Considering where I grew up, I couldn't help but reflect on the evolution of the American Dream, its impact on my life, and its varied resonance within the black community. From the Bronx to the bench, the Honorable Justice Tanya R. Kennedy joins me to share her inspiring climb to the judiciary from a single-parent household. Adding to our generational tapestry, dynamic entrepreneur Imani Blair illuminates the highs and lows of her eclectic career pursuits, from real estate gambles to the creative hustle of podcasting and music. Together, we dissect the layers of ambition and happiness, examining the changing face of success and fulfillment.   The conversation turns to the financial tightrope many of us walk. Imani's tales of her sporadic, yet substantial, freelance income injects a dose of reality into the dreams of those chasing non-traditional career paths. Amidst this, we underscore the paramount importance of financial literacy and proactive retirement planning, drawing on Justice Kennedy's wisdom of long-term professional commitment and the less discussed significance of Associate programs.   To cap off our journey, we navigate the transformative rivers of education and career decisions. My personal hurdles – from the sting of academic expulsion due to financial barriers to carving a space for myself as a minority in media – contrast Imani's flexible leap from aspiring recording artist to podcasting success, offering an honest look at the shifting educational landscape. We question the future of higher education in a world where acquired skills are rapidly overriding degrees, and look ahead to how the evolving job market and generational perspectives on work-life balance are reshaping what we strive for and how we get there.  RATE, REVIEW, AND FOLLOW ON APPLE PODCAST ‌🎥 Watch Across Generations on YOUTUBE: Follow us on social media: ‌📱INSTAGRAM: Tiffany D Cross ‌Across Generations Podcast 🐦TWITTER/X: Tiffany D Cross ‌Across Generations is produced and edited by Idea to Launch Productions See omnystudio.com/listener for privacy information.