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Why does every generation seem convinced that the generation after them is more entitled than they were?

From Baby Boomers to Gen X, Millennials, Gen Z, and Gen Alpha, the debate over entitlement has been happening for decades. But is the next generation truly more entitled—or are we viewing them through the lens of our own experiences, values, and cultural upbringing?

In this episode of ROAR OUT LOUD, Mary Street explores the strengths, challenges, and defining characteristics of each generation. She breaks down the difference between healthy entitlement and unhealthy entitlement, revealing why some expectations are rooted in personal responsibility, self-worth, and healthy boundaries, while others stem from privilege, excuses, and misplaced expectations.

You'll also discover how the culture we grow up in shapes the way we think, lead, work, communicate, and show up in life. By understanding the historical and cultural influences that have shaped each generation, we can move beyond stereotypes and learn to lead, parent, mentor, and influence others with greater wisdom and understanding.

Whether you're young trying to find your way in life, a leader, parent, entrepreneur, coach, pastor, educator, or simply curious about generational differences, this episode offers practical leadership insights to help you navigate generational tension, build stronger relationships, and bridge the gap between generations.