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Millennials: The most challenging generation?

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For a recent event I was involved in, I was asked to facilitate a roundtable on communicating across generations – Baby Boomers, Generation X, Millennials and Generation Z.

For transparency reasons, 8THIRTYFOUR employs Millennials and Generation Z, I am the only Gen X’er in the company. Yay me.

I did some in-depth research (ok I Googled) to determine the characteristics of the different generations. The research, as well as the business owners’ experiences with millennials specifically was fascinating and very similar.

Baby Boomers (born 1946-1964)

  • Live to work
  • Self-worth = work ethic
  • Loyal to employer
  • Competitive
  • Goal-centric
  • Process-oriented
  • Focused
  • Disciplined
  • Enjoy working in teams and proving themselves to the team
  • Need to know that they are valued
  • Want to make a difference

Generation X (born 1965-1980)

  • Work to live
  • Crave independence
  • Skepticism
  • Focused on results
  • Think Globally
  • Adapt to change
  • Eager to learn
  • Thrive on flexibility
  • Education is a necessary means to succeed

Millennials (Generation Y, born 1981-1996)

  • Fully transparent, shares everything
  • Do well with detailed instructions
  • Desire to make an impact
  • Commerce & conscience together
  • Value Diversity
  • Love technology
  • Education is a highly expensive necessity
  • Do not perform at their best in a traditional work environment
  • Find solutions using technology

Generation Z (born since 1996)

  • Tech-innate (first generation to grow up with modern technology)
  • Accepting of others
  • Make things
  • Realists
  • Individualistic
  • Competitive
  • Transparent
  • Entrepreneurial and inventive spirit
  • Concerned about the cost of education

Besides determining that Gen X’ers are the best generation (kidding), the general consensus was that those born between 1981 and 1996, Millennials, seem to be the most challenging to manage. Here is some of the business owner’s feedback:

  • They have unrealistic expectations. They expect to make upwards of $45,000 in their first job out of college.
  • When asked where she wanted to be in 5 years, she responded “CEO of the company.”
  • They want all the perks, with none of the work.
  • They have a sense of entitlement, want things handed to them.
  • Lack of problem-solving skills need things spelled out for them.
  • Lack of loyalty, the grass is always greener.
  • Disrespectful.

Obviously, this is only one small group’s experience, but millennials tend to be the topic of everyone’s conversations, why is that?

According to the Center for Generational Kinetics’, in the last several years, Millennials have become the largest generation in the U.S. workforce. Millennials are also the fastest-growing generation of customers in the marketplace, bringing the greatest lifetime value. In addition, Millennials exhibit different attitudes toward employmentsales, and marketing, which are challenging many conventional strategies and approaches.

A Time Magazine article published in 2013 titled, Millennials: The Me Me Me Generation stated, “This generation has the highest likelihood of having unmet expectations with respect to their careers and the lowest levels of satisfaction with their careers at the stage that they’re at.”

Here is what I do know, every generation has despised the generation that follows or precedes it. One thing Gen X’ers, Millennials and Gen Z seem to agree on is their dislike of Baby Boomers.

I think what makes most of us uncomfortable…especially business owners is we just don’t know how to manage millennials.

Tom Brokaw, champion of the Greatest Generation, loves millennials. He calls them the Wary Generation, and he thinks their cautiousness in life decisions is a smart response to their world. “Their great mantra has been: Challenge convention. Find new and better ways of doing things.”

In future blogs, I’ll explore the challenges and benefits of employing millennials. I would love your feedback, drop it in the comments below.

Join Me for Uncomfortable Conversations: The Skills Crisis

April 28, 2026

We’re putting employers and Gen Z in the same room, across a table from each other. They’ll discuss what’s working, what’s missing, and what they wish the other side understood.

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