Jason Dorsey: How Travel Advisors Can Win the Next Generation of Clients

Travel advisors who want to attract multiple generations of clients need to understand how different cohorts communicate, build trust and make buying decisions.

That was the message from generational researcher and keynote speaker Jason Dorsey at Travel Market 2026 in San Antonio, where he offered a fast-paced and humorous look at the behavioural differences separating Gen Z, millennials, Gen X and baby boomers. Several advisors later told Travel Market Report Canada that the presentation was among the most valuable at the event.

Dorsey argued that one of the biggest influences shaping a generation isn’t technology, social media or economics. It’s parenting.

“Parenting is the most influential,” he told attendees, although he stressed that it isn’t deterministic. The environment people grow up in helps shape expectations around work, money, communication and relationships. 

“How many of you are still paying the phone bills of children in their 20s,” Dorsey asked the audience to loud laughter.

Success Comes from Understanding Generational Needs

Technology is another powerful differentiator, but Dorsey offered an important distinction: “Technology is only new if you remember it the way it was before. Otherwise, it’s all you’ve ever known.”

For younger travellers, communicating by text, FaceTime, social media or AI isn’t adopting technology — it’s simply communicating.

That distinction will become increasingly important as Gen Z enters the workforce, accumulates wealth and becomes a larger travel-buying force.

“Whoever takes the time to understand how they want to communicate, how they want to learn and how they want to emotionally connect will get the business [and] the loyalty,” Dorsey said.

Gen Z Wants Stability & a Human Connection

For advisors, Dorsey sees an especially significant opportunity with Gen Z.

Having come of age through COVID, economic uncertainty and an intensely polarized political environment, he said Gen Z has experienced significant instability. As a result, one of the things members of the generation value most is stability.

For travel advisors, that creates an opportunity to demonstrate that there is a real person standing behind a trip when something goes wrong.

“They want to hear someone like you say, ‘We have your back,’” Dorsey said.

He also challenged the perception that Gen Z is interested primarily in digital experiences. Instead, he sees increasing demand for travel, unique experiences and in-person connections.

“This is the best time ever to attract Gen Z as your clients,” he said. “They’re determining their loyalty right now.”

Social media plays an important role in establishing that relationship, but Dorsey said younger consumers aren’t necessarily looking for a highly polished corporate presence.

Instead, they’re looking for a human touch they can relate to. In response, advisors should let prospective clients see something of the person behind the professional title, including their interests, preferences and personality.

While “authenticity” has become a marketing buzzword, Dorsey suggested vulnerability is a better description of what younger consumers respond to.

Older generations were often taught to present a highly polished image, he said. Younger generations are more comfortable seeing and sharing imperfection.

Dorsey also said Gen Z is particularly powerful when it comes to generating new business through friends. But he cautioned advisors about the language they use.

“Referral is a negative word,” he said. Rather than asking younger clients for referrals, he suggested asking: “Do you have any friends I can help?”

Millennials Are All Grown Up Now

Dorsey reminded attendees that millennials are much older than many marketers perceive them to be, with the oldest members of the generation now approaching their late 40s.

He describes one important millennial life stage as “delayed adulthood.” Traditional milestones such as marriage, children and home ownership, are not being rejected, but are often delayed.

Another misconception, he said, is that millennials are inherently tech-savvy.

“We are tech-dependent,” he said. “We don’t care how it works. We just expect it to work.”

For travel sellers, that means removing friction and making interactions as straightforward as possible.

“How simple can you make it so it just works?” he asked.

Gen X, for its part, tends to be naturally sceptical, Dorsey said — a characteristic advisors should be aware of when working to establish credibility and trust.

He also highlighted “cuspers,” people born within a few years of the dividing line between generations. Because they often identify with characteristics on both sides of that line, Dorsey describes them as “natural behavioural bridges,” noting that they frequently gravitate toward entrepreneurship and sales.

Every Generation Brings Its Own Value

Despite the differences between generations, Dorsey stressed that one should not be considered more valuable than another.

“Every generation is equally valuable,” he said. “Every generation brings something we need.”

For advisors selling to Gen Z and millennials, however, Dorsey offered one particularly simple piece of advice: position travel as being “as unique as you are.” He argues that younger consumers respond more strongly to the idea that something has been created specifically around who they are and what they want.

It also illustrates the larger point behind his presentation.

Technology and AI will continue transforming how travellers research and purchase trips, but Dorsey doesn’t believe being younger automatically provides an advantage.

Instead, the advantage goes to the advisor who understands how a client wants to communicate, what makes them feel confident and how they want to connect.

For Gen Z in particular, Dorsey said the opportunity is substantial.

“At the end of the day, what we see is that Gen Z wants a human being they can count on when they need it.”