ORLANDO, Fla. — While communicating with different generations on both sides of the counter can be a daunting task for dry cleaners, understanding the experiences of each age range and how they have shaped their outlook is an important step toward connection.
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.
In Part 1 of this series, we looked at some of the challenges of changing your mindset about connecting with different generations. Today, we’ll continue by digging into what makes the baby boom and Gen X generations tick.
Baby Boomers: The Foundation Builders
Baby boomers, now roughly 61 to 79 years old, came of age during a time of societal upheaval — the Kennedy assassinations, the Vietnam War, Woodstock, the moon landing, Watergate and numerous social movements. Despite this turmoil, Stollings-Holder says, this generation developed an optimistic outlook bolstered by a booming post-war economy and belief in the American dream.
At their peak, boomers numbered as high as 80 million. This massive group meant intense competition for jobs and advancement, which created what Stollings-Holder identifies as a linkage between sacrifice and success.
“That means when your business is opening, I’m not just walking in,” she says. “I’m already working. I’ve gotten everything ready the night before and sometimes a guilt for leaving at 5.”
This brings up what Stollings-Holder calls “probably the most significant conflict” in today’s workplace: disagreements over work ethic. For baby boomers, hard work is naturally associated with time and place — being there early, staying late and putting in the hours.
This is different from the generation now entering the workplace, she says. “It has everything to do with the outcome they produce.”
This fundamental disconnect means everyone believes they’re working hard while simultaneously thinking others aren’t. The solution? Creating shared definitions.
“I encourage you, within your business, to create shared pools of meaning,” Stollings-Holder says. “‘Here is what hard work means at our company. Here’s how we measure it.’”
For engaging baby boomers, Stollings-Holder recommends taking time to say “thank you” for the foundations they’ve built, keeping them up to speed on technology and changes, and — critically — capturing their knowledge and wisdom. With 10,000 boomers turning 65 every day, the window for preserving institutional knowledge is closing rapidly.
Generation X: The Skeptical Independents
Generation X, roughly 45 to 60 years old, holds 51% of global leadership positions today. Members of this smaller generation, Stollings-Holder says, earned their reputation for skepticism and independence through hard experience.
As Gen X came of age, they witnessed scandals in government and religious institutions, both parents entering the workforce — often missing important moments — and the mass layoffs of the early 1980s. Divorce rates tripled, creating a generation of “latchkey kids” who went to after-school programs or stayed home alone.
“When it comes to partnering and trusting you, they’re going to take a step back to see if your words and actions align,” Stollings-Holder says. “For them, truth equals behavior over time.”
Generation X values efficiency and directness. They communicate in an easygoing style — you may get everything you need in an email subject line, punctuation optional. They ask questions not to challenge authority but to ensure processes still add value in a changing world.
Critically, Gen Xers cannot stand micromanagement, and don’t like to do it themselves as leaders.
“If they’re not hovering over your shoulder, that’s a great compliment because that means that they can trust you,” Stollings-Holder says.
Many Gen Xers missed parental involvement growing up, she says, which led them to overcompensate by becoming highly active parents themselves. This doesn’t mean a lack of work engagement — it simply reflects a high value for family, which is especially important for family-owned drycleaning businesses to understand.
Come back Thursday for the conclusion, where we’ll get into the minds of the millennial and Gen Z generations, and share some thoughts on how to bring everyone together. For Part 1 of this series, click HERE.
Have a question or comment? E-mail our editor Dave Davis at [email protected].
