Join Jason for an insightful, heartfelt conversation with his daughter Bailey, a high school senior and returning guest who brings a fresh, next-generation perspective on work, communication, and the rapidly changing world of careers.

As the year comes to a close, Bailey returns to reflect on her early work experiences, lessons in workplace culture, and what the future holds. As a member of Gen Z looking towards college and preparing for a career in the age of AI, she offers valuable insight into the expectations of tomorrow’s workforce.

Bailey shares her takes on what makes for a good work experience, what she looks for when considering a part-time job (including the "vibe" of the place), and how she and her peers are thinking about their career prospects beyond high school graduation.

Some highlights from Bailey's perspective include:

👉 Prioritize people and communicate consistently; your hardest workers check out long before you notice if you neglect to follow up or show genuine care.

👉 Authentic happiness at work matters; employees can sense when colleagues are “putting on a show” versus truly enjoying their environment.

👉 Candidates evaluate your culture (the “vibes”) from the moment they interact with your organization, make it a two-way street, not just an act for outsiders.

👉 Today’s young workers are practical and pragmatic. They’re weighing their education and career choices against a backdrop of cost, job stability, and AI disruption.

👉 Teach and encourage healthy skepticism: critical thinking is now a survival skill when technology can fabricate reality at scale.

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Connect with Jason:

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