Ashan Singh, correspondent for ABC News Nightline, joins middle schooler Kali to share how curiosity, asking questions, and being open to unexpected paths led him into journalism after initially pursuing law.

Kali learns from Ashan why good storytelling starts with a question, how taking on hard things builds confidence, and why making mistakes (and owning them) can help you grow and keep moving forward.

Elise Kirban, Global Chief Counsel of Competition at Aon, joins middle schooler Brielle to share how a path that began in theater led her into a career in antitrust law as her interests evolved along the way..

Brielle learns from Elise why asking questions early, staying curious, and breaking big problems into smaller steps can help you succeed in school and beyond.

Jackie Bravo, Executive Vice President and Corporate Secretary at BankUnited, joins middle schooler Maurice to share how her love of math, structure, and problem-solving led her to a leadership role in banking.

Maurice learns from Jackie why leaning into challenges builds confidence, how being honest and accountable helps you grow, and why doing what you’re good at—and speaking up for yourself—can open doors you didn’t expect.

Alessandra Agarita, Director of Volunteerism at United Way of New York City, joins middle schooler Alondra to share how she built a career focused on helping others and making a difference in our communities.

Alondra learns from Alessandra how confidence grows by stepping outside your comfort zone, why saying yes to opportunities matters, and how volunteering can create real impact.

Diana Arias, Director of Communications at the New York Jobs CEO Council, joins middle schooler Sarah to share how curiosity and creativity helped shape her career. From writing and storytelling to producing videos and social media content, Diana explains how a career in communications can open doors and help people connect.

Sarah learns how trying new things, even in small steps, can lead to unexpected passions, why mistakes are part of the process, and how skills like talking, listening, and thinking outside the box can land you an exciting career.

Steven Milner, founder of US Mortgage Corporation, joins middle schooler Jahlil to share how his career took unexpected turns, from engineering to teaching to entrepreneurship, and why taking risks played a key role in his journey.Steven also tells us about a tough experience that tested him and what he looks for in a strong team.

Jahlil learns from Steven how planning ahead, staying motivated, and doing the right thing can shape your future.

Divinity Roxx, bassist and music producer, joins middle schooler Izzy to talk about her journey in finding her unique voice as an artist.. She shares with us how she unexpectedly fell in love with the bass, the major setback that shifted her career path, and what it really takes to grow as an artist beyond what you see on social media.

Izzy learns from Divinity how staying open, putting in the work, and embracing change can lead to new opportunities.

Lester Marks, VP of Strategy and Impact at the Mother Cabrini Health Foundation, joins middle schooler Ariana to share how his career took unexpected turns, from a love of sports and sports broadcasting to a path in government and nonprofit work.

Ariana learns from Lester why being prepared can open doors, how confidence grows over time, and why it’s important to speak up and take chances even when things feel uncertain. He also shares lessons about teamwork, owning mistakes, and finding balance while building a meaningful career.