generation has essentially grown up in a different world, making miscommunication not only possible but likely. For drycleaning businesses competing in an era where customers expect personal service and instant gratification, understanding these generational differences isn’t just a “nice to have” factor — it’s essential for survival.
A Lens, Not a Label
Before diving into specific generations, Stollings-Holder established an important ground rule: View generations as a factor for understanding rather than a method for stereotyping.
“We’re not saying that if you are this generation, you have these 3.5 robotic qualities,” she says. “Today, I encourage us to think of generations as a lens, not a label, to better understand ourselves and relate to others.”
She compares studying generations to examining trees in a forest. While each is unique, those growing in similar soil with similar exposure to sunlight and rainfall share certain characteristics. The same applies to people shaped by common historical events and cultural influences during their formative years.
Generational theory supports this outlook, she says, which suggests that each generation tends to overcompensate for perceived lacks in the previous generation, creating recurring cycles throughout history.
Stollings-Holder notes that we’re currently at the end of a full generational cycle, known as a “fourth turning” or crisis cycle — similar to periods like the Great Depression and World War II.
“It means that many of the systems that were built start to break,” she says. “And all of a sudden, we have to think about new ways to build them. In other words, what got us here in the past simply can’t carry us forward into the future.”
While this can create tension and frustration, Stollings-Holder frames it as an opening.
“Spring is coming, but in the middle of this friction and frustration, some breakage is happening,” she says. “We have the opportunity to ask, ‘What are we going to build? How can it be better? And how can we do it together?’”
The Power of Story
To demonstrate the value of understanding generational experiences, Stollings-Holder led attendees through a story-sharing exercise in which partners from different generations took turns describing the decade they grew up in — the headlines, the music, the devices they thought were cool, what was on their Christmas lists, and so on.
The exercise revealed something interesting: Story sharing creates human connection. Some research has shown storytelling actually syncs the brains between storyteller and listener. This makes it one of the most effective forms of communication, and one that can be used at any time.
“When you have that moment where someone shares a memory, it’s like we really connect and really vibe,” Stollings-Holder says. “That is the power of human connection.”
Come back Tuesday for Part 2 of this series, where we’ll dig into what makes the baby boom and Gen X generations tick.
Have a question or comment? E-mail our editor Dave Davis at [email protected].
